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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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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

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)
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)
Chemoselective Zinc/HCl Reduction of Halogenated β-Nitrostyrenes: Synthesis of Halogenated Dopamine Analogues.
Maresh JJ, et al.
Synlett, 25, 2891-2894 (2014)
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