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429120

Sigma-Aldrich

3-Methoxybenzyl bromide

98%

Synonym(s):

1-Bromomethyl-3-methoxybenzene

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5 ML
€92.50
25 ML
€134.00

About This Item

Linear Formula:
CH3OC6H4CH2Br
CAS Number:
874-98-6
Molecular Weight:
201.06
MDL number:
MFCD00216590
UNSPSC Code:
12352100
PubChem Substance ID:
24866839
NACRES:
NA.22

€92.50

In StockDetails

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Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.575 (lit.)

bp

152 °C (lit.)

density

1.436 g/mL at 25 °C (lit.)

functional group

bromo

SMILES string

COc1cccc(CBr)c1

InChI

1S/C8H9BrO/c1-10-8-4-2-3-7(5-8)6-9/h2-5H,6H2,1H3

InChI key

ZKSOJQDNSNJIQW-UHFFFAOYSA-N

General description

3-Methoxybenzyl bromide is a benzyl bromide derivative.

Application

3-Methoxybenzyl bromide (1-bromomethyl-3-methoxybenzene) may be used in the diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives.[1]
It may be used in the synthesis of the following:
  • 6-(3-methoxyphenyl)-hexane-2,4-dione[2]
  • N-(3-methoxybenzyl)-N-(1-methyl-1-phenylethyl)-amine[3]
  • 2-(3-methoxybenzyl)-3-[(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]-(3S)-2-thionia-bicyclo [2.2.1]- heptane tetrafluoroborate[4]
  • 1-(3-methoxybenzyl)-5-(1-methyl-1H-imidazol-5-yl)-1H-1,2,3-triazole[5]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL8646
MKBT8591V
MKBL8798V
MKBF5585V
MKBF5585

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Highly diastereoselective alkylation of vicinal dianions of chiral succinic acid derivatives: a new general strategy to (R)-?-arylmethyl-?-butyrolactones.
Pohmakotr M, et al.
Tetrahedron Letters, 45(22), 4315-4318 (2004)
Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization.
Clayden J, et al.
Tetrahedron, 58(23), 4727-4733 (2002)
Application of sulfur ylide mediated epoxidations in the asymmetric synthesis of ?-hydroxy-d-lactones. Synthesis of a mevinic acid analogue and (+)-prelactone B.
Aggarwal VK, et al.
Tetrahedron Asymmetry, 60(43), 9725-9733 (2004)
Yang Zhang et al.
The Journal of organic chemistry, 71(12), 4516-4520 (2006-06-06)
A mild protocol for the conversion of beta-ketoesters and beta-diketones to carboxylic acids with use of CAN in CH3CN is described. The method is compatible with a number of functional groups, and can generate carboxylic acids under neutral conditions at
Johan R Johansson et al.
The Journal of organic chemistry, 76(7), 2355-2359 (2011-03-11)
An experimentally simple sequential one-pot RuAAC reaction, affording 1,5-disubstituted 1H-1,2,3-triazoles in good to excellent yields starting from an alkyl halide, sodium azide, and an alkyne, is reported. The organic azide is formed in situ by treating the primary alkyl halide
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