Oxalyl chloride

• Catalog No.: A18012
• CAS Number: 79-37-8
• M. F.: C2Cl2O2
• M. W.: 126.9262
• Purity: 98%

SYNONYMS

• Title: 草酰氯
• IUPAC name: oxalic dichloride
• IUPAC Traditional name: oxalyl chloride

DATABASE IDS

• Merck Index: 146914
• MDL Number: MFCD00000704
• Beilstein Number: 1361988
• CAS Number: 79-37-8
• EC Number: 201-200-2

PROPERTIES

• Purity: 98%
• Boiling Point: 63-64°C
• Density: 1.455
• Melting Point: -12°C
• Refractive Index: 1.4290
• GHS Hazard statements: H331-H302-H314-H318
• European Hazard Symbols: Toxic (T)
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310-P402+P404
• Risk Statements: 14-22-23-29-34
• RTECS: KI2950000
• Safety Statements: 4-7/8-9-20-23-26-30-36/37/39-45-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2927
• Packing Group: II

REFERENCES

• 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.
• 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.
• 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).
• 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).