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748838

Sigma-Aldrich

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
MDL number:
MFCD21608484
UNSPSC Code:
12352005
PubChem Substance ID:
329765937
NACRES:
NA.22
Pricing and availability is not currently available.

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.[1]
  • Esters and amides via chemoselective esterification and amidation of carboxylic acids.[2]
  • Carbamoylimidazolium iodides and their derivatives such as ureas, thioureas, carbamates, and amides upon reacting with amines, alcohols, thiols, and carboxylic acids.[3]

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

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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Heller Group – Prof. Product Portal

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

Heller Group – Prof. Product Portal

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

Heller Group – Prof. Product Portal

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

Heller Group – Prof. Product Portal

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

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