Oxalyl chloride

Oxalyl chloride
	Carbon, C Oxygen, O Chlorine, Cl
Names
	Preferred IUPAC name Oxalyl dichloride
	Systematic IUPAC name Ethanedioyl dichloride
	Other names Oxalic acid chloride; Oxalic acid dichloride (1:2); Oxalic dichloride; Oxaloyl chloride;
Identifiers
CAS Number	79-37-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	59021 ;
ECHA InfoCard	100.001.092
EC Number	201-200-2;
PubChem CID	65578;
RTECS number	KI2950000;
UNII	R4Y96317DW ;
CompTox Dashboard (EPA)	DTXSID3058822 ;
	InChI InChI=1S/C2Cl2O2/c3-1(5)2(4)6 Key: CTSLXHKWHWQRSH-UHFFFAOYSA-N ; InChI=1/C2Cl2O2/c3-1(5)2(4)6 Key: CTSLXHKWHWQRSH-UHFFFAOYAG;
	SMILES ClC(=O)C(=O)Cl;
Properties
Chemical formula	C2O2Cl2
Molar mass	126.92 g·mol−1
Appearance	Colorless liquid
Odor	Phosgene-like
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
Solubility in water	Reacts
Refractive index (nD)	1.429
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic, corrosive, lachrymator
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314, H331
Precautionary statements	P261, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 1 2 W
Safety data sheet (SDS)	External MSDS
Related compounds
Related acyl chlorides	Malonyl chloride; Succinyl chloride; Phosgene;
Related compounds	Oxalic acid; Diethyl oxalate; Oxamide; Oxalyl hydrazide; Cuprizon 1;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

^ ^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.
^ Oxalyl chloride: odor
^ ^a ^b ^c ^d ^e Oxalyl chloride MSDS
^ Salmon, R. (2001). "Oxalyl Chloride". Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley & Sons. doi:10.1002/047084289X.ro015. ISBN 0471936235.