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808598

Sigma-Aldrich

CLAmP

Synonym(s):

N-Methoxy-N-methyl-1H-pyrrole-1-carboxamide, Heller-Sarpong Reagent

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About This Item

Empirical Formula (Hill Notation):
C7H10N2O2
Molecular Weight:
154.17
UNSPSC Code:
12352000
PubChem Substance ID:
329769111

form

liquid

refractive index

n/D 1.510

density

1.126 g/mL

storage temp.

2-8°C

SMILES string

O=C(N(OC)C)N1C=CC=C1

InChI

1S/C7H10N2O2/c1-8(11-2)7(10)9-5-3-4-6-9/h3-6H,1-2H3

InChI key

NLSJGNBOCVXWHS-UHFFFAOYSA-N

Application

The CLAmP (Carbonyl Linchpin N, O-dimethylhydroxylamine pyrrole) reagent, reported by Sarpong and Heller, is a useful building block for the efficient synthesis of unsymmetrical ketones. CLAmP shows high versatility based on compatibility with both highly reactive, thermally unstable nucleophiles as well as less reactive stable nucleophiles. It reacts with Grignard reagents to form the corresponding Weinreb amides.[1]

Other Notes

One-pot Unsymmetrical Ketone Synthesis Employing a Pyrrole-Bearing Formal Carbonyl Dication Linchpin Reagent

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F

flash_point_c

110 °C

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One-pot Unsymmetrical Ketone Synthesis Employing a Pyrrole-Bearing Formal Carbonyl Dication Linchpin Reagent.
Heller ST, et al.
Angewandte Chemie (International Edition in English), 54(34), 9839-9843 (2015)

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

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