ChemicalBook > CAS DataBase List > Oxalyl chloride

Oxalyl chloride

Product Name
Oxalyl chloride
CAS No.
79-37-8
Chemical Name
Oxalyl chloride
Synonyms
OXALYL DICHLORIDE;Oxalyl;OC;formyl chloride;Oxalic dichloride;COX;ETHANEDIOYL DICHLORIDE;Oxalic chloride;Oxaloyl chloride;Oxalyl chloride solution 2.0 M in methylene chloride
CBNumber
CB7854408
Molecular Formula
C2Cl2O2
Formula Weight
126.93
MOL File
79-37-8.mol
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Oxalyl chloride Property

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)
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Safety

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
9-19-21
Hazard Note 
Toxic/Corrosive/Store Cold/Lacrymatory
TSCA 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29171990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H260In contact with water releases flammable gases which may ignite spontaneously

H314Causes severe skin burns and eye damage

Precautionary statements

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
221015
Product name
Oxalyl chloride
Purity
ReagentPlus , ≥99%
Packaging
5g
Price
$27.8
Updated
2024/03/01
Sigma-Aldrich
Product number
221015
Product name
Oxalyl chloride
Purity
ReagentPlus , ≥99%
Packaging
10kg
Price
$2040
Updated
2024/03/01
TCI Chemical
Product number
O0082
Product name
Oxalyl Chloride
Purity
>98.0%(GC)(T)
Packaging
25g
Price
$28
Updated
2024/03/01
TCI Chemical
Product number
O0082
Product name
Oxalyl Chloride
Purity
>98.0%(GC)(T)
Packaging
100g
Price
$62
Updated
2024/03/01
Alfa Aesar
Product number
A18012
Product name
Oxalyl chloride, 98%
Packaging
50g
Price
$45.9
Updated
2023/06/20
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Oxalyl chloride Chemical Properties,Usage,Production

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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View Lastest Price from Oxalyl chloride manufacturers

Hebei Weibang Biotechnology Co., Ltd
Product
Oxalyl chloride 79-37-8
Price
US $1.00/PCS
Min. Order
1PCS
Purity
99%
Supply Ability
100mt
Release date
2024-11-04
Hebei Yanxi Chemical Co., Ltd.
Product
Oxalyl chloride 79-37-8
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-10-09
Hebei Chuanghai Biotechnology Co,.LTD
Product
Oxalyl chloride 79-37-8
Price
US $10.60/KG
Min. Order
1KG
Purity
98%
Supply Ability
5000kg
Release date
2024-08-21

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