Methyl Chloroglyoxylate TCI C1561

Chemical Identity

Other names: Chloroglyoxylic Acid Methyl Ester · Methyl Oxalyl Chloride
CAS No.: 5781-53-3
Formula: C3H3ClO3
Molecular weight: 122.50 g/mol
Purity: >98.0%(GC)(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: methyl 2-chloro-2-oxoacetate
SMILES: COC(=O)C(=O)Cl
InChIKey: ZXUQEPZWVQIOJE-UHFFFAOYSA-N
MDL: MDL00000705
PubChem: CID 79846

Rp 3.763.200,00

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TCI C1561 Methyl chloroglyoxylate, also known as methyl oxalyl chloride, is a highly reactive acyl chloride bearing an adjacent methyl ester group. It acylates amines, alcohols, and electron-rich aromatics readily, giving oxamates, oxalate esters, and ketoester products under mild conditions. A particularly popular modern application is the preparation of oxalyl esters that serve as acyl radical precursors in photoredox catalysis. AMI Scientific supplies this TCI reagent in 25 g and 250 g packs; it is corrosive and moisture sensitive, so dry solvents, dried glassware, and inert atmosphere handling are strongly recommended.

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Bayat et al. (2011). ChemInform Abstract: One‐Pot Synthesis of Functionalized 2H‐Chromene (=2H‐1‐Benzopyran) Derivatives via a Three‐Component Reaction Between a CH‐Acid, a Dialkyl Acetylenedicarboxylate, and Methyl Chloroglyoxylate or Benzyl Carbonochloridate Mediated by Triphenylphosphine.. ChemInform doi:10.1002/chin.201111154
Bayat et al. (2010). One‐Pot Synthesis of Functionalized 2H‐Chromene (=2H‐1‐Benzopyran) Derivatives via a Three‐Component Reaction between a CH‐Acid, a Dialkyl Acetylenedicarboxylate, and Methyl Chloroglyoxylate or Benzyl Carbonochloridate Mediated by Triphenylphosphine. Helvetica Chimica Acta doi:10.1002/hlca.201000030

References were compiled automatically from Crossref and every DOI was verified to exist. AMI Scientific is not affiliated with the authors or the publishers.