2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE Chemical Properties

Melting point:

81-83°C

Boiling point:

326.5±27.0 °C(Predicted)

Density 

1.422±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Dichloromethane, Ether, Methanol

form 

Solid

color 

Off-White to Light Grey

InChI

InChI=1S/C10H11BrO3/c1-13-9-4-3-7(8(12)6-11)5-10(9)14-2/h3-5H,6H2,1-2H3

InChIKey

NUAIPKMBWNVQIM-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1835-02-5(CAS DataBase Reference)

Safety Information

RIDADR 

UN1759

HazardClass 

IRRITANT

HS Code 

2934999090

2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE Usage And Synthesis

Chemical Properties

Off-White Solid

Preparation

Obtained by reaction of bromine with acetoveratrone in chloroform at r.t. (84%).

Synthesis

General procedure for the synthesis of 2-bromo-1-(3,4-dimethoxyphenyl)ethanone from 3,4-dimethoxyacetophenone: Benzyltrimethylammonium tribromide (2.16 g, 5.55 mmol) was added to a stirred mixture of 1-(3,4-dimethoxyphenyl)ethanone (1.0 g, 5.55 mmol) in a mixed solution of dichloromethane (6 mL) and methanol (3 mL). The reaction mixture was stirred at room temperature for 16 hours before dilution with dichloromethane (80 mL) and water (40 mL) to separate the organic layer. The aqueous phase was extracted twice with dichloromethane (80 mL x 2). All organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 2-bromo-1-(3,4-dimethoxyphenyl)ethanone (1.20 g, 4.63 mmol, 83% yield) as a brown solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.63 (s, 1H), 7.57 (d, J=2.1Hz, 1H), 6.94 (d, J=8.4Hz, 1H), 4.43 (s, 2H), 3.98 (s, 6H).

References

[1] European Journal of Organic Chemistry, 2002, # 13, p. 2126 - 2135
[2] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 15, p. 4223 - 4227
[3] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2720 - 2728
[4] RSC Advances, 2014, vol. 4, # 107, p. 62308 - 62320
[5] Tetrahedron Asymmetry, 2009, vol. 20, # 10, p. 1138 - 1143

2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE(1835-02-5)Related Product Information

• 2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE
• 2,5-dimethoxyphenacyl bromide ,2-bromo1-(2,5-dimethoxyphenyl)ethanone,2-BROMO-1-(2,5-DIMETHOXYPHENYL)ETHANONE
• 2-Bromo-2′,4′-dimethoxyacetophenone
• 3,4-Dimethoxyacetophenone
• 2-BROMO-1-(3,4-DIHYDRO-2H-1,5-BENZODIOXEPIN-7-YL)ETHAN-1-ONE
• 2-BROMO-1-(2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)ETHAN-1-ONE
• 2-Bromo-1-(3,4,5-trimethoxy-phenyl)-ethanone
• 2-BROMO-1-(2,3,4-TRIMETHOXY-PHENYL)-ETHANONE
• 2-BROMO-2,3-DIHYDRO-5,6-DIMETHOXY-1H-INDEN-1-ONE
• 2-BROMO-1-(4,5-DIMETHOXY-2-NITRO-PHENYL)ETHANONE
• 2-BROMO-1-(2,6-DIMETHOXYPHENYL)ETHANONE
• 2-BROMO-1-(3,5-DIMETHOXYPHENYL)ETHANONE
• 2-BROMO-1-(2,3-DIMETHOXYPHENYL)ETHANONE
• CARBONIC ACID 2-(2-BROMO-ACETYL)-4,5-DIMETHOXY-PHENYL ESTER ETHYL ESTER
• N-[2-(2-BROMO-PROPIONYL)-4,5-DIMETHOXY-PHENYL]-4-METHYL-BENZENESULFONAMIDE
• 2-BROMO-1-[4-(DIFLUOROMETHOXY)-3-METHOXYPHENYL]ETHANONE
• 2-BROMO-1-(3,4-DIMETHOXY-PHENYL)-PENTAN-1-ONE
• N-[2-(2-BROMO-ACETYL)-4,5-DIMETHOXY-PHENYL]-4-METHYL-BENZENESULFONAMIDE