Malonyl chloride

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Malonyl chloride
CH2(COCl)2.png
Names
Preferred IUPAC name
Propanedioyl dichloride[1]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.249 Edit this at Wikidata
EC Number
  • 216-772-9
UNII
  • InChI=1S/C3H2Cl2O2/c4-2(6)1-3(5)7/h1H2
    Key: SXYFKXOFMCIXQW-UHFFFAOYSA-N
  • C(C(=O)Cl)C(=O)Cl
Properties
C3H2Cl2O2
Molar mass 140.95 g·mol−1
Appearance colorless liquid
Boiling point 58 °C (136 °F; 331 K) 28 mm Hg
Hazards
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Malonyl chloride is the organic compound with the formula CH2(COCl)2. It is the acyl chloride derivative of malonic acid. It is a colorless liquid although samples are often deeply colored owing to impurities. The compound degrades at room temperature after a few days. It used as a reagent in organic synthesis.[2]

Synthesis and reactions[edit]

Malonyl chloride can be synthesized from malonic acid in thionyl chloride.[3] As a bifunctional compound, it is used in the preparation of a number of cyclic compounds by diacylation. Heating in the presence of non-nucleophilic base gives the ketene derivative O=C=C(H)COCl.

References[edit]

  1. ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 797. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. ^ Thomas Ziegler (2001). "Malonyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm016. ISBN 0471936235.
  3. ^ Chittaranjan Raha (1953). "Di-tert-Butyl Malonate". Organic Syntheses. 33: 20. doi:10.15227/orgsyn.034.0026.