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Merck
CN

748838

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

≥95%

Synonym(s):

Heller-Sarpong reagent, WImC

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About This Item

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

Key Documents

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Product Name

N-Methoxy-N-methyl-1H-imidazole-1-carboxamide, ≥95%

InChI

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

SMILES string

CON(C)C(=O)n1ccnc1

InChI key

DOQREVDTYAHWSN-UHFFFAOYSA-N

assay

≥95%

form

liquid

refractive index

n20/D 1.508

density

1.204 g/mL at 25 °C

storage temp.

2-8°C

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBW4563
MKBJ4070V

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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)

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Professor Heller's research focuses on mild acylation reactions using carbonylimidazole-derived reagents.

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