50670-58-1|4'-Bromo-[1,1'-biphenyl]-4-carbaldehyde| Ambeed

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Quality Control of [ 50670-58-1 ] Purity: 95% SDS Specification

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Product Details of [ 50670-58-1 ]

CAS No. :	50670-58-1
Formula :	C₁₃H₉BrO
M.W :	261.11
SMILES Code :	O=CC1=CC=C(C2=CC=C(Br)C=C2)C=C1
MDL No. :	MFCD05980925
InChI Key :	AZDGDDGUHUQQMO-UHFFFAOYSA-N
Pubchem ID :	1392819

Safety of [ 50670-58-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 50670-58-1 ]

* 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 [ 50670-58-1 ]

[ 50670-58-1 ] Synthesis Path-Downstream 1~35

1
[ 92-86-4 ]
[ 33513-42-7 ]
[ 50670-58-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 1141 - 1146.
[2]Tetrahedron Letters,2008,vol. 49,p. 5024 - 5027.
[3]Tetrahedron Letters,2005,vol. 46,p. 7589 - 7592.
[4]Dalton Transactions,2020,vol. 49,p. 16683 - 16692.
[5]Chemical Communications,1997,p. 1105 - 1106.
[6]Tetrahedron,2006,vol. 62,p. 5092 - 5098.
[7]Chemical Communications,2008,p. 4816 - 4818.
[8]Organic Letters,2013,vol. 15,p. 1456 - 1459.
[9]European Journal of Inorganic Chemistry,2013,p. 5862 - 5870.

2
[ 50670-58-1 ]
[ 107-21-1 ]
[ 214745-69-4 ]

Yield	Reaction Conditions	Operation in experiment
		4-Bromo-dibenzaldehyde (0.1 mmol) and ethylene glycol (0.1, 0.2, 0.3 mmol, respectively) were weighed and put into a single-neck bottle containing 50 mL of toluene solvent, and heated to 50 degrees Celsius for half an hour. A catalytic amount (0.005 mmol) of p-toluenesulfonic acid was rapidly added, heated to 120 degrees Celsius, and refluxed for 12 hours. After the reaction was completed, the reaction solution was cooled. Toluene in the reaction flask was removed by rotary evaporation, dissolved in dichloromethane, mixed with silica gel, dry loaded, and purified by column using petroleum ether as a developing solvent to obtain the intermediate 4-bromo-diphenyldioxolane, The fractions yielded 90%, 85% and 91% yields.

References: [1]Organic Letters,2013,vol. 15,p. 1456 - 1459.
[2]Chemical Communications,1997,p. 1105 - 1106.
[3]Journal of Organic Chemistry,2005,vol. 70,p. 8568 - 8571.
[4]Patent: CN114230448,2022,A .Location in patent: Paragraph 0026; 0059; 0062-0063.

3
[ 5467-74-3 ]
[ 1122-91-4 ]
[ 50670-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 130℃;Microwave irradiation; Sealed tube;	General procedure: To a solution of a 3- or 4-bromobenzaldehyde in a mixture DMF/water (3:1; 14.8mL/mmol) were added boronic acid derivative (1.5 equiv.), Pd(PPh3)4 (5mol%), and K2CO3 (2 equiv.). The reaction mixture was heated under microwave irradiation (130C) until TLC showed complete conversion of the starting material (0.5-1h). After cooling, the mixture was extracted with dichloromethane. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered off, and concentrated under reduced pressure to afford the corresponding crude product 2. (0027) Compounds 2a-2p were synthesized following the procedure described above from the corresponding boronic acids.

References: [1]Applied Organometallic Chemistry,2019,vol. 33.
[2]Letters in Organic Chemistry,2022,vol. 19,p. 118 - 125.
[3]Bioorganic and Medicinal Chemistry,1998,vol. 6,p. 15 - 30.
[4]European Journal of Medicinal Chemistry,2016,vol. 115,p. 453 - 462.

4
[ 50670-58-1 ]
[ 5731-11-3 ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 4293 - 4299.
[2]Russian Journal of General Chemistry,2014,vol. 84,p. 782 - 788.
Zh. Obshch. Khim.,2014,vol. 84,p. 782 - 788,7.
[3]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 437 - 448.
[4]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.
[5]Journal of Medicinal Chemistry,2008,vol. 51,p. 4796 - 4803.

5
[ 589-87-7 ]
[ 87199-17-5 ]
[ 50670-58-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Inert atmosphere;	A mixture of (4-formylphenyl)boronic acid (0.6 g, 4 mmol), 1-bromo-4-iodobenzene (1.3 g, 4.3 mmol), Pd(PPh3)4 (46 mg,0.04 mmol), K2CO3 (2.0 M aqueous solution, 60 mL), toluene(60 mL) and ethanol (30 mL) were stirred under nitrogen at 90 Cfor 12 h. After cooling to room temperature, the reaction mixturewas extracted with dichloromethane and further purified by columnchromatography to obtain a white solid (1 g, yield: 95%). 1HNMR (400 MHz, CDCl3) δ [ppm]: 10.06 (s, 1H), 7.96 (d, J = 8.0 Hz,2H), 7.72 (d, J = 8.0 Hz, 2H), 7.61 (d, J = 8.0 Hz, 2H), 7.51 (d,J 8.4 Hz, 2H).
71%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 20℃; for 0.166667h;Inert atmosphere;	To a solution of 1-bromo-4-iodobenzene 9 (564 mg, 2 mmol) in 6 mL of toluene was added a catalytic amount (0.4% mol) of tetrakis-triphenylphosphine palladium(0) and 0.5 mL of aqueous 2 M Na2CO3. A solution of 4-formyl phenylboronic acid 10 (300 mg 2 mmol) in 2 mL of ethanol was added, stirred at room temperature under a nitrogen atmosphere. After 10 min, the solution was heated to reflux for 2-3 h in an argon atmosphere. Reaction is monitored by the TLC. After completion of the reaction, reaction mixture is cooled to room temperature and extracted with ethyl acetate (3 x 30 mL) and the organic phase was washed with water and brine solution, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to obtain the crude product. This product was further purified by column chromatography using ethyl acetate and hexane to afford the pure bromobiphenyl aldehyde (11) as a white solid, 370 mg in 71% yield; mp: 136-137 C; 1H NMR (300 MHz, CDCl3): δ 7.47-7.52 (m, 2H), 7.58-7.63 (m, 2H), 7.69 (d, 2H, J = 8.3 Hz), 7.93-7.97 (m, 2H), 10.05 (s, 1H); (ESI) MS: m/z 261 (M+H)+.
68%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 2h;Reflux; Inert atmosphere;	To a solution of 1-bromo-4-iodobenzene (4, 282 mg, 1 mmol) in 3 mL of toluene was added a catalytic amount (0.4% mol) of tetrakis-triphenylphosphine palladium (0) and 0.5 mL of aqueous 2 M Na2CO3. A solution of 4-formyl phenylboronic acid (5, 150 mg 1 mmol) in 1 mL of ethanol was added, stirred at room temperature under a nitrogen atmosphere. After 10 min, the solution was heated to reflux for 2 h in an argon atmosphere. TLC showed disappearance of starting materials, this reaction mixture is cooled to room temperature and extracted with ethyl acetate (3 × 30 mL) and the organic phase was washed with water and brine, dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to get the crude product. This residue was further purified by column chromatography using ethyl acetate and hexane to afford the pure bromobiphenylaldehyde (6) as a white solid, mp: 138-140 C: Yield 176 mg, 68%: 1H NMR (CDCl3, 300 MHz): δ 10.06 (s, 1H, -CHO), 7.96 (d, 2H, J = 8.6 Hz, ArH), 7.72 (d, 2H, J = 8.6 Hz, ArH), 7.61 (d, 2H, J = 9.2 Hz, ArH), 7.50 (d, 2H, J = 9.2 Hz, ArH); MS (ESI): m/z 260 (M + 1)+.

54%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 110℃; for 3h;Inert atmosphere;	To a mixture of 1-bromo-4-iodo-benzene (6.0 g, 21 mmol, 1.0 eq), Pd(PPh3)4 (1.2 g, 1.1 mmol, 0.050 eq), and Na2CO3 (2.0 M, 11 mL, 1.0 eq) in toluene (60 mL) was added (4-formylphenyl)boronic acid (3.5 g, 23 mmol, 1.1 eq) in ethanol (20 mL) under Ar, and the mixture was stirred at 110 C. for 3 hours. The mixture was poured into water and extracted with ethyl acetate (100 mL×2). The combined organic phase was washed with brine (100 mL), dried with anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=100:1 to 10:1) to give 4-1 (3.0 g, 11 mmol, 54% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.07 (s, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.73 (d, J=8.0 Hz, 2H), 7.62 (d, J=8.8 Hz, 2H), 7.54-7.49 (m, 2H).
54%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 110℃; for 3h;Inert atmosphere;	To a mixture of 1-bromo-4-iodo-benzene (6.0 g, 21 mmol, 1.0 eq), Pd(PPh3)4 (1.2 g, 1.1 mmol, 0.050 eq), and Na2CO3 (2.0 M, 11 mL, 1.0 eq) in toluene (60 mL) was added (4-formylphenyl)boronic acid (3.5 g, 23 mmol, 1.1 eq) in ethanol (20 mL) under Ar, and the mixture was stirred at 110 C. for 3 hours. The mixture was poured into water and extracted with ethyl acetate (100 mL×2). The combined organic phase was washed with brine (100 mL), dried with anhydrous Na2SO4, filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, petroleum ether:ethyl acetate=100:1 to 10:1) to give 4-1 (3.0 g, 11 mmol, 54% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.07 (s, 1H), 7.97 (d, J=8.4 Hz, 2H), 7.73 (d, J=8.0 Hz, 2H), 7.62 (d, J=8.8 Hz, 2H), 7.54-7.49 (m, 2H).

References: [1]Dyes and Pigments,2017,vol. 140,p. 328 - 336.
[2]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2714 - 2723.
[3]European Journal of Medicinal Chemistry,2012,vol. 50,p. 9 - 17.
[4]Tetrahedron Letters,2003,vol. 44,p. 3005 - 3008.
[5]Journal of Medicinal Chemistry,2005,vol. 48,p. 4293 - 4299.
[6]Physical Chemistry Chemical Physics,2020,vol. 22,p. 25514 - 25521.
[7]Patent: US2022/2317,2022,A1 .Location in patent: Paragraph 0554; 0555.
[8]Patent: US2022/2317,2022,A1 .Location in patent: Paragraph 0554; 0555.
[9]Journal of Medicinal Chemistry,2008,vol. 51,p. 4796 - 4803.
[10]Dalton Transactions,2014,vol. 43,p. 1424 - 1433.
[11]Patent: WO2004/99171,2004,A2 .Location in patent: Page 46.
[12]Journal of Materials Chemistry C,2022,vol. 10,p. 1204 - 1211.

6
[ 50670-58-1 ]
[ 84337-86-0 ]

References: [1]Helvetica Chimica Acta,2003,vol. 86,p. 2671 - 2686.
[2]Dalton Transactions,2020,vol. 49,p. 16683 - 16692.

7
[ 92-86-4 ]
[ 33513-42-7 ]
[ 50670-58-1 ]
[ 66-98-8 ]

References: [1]Helvetica Chimica Acta,2003,vol. 86,p. 2671 - 2686.
[2]Organic Letters,2007,vol. 9,p. 3591 - 3594.
[3]Journal of Organic Chemistry,2009,vol. 74,p. 8510 - 8515.

8
[ 21211-65-4 ]
[ 50670-58-1 ]
[ 348081-91-4 ]
5-(3,5-dioctyloxyphenyl)-15-[4-(4-bromophenyl)phenyl]porphyrin [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 16187 - 16198.

9
[ 50670-58-1 ]
[ 5720-07-0 ]
[ 1099-45-2 ]
ethyl 3-(4''-methoxy-p-terphenyl)acrylate [ No CAS ]

References: [1]Journal of Chemical Research,2004,p. 723 - 727.

10
[ 50670-58-1 ]
[ 5122-94-1 ]
[ 1099-45-2 ]
ethyl 3-(quaterphenyl)acrylate [ No CAS ]

References: [1]Journal of Chemical Research,2004,p. 723 - 727.

11
[ 67-56-1 ]
[ 50670-58-1 ]
[ 89901-03-1 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 7589 - 7592.

12
[ 50670-58-1 ]
[ 603-35-0 ]
(4'-formyl-1,1'-biphenyl-4-yl)(triphenyl)phosphonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%		In an inert atmosphere of argon (with a high flow), 4-(4- bromophenyl) benzaldehyde (4 g, 15.33 mmol), PPh3 (6.11 g, 22.99 mmol), and dry NiBr2 (1.70 g, 7.66 mmol) were suspended in PhCN (160 ml). The resulting green reaction mixture was stirred at 200 C for 4 h, and then cooled to r. t. The deep green reaction vessel was quenched with a 10% aq. soln. of KBr (200 ml), and extracted with CH2C12 (2x 200 ml). The combined organic phases were washed with H20 (2x 500 ml), brine (2x 500 ml), dried (Na2S04), and concentrated in vacuo to afford a brown oil. The resulting brown oil was taken up (in a flask) with hexane (500 ml), and the crude product glued on the faces of the flask as a thick oil. The hexane layer was separated, and this operation was carried out twice. The resulting thick oil was taken up with CH2C12 (small amount), and Et20 (200 ml) was added in order to precipitate the phosphonium salt. The flask was rotated vigorously, and the organic phase was decanted. This operation was done twice, affording the desired compound (11) as a yellow residue, which was pure enough to continue (4.4 g, 55%), has been characterized has follows: 1H-NMR (400 MHz, CDCl3): 8 10.02 (s, 1 H), 8.02 (d, J= 6.72, 2 H), 7.94 (d, J= 8.08, 2 H), 7.83 (m, 5 H), 7.72 (m, 8 H), 7.58 (m, 6 H). 13C-NMR (25 MHz, CDCl3) : # 192.21, 147.00 (d, J= 12.30), 144.17, 136.63,136.24 (d, J= 0.95), 135.48 (d, J= 3.55), 134.71 (d, J= 3.45), 131.26 (d, J= 4.27), 130.87, 129.95 (d, J= 4.40), 128.72, 118.21, 117.03 . 31P (162 MHZ, CDCl3) : δ 24.22 (s).

References: [1]Journal of Organic Chemistry,2008,vol. 73,p. 590 - 593.
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 5011 - 5014.
[3]Patent: WO2005/97812,2005,A1 .Location in patent: Page/Page column 36.

13
[ 50670-58-1 ]
[ 603-35-0 ]
(4'-formyl-1,1'-biphenyl-4-yl)triphenylphosphonium perchlorate [ No CAS ]

References: [1]Journal of Organic Chemistry,2009,vol. 74,p. 8510 - 8515.
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 5011 - 5014.

14
[ 2033-24-1 ]
[ 50670-58-1 ]
[ 1896-62-4 ]
(7β,11β)-7-(4'-bromobiphenyl-4-yl)-3,3-dimethyl-11-phenyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 7120 - 7124.

15
[ 50670-58-1 ]
C₃₆H₃₃NOP⁽¹⁺⁾*CF₃SO₃^(1-) [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 5011 - 5014.
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 5011 - 5014.
[3]Angewandte Chemie - International Edition,2007,vol. 46,p. 5011 - 5014.
[4]Angewandte Chemie - International Edition,2007,vol. 46,p. 5011 - 5014.

16
[ 50670-58-1 ]
(4'-(bromomethyl)-1,1'-biphenyl-4-yl)(triphenyl)phosphonium perchlorate [ No CAS ]