2-Bromo-4'-methylacetophenone Chemical Properties

Melting point:

45-49 °C(lit.)

Boiling point:

238-239 °C(lit.)

Density 

0.993 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.528(lit.)

Flash point:

229 °F

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate

form 

Crystalline Powder or Needles

color 

White to light yellow

BRN 

607041

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

InChI

InChI=1S/C9H9BrO/c1-7-2-4-8(5-3-7)9(11)6-10/h2-5H,6H2,1H3

InChIKey

KRVGXFREOJHJAX-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

619-41-0(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 2-bromo-1-(4-methylphenyl)-(619-41-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-27-37/39

RIDADR 

UN 2811

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

6.1

PackingGroup 

III

HS Code 

29147000

MSDS

• Language:English Provider:2-Bromo-1-(4-methylphenyl)ethan-1-one
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Bromo-4'-methylacetophenone Usage And Synthesis

Chemical Properties

White to light yellow crystal powder

Uses

2-Bromo-4′-methylacetophenone was used in the general fluorous thiol quenching method. It was also used in the preparation of hydroxyquinolinone and N-derivatized carboxamides.

General Description

2-Bromo-4′-methylacetophenone is an α-bromoketone.

Synthesis

General procedure: 4-methylstyrene (1 mmol) was dissolved in a solvent mixture of acetone (3 mL) and water (0.1 mL) at room temperature. Subsequently, dibromo-p-toluenesulfonamide (TsNBr2, 2.2 mmol) was slowly added to this solution. After the reaction was complete, sodium thiosulfate (~200 mg) was added to quench the reaction and stirring was continued for 10 minutes. The reaction mixture was extracted with ethyl acetate and the organic phase was dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure to remove the solvent. The crude product was purified by column chromatography on silica gel (230-400 mesh), the eluent being a mixed petroleum ether-ethyl acetate solvent, to give the final pure 2-bromo-4'-methylacetophenone.

References

[1] Tetrahedron Letters, 2015, vol. 56, # 2, p. 356 - 358
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 48, p. 11389 - 11395
[3] Green Chemistry, 2013, vol. 15, # 8, p. 2175 - 2179
[4] Synlett, 2010, # 15, p. 2335 - 2339
[5] Organic Letters, 2015, vol. 17, # 11, p. 2704 - 2707

2-Bromo-4'-methylacetophenone(619-41-0)Related Product Information

• 4'-Methylacetophenone
• 3'-Methylacetophenone
• Acetophenone
• 2',4'-Dichloroacetophenone
• 4'-Hydroxyacetophenone
• Chalcone
• 4'-(Trifluoromethyl)acetophenone
• PIPERACETAZINE (250 MG)
• 3-Nitroacetophenone
• 4'-Bromoacetophenone
• 2-Bromoacetophenone
• 4-(Trifluoromethyl)phenacyl bromide
• 2-BROMO-1-(2,4-DIMETHYLPHENYL)ETHAN-1-ONE
• Methyl bromide
• 2-BROMO-4'-PHENYLACETOPHENONE
• 2-BROMO-1-(3-CHLORO-4-METHYLPHENYL)PROPAN-1-ONE
• 4,4'-Bis(2-bromoacetyl)biphenyl
• Bromine