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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

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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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)
(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)
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)
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
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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