111-86-4|N-octylamine| Ambeed

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Structure of 111-86-4

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Quality Control of [ 111-86-4 ] Purity: 99% SDS Specification

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Product Details of [ 111-86-4 ]

CAS No. :	111-86-4
Formula :	C₈H₁₉N
M.W :	129.24
SMILES Code :	NCCCCCCCC
MDL No. :	MFCD00008247
InChI Key :	IOQPZZOEVPZRBK-UHFFFAOYSA-N
Pubchem ID :	8143

Safety of [ 111-86-4 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H226-H301+H311-H314-H332-H335-H410
Precautionary Statements:	P210-P280-P301+P310+P330-P303+P361+P353-P304+P340+P310-P305+P351+P338
Class:	8
UN#:	2735
Packing Group:	Ⅱ

Application In Synthesis of [ 111-86-4 ]

* 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.

Upstream synthesis route of [ 111-86-4 ]
Downstream synthetic route of [ 111-86-4 ]

[ 111-86-4 ] Synthesis Path-Upstream 1~6

1
[ 111-86-4 ]
[ 19524-06-2 ]
[ 64690-19-3 ]

References: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596.
[2] Organic Letters, 2008, vol. 10, # 18, p. 4109 - 4112.

2
[ 111-86-4 ]
[ 7379-35-3 ]
[ 64690-19-3 ]

Yield	Reaction Conditions	Operation in experiment
78.5%	at 130℃; for 2 h; Large scale	Into 200L reactor was pumped n-octylamine 100kg,30kg of 4-chloropyridine hydrochloride and 10kg of sodium fluoride were added, the temperature was raised to 130 ° C, and the mixture was stirred for 2 hours while keeping warm,Decompression recovery n-octylamine, while hot sodium carbonate aqueous solution to adjust the pH to about 7, adding ethyl acetate 120kg, separating the aqueous layer, the organic layer was cooled, filtered,Dried to give 4-octylaminopyridine 32.3kg,Purity was 99.3percent, yield was 78.5percent.

References: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596.
[2] Patent: CN107501173, 2017, A, . Location in patent: Paragraph 0018.

3
[ 111-86-4 ]
[ 36316-71-9 ]
[ 64690-19-3 ]

References: [1] Angewandte Chemie - International Edition, 2005, vol. 44, # 9, p. 1371 - 1375.

4
[ 15854-87-2 ]
[ 111-86-4 ]
[ 64690-19-3 ]

References: [1] Journal of the American Chemical Society, 2008, vol. 130, # 20, p. 6586 - 6596.

5
[ 626-61-9 ]
[ 111-86-4 ]
[ 64690-19-3 ]

References: [1] Synlett, 2000, # 1, p. 116 - 118.

6
[ 75-21-8 ]
[ 111-86-4 ]
[ 15520-05-5 ]

References: [1] European Journal of Medicinal Chemistry, 1976, vol. 11, p. 115 - 124.

[ 111-86-4 ] Synthesis Path-Downstream 1~35

1
[ 111-86-4 ]
[ 57-92-1 ]
(1R)-N,N'-dicarbamimidoyl-O⁴-[O²-(2-methylamino-2-deoxy-α-L-glucopyranosyl)-3-(octylamino-methyl)-5-deoxy-α-L-lyxofuranosyl]-streptamine [ No CAS ]

References: [1]Journal of the American Chemical Society,1950,vol. 72,p. 3969.

2
[ 75-21-8 ]
[ 111-86-4 ]
[ 15520-05-5 ]

References: [1]European Journal of Medicinal Chemistry,1976,vol. 11,p. 115 - 124.

3
[ 1194-21-4 ]
[ 111-86-4 ]
2-Amino-6-octylamino-3H-pyrimidin-4-one [ No CAS ]

References: [1]Journal of medicinal chemistry,1993,vol. 36,p. 3431 - 3436.

4
[ 111-86-4 ]
[ 2258-42-6 ]
[ 2439-54-5 ]

References: [1]Tetrahedron Letters,1982,vol. 23,p. 3315 - 3318.

5
[ 67-56-1 ]
[ 111-86-4 ]
[ 7378-99-6 ]
[ 2439-54-5 ]

Yield	Reaction Conditions	Operation in experiment
64%Chromat.; 23%Chromat.	With platinum on carbon; sodium hydroxide; at 150℃; under 750.075 Torr; for 36h;Inert atmosphere; Autoclave;	General procedure: After the reduction under a flow of H2 at 300C for 0.5h, we carried out catalytic tests without exposing the catalyst to air as follows. Methanol (30mmol) was injected to the reduced catalyst inside the glass tube through a septum inlet, thus the catalyst was covered with a layer of methanol to restrict it from air exposure. After removal of the septum under air, amine (1mmol), solid NaOH (1mmol), n-dodecane (0.25mmol) and a magnetic stirrer bar were placed in the tube. The tube was inserted into a stainless-steel autoclave (28cm3) and purged with N2 gas. Finally, the resulting mixture was heated at 150C and stirred under 1barN2. For the model reaction of n-octylamine, the catalyst screening, optimization of reaction conditions, kinetic studies and control reactions, the conversion of n-octylamine and yields of products were determined by GC analyses, using n-dodecane as an internal standard by applying the GC sensitivity of the isolated or commercial products. For the substrate scope study, the products were isolated by column chromatography with silica gel 60 (spherical, 60-100mum, Kanto Chemical Co., Ltd.) using hexane/ethyl acetate or ethyl acetate/methanol as the eluting solvent. The yields of the isolated amine derivatives were determined and identified by 1H and 13C NMR and GC-MS methods.

References: [1]Tetrahedron Letters,1999,vol. 40,p. 3689 - 3592.
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 6166 - 6170.
Angew. Chem.,2018,vol. 130,p. 6274 - 6278,5.
[3]Journal of Catalysis,2019,vol. 371,p. 47 - 56.

6
[ 111-86-4 ]
[ 19829-72-2 ]
2,3-dihydroxy-N,N'-dioctyl-terephthalamide [ No CAS ]

References: [1]Organic Letters,2001,vol. 3,p. 2827 - 2830.

7
[ 111-86-4 ]
[ 97-08-5 ]
N-octyl-4-chloro-3-nitrobenzenesulfonamide [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 3677 - 3680.

8
[ 57876-69-4 ]
[ 111-86-4 ]
N-(1-octyl)-2-amino-3-methylquinoline [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 1371 - 1375.

9
[ 111-86-4 ]
[ 4023-02-3 ]
[ 1458-01-1 ]
N-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-N'-octyl-guanidine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 4098 - 4115.

10
[ 126-83-0 ]
[ 111-86-4 ]
1-(N-octylamino)-2-hydroxy-1-propanesulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3%		Preparation of 1-(N-octylamino)-2-hydroxy-1-propanesulfonic acid (Compound JW); A solution of 3-chloro-2-hydroxy-1-propanesulfonic acid, sodium salt (4 g, 20 mmol) in water (17.5 mL total volume) was added over 2 hours to a mixture of octylamine (8 mL), water (20 mL) and 1,4-dioxane (11 mL) at 70-75 C. The mixture was stirred at this temperature for another 2 hours after the end of the addition. The 1,4-dioxane was removed under reduced pressure and the mixture was diluted with water (10 mL). The mixture was extracted with 40% ethyl acetate/hexane (3×40 mL). The aqueous layer was concentrated then the mixture was passed over a column of Dowex 50×8 (125 g). The fractions containing the pure product were concentrated to a thick oil then freeze-dried. The desired material was obtained as a white fluffy solid (150 mg, 0.56 mmol, 3%). The 1H and 13C NMR and MS were consistent with the structure.

References: [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 145.

11
[ 111-86-4 ]
[ 21252-69-7 ]

Yield	Reaction Conditions	Operation in experiment
71.3%	In propan-1-ol;	EXAMPLE 3 Preparation of 1-octylimidazole 64.6 parts of n-octylamine and 34 parts of 25percent strength aqueous ammonia aredissolved in 186 parts of propanol and are introduced dropwise over 30 minutes, simultaneously with a mixture of 72.5 parts of 40percent strength aqueous glyoxal solution and 37.5 parts of 40percent strength aqueous formaldehyde solution, into a stirred flask. The temperature is kept at 65° C. After all has been introduced, stirring is continued for 20 minutes at 65° C., and the mixture is then worked up by distillation. 64.2 parts of 1-octylimidazole (boiling point 110° C./1 mm Hg) are obtained, corresponding to a yield of 71.3percent of theory.

References: [1]Patent: US4450277,1984,A .

12
[ 111-86-4 ]
[ 15441-06-2 ]
[ 33312-01-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	In methanol; at 5℃; for 120h;	Example 1 Preparation of N,N'-di-n-octyl-3,3'-dithiodipropionamide The reaction scheme is as follows: (SCH2CH2CO2CH3)2+2C8H17NH2-->(SCH2CH2CONHC8H17)2+2CH3OH 238 g (1 mol) of dimethyl 3,3'-dithiodipropionamide and 280 g (2.17 mol) of n-octylamine were added into 300 ml of methanol in a 1,000 ml reaction flask, and the reactants stirred at 5° C. for 5 days (under nitrogen atmosphere, if desired). The reaction mixture was then cooled to -10° C., and separated by centrifuging to give 329 g of a solid of N,N'-di-n-octyl-3,3'-dithiodipropionamide (purity >95percent, yield 76percent). The mother liquor was recycled after methanol was recovered by evaporation.

References: [1]Patent: US2008/227986,2008,A1 .Location in patent: Page/Page column 3.

13
[ 111-86-4 ]
[ 4214-79-3 ]
[ 1028224-23-8 ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 6586 - 6596.

14
[ 4282-29-5 ]
[ 111-86-4 ]
[ 773881-43-9 ]

References: [1]Journal of the American Chemical Society,2010,vol. 132,p. 5330 - 5331.
[2]Advanced Functional Materials,2011,vol. 21,p. 718 - 728.
[3]Macromolecules,2012,vol. 45,p. 6906 - 6914,9.
[4]Journal of Organic Chemistry,2012,vol. 77,p. 8167 - 8173,7.
[5]Patent: WO2014/29014,2014,A1 .Location in patent: Paragraph 00111.

15
[ 41014-43-1 ]
[ 111-86-4 ]
[ 1297605-67-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In methanol; at 20℃;	General procedure: A solution of compound 2 (1.66 g, 0.01 mol) in MeOH (25 mL) was added dropwise to the suspension of hexan-1-amine (3.04 g, 0.03 mol) and anhydrous K2CO3 (2.76 g, 0.02 mol) in MeOH (10 mL). The mixture was stirred at room temperature for 0.5 h. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (CH2Cl2: MeOH 100:2, v/v) to give 3a as yellow oil (0.28 g, 12.1%).

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 1706 - 1712.

16
[ 6007-85-8 ]
[ 111-86-4 ]
[ 773881-43-9 ]

References: [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 3761 - 3768.
[2]Chemistry of Materials,2010,vol. 22,p. 2696 - 2698.
[3]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 3758 - 3766.

17
[ 111-86-4 ]
[ 6492-86-0 ]
[ 58862-54-7 ]

Yield	Reaction Conditions	Operation in experiment
67.9%	In ethanol; for 3h;Reflux;	A solution of 2b (8.7 g, 0.041 mol) and n-octyl amine (26.5 g, 0.21 mol) in ethanol (100 ml) was refluxed for 3 hrs. The hot solution was poured into 2 L of ice water carefully and left standing at room temperature for 1 day. The suspension was filtered and the filter cake was washed with 200 ml of distilled water, re-crystallized from ethanol, dried in vacuum to give the yellow product 2c (9.0 g, 67.9 %, Mp:162-163 ºC). 1H NMR (400 MHz, DMSO-d6) delta 8.61 (dd, 1H, J1 = 8.4 Hz, J2 = 0.9 Hz); 8.42 (dd, 1H, J1 = 7.3 Hz, J2 = 0.9 Hz); 8.19 (d, 1H, J = 8.4 Hz); 7.65 (dd, 1H, J1 = 8.3 Hz, J2 = 7.4 Hz); 7.44 (s, 2H,); 6.84 (d, 1H, J = 8.4 Hz); 4.06 - 3.92 (m, 2H); 1.66 - 1.51 (m, 2H); 1.33 - 1.18(complex m, 10H); 0.84 (t, 3H, J = 6.9 Hz).

References: [1]Tetrahedron Letters,2012,vol. 53,p. 6414 - 6417.

18
[ 111-86-4 ]
[ 21906-31-0 ]
[ 42951-39-3 ]

References: [1]Organic Letters,2013,vol. 15,p. 1666 - 1669.

19
[ 111-86-4 ]
[ 21906-31-0 ]
C₁₇H₂₆BrN [ No CAS ]

References: [1]Organic Letters,2013,vol. 15,p. 1666 - 1669.

20
[ 3141-26-2 ]
[ 111-86-4 ]
[ 201230-82-2 ]
[ 773881-43-9 ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 3430 - 3434.

21
[ 3141-26-2 ]
[ 111-86-4 ]
[ 201230-82-2 ]
[ 773881-43-9 ]
4-bromo-N-octylthiophene-3-carboxamide [ No CAS ]

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 3430 - 3434.
[2]European Journal of Organic Chemistry,2015,vol. 2015,p. 3430 - 3434.

22
[ 111-86-4 ]
[ 15666-97-4 ]
[ 927-63-9 ]
octyl (2E,4E)-2-cyano-5-(dimethylamino)penta-2,4-dienoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		Example 7 Preparation of octyl (2E,4E)-2-cyano-5-(dimethylamino)penta-2,4-dienoate N,N-Dimethylacrolein (37.4 ml, 0.374 mol) is dissolved in 500 ml of toluene while bubbling with nitrogen and the catalyst, a mixture of acetic acid (4.1 ml, 0.2 equiv.) and of n-octylamine (1.8 ml, 0.03 equiv.), is added. The mixture is heated to reflux and <strong>[15666-97-4]n-<strong>[15666-97-4]octyl cyanoacetate</strong></strong> (76 ml, 0.359 mol) is added dropwise over 25 minutes. The water is removed by azeotropic distillation. The reaction is halted after 2 hours. The solvent is evaporated under vacuum. 123 g of an orangey brown solid are obtained, which solid is recrystallized from isopropanol to give 118.5 g (yield: 85%) of the derivative of Example 7 in the form of pale yellow needles: M.P.: 80-81 C. UV (Ethanol): lambdamax=380 nm, E1%=2186.

References: [1]Patent: US2015/284330,2015,A1 .Location in patent: Paragraph 0230-0233.

23
[ 111-86-4 ]
[ 4506-66-5 ]
N1,N2,N4,N5-tetraoctyl-2,5-diamino-1,4-benzoquinonediimine [ No CAS ]

References: [1]Organic Letters,2016,vol. 18,p. 5340 - 5343.

24
[ 111-86-4 ]
[ 96-81-1 ]
C₁₅H₃₀N₂O₂ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3847 - 3851.
Angew. Chem.,2017,vol. 129,p. 3905 - 3909,5.

25
[ 25834-16-6 ]
[ 111-86-4 ]
4,7-dibromooctylisoindoline-1,3-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With acetic acid; for 2.0h;Reflux; Inert atmosphere; Schlenk technique;	3, 6-dibromo phthalic anhydride (1.53 g, 5 mrnol), n-octylamine (0.84 g, 6.5 mmol) and glacial acetic acid (30 ml) were combined and refluxed under Ar for 2 h. After the acetic acid was removed under reduced pressure, the target compound 13 was purified via column chromatography (silica gel, dichloromethane:hexanes 1:2). The resulting white solid was further purified via recrystallization from hexanes to afford a white crystal as the product (1.88 g, 90 %).?H NMR (400 MHz, CDC13, ppm): 7.64 (s, 2H), 3.73-3.61 (t, 2H), 1.74-1.63 (m, 2H), 1.29 (m, 1OH), 0.86 (t, 3H). ?3C NMR (100 MHz, CDC13, ppm): 164.87, 139.49, 131.31, 117.50, 38.68, 31.78, 29.11, 28.32, 26.84, 22.63, 14.10. Anal. Calcd for C,6H,9Br2NO2 (%): C, 46.07; H, 4.59; N, 3.36; 5, 0. Found (%): C, 46.08; H, 4.47; N, 3.23; 5, 0.03.

References: [1]Patent: WO2017/152354,2017,A1 .Location in patent: Page/Page column 34.

26
[ 111-86-4 ]
[ 58656-98-7 ]
[ 1068160-34-8 ]