3,4-DICHLOROPHENACYL BROMIDE

3,4-DICHLOROPHENACYL BROMIDE Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

3,4-DICHLOROPHENACYL BROMIDE Chemical Properties,Usage,Production

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