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144088

Sigma-Aldrich

4-Hydroxybenzaldehyde

98%

Synonym(s):

4-Formylphenol, 4-Hydroxybenzaldehyde, Parahydroxybenzaldehyde, p-Formylphenol, p-Hydroxybenzaldehyde, p-Oxybenzaldehyde

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About This Item

Linear Formula:
HOC6H4CHO
CAS Number:
Molecular Weight:
122.12
Beilstein/REAXYS Number:
471352
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

form

solid

mp

112-116 °C (lit.)

SMILES string

[H]C(=O)c1ccc(O)cc1

InChI

1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H

InChI key

RGHHSNMVTDWUBI-UHFFFAOYSA-N

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Application

4-Hydroxybenzaldehyde can be used as a reactant to synthesize:
  •  4-Hydroxybenzaldehydesemicarbazone by a condensation reaction with semicarbazide.    
  • Vanillin via bromination followed by copper-catalyzed coupling reaction with sodium methoxide.      
  • Oligo-4-hydroxybenzaldehyde by an oxidative polycondensation reaction with hydrogen peroxide (H2O2) in an alkaline medium.
  • (−)-Centrolobine, a diarylheptanoid.

pictograms

CorrosionExclamation mark

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - STOT SE 3

target_organs

Respiratory system

wgk_germany

WGK 2

flash_point_f

345.2 °F

flash_point_c

174 °C

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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The synthesis, characterization and thermal stability of oligo-4-hydroxybenzaldehyde
Mart H, et al.
Polymer Degradation and Stability, 83(3), 395-398 (2004)
Vanillin synthesis from 4-hydroxybenzaldehyde
Taber Douglass F, et al.
Journal of Chemical Education, 84(7), 1158-1158 (2007)
Stereoselective synthesis of (-)-centrolobine
Lee Eun, et al.
Bulletin of the Korean Chemical Society,, 25(11), 1609-1610 (2004)
Nadja Schultz-Jensen et al.
Applied biochemistry and biotechnology, 165(3-4), 1010-1023 (2011-07-06)
The potential of wheat straw for ethanol production after pretreatment with O(3) generated in a plasma at atmospheric pressure and room temperature followed by fermentation was investigated. We found that cellulose and hemicellulose remained unaltered after ozonisation and a subsequent
Hypomethylating agents (HMAs) effect on myelodysplastic/myeloproliferative neoplasm unclassifiable (MDS/MPN-U): single institution experience.
Aref Al-Kali et al.
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