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Merck
CN

549800

4-Bromo-2,3-dimethylanisole

96%

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About This Item

Linear Formula:
Br(CH3)2C6H2OCH3
CAS Number:
Molecular Weight:
215.09
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
Assay:
96%
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InChI

1S/C9H11BrO/c1-6-7(2)9(11-3)5-4-8(6)10/h4-5H,1-3H3

SMILES string

COc1ccc(Br)c(C)c1C

InChI key

WOWNZZYJCUUIFC-UHFFFAOYSA-N

assay

96%

refractive index

n20/D 1.566 (lit.)

bp

197 °C (lit.)

density

1.36 g/mL at 25 °C (lit.)

General description

4-Bromo-2,3-dimethylanisole can be prepared from 2,3-dimethylanisole via bromination using N-bromosuccinimide-acetonitrile (NBS-CH3CN) system.

Application

4-Bromo-2,3-dimethylanisole may be used in the preparation of:
  • 4,6-Dibromo-2,3-dimethylanisole via bromination using NBS-CH3CN system.
  • 4-Methoxy-2,2′,3,3′-tetramethyldiphenyl ether by reacting with 2,3-dimethylphenol.
  • A novel arylsulfonamide derivative with potent glucocorticoid receptor (GR) agonist activity.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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N-Bromosuccinimide in acetonitrile: A mild and regiospecific nuclear brominating reagent for methoxybenzenes and naphthalenes.
Carreno MC, et al.
The Journal of Organic Chemistry, 60(16), 5328-5331 (1995)
Substituted phenyl as a steroid A-ring mimetic: Providing agonist activity to a class of arylsulfonamide nonsteroidal glucocorticoid ligands.
Darren D, et al.
Bioorganic & Medicinal Chemistry Letters, 23(24), 6645-6649 (2013)
Oxidative coupling of phenols. Part 9. The role of steric effects in the oxidation of methyl-substituted phenols.
Armstrong DR, et al.
J. Chem. Soc. Perkin Trans. II, 5, 581-585 (1983)

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