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410470

Sigma-Aldrich

5-Bromo-2-hydroxy-3-methoxybenzaldehyde

97%

Synonym(s):

5-Bromo-3-methoxysalicylaldehyde

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About This Item

Linear Formula:
BrC6H2(OH)(OCH3)CHO
CAS Number:
5034-74-2
Molecular Weight:
231.04
MDL number:
MFCD00016593
UNSPSC Code:
12352100
PubChem Substance ID:
24865528
NACRES:
NA.22

Assay

97%

form

solid

mp

125-127 °C (lit.)

SMILES string

COc1cc(Br)cc(C=O)c1O

InChI

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

InChI key

MMFKBTPDEVLIOR-UHFFFAOYSA-N

Related Categories

Application

5-Bromo-2-hydroxy-3-methoxybenzaldehyde may be employed for the following syntheses:
  • ailanthoidol, via Stille coupling
  • 6-bromo-8-methoxy-3-(methoxycarbonyl)-2H-chromen-2-one
  • benzimidazole-based ligand, 2-(1H-benzoimidazol-2-yl)-4-bromo-6-methoxy-phenol (HL)
  • chromogenic reagent, 5-bromo-2-hydroxy-3-methoxybenzaldehyde-p-hydroxy benzoic hydrazone
  • (E)-N′-(5-bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide monohydrate

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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(E)-N'-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-2-hydroxybenzohydrazide monohydrate.
Zhao S, et al.
Acta Crystallographica Section E, Structure Reports Online, 68(7), 2040-2040 (2012)
Direct Spectrophotometric Determination of Ni (II) Using 5-Bromo-2-hydroxyl-3-methoxybenzaldehyde-4-hydroxy benzoichydrazone.
Saritha B and Reddy TS.
J. Appl. Chem., 7(3), 22-26 (2014)
Shun-Yu Lin et al.
The Journal of organic chemistry, 68(7), 2968-2971 (2003-03-29)
Ailanthoidol 1, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only six steps in 48% overall yield from commercially available 5-bromo-2-hydroxy-3-methoxybenzaldehyde. The key transformations in the synthesis are the Stille coupling
Transformation of a luminescent benzimidazole-based Yb3 cluster into a one-dimensional coordination polymer.
Yang X, et al.
Crystal Growth & Design, 10(2), 970-976 (2009)
Pedro Verdía et al.
Molecules (Basel, Switzerland), 16(6), 4379-4388 (2011-05-31)
The ionic liquid 1,3-dimethylimidazolium methyl sulfate, [MMIm][MSO₄], together with a small amount of water (the amount taken up by the ionic liquid upon exposure to air), acts efficiently as both solvent and catalyst of the Knoevenagel condensation reactions of malononitrile

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