| Identification | More | [Name]
4-Aminophenylacetic acid | [CAS]
1197-55-3 | [Synonyms]
2-(4-AMINOPHENYL)ACETIC ACID
4-AMINOPHENYLACETIC ACID
ACETIC ACID 4-AMINOPHENYL ESTER
AKOS BBS-00006880
H-4-APH-OH
H-APH(4)-OH
P-AMINOPHENYLACETIC ACID
RARECHEM AL BO 0220
(p-aminophenyl)-aceticaci
(para-Aminophenyl)acetic acid
4-Aminobenzeneacetic acid
4-amino-benzeneaceticaci
4-aminobenzeneaceticacid
4-Carboxymethylaniline
Acetic acid, (p-aminophenyl)-
p-Amino-alpha-toluic acid
p-amino-alpha-toluicacid
Phenylglycine base
4-Aminophenylacetic
Benzeneacetic acid, 4-amino- | [EINECS(EC#)]
214-828-7 | [Molecular Formula]
C8H9NO2 | [MDL Number]
MFCD00007916 | [Molecular Weight]
151.16 | [MOL File]
1197-55-3.mol |
| Chemical Properties | Back Directory | [Appearance]
light yellow to beige powder | [Melting point ]
201 °C (dec.) (lit.) | [Boiling point ]
273.17°C (rough estimate) | [density ]
1.2023 (rough estimate) | [refractive index ]
1.5635 (rough estimate) | [Fp ]
201°C | [storage temp. ]
Store below +30°C. | [form ]
Powder | [pka]
pK1: 3.60;pK2: 5.26 (20°C) | [color ]
Light yellow to beige | [Water Solubility ]
Very soluble in water. | [Decomposition ]
201 ºC | [Usage]
It is a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1 | [Detection Methods]
HPLC,NMR | [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]
1197-55-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [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. |
| Hazard Information | Back Directory | [Chemical Properties]
light yellow to beige powder | [Uses]
It is a non-translocated competitive inhibitor of the epithelial peptide transporter PepT1 | [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. |
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