2-Bromo-2'-chloroacetophenone Chemical Properties

Boiling point:

105 °C1 mm Hg(lit.)

Density 

1.602 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.5900(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

Acetone, Chloroform, Ethyl Acetate, Methanol

form 

Liquid

Specific Gravity

1.602

color 

Colorless to pale yellow

Sensitive 

Lachrymatory

InChI

InChI=1S/C8H6BrClO/c9-5-8(11)6-3-1-2-4-7(6)10/h1-4H,5H2

InChIKey

WZWWEVCLPKAQTA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

5000-66-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2922 8/PG 2

WGK Germany 

3

Hazard Note 

Corrosive/Lachrymatory/Keep Cold

HazardClass 

8

PackingGroup 

II

HS Code 

29143900

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials

Hazard Classifications

Skin Corr. 1B

MSDS

• Language:English Provider:SigmaAldrich

2-Bromo-2'-chloroacetophenone Usage And Synthesis

Chemical Properties

Colourless Liquid

Uses

2’-Chloro-2-bromoacetophenone (cas# 5000-66-8) is a compound useful in organic synthesis.

Preparation

2-Bromo-2'-chloroacetophenone can be prepared by bromination of o-chloroacetophenone.

Hazard

2-Bromo-2'-chloroacetophenone has acute oral toxicity,it causes skin corrosion/irritation nad serious eye damage/eye irritation.

Synthesis

The general procedure for the synthesis of 2-bromo-2'-chloroacetophenone from o-chloroacetophenone is as follows: in a reaction system, 1.2 g (10 mmol) of o-chloroacetophenone 1a was mixed and stirred with 0.121 g (0.5 mmol) of Cu(NO3)2-3H2O while an oxygen bulb (ca. 0.5-1 L) was attached. Subsequently, an aqueous 8 mol/L hydrobromic acid solution (1.5 mL, 12 mmol) was slowly added dropwise to the mixture. The reaction mixture was stirred continuously at 70 °C and the reaction progress was monitored by TLC or GC. After completion of the reaction, the mixture was extracted with CH2Cl2. The organic extract was washed sequentially with 5% sodium sulfite solution, saturated sodium bicarbonate solution and water and finally dried with anhydrous magnesium sulfate. The solvent was removed under vacuum and the residue was purified by column chromatography (silica gel as stationary phase, petroleum ether/dichloromethane 3:1 v/v/v) to afford the target product 2-bromo-2'-chloroacetophenone (2a) in a yield of 1.81 g in 91%.

References

[1] Synthetic Communications, 2016, vol. 46, # 2, p. 165 - 168
[2] Patent: US2004/44057, 2004, A1
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 2, p. 692 - 702
[4] Tetrahedron, 1998, vol. 54, # 43, p. 13059 - 13072
[5] Tetrahedron Letters, 2012, vol. 53, # 2, p. 191 - 195

2-Bromo-2'-chloroacetophenone(5000-66-8)Related Product Information

• 4'-Bromoacetophenone
• Acetophenone
• 2',6'-Dichloroacetophenone
• 2-Chlorophenol
• Dichloroacetonitrile
• 2-Chlorobenzoic acid
• 2-Chlorobenzaldehyde
• 2',4'-Dichloroacetophenone
• 3'-Chloroacetophenone
• 4'-Chloroacetophenone
• alpha-Bromo-2-chlorophenylacetic acid
• 3-Nitroacetophenone
• 3-Aminoacetophenone
• 2,2',4'-Trichloroacetophenone
• 2-Chlorophenylacetic acid
• 2-Bromoacetophenone
• 4'-Hydroxyacetophenone
• 4-Nitroacetophenone