4-Aminophenylacetic acid
Basic information
- CAS
1197-55-3- Standard SMILES
Nc1ccc(CC(=O)O)cc1- InChIKey
CSEWAUGPAQPMDC-UHFFFAOYSA-N- Molecular formula
- C8H9NO2
- Average molar mass
- 151.16 g/mol
- Monoisotopic mass
- 151.06332853
Overview
peptide mimic; structure in first source
Names & identifiers
- Preferred name
- 4-Aminophenylacetic acid
- IUPAC
- 2-(4-aminophenyl)acetic acid
- English name
- 4-Aminophenylacetic acid
- Molecular formula
- C8H9NO2
- Molecular weight
- 151.16
Names & synonyms
4-Aminophenylacetic acid1197-55-3Benzeneacetic acid, 4-amino-P-AMINOPHENYLACETIC ACID4-Aminobenzeneacetic acidAcetic acid, (p-aminophenyl)-p-Amino-alpha-toluic acid1IED47A544NSC-7929DTXSID1061609RefChem:978634-APAA
Show more names
H-4-APH-OH4-AminophenylaceticNSC 7929H-APH(4)-OH4-AMino acidp-Amino-alphAKOS BBS-00006880Desacetyl Actarit
DTXCID3033519214-828-72-(4-aminophenyl)acetic acid(4-aminophenyl)acetic acid4-Carboxymethylaniline(para-Aminophenyl)acetic acidMFCD00007916(p-Aminophenyl)acetic acid
Database identifiers
- CAS
1197-55-3- PubChem CID
- 14533
- DTXSID
DTXSID1061609- ChEMBL
CHEMBL3278327- UNII
- 1IED47A544
- EC Number
- 214-828-7
- Nikkaji
- J27.580H
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 63.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 139
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Physical DescriptionSolid; [Merck Index] Tan powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 201 °C · 201 °C (dec.) (lit.)
- Boiling point
- 273.17 °C · 273.17°C (rough estimate)
- Density
- 1.2023 · 1.2023 (rough estimate)
- refractive index
- 1.5635 · 1.5635 (rough estimate)
- Flash point
- 201 °C · 201°C
- storage temp.
- 30 °C · Store below +30°C.
- pka
- 1 · pK1: 3.60;pK2: 5.26 (20°C)
- form
- Powder
- color
- Light yellow to beige
- Water Solubility
- Very soluble in water.
- Decomposition
- 201 · 201 ºC
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 9 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzeneacetic acid, 4-amino-
Benzeneacetic acid, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; May induce methemoglobinemia; [Alfa Aesar MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Safety data
- F
- 13
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- AF3550000
- hs_code
- 29224995
- Toxicity
- mouse,LD50,intraperitoneal,3500mg/kg (3500mg/kg),Farmaco, Edizione Scientifica. Vol. 13, Pg. 286, 1958.
Chemistry & industry
Uses & manufacturing
UsesPeptide mimic. [ChemIDplus]
General Manufacturing InformationBenzeneacetic acid, 4-amino-: ACTIVE
Applications
Uses4-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 methods
Preparationp-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%.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
150 records
Compound notes
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