4-Hydroxyphenylacetic acid

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For Research Use Only.

Category

Phenols

Cat.No.

NP4630

CAS

156-38-7

Product Name

4-Hydroxyphenylacetic acid

Structure

Product Details

Description

4-Hydroxyphenylacetic acid is a phenolic compound found in olive oil and beer. In industry 4-Hydroxyphenylacetic acid is an intermediate used to synthesize atenolol and Daidzein.

Synonyms

2-(4-hydroxyphenyl)acetic acid

IUPAC Name

2-(4-hydroxyphenyl)acetic acid

Molecular Weight

152.15

Molecular Formula

C8H8O3

Canonical SMILES

C1=CC(=CC=C1CC(=O)O)O

InChI

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

Boiling Point

346.6 ℃ at 760 mmHg

Melting Point

150-151 ℃

Purity

98 %

Density

1.319 g/cm³

Solubility

50 g/L

Appearance

Powder

Storage

Inert atmosphere,Room Temperature

BRN

1448766

Chemical Properties

4-Hydroxyphenylacetic acid is a white to cream or light tan crystalline powder. sublimation. Insoluble in cold water, soluble in hot water, ether, ethanol, ethyl acetate. In the case of ferric chloride, it is a purple-green precipitate. It is used as a pharmaceutical raw material for the synthesis of cephalosporin antibiotics, antipyretic analgesics.

Color

White to cream or light tan

Definition

ChEBI: 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It derives from an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate.

EINECS

205-851-3

Form

Crystalline Powder

Hazard Class

HS Code

29182990

MDL

MFCD00004347

2.0-2.4 (30 g/L, H2O, 20 ℃)

pKa

4.50±0.10(Predicted)

Preparation

4-Hydroxyphenylacetic acid is synthesized by diazotization and hydrolysis of 4-aminophenylacetic acid. 4-aminophenylacetic acid and alkali solution are prepared into sodium salt, and then sulfuric acid is added. Cool to 0°C, control the temperature at 0-5°C, and add sodium nitrate solution dropwise, and the reaction is completed for 0.5h. The obtained diazonium was added dropwise to dilute sulfuric acid at 90-95°C for about 1 hour, and the reaction was continued for 1 hour. The reaction solution was decolorized and filtered, cooled and extracted with ethyl acetate, and the extract was recovered with ethyl acetate to obtain 4-Hydroxyphenylacetic acid. The yield is about 85%.

Purification Methods

Crystallise the acid from water or Et2O/pet ether.

Refractive Index

1.4945 (estimate)

Risk Statements

36/37/38

RTECS

AI2680000

Safety Statements

26-36-24/25

Uses

A compound present in olive oil. An important fine chemical intermediate with broad prospects for application development.

Vapor Pressure

0.0000555 [mmHg]

Water Solubility

Soluble in dimethyl sulfoxide and methanol. Slightly soluble in water.

WGK Germany

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