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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:
123-08-0
Molecular Weight:
122.12
Beilstein:
471352
EC Number:
204-599-1
MDL number:
MFCD00006939
UNSPSC Code:
12352100
PubChem Substance ID:
24848630
NACRES:
NA.22

Quality Level

200

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H318,H335

Hazard Classifications

Eye Dam. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

345.2 °F

Flash Point(C)

174 °C

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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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
Wei Yi et al.
European journal of medicinal chemistry, 45(2), 639-646 (2009-11-26)
A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC(50)=1.22 mM). Interestingly, compound 3c
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