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Sigma-Aldrich

2-Bromo-3-hydroxy-4-methoxybenzaldehyde

97%

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About This Item

Linear Formula:
BrC6H2(OH)(OCH3)CHO
CAS Number:
2973-58-2
Molecular Weight:
231.04
MDL number:
MFCD02380230
UNSPSC Code:
12352100
PubChem Substance ID:
24871450
NACRES:
NA.22

assay

97%

mp

202-207 °C (lit.)

SMILES string

COc1ccc(C=O)c(Br)c1O

InChI

1S/C8H7BrO3/c1-12-6-3-2-5(4-10)7(9)8(6)11/h2-4,11H,1H3

InChI key

QPDFBPIHEDAUKK-UHFFFAOYSA-N

Related Categories

General description

2-Bromo-3-hydroxy-4-methoxybenzaldehyde, also known as 2-bromo-isovanillin, can be synthesized by the bromination of 3-hydroxy-4-methoxybenzaldehyde.

Application

2-Bromo-3-hydroxy-4-methoxybenzaldehyde (2-Bromo-isovanillin) may be used in the preparation of:
  • 2-hydroxy-3-methoxybenzaldehyde semicarbazone (HMBS)
  • 2-cyclopentyl-7-methoxy-1-benzofuran-4-carbaldehyde
  • 3-(benzyloxy)-2-bromo-4-methoxybenzaldehyde
It may also be used as a starting material in the total synthesis of the following natural products:
  • pareitropone
  • denbinobin
  • (±)-codeine

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Total synthesis of pareitropone via radical anion coupling.
Hong SK, et al.
Organic Letters, 12(17), 3954-3956 (2010)
Growth, spectral, and thermal characterization of 2-hydroxy-3-methoxybenzaldehyde semicarbazone.
Binil PS, et al.
Journal of Thermal Analysis and Calorimetry, 112(2), 913-919 (2013)
A concise synthesis of denbinobin.
Wang YC, et al.
Tetrahedron Letters, 46(47), 8103-8104 (2005)
Synthesis and preliminary biological evaluation of novel taspine derivatives as anticancer agents.
Zhang J, et al.
European Journal of Medicinal Chemistry, 45(7), 2798-2805 (2010)
Concise syntheses of (-)-galanthamine and (?)-codeine via intramolecular alkylation of a phenol derivative.
Magnus P, et al.
Journal of the American Chemical Society, 131(44), 16045-16047 (2009)
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