ChemicalBook--->CAS DataBase List--->19213-72-0

19213-72-0

19213-72-0 Structure

19213-72-0 Structure
IdentificationBack Directory
[Name]

1-CARBETHOXYIMIDAZOLE
[CAS]

19213-72-0
[Synonyms]

EtImC
Einecs 242-883-7
1-CARBETHOXYIMIDAZOLE
Etomidate Impurity 10
N-Carboethoxyimidazole
Ethyl imidazolecarbamate
Ethyl 1-imidazolecarboxylate
ethyl imidazole-1-carboxylate
ethyl 1H-imidazole-1-carboxylate
1H-Imidazole-1-carboxylic acid, ethyl ester
Etomidate Desphenylethyl 1-Carboxylate Impurity
Etomidate Impurity 10 (Ethyl 1H-imidazole-1-carboxylate)
[EINECS(EC#)]

242-883-7
[Molecular Formula]

C6H8N2O2
[MDL Number]

MFCD00014498
[MOL File]

19213-72-0.mol
[Molecular Weight]

140.14
Chemical PropertiesBack Directory
[Boiling point ]

100 °C(Press: 16 Torr)
[density ]

1.162 g/mL at 25 °C
[refractive index ]

n20/D1.472
[Fp ]

104℃
[storage temp. ]

2-8°C
[solubility ]

Chloroform (Sparingly), Methanol (Slightly)
[form ]

Oil
[pka]

3.73±0.10(Predicted)
[color ]

Clear Colourless to Pale Yellow
[Stability:]

Volatile
[InChI]

1S/C6H8N2O2/c1-2-10-6(9)8-4-3-7-5-8/h3-5H,2H2,1H3
[InChIKey]

YICRPEGTQDSFEX-UHFFFAOYSA-N
[SMILES]

CCOC(=O)n1ccnc1
Safety DataBack Directory
[WGK Germany ]

3
[HS Code ]

2933299090
[Storage Class]

10 - Combustible liquids
Spectrum DetailBack Directory
[Spectrum Detail]

1-CARBETHOXYIMIDAZOLE(19213-72-0)1HNMR
Hazard InformationBack Directory
[Synthesis]

Imidazole

288-32-4

Ethyl chloroformate

541-41-3

1-CARBETHOXYIMIDAZOLE

19213-72-0

General procedure for the synthesis of 1-ethoxycarbonylimidazole from imidazole and ethyl chloroformate: imidazole (3.75 g, 55.0 mmol) was added to the reactor followed by 50 ml of anhydrous ether. The reaction system was cooled to 0 °C and ethyl chloroformate (2.58 ml, 27.0 mmol) was added slowly and dropwise. After stirring the reaction at 0°C for 1 hour, the reaction system was moved to room temperature and continued for 4 hours. After completion of the reaction, the reaction solution was filtered. The filtrate was redissolved in 100 ml of ether and the organic phase was washed with water and subsequently dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to give the product 1-ethoxycarbonylimidazole (1.28 g, 17% yield) as a colorless liquid.

[References]

[1] Angewandte Chemie - International Edition, 2012, vol. 51, # 33, p. 8304 - 8308
[2] Organic Letters, 2010, vol. 12, # 20, p. 4572 - 4575
[3] Patent: CN105566347, 2016, A. Location in patent: Paragraph 0033; 0034; 0035
[4] Patent: CN105503932, 2016, A. Location in patent: Paragraph 0045; 0046; 0047
[5] Justus Liebigs Annalen der Chemie, 1957, vol. 609, p. 75,82
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