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[3]
GHS labelling:
Pictograms
[3]
Signal word
Danger[3]
Hazard statements
H314, H331[3]
Precautionary statements
P261, P280, P305+P351+P338, P310[3]
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).
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Infobox references
Chemical compound
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]
^ abNomenclature 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
^ abcdeOxalyl 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.
Oxalylchloride is an organic chemical compound with the formula Cl−C(=O)−C(=O)−Cl. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic...
the liberated chloride, forming the acid anhydride and releasing regenerated molecule of DMF. Relative to thionyl chloride, oxalylchloride is more expensive...
(m.p. 52.5 to 53.5 °C, 126.5 to 128.3 °F). It forms an acid chloride called oxalylchloride. Transition metal oxalate complexes are numerous, e.g. the...
alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalylchloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine...
thionyl chloride could be used to make acid anhydrides and acyl chlorides from carboxylic acids and to make alkyl chlorides from alcohols. Oxalylchloride Phosphorus...
chlorides, it can be generated from the parent acid and standard chlorinating agents such as phosphorus pentachloride, thionyl chloride, and oxalyl chloride...
chlorinating agents including oxalylchloride and thionyl chloride. This compound undergoes the reactions common for acid chlorides. For example, it reacts...
vinylene carbonate, which is used in polymers and in organic synthesis. Oxalylchloride is produced commercially from ethylene carbonate. Photochlorination...
activator for the Pummerer rearrangement. It can be used in place of oxalylchloride in the Swern oxidation, allowing temperatures up to −30 °C. With sodium...
receptor ligand.: Cyanuric chloride can also be used as an alternative to oxalylchloride in the Swern oxidation. Thiazyl chloride trimer – structural analogue...
decomposition of certain oxalates and certain chemoluminescent reactions of oxalylchloride. 1,2-dioxetanedione α-acetolactone Paolo Strazzolini; Alberto Gambi;...
Paolo Strazzolini and others synthesized this compound by reacting oxalylchloride (COCl)2 or the bromide (COBr)2 with a suspension of silver oxalate...
special precautions. A laboratory-safe variation masks the phosgene as oxalylchloride. Another route to isocyanates entails addition of isocyanic acid to...
colorless liquid is prepared by reaction of sodium fluoride with oxalylchloride. Oxalyl fluoride is being investigated for use in etching as a replacement...
Malaysia Airlines A330-300 suffered structural damage due to leaking oxalylchloride, a corrosive chemical substance that had been improperly labeled before...
thionyl chloride to the corresponding acyl chloride. The tendency towards DMCC formation depends on the chlorination reagent (thionyl chloride > oxalyl chloride...
ISBN 0911910123 Allen, C. F. H.; Byers Jr., J. R.; Humphlett, W. J. (1963). "Oleoyl chloride". Organic Syntheses; Collected Volumes, vol. 4, p. 739.; Rutenberg, M....
proceeds (in the variant with trifluoroacetic anhydride instead of oxalylchloride) with a yield of 73%. Under UV irradiation, ketones react with vinylene...
as a result of the deprotection was then converted to an acyl chloride by oxalylchloride and a catalytic amount of DMF. Finally, addition of sodium azide...
isatins. In this case primary or secondary arylamines are condensed with oxalylchloride to form a chlorooxalylanilide intermediate which can then cyclize in...
iodine and triethylamine, oxidation by silver oxide, oxidation by oxalylchloride, or even electrochemical oxidation on a platinum-titanium anode. Diazirines...
iodosyl-based oxidants have been developed, e.g. IBX. Swern oxidation uses oxalylchloride, dimethylsulfoxide, and an organic base, such as triethylamine. The...
4,6-trichlorophenol in a solution of dry toluene by reaction with oxalylchloride in the presence of a base such as triethylamine. This method produces...
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