4-Aminophenylacetic acid
- CAS No.
- 1197-55-3
- Chemical Name:
- 4-Aminophenylacetic acid
- Synonyms
- 2-(4-AMINOPHENYL)ACETIC ACID;H-4-APH-OH;P-AMINOPHENYLACETIC ACID;NSC 7929;H-APH(4)-OH;4-AMino acid;p-Amino-alph;Desacetyl Actarit;AKOS BBS-00006880;Phenylglycine base
- CBNumber:
- CB6373122
- Molecular Formula:
- C8H9NO2
- Molecular Weight:
- 151.16
- MOL File:
- 1197-55-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/21 22:41:43
| 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
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a | |||||||||
| 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. | |||||||||
| NFPA 704 |
|
4-Aminophenylacetic acid Chemical Properties,Uses,Production
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] 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.
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.
4-Aminophenylacetic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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