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412015

Sigma-Aldrich

3-Bromo-4-methoxybenzaldehyde

98%

Synonym(s):

3-Bromo-p-anisaldehyde

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About This Item

Linear Formula:
BrC6H3(OCH3)CHO
CAS Number:
34841-06-0
Molecular Weight:
215.04
EC Number:
252-241-8
MDL number:
MFCD00016599
UNSPSC Code:
12352100
PubChem Substance ID:
24865781
NACRES:
NA.22

Assay

98%

mp

51-54 °C (lit.)

SMILES string

COc1ccc(C=O)cc1Br

InChI

1S/C8H7BrO2/c1-11-8-3-2-6(5-10)4-7(8)9/h2-5H,1H3

InChI key

QMPNFQLVIGPNEI-UHFFFAOYSA-N

General description

3-Bromo-4-methoxybenzaldehyde is formed by the solvent-free bromination of 4-methoxybenzaldehyde using 1,3-di-n-butylimidazolium tribromide, as a brominating reagent.

Application

3-Bromo-4-methoxybenzaldehyde may be used in the following studies:
  • Asymmetric synthesis of a novel β-hydroxy-α-amino acid derivative, via Mukaiyama aldol reaction.
  • Synthesis of 2-(3-bromo-4-methoxyphenyl)-5-fluorobenzothiazole.
  • Preparation of 5-[(Z)-2-(3-bromo-4-methoxyphenyl)vinyl]-1,2-3-trimethoxybenzene.
  • Total synthesis of engelhardione.
  • Starting reagent for the synthesis of (2E)-3-(3-bromo-4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one.

Storage Class Code

13 - Non 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

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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22287813
10th Internatl. Conf. on Organic Synthesis, Bangalore, India, December 1994 null
Aromatic bromination of aldehydes and ketones using 1, 3-di-n-butylimidazolium tribromide [BBIm] Br3 ionic liquids under solvent-free conditions.
Borikar SP and Daniel T.
Journal of the Iranian Chemical Society, 8(2), 531-536 (2011)
(2E)-3-(3-Bromo-4-methoxyphenyl)-1-(4-methylphenyl)prop-2-en-1-one.
Dutkiewicz g, et al.
Acta Crystallographica Section E, Structure Reports Online, 67(4), 1024-1024 (2011)
Yali Kong et al.
Chemistry & biology, 12(9), 1007-1014 (2005-09-27)
Targeting the microtubule system represents an attractive strategy for the development of anticancer agents. In this study, we report a class of combretastatin A-4 (CA-4) analogs derivatized with a boronic acid moiety replacing the hydroxyl group on the C-ring of
Li Shen et al.
Tetrahedron letters, 52(35), 4570-4574 (2011-09-20)
The total synthesis of the macrocyclic natural product engelhardione is reported. This effort led to the structural revision of the published structure of engelhardione to that of pterocarine. The revision reflects the change of the substitution pattern of one phenyl
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