Thionyl chloride
Other names	sulfurous oxychloride sulfurous dichloride sulfinyl chloride sulfinyl dichloride dichlorosulfoxide
Identifiers
CAS number	[7719-09-7]
Properties
Molecular formula	SOCl2
Molar mass	118. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 97 g/mol
Appearance	clear to yellow odorous liquid
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 638 g ml−1, liquid
Melting point	−104. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C
Boiling point	76 °C
Solubility in water	Reactive
Viscosity	0. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 6 cP at ? °C
Structure
Molecular shape	pyramidal
Dipole moment	1. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. Molecular geometry or molecular structure is the three- Dimensional arrangement of the Atoms that constitute a Molecule. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 4 D
Hazards
MSDS	External MSDS
EU classification	Corrosive (C)
NFPA 704	0 4 2 W
R-phrases	R14, R20/22, R29, R35
S-phrases	(S1/2), S26, S36/37/39, S45
Flash point	non flammable
Related compounds
Related compounds	Sulfuryl chloride Selenium oxydichloride
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Thionyl chloride (or thionyl dichloride) is an inorganic compound with the formula SOCl₂. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws regulations and administrative provisions relating to the classification packaging and labelling Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air Sulfuryl chloride is SO2Cl2 a compound composed of Sulfur, Oxygen, and Chlorine. Selenium oxydichloride is the chemical compound SeOCl2 a close chemical relative of Thionyl chloride, SOCl2 In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Traditionally inorganic compounds are considered to be of mineral not biological origin A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 Oxygen (from the Greek roots ὀξύς (oxys (acid literally "sharp" from the taste of acids and -γενής (-genēs (producer literally begetteris the Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and SOCl₂ is a reactive chemical reagent used in chlorination reactions. A reagent or reactant is a substance or compound consumed during a Chemical reaction. A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called It is a colorless, distillable liquid at room temperature and pressure that decomposes above 140 °C. Liquid is one of the principal States of matter. A liquid is a Fluid that has the particles loose and can freely form a distinct surface at the boundaries of Temperature is a physical property of a system that underlies the common notions of hot and cold something that is hotter generally has the greater temperature Pressure (symbol 'p' is the force per unit Area applied to an object in a direction perpendicular to the surface SOCl₂ is sometimes confused with sulfuryl chloride, SO₂Cl₂, but the chemical properties of these S(IV) and S(VI) compounds differ significantly. Sulfuryl chloride is SO2Cl2 a compound composed of Sulfur, Oxygen, and Chlorine.

Contents 1 Properties and structure 2 Production 3 Applications 3.1 Organic chemistry 3.2 Inorganic chemistry 4 Safety 5 References 6 External links

Properties and structure

The molecule SOCl₂ is pyramidal, indicating the presence of a lone pair of electrons on the S(IV) center. In contrast, COCl₂ is planar. Phosgene is the Chemical compound with the formula COCl2 This colorless gas gained infamy as a Chemical weapon during World War I

SOCl₂ reacts with water to release hydrogen chloride and sulfur dioxide.

H₂O + O=SCl₂ → SO₂ + 2 HCl

Because of its high reactivity toward water, SOCl₂ would not be expected to occur in nature. Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as

Production

The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride:^[1]

SO₃ + SCl₂ → SOCl₂ + SO₂. Sulfur trioxide (also spelled sulphur trioxide) is the chemical compound with the formula SO3 Sulfur dichloride is the Chemical compound with the formula SCl2 Sulfur trioxide (also spelled sulphur trioxide) is the chemical compound with the formula SO3 Sulfur dichloride is the Chemical compound with the formula SCl2

Other methods include

SO₂ + PCl₅ → SOCl₂ + POCl₃;

SO₂ + Cl₂ + SCl₂ → 2 SOCl₂;

SO₃ + Cl₂ + 2 SCl₂ → 3 SOCl₂. Phosphorus pentachloride is the Chemical compound with the formula PCl5 Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Sulfur trioxide (also spelled sulphur trioxide) is the chemical compound with the formula SO3

The first of the above three reactions also affords phosphorus oxychloride (or phosphoryl chloride), which resembles thionyl chloride in many of its reactions. Submit to get this template --> Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula 3

Applications

Thionyl chloride is used inside lithium-thionyl chloride batteries as the positive active material with lithium as the negative active material. In electronics a battery is a combination of two or more Electrochemical cells which store chemical Energy which can be converted into electrical energy Lithium (ˈlɪθiəm is a Chemical element with the symbol Li and Atomic number 3 It is also used as a reagent for the production of other chemical compounds or materials. A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by Mass.

In military usage, thionyl chloride is used in the "di-di" method of producing G-series nerve agents. Nerve agents (also being referred to as nerve gases, though these chemicals are liquid at room temperature are a class of Phosphorus -containing organic chemicals

Organic chemistry

Thionyl chloride is widely used to convert carboxylic acids to acyl chlorides ^[2][3]

and alcohols ^[4][5] to the corresponding alkyl chlorides via an internal nucleophilic substitution. Carboxylic acids are Organic acids characterized by the presence of a Carboxyl group, which has the formula -C(=OOH usually written -COOH or -CO2H In Organic chemistry, an acyl chloride (or acid chloride) is an Organic compound which is a reactive derivative of a Carboxylic acid. In Chemistry, an alcohol is any Organic compound in which a Hydroxyl group ( - O[[hydrogen H]]) is bound to a Carbon SNi or Substitution Nucleophilic internal stands for a specific but not often encountered nucleophilic aliphatic substitution Reaction mechanism

It is preferred over other reagents such as phosphorus pentachloride because the products of the thionyl chloride reactions, HCl and SO₂ are gaseous, simplifying the purification of the product. Phosphorus pentachloride is the Chemical compound with the formula PCl5 Excess thionyl chloride may be removed by distillation. Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture An example of a reaction of thionyl chloride with an alcohol is in a synthesis of bicifadine ^[6]:

Sulfonic acids react with thionyl chloride to produce sulfonyl chlorides. Bicifadine is a Serotonin-norepinephrine reuptake inhibitor (SNRI developed by DOV Pharmaceutical. Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH ^[7][8] Likewise, thionyl chloride will transform sulfinic acids into sulfinyl chlorides^[9][10] and phosphonic acids into phosphoryl chlorides. Sulfinic acids are Oxoacids of Sulfur with the structure RSO(OH In Inorganic chemistry, phosphonic acid is a Phosphorus Oxoacid with a formula of H3PO3, more commonly known as Phosphorous Submit to get this template --> Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula 3

Thionyl chloride will react with primary formamides to form isocyanides. Formamide, also known as methanamide is an Amide derived from Formic acid. An isocyanide (also called an isonitrile) is an Organic compound with the Functional group R-N≡C ^[11]

Amides will react with thionyl chloride to form imidoyl chlorides. In Chemistry, an amide is one of three kinds of Compounds (sometimes called acid amide the organic Functional group characterized However, primary amides under heating with thionyl chloride will continue on to form nitriles. A nitrile is any Organic compound which has a - C ≡ N Functional group. ^[12]

Inorganic chemistry

Anhydrous metal chlorides may be obtained from hydrated metal chlorides by refluxing in freshly distilled thionyl chloride:^[13]

MCl_n·xH₂O + x SOCl₂ → MCl_n + x SO₂ + 2x HCl

Safety

SOCl₂ is toxic, corrosive, and lachrymatory. As a general term a substance is said to be anhydrous if it contains no Water. Toxicity is the degree to which a substance is able to damage an exposed organism A lachrymatory agent or lachrymator (from lacrima meaning "a tear " in Latin) (commonly referred to as tear gas) is a It is a skin and inhalation hazard, as well as being odorous. The skin is the outer covering of living tissue of an animal (or plant Inhalation (also known as respiration) is the movement of air from the external environment through the air ways and into the Alveoli. It can react explosively when exposed to high concentrations of nucleophiles such as phosphites. The phosphite ion (PO33− is a Polyatomic ion with a Phosphorus central atom

Industrial production of thionyl chloride is controlled under the Chemical Weapons Convention, where it is listed in schedule 3. The Chemical Weapons Convention ( CWC) is an Arms control agreement which outlaws the production stockpiling and use of chemical weapons Its full name is Schedule 3 substances, in the sense of the Chemical Weapons Convention, are chemicals which can either be used as toxic chemical weapons themselves or used in the manufacture

References

External links

• Usage of thionyl chloride in Organic Syntheses
• International Chemical Safety Card 1409
• NIOSH Pocket Guide to Chemical Hazards

Organic Syntheses is a Scientific journal that since 1921 has provided the Chemistry community with annual collections of detailed and checked procedures

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