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Oxalyl chloride is mainly used as a catalyst in the oxidation of alcohols to the corresponding aldehydes and ketones. It is actively used for the synthesis of acid chlorides from acids. In the Fridel-Crafts acylation reaction, it reacts with aromatic compounds to get the corresponding acyl choride using aluminum chloride as catalyst. Further, it is utilized to prepare dioxane tetrketone, an oxide of carbon.
Reactive acid chloride which can be used as a phosgene substitute in many reactions.
Caution! Carbon monoxide may be evolved.
Mild reagent for conversion of sensitive acids to acid chlorides; see, e.g.: Org. Synth. Coll., 8, 486 (1993); Org. Synth. Coll., 9, 516 (1998).
Has advantages over POCl3 in the Vilsmeier formylation reaction in that cleaner reactions often occur and a much lower mass of acidic by-product is formed. See N,N-Dimethylformamide, A13547 and (Chloromethylene)dimethylammonium chloride, B24172.
Friedel-Crafts reaction with arenes give carboxylic acids via the acid chlorides; see, e.g.: Org. Synth. Coll., 5, 706 (1973); 7, 420 (1990). For other phosgene equivalents, see Trichloromethyl chloroformate, A17444, and Triphosgene, A14932.
Widely used to activate Dimethyl sulfoxide, A13280, for selective oxidation of alcohols to aldehydes or ketones (Swern oxidation) at low temperatures under very mild conditions: J. Org. Chem., 43, 2480 (1978). The reactive species is thought to be chlorodimethylsulfonium chloride: J. Org. Chem., 44, 4148 (1979). For examples of Swern oxidations, see: Org. Synth. Coll., 7, 258 (1990); 8, 501 (1993); 9, 692 (1998); Org. Synth., 76, 110 (1998). See also Trifluoroacetic anhydride, A13614.
Reaction with Grignards in the presence of LiBr and CuBr provides a route to symmetrical ɑ-diones in good yield: Tetrahedron Lett., 36, 7305 (1995).
For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1172 (2007).
Ilangovan, A.; Anandhan, K.; Kaushik, M. P. Facile and selective deprotection of PMB ethers and esters using oxalyl chloride. Tetrahedron Lett. 2015, 56 (9), 1080-1084.
Hansen, S. V.; Ulven, T. Oxalyl Chloride as a Practical Carbon Monoxide Source for Carbonylation Reactions. Org. Lett. 2015, 17 (11), 2832-2835.
Hazard Statements: H260-H301-H314-H331
In contact with water releases flammable gases which may ignite spontaneously. Toxic if swallowed. Causes severe skin burns and eye damage. Toxic if inhaled.
Precautionary Statements: P223-P231+P232-P260-P264b-P270-P271-P280-P284-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P335+P334-P363-P370+P378q-P501c
Keep away from any possible contact with water, because of violent reaction and possible flash fire. Handle under inert gas. Protect from moisture. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. Wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant