Malonyl chloride

Malonyl chloride is the organic compound with the formula CH2(COCl)2. It is the acyl chloride derivative of malonic acid and the simplest three-carbon diacid chloride. 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.[1]

Malonyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.249
EC Number
  • 216-772-9
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 pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

Malonyl chloride can be synthesized from malonic acid in thionyl chloride.[2] 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.

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References
  1. Thomas Ziegler (2001). "Malonyl Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm016.
  2. Chittaranjan Raha (1953). "Di-tert-Butyl Malonate". Organic Syntheses. 33: 20. doi:10.15227/orgsyn.034.0026.
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