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Oxalyl chloride

Not to be confused with phosgene.
Oxalyl chloride
Oxalyl chloride
Oxalyl chloride
  Carbon, C
  Oxygen, O
  Chlorine, Cl
Names
Preferred IUPAC name
Oxalyl dichloride[1]
Systematic IUPAC name
Ethanedioyl dichloride[1]
Other names
  • Oxalic acid chloride
  • Oxalic acid dichloride (1:2)
  • Oxalic dichloride
  • Oxaloyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.092 Edit this at Wikidata
EC Number
  • 201-200-2
RTECS number
  • KI2950000
UNII
  • InChI=1S/C2Cl2O2/c3-1(5)2(4)6 ☒N
    Key: CTSLXHKWHWQRSH-UHFFFAOYSA-N ☒N
  • InChI=1/C2Cl2O2/c3-1(5)2(4)6
    Key: CTSLXHKWHWQRSH-UHFFFAOYAG
  • ClC(=O)C(=O)Cl
Properties
C2O2Cl2
Molar mass 126.92 g·mol−1
Appearance Colorless liquid
Odor Phosgene-like[2]
Density 1.4785 g/mL
Melting point −16 °C (3 °F; 257 K)
Boiling point 63 to 64 °C (145 to 147 °F; 336 to 337 K) at 1.017 bar
Reacts
1.429
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, corrosive, lachrymator[3]
GHS labelling:
GHS06: Toxic GHS05: Corrosive[3]
Danger[3]
H314, H331[3]
P261, P280, P305+P351+P338, P310[3]
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
1
2
W
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oxalyl chloride is an organic chemical compound with the formula Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis.[4]

  1. ^ a b Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 797. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ Oxalyl chloride: odor
  3. ^ a b c d e Oxalyl chloride MSDS
  4. ^ Salmon, R. (2001). "Oxalyl Chloride". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.ro015. ISBN 0471936235.

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اوکسالیل کولورید AZB Clorur d'oxalil Catalan Oxalylchlorid Czech Oxalylchlorid German Oksalila klorido EO اکسالیل کلرید FA Oksalyylikloridi Finnish Chlorure d'oxalyle French ऑक्जिलिल क्लोराइड HI Oxalil-klorid Hungarian

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