523054
4-Bromo-2-methylanisole
98%
Synonym(s):
5-Bromo-2-methoxytoluene
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About This Item
Linear Formula:
BrC6H3(CH3)OCH3
CAS Number:
Molecular Weight:
201.06
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
98%
form
solid
mp
66-69 °C (lit.)
SMILES string
COc1ccc(Br)cc1C
InChI
1S/C8H9BrO/c1-6-5-7(9)3-4-8(6)10-2/h3-5H,1-2H3
InChI key
UDLRGQOHGYWLCS-UHFFFAOYSA-N
Related Categories
General description
4-Bromo-2-methylanisole can be prepared by the bromination of o-methylanisole (2-methylanisole). It can also be prepared via reaction between 1-butyl-3-methylimidazolium tribromide [(Bmim)Br3] and an activated aromatic compound. It participates as a substrate for the a-arylation of sulphonamide in a study.
Application
4-Bromo-2-methylanisole may be used in the synthesis of 4-isopropyl-2-methylphenol and 4-methoxy-3-methylphenol.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Certificates of Analysis (COA)
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The isopropyl cresols.
Carpenter MS and Easter WM.
The Journal of Organic Chemistry, 20(4), 401-411 (1955)
George Majetich et al.
The Journal of organic chemistry, 62(13), 4321-4326 (1997-06-27)
It has been shown that bromodimethylsulfonium bromide, generated in situ by treating dimethyl sulfoxide with aqueous hydrobromic acid, is a milder and more selective reagent for electrophilic aromatic bromination than elemental bromine.
Total synthesis of (?)-heliannuol D, an allelochemical from Helianthus annuus.
Vyvyan JR and Looper RE.
Tetrahedron Letters, 41(8), 1151-1154 (2000)
Gang Zhou et al.
Organic letters, 10(12), 2517-2520 (2008-05-22)
A mild catalytic system to access diversely functionalized benzylic sulfonamides has been developed. Palladium-catalyzed alpha-arylation by Negishi cross-coupling of sulfonamide-stabilized anions and a wide range of aryl iodides, bromides, and triflates constitutes a practical strategy for the synthesis of various
James R Vyvyan et al.
The Journal of organic chemistry, 69(7), 2461-2468 (2004-03-31)
Aromatic bisabolene derivatives were prepared by two methods involving cross-coupling of organozinc reagents. The first synthesis of (+/-)-glandulone A (10), as well as syntheses of (+/-)-curcuhydroquinone (8) and (+/-)-curcuquinone (9), were accomplished via coupling of a secondary alkyl zinc reagent
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