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Thionyl chloride is an inorganic compound with the chemical formula SOCl 2.It is a moderately volatile, colourless liquid with an unpleasant acrid odour.Thionyl chloride is primarily used as a chlorinating reagent, with approximately 45,000 tonnes (50,000 short tons) per year being produced during the early 1990s, [5] but is occasionally also used as a solvent.
Thionyl chloride, SOCl 2, is a common reagent used in organic synthesis to convert carboxylic acids to acyl chlorides. In organic chemistry , the thionyl group is known as a sulfoxide group or sulfinyl group, and has the general structure RS(=O)R'.
A typical representative organic reaction displaying this mechanism is the chlorination of alcohols with thionyl chloride, or the decomposition of alkyl chloroformates, the main feature is retention of stereochemical configuration. Some examples for this reaction were reported by Edward S. Lewis and Charles E. Boozer in 1952. [2]
Thionyl fluoride is the inorganic compound with the formula S O F 2. This colourless gas is mainly of theoretical interest, but it is a product of the degradation of sulfur hexafluoride, an insulator in electrical equipment. The molecule adopts a distorted pyramidal structure, with C s symmetry. The S-O and S-F distances are 1.42 and 1.58 Å ...
All are easily hydrolyzed. Indeed, thionyl chloride can be used as a dehydration agent as the water molecules are converted into gaseous products, leaving behind the anhydrous solid chloride. [11] MgCl 2 ·6H 2 O + 6 SOCl 2 → MgCl 2 + 6 SO 2 + 12 HCl. Selenium and tellurium form similar compounds and also the oxo-bridged species F 5 AOAF 5 (A ...
This Lewis basicity is exploited in the Kinnear–Perren reaction to prepare alkylphosphonyl dichlorides (RP(O)Cl 2) and alkylphosphonate esters (RP(O)(OR') 2). Alkylation of phosphorus trichloride is effected in the presence of aluminium trichloride give the alkyltrichlorophosphonium salts, which are versatile intermediates: [16]
Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis. Sulfuryl chloride is commonly confused with thionyl chloride, SOCl 2. The properties of these two sulfur oxychlorides are quite different: sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions.
The Beckmann rearrangement is often catalyzed by acid; however, other reagents have been known to promote the rearrangement. These include tosyl chloride, thionyl chloride, phosphorus pentachloride, phosphorus pentoxide, triethylamine, sodium hydroxide, trimethylsilyl iodide among others. [3]