808598

CLAmP

• Synonym(s): N-Methoxy-N-methyl-1H-pyrrole-1-carboxamide, Heller-Sarpong Reagent
• Empirical Formula (Hill Notation): C₇H₁₀N₂O₂
• Molecular Weight: 154.17
• UNSPSC Code: 12352000
• PubChem Substance ID: 329769111

Properties

• 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.

Other Notes

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

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 230.0 °F
• Flash Point(C): 110 °C