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1835-02-5

1835-02-5 Structure

1835-02-5 Structure
IdentificationMore
[Name]

2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE
[CAS]

1835-02-5
[Synonyms]

2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE
AKOS 90592
AKOS BBS-00003864
2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE, TECH
[Molecular Formula]

C10H11BrO3
[MDL Number]

MFCD03425186
[Molecular Weight]

259.1
[MOL File]

1835-02-5.mol
Chemical PropertiesBack Directory
[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 DataBack Directory
[Symbol(GHS) ]

Corrosion (GHS05)
GHS05
[Signal word ]

Danger
[Hazard statements ]

H314
[Precautionary statements ]

P310-P260-P280
[RIDADR ]

UN1759
[HazardClass ]

IRRITANT
[HS Code ]

2934999090
Hazard InformationBack Directory
[Chemical Properties]

Off-White Solid
[Preparation]

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

3,4-Dimethoxyacetophenone

1131-62-0

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

1835-02-5

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
Spectrum DetailBack Directory
[Spectrum Detail]

2-BROMO-1-(3,4-DIMETHOXYPHENYL)ETHANONE(1835-02-5)1HNMR
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