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HomeProduct name list2-Aminobenzonitrile

2-Aminobenzonitrile

Synonym(s):2-Cyanoaniline;Anthranilonitrile

  • CAS NO.:1885-29-6
  • Empirical Formula: C7H6N2
  • Molecular Weight: 118.14
  • MDL number: MFCD00007631
  • EINECS: 217-549-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-06-24 22:20:23
2-Aminobenzonitrile Structural

What is 2-Aminobenzonitrile?

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.

The Uses of 2-Aminobenzonitrile

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%.
Synthesis of 2-Aminobenzonitrile
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- .

Properties of 2-Aminobenzonitrile

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)
pka 0.77(at 25℃)
form  Crystalline Flakes
color  Yellow to beige-brown
Water Solubility  INSOLUBLE
BRN  907187
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 for 2-Aminobenzonitrile

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H317:Sensitisation, Skin
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2-Aminobenzonitrile

InChIKey HLCPWBZNUKCSBN-UHFFFAOYSA-N

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