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| | 4-Aminophenylacetic acid Basic information |
| | 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) | | 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 | | Merck | 14,463 | | BRN | 2208094 | | InChI | 1S/C8H9NO2/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4H,5,9H2,(H,10,11) | | InChIKey | CSEWAUGPAQPMDC-UHFFFAOYSA-N | | SMILES | Nc1ccc(CC(O)=O)cc1 | | 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) |
| 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 | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29224995 | | Storage Class | 13 - Non Combustible Solids | | Toxicity | mouse,LD50,intraperitoneal,3500mg/kg (3500mg/kg),Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958. |
| | 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] 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.
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| | 4-Aminophenylacetic acid Preparation Products And Raw materials |
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