[A18012] CAS 79-37-8 | Oxalyl chloride, 98%

CAS : 79-37-8
UN# : UN3130
MDL : MFCD00000704
Hazard Class : 4.3
EINECS : 201-200-2
Packing Group : I

Chemical Properties

Formula : C2Cl2O2
Formula weight : 126.93
Melting Point : -12°
Boiling Point : 63-64°
Density : 1.455
Refractive Index : 1.4290
Sensitivity : Moisture Sensitive. Store under Nitrogen. Ambient temperatures.
Form : Liquid
Solubility : Oxalyl chloride Slightly miscible with water.Miscible with ether, benzene and chloroform.

Literature References

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).

Applications

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.

Grade Specifications

GHS Hazard and Precautionary Statements

Hazard Statements : H331-H302-H314-H318Toxic if inhaled.Harmful if swallowed.Causes severe skin burns and eye damage.Causes serious eye damage.
Precautionary Statements : P280-P303+P361+P353-P305+P351+P338-P310-P402+P404Wear protective gloves/protective clothing/eye protection/face protection.IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower.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.Store in a dry place. Store in a closed container.Other References:Beilstein: 1361988Merck: 14,6914UN#: UN3130