Oxalyl chloride Chemical Properties

Melting point:

-10--8 °C (lit.)

Boiling point:

62-65 °C (lit.)

Density 

1.5 g/mL at 20 °C (lit.)

vapor density 

4.4 (vs air)

vapor pressure 

150 mm Hg ( 20 °C)

refractive index 

n20/D 1.429(lit.)

Flash point:

176-178°C

storage temp. 

Store Cold

solubility 

Chloroform (Soluble), Ethyl Acetate

form 

Liquid

color 

APHA: 0-150

Odor

penetrating odor

Water Solubility 

reacts

Decomposition 

176-178 ºC

Sensitive 

Moisture Sensitive

Merck 

14,6914

BRN 

1361988

Exposure limits

ACGIH: TWA 50 ppm
OSHA: TWA 25 ppm; STEL 125 ppm
NIOSH: IDLH 2300 ppm

Dielectric constant

3.4700000000000002

Dielectric constant

3.5（21℃）

Stability:

Stable. Incompatible with bases, alcohols, steel, oxidizing agents, alkali metals. Moisture sensitive. Reacts violently with water, liberating toxic gas.

InChIKey

CTSLXHKWHWQRSH-UHFFFAOYSA-N

CAS DataBase Reference

79-37-8(CAS DataBase Reference)

NIST Chemistry Reference

Oxalyl chloride(79-37-8)

EPA Substance Registry System

Ethanedioyl dichloride (79-37-8)

Safety Information

Hazard Codes 

C,T

Risk Statements 

14-20-29-34-40-23/24/25-37-35-23

Safety Statements 

26-36/37/39-43-45-8-24/25-23-27

RIDADR 

UN 2927 6.1/PG 2

WGK Germany 

2

RTECS 

KI2950000

F 

9-19-21

Hazard Note 

Toxic/Corrosive/Store Cold/Lacrymatory

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29171990

MSDS

• Language:English Provider:Ethanedioyl dichloride
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Oxalyl chloride Usage And Synthesis

Chemical Properties

colourless liquid with a pungent odour

Uses

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.

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

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

Oxalyl chloride 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.

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