4-BROMO-3-CHLOROANILINE Chemical Properties

Melting point:

74 °C

Boiling point:

276.3±20.0 °C(Predicted)

Density 

1.722±0.06 g/cm3(Predicted)

Flash point:

>100 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.84±0.10(Predicted)

color 

White to Light yellow

BRN 

1210160

InChI

InChI=1S/C6H5BrClN/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2

InChIKey

QLYHPNUFNZJXOQ-UHFFFAOYSA-N

SMILES

C1(N)=CC=C(Br)C(Cl)=C1

CAS DataBase Reference

21402-26-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T,Xn

Risk Statements 

20/21/22-33-36/37/38-22

Safety Statements 

28-36/37-36/37/39-26-23

RIDADR 

2811

Hazard Note 

Harmful

HazardClass 

6.1

PackingGroup 

III

HS Code 

29214200

MSDS

• Language:English Provider:ALFA

4-BROMO-3-CHLOROANILINE Usage And Synthesis

Chemical Properties

off-white powder

Uses

4-Bromo-3-chloroaniline is a precursor or building block in medicine, pesticide and dyestuffs.

Synthesis

General method: A solution was prepared by dissolving m-chloroaniline (2a or 2b) in DMF as starting material. Subsequently, another solution was prepared by dissolving NBS (92 mmol, 1.0 eq.) in 100 ml DMF. The DMF solution of m-chloroaniline was added dropwise to the DMF solution of NBS at room temperature. After the dropwise addition, the reaction mixture was stirred continuously for 3 hours at room temperature. After completion of the reaction, the reaction mixture was diluted with 500 ml of ethyl acetate and washed with 2 x 150 ml of brine. The organic phase was separated, dried with anhydrous Na2SO4, filtered and concentrated to give 4-bromo-3-chloroaniline (3a or 3b) as a brown solid in 90-92% yield. In another experiment, m-chloroaniline (2a or 2b, 0.8 mmol) was dissolved in a solvent of choice (1 ml) and a solution of NBS (0.8 mmol) in the same solvent (1 ml) was added in batches at room temperature. The reaction progression was monitored by LC-MS/MS and a final mixture containing traces of the dibrominated product was obtained.

References

[1] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 539 - 552
[2] Patent: CN107089919, 2017, A. Location in patent: Paragraph 0044; 0045; 0046; 0047
[3] Synthetic Communications, 2009, vol. 39, # 10, p. 1817 - 1824

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