| Identification | Back Directory | [Name]
2,6-Dichloronicotinic acid ethyl ester | [CAS]
58584-86-4 | [Synonyms]
ethyl 2,6-dichloronicotinate
2,6-Dichloronicotinic acid ethyl ester
Ethyl 2,6-dichloropyridine-3-carboxylate
3-Pyridinecarboxylic acid, 2,6-dichloro-, ethyl ester | [Molecular Formula]
C8H7Cl2NO2 | [MDL Number]
MFCD09757510 | [MOL File]
58584-86-4.mol | [Molecular Weight]
220.06 |
| Chemical Properties | Back Directory | [Melting point ]
50.0 to 54.0 °C | [Boiling point ]
286.0±35.0 °C(Predicted) | [density ]
1.367±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
-4.48±0.10(Predicted) | [color ]
White to Light yellow | [InChI]
InChI=1S/C8H7Cl2NO2/c1-2-13-8(12)5-3-4-6(9)11-7(5)10/h3-4H,2H2,1H3 | [InChIKey]
KKYBVLDQTWQETN-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC(Cl)=CC=C1C(OCC)=O |
| Hazard Information | Back Directory | [Synthesis]
General procedure: 2,6-dichloronicotinic acid (25.5 g, 0.1328 mol) was mixed with ethanol (200 mL) under nitrogen protection and 96% sulfuric acid (1.7 g) was added as catalyst. The reaction mixture was heated to reflux temperature for esterification. Upon completion of the reaction, ethyl 2,6-dichloronicotinate was obtained as a gray solid (24.89 g, 0.1131 mol, 85.2% yield) after conventional post-treatment. The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 8.30 (d, J = 8.1 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 4.33 (q, J = 7.2 Hz, 2H) and 1.30 (t, J = 7.2 Hz, 3H) ppm. | [References]
[1] Patent: US2015/291629, 2015, A1. Location in patent: Paragraph 0722-0723
[2] Patent: WO2009/150230, 2009, A1. Location in patent: Page/Page column 134
[3] Patent: WO2010/116282, 2010, A1. Location in patent: Page/Page column 65
[4] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4273 - 4288
[5] Patent: US2006/194801, 2006, A1. Location in patent: Page/Page column 38-39 |
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