Oxalyl chloride

Molecule structure of Oxalyl chloride (CAS NO.79-37-8):

IUPAC Name: Oxalyl dichloride 
Molecular Weight: 126.9262 g/mol
Molecular Formula: C₂Cl₂O₂ 
Density: 1.615 g/cm³ 
Melting Point: −10-−8 °C(lit.)
Boiling Point: 63.5 °C at 760 mmHg 
Flash Point: 4.5 °C
Index of Refraction: 1.449
Molar Refractivity: 21.07 cm³
Molar Volume: 78.5 cm³
Surface Tension: 40.9 dyne/cm 
Enthalpy of Vaporization: 30.57 kJ/mol
Vapour Pressure: 171 mmHg at 25 °C 
Storage Temp.: store cold
Water Solubility: reacts
Sensitive: moisture sensitive
XLogP3-AA: 1.7
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 125.927535
MonoIsotopic Mass: 125.927535
Topological Polar Surface Area: 34.1
Heavy Atom Count: 6
Canonical SMILES: C(=O)(C(=O)Cl)Cl
InChI: InChI=1S/C2Cl2O2/c3-1(5)2(4)6
InChIKey: CTSLXHKWHWQRSH-UHFFFAOYSA-N
EINECS: 201-200-2
Product Categories: Organics; Chlorination; Halogenation; Synthetic Organic Chemistry; Others; Oxidation; Synthetic Reagents

 Oxalyl chloride (CAS NO.79-37-8) is a useful reagent in organic synthesis. It is mainly used in organic synthesis for the preparation of acid chlorides from the corresponding carboxylic acids. Oxalyl chloride tends to be a milder, more selective reagent. Oxalyl chloride reacts with aromatic compounds in the presence of aluminium chloride to give the corresponding acid chloride in a process known as a Friedel-Crafts acylation. The resulting acid chloride can be hydrolysed in water to form the corresponding carboxylic acid. The combination of DMSO, oxalyl chloride and triethylamine converts alcohols to the corresponding aldehydes and ketones via the process known as the Swern oxidation. Oxalyl chloride was reportedly used in the first syhthesis of dioxane tetraketone (C₄O₆), a novel oxide  of carbon.

 Oxalyl chloride can be prepared by treating oxalic acid with phosphorus pentachloride.

Hazard Codes: C, T
Risk Statements: 14-20-29-34-40-23/24/25-37-35 
R14 :Reacts violently with water. 
R20:Harmful by inhalation. 
R29:Contact with water liberates toxic gas. 
R34:Causes burns. 
R40:Limited evidence of a carcinogenic effect. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R37:Irritating to respiratory system 
R35:Causes severe burns.
Safety Statements: 26-36/37/39-43-45-8-24/25-23-27 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S43:In case of fire use ... (there follows the type of fire-fighting equipment to be used.) 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S8:Keep container dry. 
S24/25:Avoid contact with skin and eyes. 
S23:Do not breathe vapour. 
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2927 6.1/PG 2
WGK Germany: 2
RTECS: KI2950000
F: 9-19-21
Hazard Note: Toxic/Corrosive/Store Cold/Lacrymatory
HazardClass: 8
PackingGroup: II
HS Code: 29171990
Poison. Violently decomposed by water and alcohol. Severe irritant to skin, eyes, respiratory tract. Explodes on contact with dimethyl sulfoxide. Forms shock-sensitive explosive mixtures with potassium or with K-Na alloy. Will react with water or steam to produce toxic and corrosive fumes. When heated to decomposition it emits toxic fumes of Cl^?. See also OXALIC ACID.

 Oxalyl chloride (CAS NO.79-37-8) is also named as 4-02-00-01853 (Beilstein Handbook Reference) ; BRN 1361988 ; Ethanedioyl chloride ; Oxalic acid chloride ; Oxalic acid dichloride ; Oxalic dichloride ; Oxaloyl chloride ; Oxalyl dichloride ;
Ethanedioyl dichloride . Oxalyl chloride (CAS NO.79-37-8) is colourless liquid with a pungent odour.