2-Aminobenzyl cyanide Chemical Properties

Melting point:

69-72 °C (lit.)

Boiling point:

321°C

Density 

1.120±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO, Methanol

pka

3.24±0.10(Predicted)

form 

Powder

color 

Off-white

Exposure limits

NIOSH: IDLH 25 mg/m3

CAS DataBase Reference

2973-50-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

23/24/25-36/37/38

Safety Statements 

26-36/37/39-45

WGK Germany 

3

HazardClass 

6.1

HS Code 

2926907090

MSDS

• Language:English Provider:SigmaAldrich

2-Aminobenzyl cyanide Usage And Synthesis

Chemical Properties

Brown Solid

Uses

2-Aminobenzyl cyanide may be used in the preparation of oxindole.

Synthesis

General procedure for the synthesis of o-aminophenylacetonitrile from 2-nitrophenylacetonitrile: 2-nitrophenylacetonitrile (30 g, 185 mmol) and 10% palladium/carbon catalyst (2 g) were suspended in acetic acid (450 mL). The suspension was transferred to a Parr hydrogenation unit and the hydrogenation reaction was carried out at 30 psi hydrogen pressure and room temperature for 2 hours. Upon completion of the reaction, the reaction mixture was filtered through a Celite pad to remove the catalyst. The filtrate was concentrated to dryness under reduced pressure. The resulting residue was dissolved in ethyl acetate (250 mL) and washed sequentially with water (2 x 100 mL) and saturated sodium chloride solution (50 mL). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography (100-200 mesh silica gel) using petroleum ether solution of 8% ethyl acetate as eluent to give o-aminophenylacetonitrile (13.5 g, 55% yield) as a white solid.1H NMR (CDCl3) δ ppm: 7.3-7.1 (m, 2H), 6.9-6.7 (m, 2H), 3.7 (br, 2H), 3.5 (s, 2H).

References

[1] Chemical and Pharmaceutical Bulletin, 1983, vol. 31, # 10, p. 3424 - 3445
[2] Patent: US2011/111046, 2011, A1. Location in patent: Page/Page column 17
[3] Patent: WO2011/58473, 2011, A1. Location in patent: Page/Page column 34; 35
[4] Tetrahedron Letters, 2006, vol. 47, # 2, p. 159 - 162
[5] Journal of the American Chemical Society, 1950, vol. 72, p. 3047,3049

2-Aminobenzyl cyanide(2973-50-4)Related Product Information

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• EC 2.6.1.2
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• Diphenylacetonitrile
• Acetonitrile
• Acetaminophen
• 2-Methylbenzyl cyanide
• 4-AMINOBENZYL CYANIDE,P-AMINOBENZYL CYANIDE,4-AMINOBENZYL CYANIDE / 4-AMINOPHENYLACETONITRILE
• HYDROGEN CYANIDE
• POTASSIUM CYANIDE
• p-Nitrophenylacetonitrile
• 4-AMINO-2-CHLORODIPHENYLACETONITRILE
• 2-(4-Amino-2-chloro-5-methylphenyl)-2-(4-chlorophenyl)acetonitrile
• (4-AMINOPHENYL)PHENYLACETONITRILE HYDROCHLORIDE,97%
• Benzeneacetonitrile
• ALPHA-AMINOBENZYL CYANIDE HYDROCHLORIDE,α-aminobenzyl cyanide hydrochloride,à-aminobenzyl cyanide hydrochloride
• 4-ACETAMIDOPHENYLACETONITRILE