4-(HYDROXYMETHYL)PHENYLACETIC ACID Chemical Properties

Melting point:

131-134 °C (lit.)

Boiling point:

357.8±22.0 °C(Predicted)

Density 

1.271±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

4.27±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C9H10O3/c10-6-8-3-1-7(2-4-8)5-9(11)12/h1-4,10H,5-6H2,(H,11,12)

InChIKey

FWZBPBKAANKOJQ-UHFFFAOYSA-N

SMILES

C1(CC(O)=O)=CC=C(CO)C=C1

CAS DataBase Reference

73401-74-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich

4-(HYDROXYMETHYL)PHENYLACETIC ACID Usage And Synthesis

Chemical Properties

White solid

Uses

4-(Hydroxymethyl)phenylacetic acid can serve as the main body of insoluble polypeptide. 4-(Hydroxymethyl)phenylacetic acid contains a benzen ring with substituted 1, 4 position[1].

Synthesis

The general procedure for the synthesis of 4-(hydroxymethyl)benzeneacetic acid from 4-bromomethylphenylacetic acid was as follows: 4-bromomethylphenylacetic acid (2.3 kg, 10.0 mol, 1 eq.) was added to an aqueous (90 L) solution of sodium hydroxide (1.61 kg, 40.2 mol, 4 eq.) and the resulting mixture was stirred at room temperature overnight. After confirming the complete consumption of 4-bromomethylphenylacetic acid by TLC analysis, the reaction mixture was carefully acidified with concentrated sulfuric acid (1.0 L) to a pH of about 2. Subsequently, solid sodium chloride (25 kg) was added to the mixture, followed by extraction with ethyl acetate (33 L × 3). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and concentrated until a significant amount of solid precipitated. The resulting suspension was kept at 4-6 °C overnight to promote further crystallization. The solid product was collected by filtration and the filter cake was washed with petroleum ether (2 L × 2) to afford 4-(hydroxymethyl)benzeneacetic acid (1.2 kg, yield: 71.9%). HPLC purity was 97.8% (220 nm); 1H NMR (300 MHz, DMSO-d6) δ 12.27 (s, 1H), 7.26-7.12 (m, 4H), 5.14 ( s, 1H), 4.47 (s, 2H), 3.53 (s, 2H).

References

[1] Zhou Bin, et al. Coupled peptide chain for dissolving insoluble polypeptide and its application in liquid phase chromatography separation and purification. China, CN105001307 A. 2015-10-28.

4-(HYDROXYMETHYL)PHENYLACETIC ACID(73401-74-8)Related Product Information

• (RS)-MCPG
• 4-(HYDROXYMETHYL)PHENYLACETIC ACID
• (±)-(hydroxymethyl)phenylacetic acid
• (S)-ALPHA-METHYL-4-CARBOXYPHENYLGLYCINE
• BOC-L-LYS(2-CL-Z)-O-CH2-PHI-CH2-COOH
• (S)-4-CARBOXYPHENYLGLYCINE
• BOC-L-ASP(OCHX)-O-CH2-PHI-CH2-COOH
• 4-(T-BUTYLOXYCARBONYL-GLYCYLOXYMETHYL)-PHENYLACETIC ACID
• (S)-4-CARBOXY-3-HYDROXYPHENYLGLYCINE
• BOC-L-ARG(TOS)-O-CH2-PHI-CH2-COOH DCHA
• 4-(T-BUTYLOXYCARBONYL-LEUCYLOXYMETHYL)-PHENYLACETIC ACID
• BOC-L-GLN-O-CH2-PHI-CH2-COOH
• BOC-L-GLU(OCHX)-O-CH2-PHI-CH2-COOH
• BOC-L-ASN-O-CH2-PHI-CH2-COOH
• BOC-L-CYS(PMEBZL)-O-CH2-PHI-CH2-COOH
• BOC-L-ILE-O-CH2-PHI-CH2-COOH
• (RS)-4-CARBOXY-3-HYDROXYPHENYLGLYCINE
• BOC-D-CYS(PMEBZL)-O-CH2-PHI-CH2-COOH