| Identification | More | [Name]
4-Amino-2-chlorobenzoic acid | [CAS]
2457-76-3 | [Synonyms]
2-CHLORO-4-AMINOBENZOIC ACID
4-AMINO-2-CHLOROBENZOIC ACID
4-AMINO-3-TRIFLUOROMETHYLBENZOIC ACID
4-CARBOXY-3-CHLOROANILINE
5-AMINO-2-CARBOXY-1-CHLOROBENZENE
BUTTPARK 44\09-94
RARECHEM AL BO 0877
RARECHEM AL BO 1298
TIMTEC-BB SBB008581
2-Chloro-p-aminobenzoic acid
4-amino-2-chloro-benzoicaci
o-Chloro-p-aminobenzoic acid
USAF nb-1
usafnb-1
4-Amino-2-Chlorobenzoic Acid 2-Chloro-4-Aminobenzoic Acid
4-AMINO-2-CHLOROBENZOIC ACIDCRYSTALLINE
4-AMINO-3-TRIFLUOROMETHYLBENZIOC ACID
4-Amino-2-chlorobenzoic
2-Amino-3-Benzoylphenylacetic Acid | [EINECS(EC#)]
219-540-5 | [Molecular Formula]
C7H6ClNO2 | [MDL Number]
MFCD03407960 | [Molecular Weight]
171.58 | [MOL File]
2457-76-3.mol |
| Chemical Properties | Back Directory | [Appearance]
beige to light brown powder | [Melting point ]
211 °C (dec.) (lit.) | [Boiling point ]
250°C (rough estimate) | [density ]
1.3246 (rough estimate) | [refractive index ]
1.5560 (estimate) | [storage temp. ]
−20°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
3.81±0.25(Predicted) | [color ]
Beige to light brown | [BRN ]
2803668 | [InChI]
InChI=1S/C7H6ClNO2/c8-6-3-4(9)1-2-5(6)7(10)11/h1-3H,9H2,(H,10,11) | [InChIKey]
MBDUKNCPOPMRJQ-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC=C(N)C=C1Cl | [CAS DataBase Reference]
2457-76-3(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzoic acid, 4-amino-2-chloro-(2457-76-3) | [EPA Substance Registry System]
2457-76-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
DG1575000
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29224995 |
| Hazard Information | Back Directory | [Chemical Properties]
beige to light brown powder | [Uses]
4-Amino-2-chlorobenzoic acid is the principal metabolite of 2-Chloroprocaine, a compound that is widely used for epidural analgesia in obstetrics. | [Definition]
ChEBI: 4-Aminobenzoic acid in which one of the hydrogens ortho- to the carboxylic acid group is substituted by chlorine. | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of 4-amino-2-chlorobenzoic acid from 2-chloro-4-nitrobenzoic acid was as follows: firstly, NaBH4 (1 mmol) was added as a reducing agent to methanol at room temperature and the reaction was carried out for 2 h. Ag (+1) was reduced to Ag (0). Subsequently, the Ag/MMT catalyst was obtained by filtration separation. In a standard reaction procedure, 2-chloro-4-nitrobenzoic acid (0.1 mmol), KOH (0.15 mmol), isopropanol (3 mL) and 1.01 wt% of Ag/MMT catalyst (50 mg) were mixed and the reaction was stirred at room temperature until completion (the reaction progress was monitored by GC). Upon completion of the reaction, the catalyst was removed by filtration. The product was extracted with ethyl acetate and washed repeatedly (3-4 times) with water to remove residual KOH. finally, the solvent in the extract was evaporated to dryness under vacuum to afford the target product 4-amino-2-chlorobenzoic acid. | [References]
[1] Journal of Medicinal Chemistry, 2004, vol. 47, # 27, p. 6730 - 6739
[2] Journal of the Iranian Chemical Society, 2018, vol. 15, # 2, p. 281 - 291
[3] Patent: US2014/18368, 2014, A1. Location in patent: Paragraph 0162; 0187
[4] Journal of the American Chemical Society, 1949, vol. 71, p. 4154
[5] Chemische Berichte, 1891, vol. 24, p. 706 |
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