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Sigma-Aldrich

2-Bromo-4-methylanisole

97%

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Synonym(s):
3-Bromo-4-methoxytoluene
Linear Formula:
Br(CH3)C6H3OCH3
CAS Number:
Molecular Weight:
201.06
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

refractive index

n20/D 1.565 (lit.)

bp

124-125 °C/20 mmHg (lit.)

mp

15.5 °C (lit.)

density

1.392 g/mL at 25 °C (lit.)

SMILES string

COc1ccc(C)cc1Br

InChI

1S/C8H9BrO/c1-6-3-4-8(10-2)7(9)5-6/h3-5H,1-2H3

InChI key

DHPUIKWBNXTXOB-UHFFFAOYSA-N

Related Categories

General description

2-Bromo-4-methylanisole can be prepared via bromination of 4-methylanisole using poly(4-vinylpyridinium bromochromate).

Application

2-Bromo-4-methylanisole may be used in the synthesis of:
  • 1,6-bis(2-hydroxy-5-methylphenyl)pyridine (H2mdppy)
  • 1,8-dimethoxy-4-methylanthra-quinone
  • ethyl 2-(2-methoxy-5-methylphenyl)-2-methyl-4-oxocyclopentanecarboxylate
It may be used as starting material in the multi-step synthesis of sesquiterpene (±)-herbertenolide.

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_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Unambiguous synthesis and spectral characterization of 1,8-dihydroxy-4-methylanthraquinone.
Wang A, et al.
ARKIVOC (Gainesville, FL, United States), 1, 80-84 (2002)
Total synthesis of (?)-herbertenolide by stereospecific formation of vicinal quaternary centers in a crystalline ketone.
Ng D, et al.
Organic Letters, 6(4), 645-647 (2004)
Highly efficient white organic electroluminescence from a double-layer device based on a boron hydroxyphenylpyridine complex.
Liu Y, et al.
Angewandte Chemie (International Edition in English), 41(1), 182-184 (2002)
Lipase-Promoted Access to Phenolic Herbertane-Type Sesquiterpenes: (+)-1, 14-Herbertenediol, (-)-a-Herbertenol, (-)-Herbertenediol and Their Enantiomers.
Acherar S, et al.
European Journal of Organic Chemistry, 2004(24), 5092-5099 (2004)
Poly (4-vinylpyridinium bromochromate): an efficient reagent for bromination of aromatic compounds.
Albadi J, et al.
Monatshefte fur Chemie / Chemical Monthly, 144(2), 179-181 (2013)

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