2-Bromo-2',4'-dichloroacetophenone Chemical Properties

Melting point:

25-29 °C(lit.)

Boiling point:

103-106 °C(Press: 0.4 Torr)

Density 

1.695±0.06 g/cm3(Predicted)

refractive index 

1.60

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform, Methanol

form 

Low Melting Solid

color 

White to brown

Sensitive 

Lachrymatory

InChI

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

InChIKey

DASJDMQCPIDJIF-UHFFFAOYSA-N

SMILES

C(=O)(C1=CC=C(Cl)C=C1Cl)CBr

CAS DataBase Reference

2631-72-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 3335

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

II

HS Code 

29147000

MSDS

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

2-Bromo-2',4'-dichloroacetophenone Usage And Synthesis

Chemical Properties

White to brown low melting solid

Uses

2-Bromo-2',4'-dichloroacetophenone is a metabolite of the insecticide Bromfenvinphos. It is also a useful intermediate in the preparation of substituted acetophenone derivatives.

Synthesis

General procedure for the synthesis of 2-bromo-2',4'-dichloroacetophenone from 2,4-dichloroacetophenone: N-bromosuccinimide (0.37 mmol) was slowly added to a stirred solution of 2,4-dichloroacetophenone (0.37 mol, 1 equiv) in acetonitrile (40 mL). The reaction mixture was continued to be stirred for 10-15 minutes. Subsequently, p-toluenesulfonic acid (p-TsOH, 0.74 mmol, 2 eq.) was added to the reaction system and the mixture was heated to reflux for 4-5 h. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was cooled to room temperature, washed with saturated sodium bicarbonate solution and subsequently extracted with ethyl acetate (3 x 20 mL). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of ethyl acetate and hexane (4:96, v/v), and the fractions on 100-200 mesh silica gel were collected to give the pure 2-bromo-2',4'-dichloroacetophenone.

References

[1] Farmaco, 1993, vol. 48, # 6, p. 857 - 869
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 13, p. 5679 - 5691
[3] Polish Journal of Chemistry, 1981, vol. 55, # 2, p. 399 - 409
[4] Medicinal Chemistry Research, 2016, vol. 25, # 10, p. 2335 - 2348
[5] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1665 - 1674

2-Bromo-2',4'-dichloroacetophenone(2631-72-3)Related Product Information

• 2',6'-Dichloroacetophenone
• 3-Nitroacetophenone
• 3-Bromoanisole
• 4-Nitroacetophenone
• 4'-Methylacetophenone
• Dichloroacetonitrile
• 2',5'-Dichloroacetophenone
• 4'-Bromoacetophenone
• 2-Bromoacetophenone
• 2-Chloroacetophenone
• 2,2',4'-Trichloroacetophenone
• 2',4'-Dichloroacetophenone
• Acetophenone
• 4'-Hydroxyacetophenone
• 2-bromo-2-5-dichloroacetophenone
• α-Bromo-3,4-dichloroacetophenone,2-BROMO-3',4'-DICHLOROACETOPHENONE,ALPHA-BROMO-3,4-DICHLOROACETOPHENONE
• 2-Bromo-2',6'-dichloroacetophenone
• Bromine