| 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].
| [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] 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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