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

A18012 Oxalyl chloride, 98%

Numéro CAS
79-37-8
Synonymes

Dimensions Prix ($) Quantité Disponibilité
50g 33,70
100g 55,21
250g 104,43
1000g 373,89
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Oxalyl chloride, 98%

MDL
MFCD00000704
EINECS
201-200-2

Propriétés chimiques

Formule
C2Cl2O2
Poids formulaire
126.93
Point de fusion
-12°
Point d'ébullition
63-64°
Densité
1.455
Indice de réfraction
1.4290
Sensibilité
Moisture Sensitive
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H331-H302-H314-H318

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

Mentions de prudence: P280-P303+P361+P353-P305+P351+P338-P310-P402+P404

Wear 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.

Autres références

Merck
14,6914
Beilstein
1361988
Classe de danger
6.1
Groupe d'emballage
II
Code tarifaire harmonisé
2917.19
TSCA
Yes
RTECS
KI2950000

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