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B56501

Sigma-Aldrich

4-Bromoanisole

≥99.0%

Synonym(s):

1-Bromo-4-methoxybenzene

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About This Item

Linear Formula:
BrC6H4OCH3
CAS Number:
104-92-7
Molecular Weight:
187.03
Beilstein:
1237590
EC Number:
203-252-1
MDL number:
MFCD00000097
UNSPSC Code:
12352100
PubChem Substance ID:
24891850
NACRES:
NA.22

Assay

≥99.0%

form

liquid

refractive index

n20/D 1.564 (lit.)

bp

223 °C (lit.)

mp

9-10 °C (lit.)

density

1.494 g/mL at 25 °C (lit.)

SMILES string

COc1ccc(Br)cc1

InChI

1S/C7H7BrO/c1-9-7-4-2-6(8)3-5-7/h2-5H,1H3

InChI key

QJPJQTDYNZXKQF-UHFFFAOYSA-N

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General description

4-Bromoanisole is a useful brominating reagent. It is formed as reaction product in the reaction between HOBr and anisole. Suzuki coupling of 4-bromoanisole with phenylboronic acid catalyzed by palladium pincer complexes has been studied. Heck Reaction of 4-bromoanisole with ethyl acrylates in room-temperature ionic liquids is reported to afford ethyl 4-methoxycinnamate.

Application

4-Bromoanisole was used in the synthesis of aryl 1,3-diketones.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

201.2 °F

Flash Point(C)

94 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Amy E Bryant et al.
PloS one, 12(2), e0172486-e0172486 (2017-03-01)
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Palladium bis (phosphinite)'PCP'-pincer complexes and their application as catalysts in the Suzuki reaction.
Bedford RB, et al.
New. J. Chem., 24(10), 745-747 (2000)
Dennis U Nielsen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(52), 17926-17938 (2013-11-23)
Reaction conditions for the three-component synthesis of aryl 1,3-diketones are reported applying the palladium-catalyzed carbonylative α-arylation of ketones with aryl bromides. The optimal conditions were found by using a catalytic system derived from [Pd(dba)2] (dba=dibenzylideneacetone) as the palladium source and
Yasuyuki Nakamura et al.
Applied and environmental microbiology, 84(15) (2018-05-29)
The methylotrophic yeast Pichia pastoris is widely used to produce recombinant proteins, taking advantage of this species' high-density cell growth and strong ability to secrete proteins. Circular plasmids containing the P. pastoris-specific autonomously replicating sequence (PARS1) permit transformation of P.
Charles E Wood et al.
Carcinogenesis, 36(7), 782-791 (2015-04-29)
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