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H19808

Sigma-Aldrich

3-Hydroxybenzaldehyde

≥99%

Synonym(s):

3-Formylphenol, 5-Hydroxybenzaldehyde, m-Formylphenol, m-Hydroxybenzaldehyde

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About This Item

Linear Formula:
HOC6H4CHO
CAS Number:
100-83-4
Molecular Weight:
122.12
Beilstein/REAXYS Number:
507099
EC Number:
202-892-9
MDL number:
MFCD00003368
UNSPSC Code:
12352100
PubChem Substance ID:
24895491
NACRES:
NA.22

Quality Level

200

assay

≥99%

bp

191 °C/50 mmHg (lit.)

mp

100-103 °C (lit.)

SMILES string

Oc1cccc(C=O)c1

InChI

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

InChI key

IAVREABSGIHHMO-UHFFFAOYSA-N

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Application

3-Hydroxybenzaldehyde can be used as a reactant along with ethyl acetoacetate and thiourea in the synthesis of corresponding dihydropyrimidine-2-thione (monastrol), using Yb(OTf)3 as a catalyst by Biginelli cyclocondensation reaction.
It can also be used as a starting material for the synthesis of:
  • (-)-Quinocarcin, isoxazolo[3,4-e][2,1]benzisoxazole and 3-n-propylphenol.
  • Oligo-3-hydroxybenzaldehyde (O-3HBA) by oxidative polycondensation.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

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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A novel cyclization to isoxazolo [3, 4-e][2, 1] benzisoxazole
Katritzky AR, et al.
Tetrahedron Letters, 43(18), 3449-3451 (2002)
The synthesis and thermal properties of oligo-3-hydroxybenzaldehyde synthesized by oxidative polycondensation
Mart H, et al.
Journal of Applied Polymer Science, 101(2), 892-897 (2006)
A practical synthesis of 3-n-propylphenol, a component of tsetse fly attractant blends
Ujvary I and Mikite G
Organic Process Research & Development, 7(4), 585-587 (2003)
Improved synthesis and preparative scale resolution of racemic monastrol
Dondoni A, et al.
Tetrahedron Letters, 43(34), 5913-5916 (2002)
M Parekh et al.
Letters in applied microbiology, 22(2), 115-120 (1996-02-01)
Desulfovibrio desulfuricans ATCC 27774 was screened for reactivity against aromatic compounds during lactate-dependent, nitrate-dissimilating growth. Only aromatic aldehydes (benzaldehyde, 2-hydroxybenzaldehyde, 3-hydroxybenzaldehyde, 4-hydroxybenzaldehyde, vanillin, iso-vanillin and o-vanillin) were reactive and, with the exception of 2-hydroxybenzaldehyde, were stimulatory to lactate-dependent growth. Aromatic
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