Oxalyl chloride

Chemical properties

colourless liquid with a pungent odour

The Uses of Oxalyl chloride

Oxalyl Chloride is used in the preparation of cardiolipin analogs which induce peroxidase activity by Cytochrome C. It is also used in the preparation of fluorescent indicators for cytosolic calcium.

The Uses of Oxalyl chloride

To a suspension of the SM (0.3 g, 2.38 mmol) in DCM (10 mL) was added (COCl)2 (0.3 mL, 3.6 mmol) dropwise at 0 C. The resulting mixture was stirred at RT for 1 h then heated to 70 C for 2 h. After cooling to RT the excess (COCl)2 and solvent were removed in vacuo (at <40 C) to provide the product as a gum which was taken to the next step without further purification.

Production Methods

Oxalyl Chloride is produced by the reaction of anhydrous oxalic acid and phosphorus pentachloride.

Preparation

Oxalyl chloride was first prepared in 1892 by the French chemist Adrien Fauconnier, who reacted diethyl oxalate with phosphorus pentachloride. Oxalyl chloride is also produced commercially from ethylene carbonate. Photochlorination gives the tetrachloride, which is subsequently degraded:
C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HCl
C2Cl4O2CO → C2O2Cl2 + COCl2

What are the applications of Application

Oxalyl chloride is used in organic synthesis. It may be used in the following processes:
Unncatalyzed reaction of silyl ketene acetals with oxalyl chloride yeilds symmetrical pulvinic acids.
Catalytic syntheses of N-heterocyclic ynones and ynediones by in situ activation of carboxylic acids with oxalyl chloride.
Oxalyl chloride was reportedly used in the first synthesis of dioxane tetraketone.
Preparation of Mosher′s acid chloride by reacting with Mosher′s acid in the presence of DMF.
Activation of dimethyl sulfoxide for use in the oxidation of long-chain alcohols to carbonyls.
Activation of α-keto carboxylic acids and N-heterocyclic carboxylic acids for alkynylation to form ynediones and N-heterocyclic ynones, respectively.

Reactions

Oxalyl Chloride vigorously reacts with water, alcohols, and amines, and is employed for the synthesis of agrochemicals, pharmaceuticals, and fine chemicals.

General Description

Oxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.

Health Hazard

Oxalyl chloride is a corrosive respiratory irritant and lachrymator. The vapors will attack the skin, eyes and especially the mucous membranes of the nose and throat and respiratory system. This material should be used only in a well ventilated area.

Fire Hazard

Extinguish with dry powder or carbon dioxide. Do not use water. Oxalyl chloride decomposes upon contact with water to produce toxic and corrosive fumes. When heated to decomposition, product emits toxic fumes.

Chemical Reactivity

Product is sensitive to temperatures below -10° and above 40°C. It reacts vigorously with water and hydroxyl compounds.

Safety Profile

Poison. Violently decomposed by water and alcohol. Severe irritant to skin, eyes, respiratory tract. Explodeson contact with dimethyl sulfoxide. Forms shock-sensitive explosive mixtures with potassium or with K-Na alloy. Will react with water or steam to

Waste Disposal

Carefully mix acidic compound with dry sodium bicarbonate. Dilute slowly with water and wash down the drain with copious amounts of water.