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H19808

Sigma-Aldrich

3-Hydroxybenzaldehyde

≥99%

Synonym(s):

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

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$112.00
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10 ML
$112.00
10 X 10 ML
$533.00

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

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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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5-Hydroxy-1,4-naphthoquinone 97%

H47003

5-Hydroxy-1,4-naphthoquinone

1,4-Naphthoquinone 97%

152757

1,4-Naphthoquinone

1,4-Dihydroxy-2,6-dimethoxybenzene 97%

565032

1,4-Dihydroxy-2,6-dimethoxybenzene

2-Hydroxy-5-nitropyridine 97%

H48808

2-Hydroxy-5-nitropyridine

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

mp

161-163 °C (lit.)

mp

119-122 °C (lit.)

mp

158-162 °C (lit.)

mp

188-191 °C (lit.)

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.[1]
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.[2][3][4]
  • Oligo-3-hydroxybenzaldehyde (O-3HBA) by oxidative polycondensation.[5]

Pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    WXBF2700V
    WXBF1655V
    WXBF0883V
    WXBD9480V
    WXBD6703V

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    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)
    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)
    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)
    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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