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].

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

P-nitrophenylacetic acid was synthesized as follows: water, ferric chloride and p-nitrophenylacetic acid were mixed in the ratio of 10:0.2:1 by weight under nitrogen protection and heated to 90 °C. Subsequently, a solution with hydrazine hydrate (1:1 by weight) was slowly added dropwise and the reaction was maintained at this temperature for 1 hour. After completion of the reaction, the mixture was cooled to 5°C and the solid product was collected by filtration. The filter cake was washed with an appropriate amount of water until the washing water was colorless, and finally the filter cake was dried to obtain p-aminophenylacetic acid. Note: The amount of washing water is not included in the total amount of water.

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.

4-Aminophenylacetic acid(1197-55-3)Related Product Information

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