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Sigma-Aldrich

Methyl 1H-imidazole-1-carboxylate

95%

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Synonym(s):
Heller-Sarpong Reagent, N-Carbomethoxyimidazole, MImC, Methylimidazolecarbamate, Sarpong reagent
Empirical Formula (Hill Notation):
C5H6N2O2
CAS Number:
61985-23-7
Molecular Weight:
126.11
MDL number:
MFCD00585680
UNSPSC Code:
12352005
PubChem Substance ID:
329765930
NACRES:
NA.22

Assay

95%

form

solid

mp

38-44 °C

storage temp.

−20°C

SMILES string

COC(=O)n1ccnc1

InChI

1S/C5H6N2O2/c1-9-5(8)7-3-2-6-4-7/h2-4H,1H3

InChI key

JQCPMLVMNQVRCC-UHFFFAOYSA-N

General description

Methyl 1H-imidazole-1-carboxylate is a reagent developed by Heller and Sarpong for the amidation and esterification of carboxylic acids chemoselectively.

Application

Methyl 1H-imidazole-1-carboxylate can be used to prepare fluorous β-keto esters, precursors used for the synthesis of fluorinated L-carbidopa derivatives.

WGK

WGK 3

Flash Point(F)

194.0 °F

Flash Point(C)

90 °C

Certificates of Analysis (COA)

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Fluorous l-Carbidopa Precursors: Highly Enantioselective Synthesis and Computational Prediction of Bioactivity
Granados A, et al.
The Journal of Organic Chemistry, 83(1), 303-313 (2018)
Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas
Heller ST and Sarpong R
Organic Letters, 12(20), 4572-4575 (2010)

Related Content

Heller Group – Professor Product Portal

Professor Heller and coworkers are engaged in the development of mild and chemoselective acylation reactions using carbonylazole-derived reagents. To that end, they have developed a suite of carbonylimidazole derivatives for facile and chemoselective esterification (MImC, etc.) and amidation (WImC) of carboxylic acids, in collaboration with Professor Richmond Sarpong.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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