| Template:Chembox header | Oxalyl chloride
|
| Oxalyl chloride
|
| Template:Chembox header | General
|
| Systematic name
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Oxalyl dichloride
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| Other names
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Ethanedioyl dichloride
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| Molecular formula
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C2O2Cl2
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| SMILES
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ClC(=O)C(=O)Cl
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| Molar mass
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126.93 g/mol
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| Appearance
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colorless liquid
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| CAS number
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[79-37-8]
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| Template:Chembox header | Properties
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| Density and phase
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1.4785 g/ml, liquid
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| Solubility in water
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Decomposes
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Solubility in diethyl ether,
benzene, chloroform
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Soluble
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| Melting point
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−16 °C
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| Boiling point
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63–64 °C (1.017 bar)
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| Viscosity
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? cP at ? °C
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| Template:Chembox header | Thermodynamic data
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Standard enthalpy
of
formation ΔfHoliquid
|
? kJ/mol
|
Standard molar entropy
Soliquid
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? J.K−1.mol−1
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| Template:Chembox header | Hazards
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| EU classification
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not listed
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| NFPA 704
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Template:Nfpa
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| RTECS number
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KI2950000
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| Template:Chembox header | Supplementary data page
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Structure and
properties
|
n, εr, etc.
|
Thermodynamic
data
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Phase behaviour
Solid, liquid, gas
|
| Spectral data
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UV, IR, NMR, MS
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| Regulatory data
|
Flash point,
RTECS number, etc.
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| Template:Chembox header | Related compounds
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| Related acyl chlorides
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Malonyl chloride
Succinyl chloride
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| Related compounds
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Oxalic acid
Oxalyl bromide
Diethyl oxalate
Oxamide
Oxalyl hydrazide
Cuprizon 1
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Template:Chembox header | Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox 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[1]. 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
See also
External links
