| Identification | More | [Name]
Methyl 2-chloro-6-methylpyridine-4-carboxylate | [CAS]
3998-90-1 | [Synonyms]
2-CHLORO-6-PICOLINE-4-CARBOXYLIC ACID METHYL ESTER
METHYL 2-CHLORO-6-METHYLISONICOTINATE
METHYL 2-CHLORO-6-METHYLPYRIDINE-4-CARBOXYLATE
METHYL 2-CHLORO-6-METHYLPYRIDINE-4-CARB&
ETHYL 2-CHLORO-6-METHYLISONICOTINATE
Methyl 2-chloro-6-methylpyridine-4-carboxylate 97%
2-METHOXYL-5-NITROPICOLINE
2-Chloro-6-methylisonicotinic acid methyl ester | [EINECS(EC#)]
627-727-1 | [Molecular Formula]
C8H8ClNO2 | [MDL Number]
MFCD04038391 | [Molecular Weight]
185.61 | [MOL File]
3998-90-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
58-62 °C(lit.)
| [Boiling point ]
124-125 °C7 mm Hg(lit.)
| [density ]
1.247±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
-0.19±0.10(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C8H8ClNO2/c1-5-3-6(8(11)12-2)4-7(9)10-5/h3-4H,1-2H3 | [InChIKey]
BDWMGYZSQKGUFA-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC(C)=CC(C(OC)=O)=C1 | [CAS DataBase Reference]
3998-90-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R43:May cause sensitization by skin contact. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Uses]
Methyl 2-Chloro-6-methylisonicotinate is used in the synthesis of pyridine derivatives as antitubercular agents | [Synthesis]
General procedure: 2-chloro-6-methylpyridine-4-carboxylic acid (2.37 g, 15.5 mmol) was added to a stirred solution of phosphorus oxychloride (POCl3, 10 mL, 107 mmol) and heated to reflux for 18 hours. Upon completion of the reaction, excess POCl3 was removed by distillation under reduced pressure and the residue was cooled to -5°C. Methanol (20 mL) was slowly added dropwise and stirred for 24 h at room temperature. Subsequently, methanol was removed by complete distillation and the reaction mixture was neutralized with solid sodium bicarbonate (NaHCO3) and partitioned between water (30 mL) and ethyl acetate (EtOAc, 30 mL). The aqueous layer was extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The crude product was purified by rapid chromatography on silica gel (eluent: dichloromethane, CH2Cl2) to afford methyl 2-chloro-6-methyl-isonicotinate (2 g, 10.8 mmol, 69% yield) as a white solid. Thin layer chromatography (TLC, silica gel plate, dichloromethane as unfolding agent) Rf value was 0.66. Nuclear magnetic resonance hydrogen spectrum (1H NMR, 300 MHz, CDCl3) δ 2.59 (s, 3H), 3.94 (s, 3H), 7.61 (s, 1H), 7.67 (s, 1H); nuclear magnetic resonance carbon spectrum (13C NMR, 75 MHz, CDCl3) δ 24.2, 52.9, 120.8, 121.2, 140.3, 151.4, 160.5, 164.6; mass spectrum (MS, EI, 70 eV): m/z (relative abundance) [M+H]+ 186 (100). | [References]
[1] Tetrahedron Letters, 2007, vol. 48, # 6, p. 999 - 1002
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 14, p. 4629 - 4635
[3] Chemistry - A European Journal, 2015, vol. 21, # 33, p. 11745 - 11756 |
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