Oxalyl chloride

Oxalyl chloride Basic information
Product Name:Oxalyl chloride
Synonyms:Oxalyl chloride solution 2.0 M in methylene chloride;Oxalic dichloride;oxalicdichloride;Oxaloyl chloride;OXALYL CHLORIDE;OXALYL DICHLORIDE;OXALIC ACID CHLORIDE;OXALIC ACID DICHLORIDE
CAS:79-37-8
MF:C2Cl2O2
MW:126.93
EINECS:201-200-2
Product Categories:Others;Oxidation;Organics;Chlorination;Halogenation;Synthetic Reagents;Synthetic Organic Chemistry;Agrochemicals;Pesticides intermediate;API;1;79-37-8;K00001
Mol File:79-37-8.mol
Oxalyl chloride Structure
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.)
Fp 176-178°C
storage temp. Store Cold
solubility Chloroform (Soluble), Ethyl Acetate
form Liquid
color APHA: 0-150
Odorpenetrating odor
Water Solubility reacts
Decomposition 176-178 ºC
Sensitive Moisture Sensitive
Merck 14,6914
BRN 1361988
Exposure limitsACGIH: TWA 50 ppm
OSHA: TWA 25 ppm; STEL 125 ppm
NIOSH: IDLH 2300 ppm
Stability:Stable. Incompatible with bases, alcohols, steel, oxidizing agents, alkali metals. Moisture sensitive. Reacts violently with water, liberating toxic gas.
InChIKeyCTSLXHKWHWQRSH-UHFFFAOYSA-N
CAS DataBase Reference79-37-8(CAS DataBase Reference)
NIST Chemistry ReferenceOxalyl chloride(79-37-8)
EPA Substance Registry SystemEthanedioyl 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
9-19-21
Hazard Note Toxic/Corrosive/Store Cold/Lacrymatory
TSCA Yes
HazardClass 8
PackingGroup II
HS Code 29171990
MSDS Information
ProviderLanguage
Ethanedioyl dichloride English
SigmaAldrich English
ACROS English
ALFA English
Oxalyl chloride Usage And Synthesis
Chemical Propertiescolourless liquid with a pungent odour
UsesOxalyl 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 MethodsOxalyl Chloride is produced by the reaction of anhydrous oxalic acid and phosphorus pentachloride.
PreparationOxalyl 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
ApplicationOxalyl 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.
ReactionsOxalyl Chloride vigorously reacts with water, alcohols, and amines, and is employed for the synthesis of agrochemicals, pharmaceuticals, and fine chemicals.
General DescriptionOxalyl chloride is a commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.
Health HazardOxalyl 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 HazardExtinguish 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 ReactivityProduct is sensitive to temperatures below -10° and above 40°C. It reacts vigorously with water and hydroxyl compounds.
Safety ProfilePoison. 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 DisposalCarefully mix acidic compound with dry sodium bicarbonate. Dilute slowly with water and wash down the drain with copious amounts of water.
Methylene Chloride Dichlorodifluoromethane GLUTARYL DICHLORIDE Titanocene dichloride Calcium chloride N-Acetylsulfanilyl chloride Acryloyl chloride Terephthaloyl chloride Lauroyl chloride Choline chloride Methanesulfonyl chloride Pivaloyl chloride Sulfuryl chloride Oxalyl chloride Polyvinyl chloride Benzoyl chloride 4,4'-Dichlorodiphenyl sulfone 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile

Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.