O8801

Oxalyl chloride

reagent grade, 98%

• Synonym(s): Ethanedioyl dichloride
• Linear Formula: ClCOCOCl
• CAS Number: 79-37-8
• Molecular Weight: 126.93
• Beilstein/REAXYS Number: 1361988
• EC Number: 201-200-2
• MDL number: MFCD00000704
• UNSPSC Code: 12352106
• PubChem Substance ID: 57654494
• NACRES: NA.22

Properties

• grade: reagent grade
• Quality Level: 200
• vapor density: 4.4 (vs air)
• vapor pressure: 150 mmHg ( 20 °C)
• assay: 98%
• reaction suitability: reagent type: oxidant
• impurities: ≤1.0% phosgene content
• refractive index: n20/D 1.429 (lit.)
• bp: 62-65 °C (lit.)
• mp: −10-−8 °C (lit.)
• density: 1.5 g/mL at 20 °C (lit.)
• SMILES string: ClC(=O)C(Cl)=O
• InChI: 1S/C2Cl2O2/c3-1(5)2(4)6
• InChI key: CTSLXHKWHWQRSH-UHFFFAOYSA-N

Description

General description

Oxalyl chloride is a versatile reagent in various chemical transformations, such as chlorination, dichlorination, oxidation, reduction, dehydration, decarboxylation, formylation, and ring cleavage of epoxides.

Application

Oxalyl chloride can be used as an oxidizing agent:

• To synthesize β, β′-diketodithioethers from β, β′-dihydroxydithioethers via Swern oxidation.
• In the DMSO-catalyzed Swern oxidation of primary amides or aldoximes to nitriles in the presence of triethylamine as a base.
• In the Moffatt-Swern oxidation of aryl allylic alcohols to halogenated unsaturated ketones in the presence of triethylamine.

Reactant involved in:

• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids
• Chlorination and halogenation
• Three-component [3+2] cycloadditions
• Reactions with organostannanes
• Synthesis of cyclopentenones
• Carbonylations, used as a carbonyl synthon

Safety Information

• pictograms: GHS02,GHS06,GHS05
• signalword: Danger
• hcodes: H260,H301 + H331,H314
• pcodes: P223 - P231 + P232 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B - Water-react 1
• supp_hazards: EUH014,EUH029,EUH071
• Storage Class: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• wgk_germany: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Faceshields, Gloves, Goggles