4-amino-2-bromobenzonitrile Chemical Properties

Boiling point:

355.5±32.0 °C(Predicted)

Density 

1.68

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

0.65±0.10(Predicted)

form 

Powder

color 

Yellow

InChI

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

InChIKey

OSYGPHDNNWRFJO-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(N)C=C1Br

Safety Information

Safety Statements 

24/25

TSCA 

y

HazardClass 

6.1

HazardClass 

IRRITANT

HS Code 

29269090

4-amino-2-bromobenzonitrile Usage And Synthesis

Chemical Properties

off-white Crysstalline

Synthesis

The general procedure for the synthesis of 2-bromo-4-aminobenzonitrile from the compound (CAS:1220099-39-7) was as follows: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (2.90 g, 12.8 mmol) was added to a 25 (4.03 g, 12.8 mmol) solution of 2-bromo-4-aminobenzonitrile (2,3-DCBQ) (2.90 g, 12.8 mmol) in a mixture of dichloromethane (CH2Cl2, 85 mL) and water ( H2O, 43 mL) in a stirred solution and the reaction was carried out at room temperature. The reaction mixture was stirred for 3.5 hours and then filtered to remove the precipitated solid. The filtrate was added to saturated aqueous sodium bicarbonate (NaHCO3) and extracted with dichloromethane (CH2Cl2). The organic layer was dried over magnesium sulfate (MgSO4) and concentrated. The residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 2/1) to give 26 (2.13 g, 10.8 mmol, 85% yield) as a white solid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 5, p. 1712 - 1717
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 4, p. 993 - 1005

4-amino-2-bromobenzonitrile(53312-82-6)Related Product Information

• 4-Amino-3-penten-2-one
• 2-Bromobenzonitrile