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.)
• functional group: acyl chloride
• 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.

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

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

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,GHS06,GHS05
• 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