ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE Chemical Properties

Melting point:

29-31°C

Boiling point:

110-111°C/ 0.5 mmHg

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Soluble in dichloromethane, ether, ethyl acetate and methanol.

form 

Solid

pka

4.00±0.25(Predicted)

color 

White Crystalline

InChI

InChI=1S/C7H10N2O2/c1-3-11-7(10)6-8-4-5-9(6)2/h4-5H,3H2,1-2H3

InChIKey

NOTZYDYZBOBDFE-UHFFFAOYSA-N

SMILES

C1(C(OCC)=O)N(C)C=CN=1

CAS DataBase Reference

30148-21-1

Safety Information

Hazard Codes 

T

Risk Statements 

36/37/38

Safety Statements 

26-36

Hazard Note 

Irritant

HS Code 

29339900

ETHYL 1-METHYL-1H-IMIDAZOLE-2-CARBOXYLATE Usage And Synthesis

Chemical Properties

White Crystalline Solid

Uses

Ethyl 1-methylimidazole-2-carboxylate is used as a synthetic intermediate for solid phase synthesis of polyamides containing imidazole.

Uses

Ethyl 1-methyl-1H-imidazole-2-carboxylate is a useful synthetic intermediate for solid phase synthesis of polyamides containing imidazole.

Synthesis

Synthesis of ethyl 1-methyl-1H-imidazole-2-carboxylate: triethylamine (3.40 mL, 24.4 mmol) and ethyl chloroformate (2.34 mL, 24.4 mmol) were added drop-wise to a solution of 1-methyl-1H-imidazole (1.00 g, 12.2 mmol) in acetonitrile (4.0 mL) at 0 °C. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure to remove the solvent. The resulting crude product was purified by fast column chromatography (silica gel as stationary phase and hexane/ethyl acetate as eluent) to afford ethyl 1-methyl-1H-imidazole-2-carboxylate (1.50 g, 9.73 mmol, 80% yield) as a white solid. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and ESI-MS: 1H-NMR δ 1.42 (3H, t, J = 7.2 Hz), 4.01 (3H, s), 4.40 (2H, q, J = 7.2 Hz), 7.01-7.03 (1H, m), 7.13-7.15 (1H, m); ESI-MS m /z = 155 (M + H)+.

References

[1] Journal of the American Chemical Society, 1996, vol. 118, # 26, p. 6141 - 6146
[2] Patent: EP3263565, 2018, A1. Location in patent: Paragraph 0386; 0387
[3] Patent: JP2017/66077, 2017, A. Location in patent: Page/Page column 7; 8; 9; 10; 11
[4] Patent: WO2005/33077, 2005, A1. Location in patent: Page/Page column 53
[5] Patent: WO2004/58763, 2004, A1. Location in patent: Page 43

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