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748838

Sigma-Aldrich

N-Methoxy-N-methyl-1H-imidazole-1-carboxamide

≥95%

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Synonym(s):
Heller-Sarpong reagent, WImC
Empirical Formula (Hill Notation):
C6H9N3O2
CAS Number:
862873-06-1
Molecular Weight:
155.15
MDL number:
MFCD21608484
UNSPSC Code:
12352005
PubChem Substance ID:
329765937
NACRES:
NA.22

Assay

≥95%

form

liquid

refractive index

n20/D 1.508

density

1.204 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CON(C)C(=O)n1ccnc1

InChI

1S/C6H9N3O2/c1-8(11-2)6(10)9-4-3-7-5-9/h3-5H,1-2H3

InChI key

DOQREVDTYAHWSN-UHFFFAOYSA-N

Application

N-Methoxy-N-methyl-1H-imidazole-1-carboxamide (or N-methoxy-N-methylcarbamoylimidazole) can be used as a reagent to prepare:
  • N-methoxy-N-methylcyanoformamide by reacting with trimethylsilyl cyanide.
  • Esters and amides via chemoselective esterification and amidation of carboxylic acids.
  • Carbamoylimidazolium iodides and their derivatives such as ureas, thioureas, carbamates, and amides upon reacting with amines, alcohols, thiols, and carboxylic acids.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Carbamoylimidazolium and thiocarbamoylimidazolium salts: novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides
Grzyb JA, et al.
Tetrahedron, 61(30), 7153-7175 (2005)
N-Methoxy-N-methylcyanoformamide, a Highly Reactive Reagent for the Formation of β-Keto Weinreb Amides and Unsymmetrical Ketones
Nugent J and Schwartz BD
Organic Letters, 18(15), 3834-3837 (2016)
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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