methyl 2-chloro-2-oxoacetate

• ChemBase ID: 147163
• Molecular Formular: C3H3ClO3
• Molecular Mass: 122.50712
• Monoisotopic Mass: 121.97707164
• SMILES: COC(=O)C(=O)Cl
• Canonical SMILES: COC(=O)C(=O)Cl
• InChI: InChI=1S/C3H3ClO3/c1-7-3(6)2(4)5/h1H3
• InChIKey: ZXUQEPZWVQIOJE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-chloro-2-oxoacetate
• IUPAC Traditional name: methyl 2-chloro-2-oxoacetate
• Synonyms: Chloroglyoxylic acid methyl ester; Methyl (chloroformyl)formate; Methyl 2-chloro-2-oxoacetate; Methyl chloroglyoxalate; Methyl oxalyl chloride; Monomethyl oxalyl chloride; Methyl chlorooxoacetate; Monomethyl oxalyl chloride; Methyl chloroglyoxylate; Methyl oxalyl chloride; 甲基戊酰氯; 甲基草酰氯; 草酰氯甲酯; 甲基戊酰氯; 甲基草酰氯

Database IDs

• CAS Number: 5781-53-3
• EC Number: 227-307-4
• MDL Number: MFCD00000705
• Beilstein Number: 1071541
• PubChem SID: 162241354; 24886874; 24849133
• PubChem CID: 79846

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.64880544
• LogD (pH = 7.4): 0.64880544
• Log P: 0.64880544
• Molar Refractivity: 23.0662 cm^3
• Polarizability: 9.246633 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 115-118°C; 118-120 °C(lit.)
• Flash Point: 114.8 °F; 46 °C; 46°C(114°F)
• Density: 1.332; 1.332 g/mL at 25 °C(lit.)
• Refractive Index: 1.4190; n20/D 1.419; n20/D 1.419(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2920; UN2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 10-14-22-34; 10-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314; H301-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2

Product Information

• Purity: ≥97.0% (AT); 96%; 97%
• Grade: purum
• Linear Formula: ClCOCOOCH3

DETAILS

Sigma Aldrich - 151440

Packaging
5, 10, 50 g in glass bottle
Application
Reactant involved in:
• Regioselective synthesis of fused coumarins1
• Cyclization to form substituted isoxazoles2 and heterocycles3
• Intramolecular Wittig reactions4
• Silyl enol ether acylation5
• Iron-mediated cleavage of C-C bonds6

Sigma Aldrich - 75754

Application
Reactant involved in:
• Regioselective synthesis of fused coumarins1
• Cyclization to form substituted isoxazoles2 and heterocycles3
• Intramolecular Wittig reactions4
• Silyl enol ether acylation5
• Iron-mediated cleavage of C-C bonds6

REFERENCES

• A useful synthesis of isocyanates has been described involving oxidation of monoamides of oxalic acid (prepared from methyl oxalyl chloride and a primary amine) with peroxydisulfate catalyzed by Ag and Cu salts: J. Org. Chem., 60, 5430 (1995):
  
• For other examples of reactions of monoesters of oxalyl chloride, see Ethyl oxalyl chloride, A14653.