Hydroxyphenylacetic acid | Pharmaceutical Grade | 99.99% Purity | CAS 156-38-7

4-Hydroxyphenylacetic Acid
Properties
Melting Point: 148-151 °C(lit.)
Boiling Point: 234.6°C (rough estimate)
Density: 1.2143 (rough estimate)
Vapor Pressure: 0.007Pa at 25℃
Refractive Index: 1.4945 (estimate)
Storage Condition: Inert atmosphere, Room Temperature
Solubility: 50 g/L
pKa (Acidity Coefficient): 4.50±0.10 (Predicted)
Form: Crystalline Powder
Color: White to cream or light tan
pH Value: 2.0-2.4 (30g/l, H2O, 20℃)
Aqueous Solubility: Soluble in dimethyl sulfoxide and methanol; slightly soluble in water.
BRN: 1448766
InChI: 1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChIKey: XQXPVVBIMDBYFF-UHFFFAOYSA-N
SMILES: OC(=O)Cc1ccc(O)cc1
LogP: 0.75 at 25℃
CAS Registry Number: 156-38-7 (CAS DataBase Reference)
NIST Chemical Information: Benzeneacetic acid, 4-hydroxy-(156-38-7)
EPA Chemical Information: Benzeneacetic acid, 4-hydroxy- (156-38-7)
Applications & Synthetic Routes
Physical and Chemical Properties
White needle-shaped crystals crystallized from water. Molecular weight: 152.15. Melting point: 149～151°C. Sublimable. Slightly soluble in cold water, soluble in hot water, diethyl ether, ethanol and ethyl acetate. It forms purple-green precipitate when reacting with ferric trichloride.
Biological Properties
4-Hydroxyphenylacetic acid (p-Hydroxyphenylacetic acid) naturally exists in olive oil and beer. It serves as a chemical intermediate for the synthesis of atenolol and 3,4-dihydroxyphenylacetic acid.
Chemical Properties
White or light yellow crystalline powder. Melting point: 149-151°C. Sublimable. Soluble in diethyl ether, ethanol and ethyl acetate.
Applications
Biochemical research raw material
Organic synthesis intermediate
Used for manufacturing beta-blocker atenolol and 4,7-dihydroxyisoflavone, the active ingredient extracted from pueraria lobata and soybean; also applied as pesticide intermediate.
Used as an acylation reagent for phenolic compounds and amine compounds.
Intermediate for the synthesis of 4,7-dihydroxyisoflavone and pesticide intermediates
Synthetic Methods
Synthesized via diazotization and hydrolysis of 4-aminophenylacetic acid
Dissolve 4-aminophenylacetic acid in alkaline solution to prepare sodium salt, then add sulfuric acid. Cool the mixture to 0°C, maintain temperature at 0-5°C and dropwise add sodium nitrate solution. Keep reaction for 0.5 hours after feeding. Add the resulting diazonium solution dropwise to dilute sulfuric acid at 90-95°C within around 1 hour, then maintain reaction for another 1 hour. Decolorize and filter the reaction liquid, cool down and extract with ethyl acetate. Recover ethyl acetate from extract to obtain finished product with yield of approximately 85%.
Synthetic route for 3-fluoro-4-hydroxyphenylacetic acid