2-AMINO-5-BROMOBENZONITRILE Chemical Properties

Melting point:

96-100 °C(lit.)

Boiling point:

288.4±25.0 °C(Predicted)

Density 

1.6480 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in methanol.

pka

1.11±0.10(Predicted)

form 

Crystalline Powder

color 

Off-white to pale brown

InChI

InChI=1S/C7H5BrN2/c8-6-1-2-7(10)5(3-6)4-9/h1-3H,10H2

InChIKey

OATYCBHROMXWJO-UHFFFAOYSA-N

SMILES

C(#N)C1=CC(Br)=CC=C1N

CAS DataBase Reference

39263-32-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

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

Safety Statements 

36/37-36/37/39-26-22

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-AMINO-5-BROMOBENZONITRILE Usage And Synthesis

Description

2-Amino-5-bromo-benzonitrile is a heterocyclic building block. It has been used in the synthesis of copper-ligand coordination complexes and 4-amino-3-benzimidazol-2-ylhydroquinolin-2-one-based multi-targeted receptor tyrosine kinase (RTK) inhibitors with anticancer activity.

Chemical Properties

white to light yellow crystal powder

Uses

2-Amino-5-bromobenzonitrile can react with Oxalic acid dimethyl ester to get 5-Bromo-N-methylanthranilonitrile.

Synthesis

The general procedure for the synthesis of 2-amino-5-bromobenzonitrile from 2-aminobenzonitrile was as follows: 2-aminobenzonitrile (11.8 g, 0.1 mol) was dissolved in acetic acid (120 ml) and ammonium bromide (10.3 g, 0.105 mol) and hydrogen peroxide (10.2 ml, 35% aqueous solution, 0.105 mol) were added sequentially. The reaction mixture was stirred at room temperature for about 1 hour, followed by continued stirring for 24 hours until LCMS analysis confirmed the completion of the reaction. Upon completion of the reaction, the acetic acid was removed by concentration and the residue was stirred with 30% aqueous sodium hydroxide solution to alkaline. The resulting solid was collected by filtration, washed with water and dried. The dried solid was dissolved in an excess of dichloromethane, the solution was concentrated until a precipitate began to appear and left to crystallize completely. The crystals were collected by filtration and washed with a small amount of dichloromethane to afford the target compound 2-amino-5-bromobenzonitrile as an off-white crystalline solid (19.2 g, 97% yield).1HNMR data: δ 7.61 (1H, d, J=2.5 Hz), 7.43 (1H, dd, J=9,2.5 Hz), 6.75 (1H, d, J=9 Hz), 6.28 ( 2H, br s); LC-MS retention time: 2.24 min.

References

[1] Canadian Journal of Chemistry, 2009, vol. 87, # 2, p. 440 - 447
[2] Patent: WO2007/80401, 2007, A1. Location in patent: Page/Page column 26
[3] Synthetic Communications, 2010, vol. 40, # 6, p. 868 - 876
[4] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232
[5] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 206, p. 205 - 221

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