Cookies disclaimer

I agree Our site saves small pieces of text information (cookies) on your device in order to deliver better content and for statistical purposes. You can disable the usage of cookies by changing the settings of your browser. By browsing our website without changing the browser settings you grant us permission to store that information on your device.

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

A18012 Oxalyl chloride, 98%

CAS-Nummer
79-37-8
Synonyme

Größe Preis ($) Menge Verfügbarkeit
50g 33,60
100g 56,00
250g 106,00
1000g 367,00
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Oxalyl chloride, 98%

MDL
MFCD00000704
EINECS
201-200-2

Chemische Eigenschaften

Formel
C2Cl2O2
Molmasse
126.93
Schmelzpunkt
-12°
Siedepunkt
63-64°
Dichte
1.455
Brechungsindex
1.4290
Sensitivität
Moisture Sensitive
Löslichkeit
Oxalyl chloride Slightly miscible with water.Miscible with ether, benzene and chloroform.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H302-H331-H314-H318

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

Sicherheitshinweise: 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. Store in a dry place. Store in a closed container.

Weitere Referenzen

Merck
14,6914
Beilstein
1361988
Gefahrenklasse
6.1
Verpackungsgruppe
II
Harmonized Tariff Code
2917.19
TSCA
Yes
RTECS
KI2950000

Empfohlen

Kürzlich angesehen

Chemikalien

Life science

Metalle und Stoffe

Katalysatoren

Forschungs- und Laborbedarf