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748730

Sigma-Aldrich

Methyl 1H-imidazole-1-carboxylate

95%

Synonym(s):

Heller-Sarpong Reagent, N-Carbomethoxyimidazole, MImC, Methylimidazolecarbamate, Sarpong reagent

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About This Item

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

194.0 °F

Flash Point(C)

90 °C

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Certificates of Analysis (COA)

Lot/Batch Number
SLBV0084
MKBJ4071V

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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)

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