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| | 4-Amino-2-chlorobenzoic acid Basic information |
| | 4-Amino-2-chlorobenzoic acid Chemical Properties |
| Melting point | 211 °C (dec.) (lit.) | | Boiling point | 250°C (rough estimate) | | density | 1.3246 (rough estimate) | | refractive index | 1.5560 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 3.81±0.25(Predicted) | | form | Powder | | color | Beige to light brown | | BRN | 2803668 | | Major Application | peptide synthesis | | 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 | Benzoic acid, 4-amino-2-chloro- (2457-76-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | WGK Germany | 3 | | RTECS | DG1575000 | | TSCA | TSCA listed | | HazardClass | IRRITANT | | HS Code | 29224995 | | Storage Class | 11 - Combustible Solids |
| | 4-Amino-2-chlorobenzoic acid Usage And Synthesis |
| 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 |
| | 4-Amino-2-chlorobenzoic acid Preparation Products And Raw materials |
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