221015

Oxalyl chloride

ReagentPlus^®, ≥99%

• Synonym(s): Ethanedioyl dichloride
• Linear Formula: ClCOCOCl
• CAS Number: 79-37-8
• Molecular Weight: 126.93
• Beilstein: 1361988
• EC Number: 201-200-2
• MDL number: MFCD00000704
• UNSPSC Code: 12352106
• PubChem Substance ID: 24853204
• NACRES: NA.22

Properties

• vapor density: 4.4 (vs air)
• Quality Level: 200
• vapor pressure: 150 mmHg ( 20 °C)
• product line: ReagentPlus^®
• Assay: ≥99%
• form: liquid
• reaction suitability: reagent type: oxidant
• impurities: <10 ppb Heavy metals
• color: APHA: 0-150
• 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 commonly used chlorinating reagent that can be prepared by the reaction of oxalic acid and phosphorus pentachloride.

Application

Oxalyl chloride may be used in the following processes:

• 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.

Suitable for the synthesis of acid chlorides used to produce liquid crystals.

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

Packaging

The 5g, 25g and 100g units sold in the US are packaged in ampules.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS02,GHS05,GHS06
• Signal Word: Danger
• Hazard Statements: H225 - H260 - H301 + H331 - H314
• Precautionary Statements: P210 - 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 - Flam. Liq. 2 - Skin Corr. 1B - Water-react 1
• Supplementary Hazards: EUH014 - EUH029 - EUH071
• Storage Class Code: 4.3 - Hazardous materials, which set free flammable gases upon contact with water
• WGK: WGK 1
• Flash Point(F): 51.8 °F - closed cup
• Flash Point(C): 11.0 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves