57774-35-3|4'-Bromo-[1,1'-biphenyl]-4-carbonitrile| Ambeed

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Quality Control of [ 57774-35-3 ] Purity: 95% SDS Specification

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Product Details of [ 57774-35-3 ]

CAS No. :	57774-35-3
Formula :	C₁₃H₈BrN
M.W :	258.11
SMILES Code :	N#CC1=CC=C(C2=CC=C(Br)C=C2)C=C1
MDL No. :	MFCD05980943
InChI Key :	BHVHKOVPWZKVCC-UHFFFAOYSA-N
Pubchem ID :	1394462

Safety of [ 57774-35-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 57774-35-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 57774-35-3 ]

[ 57774-35-3 ] Synthesis Path-Downstream 1~35

1
[ 128-39-2 ]
[ 57774-35-3 ]
[ 139780-23-7 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 491 - 494.
[2]Journal of Organic Chemistry,1994,vol. 59,p. 4482 - 4489.

2
[ 57774-35-3 ]
[ 130447-21-1 ]
[ 130447-12-0 ]

References: [1]Journal of Organometallic Chemistry,1990,vol. 390,p. 389 - 398.

3
[ 57774-35-3 ]
[ 130447-20-0 ]
[ 130447-15-3 ]

References: [1]Journal of Organometallic Chemistry,1990,vol. 390,p. 389 - 398.

4
[ 57774-35-3 ]
[ 93296-10-7 ]
[ 130447-13-1 ]

References: [1]Journal of Organometallic Chemistry,1990,vol. 390,p. 389 - 398.

5
[ 623-00-7 ]
[ 130447-21-1 ]
[ 57774-35-3 ]

References: [1]Journal of Organometallic Chemistry,1990,vol. 390,p. 389 - 398.

6
[ 57774-35-3 ]
[ 73183-34-3 ]
[ 406482-72-2 ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 8290 - 8294.
Angew. Chem.,2017,vol. 129,p. 8405 - 8410,6.
[2]Journal of Organic Chemistry,2002,vol. 67,p. 1699 - 1702.
[3]Journal of Materials Chemistry C,2015,vol. 3,p. 3960 - 3970.
[4]Chemical Communications,2015,vol. 51,p. 12641 - 12644.
[5]Journal of the American Chemical Society,2009,vol. 131,p. 3881 - 3883.

7
[ 57774-35-3 ]
[2,4,6-tris(4'-bromo[1,1'-biphenyl]-4-yl)-1,3,5-triazine] [ No CAS ]

References: [1]Dalton Transactions,2006,vol. 6,p. 1721 - 1728.
[2]Journal of Materials Chemistry A,2018,vol. 6,p. 15154 - 15161.
[3]CrystEngComm,2012,vol. 14,p. 768 - 770.

8
[ 57774-35-3 ]
[ 406482-73-3 ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 1699 - 1702.
[2]Chemical Communications,2015,vol. 51,p. 12641 - 12644.

9
[ 57774-35-3 ]
ethyl N-(4'-cyanobiphenyl-4-yl)-5-formylpyrrole-3-glyoxalate [ No CAS ]

References: [1]Journal of Organic Chemistry,2002,vol. 67,p. 1699 - 1702.

10
[ 57774-35-3 ]
[ 130447-14-2 ]

References: [1]Journal of Organometallic Chemistry,1990,vol. 390,p. 389 - 398.

11
[ 106-37-6 ]
[ 126747-14-6 ]
[ 57774-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 60℃; for 12h;	Add 100mmol of 1,4-dibromonaphthalene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of tetrahydrofuran (THF), 200ml of water and Pd(PPh3)4 in the reaction flask, at 60 After reacting at for 12h, stop the reaction after the reaction is completed, and cool the reactant to room temperature, add water, filter, and wash with water. The solid obtained is recrystallized and purified with toluene to obtain white powder M1, in which Pd(PPh3)4 is added The amount is 1 mol% of 1,4-dibromonaphthalene
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 120℃; for 12h;	100mmol of 1,4-dibromobenzene, 100mmol of 4-cyanophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water were added to the reaction flask, and 1mol% of Pd(PPh3)4 was added. React at 120C for 12h. After the completion of the reaction, the reaction was stopped, the reactant was cooled to room temperature, water was added, and the organic phase was concentrated to obtain a white solid, which was filtered and washed with water. The obtained solid was recrystallized and purified with toluene to obtain a white powder M1. Among them, the added amount of Pd(PPh3)4 is 1 mol% of 1,4-dibromobenzene.

References: [1]Patent: WO2005/40132,2005,A1 .Location in patent: Page/Page column 76.
[2]Patent: CN112159361,2021,A .Location in patent: Paragraph 0110-0111; 0120-0121.
[3]Patent: CN113307764,2021,A .Location in patent: Paragraph 0151-0153.

12
[ 92-86-4 ]
copper(l) cyanide [ No CAS ]
[ 57774-35-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	In N,N-dimethyl-formamide; for 12h;Inert atmosphere; Reflux;	4,4'-dibromobiphenyl(15 g, 48.08 mmol) and 4.31 g (48.08 mmol) of CuCN (CAUTION, keep water away from) the round Plastic tested in 20mL DMF and then dissolved in nitrogen 12 hr reflux in state condition, and stirred. After the reaction was completed down to room temperature, the organic layer was dried with MgSO4 and the solvent removed under reduced pressure and purified by column chromatography (silica, CH2Cl2: 1: 1 = hexane) was isolated the product as a. The yield was 93%.

References: [1]Patent: KR101489184,2015,B1 .Location in patent: Paragraph 0063; 0142-0144.
[2]Journal of Materials Chemistry C,2015,vol. 3,p. 3960 - 3970.
[3]Chemistry - A European Journal,2013,vol. 19,p. 15545 - 15555.
[4]Journal of the American Chemical Society,2009,vol. 131,p. 3881 - 3883.

13
[ 889676-34-0 ]
[ 57774-35-3 ]
[ 1214278-85-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 557 - 566.

14
[ 57774-35-3 ]
[ 1028752-21-7 ]
[ 1214278-84-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 557 - 566.

15
[ 3058-39-7 ]
[ 5467-74-3 ]
[ 57774-35-3 ]

Yield	Reaction Conditions	Operation in experiment
1.1 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In methanol; water; toluene; for 16h;Inert atmosphere; Reflux;	Step-1 :- Preparation of 4'-bromo-[ 1,1 '-biphenyl] -4-carbonitrile To a solution of 4-iodobenzonitrile (1.0 g, 4.365 mmol) in MeOH /toluene (1 : 1 ratio, 20 mL) was added (4-bromophenyl)boronic acid (0.964 g, 4.824 mmol). The reaction mixture was de-gassed under vacuum for 10 mins, followed by addition of tetrakis(triphenylphosphine)Pd(0) (49.0 mg, 0.043 mmol) and aq. Na2C03 (0.683 g, 6.45 mmol) under nitrogen atmosphere. The reaction mixture was heated at reflux for 16 h. Then the reaction mixture was cooled to RT and quenched with water and extracted with EtOAc. The organic layer was washed with water, brine and the organic portion was separated, dried, concentrated and further purified by column chromatography to afford 1.1 g of title product. 1H NMR (300 MHz, CDC13 ): δ 7.75 (d, 2H), 7.72- 7.60 (m, 4H) , 7.47- 7.44(d, = 8.7 Hz, 2H).

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 557 - 566.
[2]Chemical Communications,2015,vol. 51,p. 12641 - 12644.
[3]Patent: WO2016/46782,2016,A1 .Location in patent: Page/Page column 73.
[4]Patent: US2018/212158,2018,A1 .Location in patent: Paragraph 0548.
[5]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.

16
[ 57774-35-3 ]
[ 2920-38-9 ]

References: [1]Journal of Chemical Research,2012,vol. 36,p. 407 - 410.

17
[ 57774-35-3 ]
[ 1219958-86-7 ]
[ 1219958-87-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; triphenylphosphine;palladium diacetate; In 1,2-dimethoxyethane; water; for 2h;Reflux;	Synthesis of Compound R-2 Raw material compound 2 (0.5 g) (1.3 mmol) and 0.33 g of raw material compound 3 (1.3 mmol) are dissolved in a mixed solvent of 20 ml of distilled water and of 14 ml of ethylene glycol dimethyl ether, and then 14.6 mg of palladium acetate (0.065 mmol), 34 mg of triphenylphosphine (0.13 mmol), and 0.97 g of potassium carbonate (7 mmol) are added thereto, and the reaction system is refluxed with heating for 2 hour. After the reaction solution is allowed to be cooled, distilled water and dichloromethane are added and extraction is performed. After removing an aqueous layer and separating an organic layer, the system is dried with magnesium sulfate. The filtrate from which magnesium sulfate is filtered out is evaporated to dryness in a rotary evaporator to obtain a crude product. The obtained crude product is refined by sublimation to thereby obtain 0.11 g of an objective product (yield: 19%). The obtained compound is confirmed to be objective compound R-2 by mass spectrum and 1H NMR spectrum.1H NMR (CDCl3) 7.52 (t, 2H), 7.62 (t, 1H), 7.71 (d, 2H), 7.78 (m, 12H), 7.86 (d, 2H), 7.93 (d, 2H)

References: [1]Patent: US2012/319059,2012,A1 .Location in patent: Page/Page column 26-27.

18
[ 589-87-7 ]
[ 126747-14-6 ]
[ 57774-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine)platinum; In N,N-dimethyl-formamide; at 120℃; for 8h;Inert atmosphere;	Synthesis of Raw Material Compound 3 4-cyanobenzeneboronic acid (1.76 g) (12 mmol) and 2.8 g of 1-bromo-4 iodobenzene (10 mmol) are dissolved in 60 ml of DMF, and then 0.6 g of tetrakis(triphenylphosphine) platinum (0.5 mmol) and 6.5 g of cesium carbonate (20 mmol) are added thereto, and the reaction system is subjected to heating for 8 hour at 120 C. under nitrogen flow. After the reaction solution is allowed to be cooled, distilled water and about 600 ml of ethyl acetate are added and extraction is performed. After removing an aqueous layer and separating an organic layer, the system is dried with magnesium sulfate. The filtrate from which magnesium sulfate is filtered out is evaporated to dryness in a rotary evaporator, and refined by silica gel column (ethyl acetate/hexane: 1/10) to obtain 0.53 g of colorless raw material compound 3 (yield: 21%). The obtained compound 3 is confirmed to be an objective compound by mass spectrum and 1H NMR spectrum.

References: [1]Organic Letters,2014,vol. 16,p. 2838 - 2841.
[2]Patent: US2012/319059,2012,A1 .Location in patent: Page/Page column 26.
[3]Physical Chemistry Chemical Physics,2021,vol. 23,p. 12600 - 12611.

19
[ 57774-35-3 ]
[ 75-36-5 ]
[ 1428763-50-1 ]

Yield	Reaction Conditions	Operation in experiment
59%		Compound 4 was obtained in an analogous manner. Briefly, to a solution of 4-bromo-4′-cyanobiphenyl (258 mg) and lithium bis(trimethylsilyl)amide (1.1 mL of a 1 M soln in tetrahydrofuran) dry benzene (4 mL) a solution of Pd(OAc)2 (11 mg) and 23 mg RuPhos [23] in benzene (1 mL) was added, followed by a solution of Cy3SiSeH (357 mg) in benzene (5 mL). After stirring overnight, acetyl chloride (350 μl) and tetra-n-butylammonium fluoride (1.2 mL, 1 M in tetrahydrofuran) were added and stirring was continued for 3 h. Extraction with ethyl acetate, water, and brine yielded an organic phase that was evaporated onto silica (1.8 g). Chromatography (hexane/ethyl acetate 400/1 to 50/1) yielded a pink compound, which was recrystallized from methylcyclohexane to yield 180 mg (59%) crystals suitable for X-ray diffraction. Mp 130 C; 1H NMR (300.1 MHz, CDCl3): δ 7.72 (m, 4H), 7.60 (m, 4H), 2.51 (s, 3H); 13C NMR (75.5 MHz, CDCl3): δ 196.3, 145.0, 140.0, 136.5, 132.9, 128.3, 128.0, 127.5, 119.0, 111.5, 34.5; IR: see Section 3.2, Table 8; MS(EI+): m/z (%) = 43.2 (100), 301.0 (10, [M]+); Anal. Calcd. [C15H11SeNO]: C 60.01, H 3.69, N 4.66%; Found: C 60.01, H 3.63, N 4.48%.

References: [1]Journal of Molecular Structure,2013,vol. 1039,p. 61 - 70.

20
[ 92-84-2 ]
[ 57774-35-3 ]
4'-(10H-phenothiazine-10-yl)biphenyl-4-carbonitrile [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 15545 - 15555.

21
[ 57774-35-3 ]
4'-(3,7-bis(4-(2-ethylhexyloxy)phenyl)-10H-phenothiazine-10-yl)biphenyl-4-carbonitrile [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 15545 - 15555.

22
[ 57774-35-3 ]
4'-(3,7-bis(4-(2-ethylhexyloxy)phenyl)-10H-phenothiazine-10-yl)biphenyl-4-carboxylic acid [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 15545 - 15555.

23
[ 57774-35-3 ]
4'-(3,7-dibromo-10H-phenothiazin-10-yl)biphenyl-4-carbonitrile [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 15545 - 15555.

24
[ 453530-47-7 ]
[ 57774-35-3 ]
[ 1448709-43-0 ]

References: [1]Patent: EP2711359,2014,A1 .

25
[ 92-86-4 ]
[ 57774-35-3 ]

Yield	Reaction Conditions	Operation in experiment
20%	With copper(l) cyanide; In tetrahydrofuran; for 24h;Reflux;	4-5: Synthesis of 4’-bromobiphenyl-4-carbonitrile: 4,4’-dibromobiphenyl (10.0 g, 32.05 mmol) and copper cyanide (CuCN) (2.87 g, 32.05 mmol) were dissolved in THF (50 mL) to prepare a mixed solution. Then, the mixed solution was reacted for 24 hours in the state ofreflux. Afterthe reaction ofthe mixed solution, a solvent was removed, and the reacted mixed solution was extracted with water andethyl ac etate to obtain an extract. The extract was dried by magnesium sulfate (MgSO4), and then a reaction productwas separated by column chromatography (n-hexane/chloroform = 1/1). The yield of the reaction product was 20% (1.7 g).1HNMR(300 MHz,CDCl3) 87.74-7.71(d, -Ar, 2H), 7.66-7.59(m, -Ar, 4H), 7.46-7.43(d, -Ar, 2H)

References: [1]Patent: EP2711359,2014,A1 .Location in patent: Paragraph 0041; 0096; 0097.

26
[ 453530-47-7 ]
[ 57774-35-3 ]
4'-(3,6-bis(4-(2-ethylhexyloxy)phenyl)-9H-carbazole-9-yl)biphenyl-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In 1,2-dichloro-benzene; at 180℃; for 24h;	4-6: Synthesis of 4’-(3,6-bis(4-(2-ethylhexyloxy)phenyl)-9H-carbazole-9-yl)biphenyl-4-carbonitrile: 4’-bromobiphenyl-4-carbonitrile (1.9 g, 7.3 mmol) and 3,6-bis(4-(2-ethylhexyloxy)phenyl)-9H-carbazole (4.0 g,7.42 mmol) were mixed with CuI (1.87 g, 9.83 mmol), 18-crown-6 (0.65 g, 2.46 mmol), K2CO3 (13.58 g, 98.25 mmol)and O-dichlorobenzene (30 ml) and then stirred at 180C for 24 hours. After the reaction of the mixture, a solvent wasremoved, and the reaction mixture was extracted with water and ethyl acetate and dried by magnesium sulfate (MgSO4),and then a reaction product was separated by column chromatography (n-hexane/EtOAc = 2/1). The yield of the reactionproduct was 64% (2.5 g).1HNMR(300 MHz,CDCl3) δ8.27(s, Ar-H, 2H), 7.74-7.71(d, -Ar, 2H), 7.66-7.59(m, -Ar, 4H), 7.46-7.43(d, -Ar, 2H),7.65-7.61(d, Ar-H, 4H), 7.49-7.46(d, Ar-H, 2H), 7.03-7.00(d, Ar-H, 2H), 3.80-3.79(d, 2H, CH2-O),1.73-1.67(m,1H,(CH2)3-H),1.53-1.28(m,8H,-CH2),0.97-0.88(t,6H,-CH3)

References: [1]Patent: EP2711359,2014,A1 .Location in patent: Paragraph 0041; 0098; 0099.

27
[ 105946-82-5 ]
potassium ferrocyanide [ No CAS ]
[ 57774-35-3 ]

References: [1]RSC Advances,2014,vol. 4,p. 37773 - 37778.

28
[ 57774-35-3 ]
{5,10-Bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-porphyrinato-κN²¹,κN²²,κN²³,κN²⁴}zinc(II) [ No CAS ]
{5,10-bis[3,5-di(tert-butyl)phenyl]-15,20-bis(4'-cyanobiphenyl-4-yl)porphyrinato-κN²¹,κN²²,κN²³,κN²⁴}zinc(II) [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 14473 - 14476.

29
[ 589-87-7 ]
[ 171364-82-2 ]
[ 57774-35-3 ]

References: [1]Chemical Communications,2015,vol. 51,p. 14473 - 14476.

30
[ 57774-35-3 ]
N-hydroxy-4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-carboximidamide [ No CAS ]

References: [1]Patent: WO2016/46782,2016,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.

31
[ 57774-35-3 ]
4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/46782,2016,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.

32
[ 57774-35-3 ]
5-(4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-yl)-2H-tetrazole [ No CAS ]

References: [1]Patent: WO2016/46782,2016,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.

33
[ 57774-35-3 ]
3-(4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-yl)-1,2,4-oxadiazol-5(2H)-one [ No CAS ]

References: [1]Patent: WO2016/46782,2016,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.

34
[ 288-32-4 ]
[ 57774-35-3 ]
4'-(1H-imidazol-1-yl)-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.850 g	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In dimethyl sulfoxide; at 100℃; for 16h;Sealed tube;	Step-2:- Preparation of 4'-(lH-imidazol- l-yl)-[l, -biphenyl]-4-carbonitrile To a solution of 4'-bromo-[l, -biphenyl]-4-carbonitrile (Step- 1, intermediate, 1.0 g, 3.875 mmol) in DMSO (5 mL) was added imidazole (0.527 g, 7.75 mmol), Cul (72 mg, 0.38 mmol), K2C03 (0.534 g, 3.875 mmol) and 1, 10 phenanthroline (68 mg, 0.38 mmol). The reaction mixture was heated to 100C in sealed tube for 16 h. The reaction mixture was then cooled to RT and quenched with water and extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2S04 and concentrated. The product was purified by column chromatography to afford 0.850 g of title product.1 NMR (300 MHz, DMSO d6): δ 9.10 (s, 1H), 8.51- 8.48 (d, = 7.8 Hz, 1H), 8.38 (s, lH), 7.95- 7.86 (m, 4H), 7.83-7.77 (m, 2H), 7.688 (s, 1H), 7.14 (s, 1H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3766 - 3773.
[2]Patent: WO2016/46782,2016,A1 .Location in patent: Page/Page column 73; 74.

35
[ 623-03-0 ]
[ 872088-07-8 ]
[ 57774-35-3 ]

Yield	Reaction Conditions	Operation in experiment
96.2%	With bis(triphenylphosphine)nickel(II) chloride; zinc(II) chloride; In tetrahydrofuran; at 10 - 15℃; for 7h;Inert atmosphere;	In another four 1L reaction flask, a nitrogen atmosphere, followed by adding 219.54g of tetrahydrofuran,73.18g (0.532mol) of chlorobenzonitrile, 0.73g (0.00532mol) zinc chloride, 0.35g (0.000532mol)Bis (triphenylphosphine) nickel chloride, open mixing, cooling to 10 ~ 15 the reaction system, and a solution ofMagnesium iodide, 4-bromophenyl Grignard reagent to produce a system, maintaining the temperature 10 ~ 15 , dropping time3 hours, the dropwise addition, heat 4h, sample detection reaction, dilute hydrochloric acid was added dropwise to the reaction mixture,The reaction was quenched by stirring 10min, allowed to stand, stratification, the organic layer was washed with 5% sodium chloride solution, was allowed to standThe layers were separated and the organic layer was added activated carbon, warmed to reflux, filtered hot and the filtrate was concentrated under reduced pressure off tetrahydrofuranNom to not far, down to 20 ~ 25 , to give a white flaky solid, as 4'-bromo-4-cyanobiphenyl,The solid was weighed 132.1g, a yield of 96.2% (in terms of chlorobenzene nitrile), purity (GC) ≥99.0%.
96.2%	With bis(triphenylphosphine)nickel(II) chloride; zinc(II) chloride; In tetrahydrofuran; at 10 - 15℃; for 7h;Inert atmosphere;	In another 1L four-neck reaction flask, under nitrogen protection, 219.54g tetrahydrofuran, 73.18g (0.532mol) p-chlorobenzoic acid, 0.73g (0.00532mol) zinc chloride, 0.35g (0.000532mol) double (three Phenylphosphine) nickel chloride, start stirring, reduce the reaction system to 10 ~ 15 C, add the 4-bromophenyl magnesium iodide Grignard reagent produced in step 1 to the system, keep the temperature 10 ~ 15 C, drop Adding time is 3 hours, adding dropwise, keeping for 4h, sampling and testing reaction is completed, dilute hydrochloric acid is added dropwise to the reaction solution, quenching reaction, stirring for 10min, standing, layering, organic layer with 5% sodium chloride solution Washing, standingLayering, the organic layer is added with activated carbon, heated to reflux, filtered while hot, and the filtrate is concentrated under reduced pressure to remove tetrahydrofuran until it is lowered.Warm to 20 ~ 25 C, to obtain a white flake solid, 4'-bromo-4-cyanobiphenyl, solid weighing 132.1g, yield 96.2% (based on p-chlorobenzoic acid), purity (GC) ≥99.0%.

References: [1]Patent: CN105294492,2016,A .Location in patent: Paragraph 0121; 0122.
[2]Patent: CN105198682,2018,B .Location in patent: Paragraph 0119; 0122; 0123.

Historical Records

Technical Information

• Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blaise Reaction • Blanc Chloromethylation • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Ritter Reaction • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Thorpe-Ziegler Reaction • Vilsmeier-Haack Reaction

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[ 57774-35-3 ]

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3'-Bromo-[1,1'-biphenyl]-4-carbonitrile

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A578932 [1129527-54-3]

5-Bromo-[1,1'-biphenyl]-3-carbonitrile

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Nitriles

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3'-Bromo-[1,1'-biphenyl]-4-carbonitrile

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 57774-35-3

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