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808598 Sigma-Aldrich

CLAmP

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

  • Empirical Formula (Hill Notation) C7H10N2O2

  • Molecular Weight 154.17

  •  PubChem Substance ID 329769111

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Properties

Related Categories Alkyl Transfer, C-X Bond Formation (Non-Halogen), Chemical Synthesis, Heller-Sarpong Reagents, Protecting and Derivatizing Reagents,
Quality Level   100
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

Description

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.

Packaging

1 g in glass bottle

Other Notes

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

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
230.0 °F
Flash Point(C) 
110 °C

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Stephen Heller Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Stephen Heller Group - Professor Product Portal
Keywords: Acylations, Amidations, Catalysis, Esterifications

Peer-Reviewed Papers
15

References

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