4-Hydroxybenzaldehyde
Names | |
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Preferred IUPAC name
4-Hydroxybenzaldehyde | |
Other names
p-Hydroxybenzaldehyde, 4-formylphenol[1]
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard
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100.004.182 |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C7H6O2 | |
Molar mass | 122.123 g·mol−1 |
Appearance | yellow to tan powder |
Density | 1.129 g/cm3 (130 °C)[1] |
Melting point | 116 °C (241 °F; 389 K)[1] |
Boiling point | 310 to 311 °C (590 to 592 °F; 583 to 584 K) |
12.9 g/L[2] | |
Acidity (pKa) | 7.61 (25 °C)[3] |
-78.0·10−6 cm3/mol | |
Refractive index (nD)
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1.57051 (130 °C)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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4-Hydroxybenzaldehyde (2-hydroxybenzaldehyde) is an
3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde
.
Synthesis, reactions, uses
4-Hydroxybenzaldehyde is prepared by reaction of phenol with chloroform, which gives isomeric hydroxybenzal chlorides. Hydrolysis of the C-Cl bonds gives the aldehyde.[5]
4-Hydroxybenzaldehyde is a precursor to 4-hydroxyphenylglycine, a precursor to penicillins. In the Dakin oxidation, 4-hydroxybenzaldehyde reacts with hydrogen peroxide in base to form hydroquinone.
Metabolism and occurrence
p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).[6]
4-Hydroxybenzaldehyde is found in the orchids Gastrodia elata,[7] Galeola faberi,[8] and the Vanilla orchids.
See also
- Salicylaldehyde (2-hydroxybenzaldehyde)
References
Cited sources
- Haynes, William M., ed. (2016). ISBN 9781498754293.