H19808
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:
Molecular Weight:
122.12
Beilstein:
507099
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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:
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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)
A novel cyclization to isoxazolo [3, 4-e][2, 1] benzisoxazole
Katritzky AR, et al.
Tetrahedron Letters, 43(18), 3449-3451 (2002)
Yan-Chao Wu et al.
Journal of the American Chemical Society, 130(22), 7148-7152 (2008-05-06)
(-)-Quinocarcin (1) has been synthesized in a longest linear sequence of 22 steps from 3-hydroxybenzaldehyde in 16% overall yield. The Pictet-Spengler reaction of L-tert-butyl-2-bromo-5-hydroxy phenylalanate (17), synthesized according to Corey-Lygo's enantioselective alkylation process, with benzoxyacetaldehyde (12) under mild acidic conditions
B A Stamboliyska et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 59(7), 1541-1548 (2003-04-26)
The spectral and structural changes, caused by the conversion of the 3-hydroxybenzaldehyde molecule into the corresponding oxyanion have been studied by IR spectra, and MP2 and DFT force field calculations. The conversion causes a 13 cm(-1) decrease in the frequency
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