Substance
ID:719068
Names and Identifiers
IUPAC name
oxalic dichloride
IUPAC Traditional name
oxalyl chloride
Synonyms
草酰氯Oxalyl chloride
Registration numbers
MDL Number
EC Number
Beilstein Number
CAS Number
Merck Index
Properties
Physical Property
Melting Point
-12°C
Density
1.455
Refractive Index
1.4290
Boiling Point
63-64°C
Safety Information
GHS Pictograms
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
Risk Statements
14-22-23-29-34
Safety Statements
4-7/8-9-20-23-26-30-36/37/39-45-60
Storage Warning
Moisture Sensitive
European Hazard Symbols
Toxic (T)RTECS
KI2950000
Packing Group
II
TSCA Listed
是
UN Number
UN2927
Hazard Class
6.1
GHS Hazard statements
H331-H302-H314-H318
GHS Precautionary statements
P280-P303+P361+P353-P305+P351+P338-P310-P402+P404
Product Information
Purity
98%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• 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).
• 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.
• 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.
• 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).