3,4-DICHLOROPHENACYL BROMIDE Chemical Properties

Melting point:

54 °C

Boiling point:

339℃

Density 

1.695

Flash point:

159℃

storage temp. 

2-8°C

form 

powder to crystal

color 

White to Light yellow

BRN 

511981

InChI

InChI=1S/C8H5BrCl2O/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3H,4H2

InChIKey

PAKFHEFMTRCFAU-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(Cl)C(Cl)=C1)CBr

CAS DataBase Reference

2632-10-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

20/21/22-34-36/37-36/37/38-36-25

Safety Statements 

26-27-36/37/39-36-45

RIDADR 

1759

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29147000

MSDS

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3,4-DICHLOROPHENACYL BROMIDE Usage And Synthesis

Uses

2-Bromo-3',4'-dichloroacetophenone is a chemical ragent used in the synthesis of 2-aroylbenzoxazoles. As well, it is used in the synthesis of aminoarylthiazole derivatives as correctors of chloride transport defect in cystic fibrosis patients.

Synthesis

General procedure for the synthesis of alpha-bromo-3,4-dichloroacetophenone from 3,4-dichloroacetophenone: to a solution of 3,4-dichloroacetophenone (18.8 g, 0.1 mol, 1.0 eq.) in acetonitrile (100 ml) was added p-toluenesulfonic acid (25.8 g, 0.15 mol, 1.5 eq.) and N-bromosuccinimide (17.7 g, 0.1 mol. 1.0 equiv). The reaction mixture was refluxed at 80 °C for 5 hours. After completion of the reaction, the organic phase was extracted and concentrated, and purified by silica gel column chromatography to afford α-bromo-3,4-dichloroacetophenone (95% yield).

References

[1] Russian Journal of Organic Chemistry, 1994, vol. 30, # 6.1, p. 881 - 887
[2] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 6, p. 827 - 832
[3] Patent: CN107266388, 2017, A. Location in patent: Paragraph 0098; 0099; 0100
[4] ChemMedChem, 2018, vol. 13, # 11, p. 1102 - 1114
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 21, p. 7146 - 7153

3,4-DICHLOROPHENACYL BROMIDE(2632-10-2)Related Product Information

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