4-Aminophenylacetic acid Chemical Properties

Melting point:

201 °C (dec.) (lit.)

Boiling point:

273.17°C (rough estimate)

Density 

1.2023 (rough estimate)

refractive index 

1.5635 (rough estimate)

Flash point:

201°C

storage temp. 

Store below +30°C.

pka

pK1: 3.60;pK2: 5.26 (20°C)

form 

Powder

color 

Light yellow to beige

Water Solubility 

Very soluble in water.

Decomposition 

201 ºC

Merck 

14,463

BRN 

2208094

LogP

0.220 (est)

CAS DataBase Reference

1197-55-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneacetic acid, 4-amino-(1197-55-3)

EPA Substance Registry System

Benzeneacetic acid, 4-amino- (1197-55-3)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

AF3550000

F 

13

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29224995

Toxicity

mouse,LD50,intraperitoneal,3500mg/kg (3500mg/kg),Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958.

MSDS

• Language:English Provider:p-Aminophenylacetic acid
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Aminophenylacetic acid Usage And Synthesis

Chemical Properties

light yellow to beige powder. Soluble in alcohols and alkalis, slightly soluble in hot water.

Uses

4-Aminophenylacetic acid is used as a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1. It can be detected using HPLC, NMR techniques.

Preparation

p-aminophenylacetic acid is obtained by the reduction of 4-nitrophenylacetic acid. In a reactor, water, 4-nitrophenylacetic acid, and acetic acid are added. The mixture is stirred and heated to 90-95℃. Iron powder is added in portions and refluxed for 2 hours. The mixture is cooled to 40-50℃ and neutralized with sodium carbonate to pH=9, then filtered. The filtrate is further neutralized with acetic acid until pH=4, resulting in the precipitation of 4-aminophenylacetic acid. The yield is 95%.

benefits

4-Aminophenylacetonitrile (4-APAN) is an arylacetonitrile and an active substrate for arylacetonitrilase, which gives 4-aminophenylacetic acid (4-APAA) on hydrolysis. 4-APAA is a precursor of 4-acetylaminophenylacetic acid, used in treating rheumatoid arthritis and actarit drugs. 4-APAA also possesses tuberculostatic activity and is helpful as a fibrinolysis inhibitor. In addition to the medical importance of this acid, several derivatives and compounds obtained from 4-APAA showed antimicrobial activity[1].

Purification Methods

Crystallise the acid from hot water (60-70mL/g). [Beilstein 14 III 1182.]

References

[1] Neerja Thakur. “Bioprocess Development for the Synthesis of 4-Aminophenylacetic Acid Using Nitrilase Activity of Whole Cells of Alcaligenes faecalis MTCC 12629.” Catalysis Letters 149 10 (2019): 2854–2863.

References

[1] BEDAIRAHMED H. Preparation of 4-aminophenylacetic acid derivatives with promising antimicrobial activity.[J]. Acta Pharmaceutica, 2006, 56 3: 273-284.
[2] MENGYIFAN ZareRichard N GnanamaniElumalai. One-Step Formation of Pharmaceuticals Having a Phenylacetic Acid Core Using Water Microdroplets.[J]. Journal of the American Chemical Society, 2023, 145 14: 7724-7728. DOI:10.1021/jacs.3c00773.

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