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79-37-8 - Oxalyl chloride, 98% - A18012 - Alfa Aesar

A18012 Oxalyl chloride, 98%

CAS Number
79-37-8
Synonyms

Size Price ($) Quantity Availability
50g 33.60
100g 56.00
250g 106.00
1000g 367.00
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Oxalyl chloride, 98%

MDL
MFCD00000704
EINECS
201-200-2

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
Solubility
Oxalyl chloride Slightly miscible with water.Miscible with ether, benzene and chloroform.

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.

Notes

Moisture sensitive. Incompatible with bases, alcohols, water, amines and metals.

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).

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H331-H314-H318

Harmful if swallowed. Toxic if inhaled. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P201-P280-P304+P340-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves/protective clothing/eye protection/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,6914
Beilstein
1361988
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2917.19
TSCA
Yes
RTECS
KI2950000

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