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| | 4-Amino-3-chloro-benzoic acid ethyl ester Basic information |
| Product Name: | 4-Amino-3-chloro-benzoic acid ethyl ester | | Synonyms: | ethyl 4-amino-3-chlorobenzoate(SALTDATA: FREE);Benzoic acid, 4-aMino-3-chloro-, ethyl ester;4-AMINO-3-CHLORO-BENZOIC ACID ETHYL ESTER;AKOS BB-3099;4-amino-3-chloro-2-ethylbenzoate;Benzoic acid, 4-amino-3-chloro-, ethyl ester (9CI, ACI);4-amino-3-chloro-Benzoic acid ethyl ester (9CI ACI) | | CAS: | 82765-44-4 | | MF: | C9H10ClNO2 | | MW: | 199.63 | | EINECS: | | | Product Categories: | | | Mol File: | 82765-44-4.mol |  |
| | 4-Amino-3-chloro-benzoic acid ethyl ester Chemical Properties |
| Melting point | 83-84°C | | Boiling point | 110-115 °C(Press: 0.001 Torr) | | density | 1.262±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | pka | 0.56±0.10(Predicted) | | Appearance | White to off-white Solid |
| | 4-Amino-3-chloro-benzoic acid ethyl ester Usage And Synthesis |
| Uses | 4-Amino-3-chloro-benzoic acid ethyl ester is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research. | | Synthesis | To a solution of ethyl 4-aminobenzoate (2.0 mmol) in acetonitrile (2 mL) was added N-chlorosuccinimide (NCS, 2.05 mmol). The reaction mixture was heated to reflux for 5 hours. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate and the organic layer was washed with 5% sodium hydroxide solution and subsequently dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the crude product. Purification by recrystallization in hexane afforded ethyl 4-amino-3-chlorobenzoate (27c) as purple crystals (melting point 81-83 °C) in 86% yield. The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz, CDCl3): 1H NMR δ 1.33 (t, 3H, J=7.0 Hz, CH3), 4.29 (q, 2H, J=7.0 Hz, CH2), 6.70 (d, 1H, J=8.5 Hz, Ar-H), 7.72 (dd , 1H, J=8.4,1.9 Hz, Ar-H), 7.92 (d, 1H, J=1.9 Hz, Ar-H); 13C NMR δ 14.30, 60.62, 114.35, 118.06, 120.63, 129.52, 131.12, 146.97, 165.74. | | References | [1] Organic Letters, 2008, vol. 10, # 1, p. 113 - 116
[2] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 1, p. 109 - 124
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 27, p. 6973 - 6982
[4] Patent: US5502073, 1996, A
[5] Patent: US5516774, 1996, A |
| | 4-Amino-3-chloro-benzoic acid ethyl ester Preparation Products And Raw materials |
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