Oxalyl chloride
ALDRICH/O8801 - reagent grade, 98%
Synonym: Ethanedioyl dichloride
CAS Number: 79-37-8
Empirical Formula (Hill Notation): C2Cl2O2
Molecular Weight: 126.93
EC Number: 201-200-2
MDL Number: MFCD00000704
Linear Formula: ClCOCOCl
Product Type: Chemical
| assay | 98% |
| bp | 62-65 °C (lit.) |
| density | 1.5 g/mL at 20 °C (lit.) |
| grade | reagent grade |
| impurities | ≤1.0% phosgene content |
| InChI | 1S/C2Cl2O2/c3-1(5)2(4)6 |
| InChI key | CTSLXHKWHWQRSH-UHFFFAOYSA |
| mp | −10-−8 °C (lit.) |
| Quality Level | 200  |
| reaction suitability | reagent type: oxidant |
| refractive index | n |
| SMILES string | ClC(=O)C(Cl)=O |
| vapor density | 4.4 (vs air) |
| vapor pressure | 150 mmHg ( 20 °C) |
| 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. |
| Application: | 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 |
| 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. |
| Symbol |    GHS02,GHS05,GHS06 |
| Signal word | Danger |
| Hazard statements | H260 - H314 - H331 - H335 |
| Precautionary statements | P223 - P231 + P232 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 |
| Hazard Codes | T |
| Risk Statements | 14-23-29-34-37 |
| Safety Statements | 26-36/37/39-45 |
| RIDADR | UN 2922 6.1(8) / PGI |
| WGK Germany | WGK 2 |
| Supplemental Hazard Statements | EUH014 - EUH029 |
| Purity | 98% |
| bp | 62-65 °C (lit.) |
| mp | −10-−8 °C (lit.) |
| Density | 1.5 g/mL at 20 °C (lit.) |
| Refractive Index | n |
| UNSPSC | 12352106 |