Oxalyl chloride
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| 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 |
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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 |
[edit] Precautions
Oxalyl chloride reacts violently with water liberating HCl gas.
[edit] References
- ^ 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).
[edit] See also
[edit] External links
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