Sources
open directory project
Help build the largest human-edited directory on the web.
Submit a site - Become an editor
Wikipedia. Licensed under the GNU Free Documentation License.
Are you an expert in this subject? Join the discussion and share your knowledge at Wikipedia.org.
Oxalyl chloride
From Wikipedia, the free encyclopedia
| Oxalyl chloride | |
|---|---|
 |
|
| General | |
| Systematic name | Oxalyl dichloride |
| Other names | Ethanedioyl dichloride Oxalic acid chloride Oxalic acid dichloride Oxalyl dichloride Oxalic dichloride Oxaloyl chloride |
| Molecular formula | C2O2Cl2 |
| SMILES | ClC(=O)C(=O)Cl |
| Molar mass | 126.93 g/mol |
| Appearance | colorless liquid |
| CAS number | [79-37-8] |
| Properties | |
| Density and phase | 1.4785 g/mL, liquid |
| Solubility in water | Decomposes |
| Solubility in diethyl ether, benzene, chloroform |
Soluble |
| Melting point | −16 °C |
| Boiling point | 63–64 °C (1.017 bar) |
| Viscosity | ? cP at ? °C |
| Thermodynamic data | |
| Standard enthalpy of formation ΔfH |
? kJ/mol |
| Standard molar entropy S |
? J.K−1.mol−1 |
| Hazards | |
| EU classification | not listed |
| NFPA 704 |
0
3
1
|
| RTECS number | KI2950000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Regulatory data | Flash point, RTECS number, etc. |
| Related compounds | |
| Related acyl chlorides | Malonyl chloride Succinyl chloride |
| Related compounds | Oxalic acid Oxalyl bromide Diethyl oxalate Oxamide Oxalyl hydrazide Cuprizon 1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Oxalyl chloride is chemical compound with the formula (COCl)2. This colourless liquid, the diacid chloride of oxalic acid, is a useful reagent in organic synthesis.
Oxalyl chloride reacts with aromatic compounds in the presence of aluminum chloride to give the corresponding acid chloride in a process known as a Friedel-Crafts acylation.[1][2]The resulting acid chloride can be hydrolysed in water to form the corresponding carboxylic acid.
Reaction of oxalyl chloride with phenol gives phenyl oxalate ester, also known as Cyalume - the active ingredient in glow sticks.
Contents |
Oxalyl chloride reacts violently with water liberating HCl gas.
- ^ Neubert, M. E.; Fishel, D. L. Organic Syntheses, Coll. Vol. 7, p.420 (1990); Vol. 61, p.8 (1983). (Article
- ^ Sokol, P. E. "Mesitoic Acid" Organic Syntheses, Collected Volume 5, p.706 (1973).
 |
This article about an organic compound is a stub. You can help Wikipedia by expanding it. |