3-Aminobenzonitrile Chemical Properties

Melting point:

48-53 °C(lit.)

Boiling point:

288-290 °C

Density 

1.5511 (rough estimate)

refractive index 

1.5500 (estimate)

Flash point:

112 °C

solubility 

soluble in Methanol

form 

Crystalline Solid

pka

2.75(at 25℃)

color 

Brown

BRN 

636498

InChI

InChI=1S/C7H6N2/c8-5-6-2-1-3-7(9)4-6/h1-4H,9H2

InChIKey

NJXPYZHXZZCTNI-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=CC(N)=C1

CAS DataBase Reference

2237-30-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzonitrile, 3-amino-(2237-30-1)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-43-22-36/37/38

Safety Statements 

36/37-36-26

RIDADR 

3276

WGK Germany 

3

RTECS 

DI2454000

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Skin Sens. 1

MSDS

• Language:English Provider:m-Cyanoaniline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Aminobenzonitrile Usage And Synthesis

Chemical Properties

BROWN CRYSTALLINE SOLID

Uses

3-Aminobenzonitrile was used in the synthesis of series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinoxalin-6-yl)pyrazoles. It was also used in the preparation of highly substituted γ-lactam analogues of a thiazolidinone follicle stimulating hormone receptor agonist.

General Description

3-Aminobenzonitrile on condensation reaction with 4-isothiocyanato-4-methyl pentane-2-one gives condensed monocyclic pyrimidine derivatives.

Synthesis

Dehydration: In the 1000ml reaction flask with brine-cooled reflux device, add 510g of toluene, 102g of 3-aminobenzamide (0.75mol), raise the temperature to 90-100??, slowly add 205g of sulfoxide chloride (1.72mol), there is a large amount of off-gas generation (HCl + SO2), sulfoxide drops after the end of, and continue to hold the temperature to the material is all dissolved clear and no off-gas After the sulfoxide chloride drop, continue to keep warm until the material is all dissolved and no exhaust gas is released. Cooled to 50 ~ 60 ??, that is, the dehydration of liquid, insulation for use. _x000D
Hydrolysis: add 102g of water in 1000ml reaction bottle, stirring temperature to 50-60 ??, add the above dehydration solution, at this time there is tail gas (SO2), control the drop acceleration, drop stirring to no tail gas release, while hot, 30% sodium hydroxide solution to adjust the aqueous layer of pH to 6.5-7.5. Static layering, the organic layer of slow stirring and cooling to 0-5 ??, filtration, appropriate amount of 0-5 ?? toluene wash, filtering, and the water is not used. Appropriate amount of 0-5 ?? toluene washing, drying to obtain m-aminobenzonitrile 80.8g, yield 91.3%, GC purity 99.6%.

3-Aminobenzonitrile(2237-30-1)Related Product Information

• Benzonitrile
• 3-Aminophenol
• 3-Aminobenzaldehyde
• 3-Aminophenylurea
• EC 2.6.1.2
• 3-Aminobenzoic acid
• 2-Cyanophenol
• Acetaminophen
• 4-Nitrobenzonitrile
• 3-Aminophenylacetic acid
• p-Tolunitrile
• 3-Aminopyridine
• 3-Aminoacetophenone
• 3-Aminobenzotrifluoride
• m-Anisidine
• Metanilic acid
• 4-Aminobenzonitrile
• 3,5-Dinitrobenzonitrile