Cookies disclaimer

Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular

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

A18012 Oxalyl chloride, 98%

Número CAS
79-37-8
Nombre Alternativo

Tamaño Precio ($) Cantidad Disponibilidad
50g 33,60
100g 56,00
250g 106,00
1000g 367,00
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

Oxalyl chloride, 98%

MDL
MFCD00000704
EINECS
201-200-2

Propiedades químicas

Fórmula
C2Cl2O2
Peso molecular
126.93
Punto de fusión
-12°
Punto de ebullición
63-64°
Densidad
1.455
Índice de refracción
1.4290
Sensibilidad
Moisture Sensitive
Solubilidad
Oxalyl chloride Slightly miscible with water.Miscible with ether, benzene and chloroform.

Aplicaciones

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.

Notas

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

Referencias documentales

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.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H331-H314-H318

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

Indicaciones de precaución: P280-P303+P361+P353-P305+P351+P338-P310a-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/doctor Store in a dry place. Store in a closed container.

Otras referencias

Merck
14,6914
Beilstein
1361988
Clase de peligro
6.1
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2917.19
TSCA
Yes
RTECS
KI2950000

Recomendado

Visto recientemente

Productos químicos

Ciencias de la vida

Metales & materiales

Catalizadores

Análisis y material de laboratorio