Oxalyl chloride
Encyclopedia : O : OX : OXA : Oxalyl chloride
| Oxalyl chloride | |
|---|---|
| |
| General | |
| Systematic name | Oxalyl dichloride |
| Other names | Ethanedioyl dichloride |
| 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 | |
| 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 hydrazideCuprizon 1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
Oxalyl chloride (also known as ethanedioyl chloride, oxalic acid chloride, oxalic acid dichloride, oxalyl dichloride, oxalic dichloride, and oxaloyl chloride) is the di-acid chloride of oxalic acid.
Oxalyl chloride will react with aromatic rings in the presence of aluminum chloride to form the corresponding aromatic acid chloride in a process known as a Friedel-Crafts acylation[#endnote_Neubert1983]. The product can be hydrolysed in water to form the corresponding carboxylic acid.
Could be reacted with phenol to form phenyl oxalate ester, also known as Cyalume - a key ingredient in glow sticks
Precautions
Oxalyl chloride reacts violently with water liberating HCl gas.References
- ↑ Neubert, M. E.; Fishel, D. L. Organic Syntheses, Coll. Vol. 7, p.420 (1990); Vol. 61, p.8 (1983). ([Article])
See also
External links
- For a full list of external links to MSDSs, spectroscopic data, commercial chemicals suppliers etc. for this compound, see [Chemical sources].
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