ethyl 5-methylpyridine-2-carboxylate

ethyl 5-methylpyridine-2-carboxylate Property

Boiling point:

123-124 °C(Press: 15 Torr)

Density 

1.077±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.12±0.10(Predicted)

Appearance

Colorless to light yellow Liquid

Safety

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H332Harmful if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P322Specific measures (see …on this label).

P330Rinse mouth.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

ethyl 5-methylpyridine-2-carboxylate Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of ethyl 5-methylpyridine-2-carboxylate from 2-cyano-5-methylpyridine and ethanol: To a solution of 2-cyano-5-methylpyridine (5 g, 42.3 mmol, 1.00 equiv) in ethanol (40 mL) was added concentrated sulfuric acid (10 mL, 4.00 equiv). The resulting solution was stirred at 80 °C for 48 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature (25 °C). Subsequently, the mixture was concentrated under reduced pressure to remove the solvent. The concentrated residue was diluted with water (100 mL) and the pH was adjusted with potassium carbonate to 8-9. The aqueous phase was extracted with ethyl acetate (3 x 100 mL) and the organic phases were combined. The organic phase was washed sequentially with water (3 × 50 mL) and saturated saline (3 × 50 mL). Finally, the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford ethyl 5-methylpyridine-2-carboxylate (3 g, 43% yield) as a light yellow oil.LC-MS analysis showed the molecular ion peak of the target product m/z = 166 [M + H]+ .

References

[1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 3026 - 3032
[2] Patent: US2018/79742, 2018, A1. Location in patent: Paragraph 0322; 0323