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523054

Sigma-Aldrich

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:
14804-31-0
Molecular Weight:
201.06
MDL number:
MFCD01321139
UNSPSC Code:
12352100
PubChem Substance ID:
24874293
NACRES:
NA.22

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

523054-VAR:
523054-BULK:
523054-25G:
523054-5G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
The isopropyl cresols.
Carpenter MS and Easter WM.
The Journal of Organic Chemistry, 20(4), 401-411 (1955)
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
(Bmim) Br3 as a New Reagent for Regioselective Monobromination of Phenols and Several Activated Aromatics under Solvent-free Conditions.
Le ZG, et al.
Chin. J. Chem., 23(11), 1537-1540 (2005)
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