2-Aminobenzonitrile Chemical Properties

Melting point:

45-48 °C (lit.)

Boiling point:

267-268 °C (lit.)

Density 

1.11 g/cm3 (50℃)

refractive index 

1.5500 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Crystalline Flakes

pka

0.77(at 25℃)

color 

Yellow to beige-brown

Water Solubility 

INSOLUBLE

BRN 

907187

InChIKey

HLCPWBZNUKCSBN-UHFFFAOYSA-N

LogP

0.901

CAS DataBase Reference

1885-29-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzonitrile, 2-amino-(1885-29-6)

EPA Substance Registry System

Benzonitrile, 2-amino- (1885-29-6)

Safety Information

Hazard Codes 

Xn,T,Xi

Risk Statements 

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

Safety Statements 

26-36/37-36

RIDADR 

3276

WGK Germany 

2

RTECS 

CB4575000

TSCA 

T

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269095

Toxicity

LD50 ivn-mus: 180 mg/kg CSLNX* NX#00381

MSDS

• Language:English Provider:2-Aminobenzonitrile
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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2-Aminobenzonitrile Usage And Synthesis

Chemical Properties

It is a chemically stable yellow solid that readily forms salts when it encounters acid. It can be oxidized to nitrogen oxide by oxidants but has certain toxicity. The substance is easily soluble in common organic solvents but hardly soluble in low-polarity solvents, and it is insoluble in water.

Uses

2-Aminobenzonitrile is used for induction of nitrilase activity in Arthrobacter and for radioprotective agent.

Preparation

Synthesis of 2-Aminobenzonitrile: 2-Aminobenzamide was dehydrated to 2-aminobenzonitrile without protection of the amino group in the presence of phenylphosphonyl dichloride and pyridine. The highest yield of 96% was obtained using reagent 2d, while reagents 2a-c yielded less than 60%.

The reagents used for the reaction included phosphoryl chloride (2a), phenyl phosphoryl dichloride (2b), 4-chlorophenyl phosphoryl dichloride (2c), and phenylphosphonic dichloride (2d) in pyridine.
synthesis of aminobenzonitrile by dehydration of aminobenzamide using phenylphosphonic dichloride in pyridine

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 5933, 1974 DOI: 10.1021/ja00825a039
The Journal of Organic Chemistry, 43, p. 944, 1978 DOI: 10.1021/jo00399a030
Tetrahedron Letters, 32, p. 1007, 1991 DOI: 10.1016/S0040-4039(00)74473-X
Improving a process for the preparation of 2-aminobenzonitrile by reduction of 2-nitrobenzonitrile.

Safety Profile

Poison by intravenous route. Seealso NITRILES. When heated to decomposition it emitstoxic fumes of NOx and CN^- .

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