Names | |
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IUPAC name Sulfuryl chloride | |
Other names Sulfonyl chloride Sulfuric chloride Sulfur dichloride dioxide | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.029.314 |
EC Number |
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2256 | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 1834 |
CompTox Dashboard (EPA) | |
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Properties | |
SO2Cl2 | |
Molar mass | 134.9698 g mol−1 |
Appearance | Colorless liquid with a pungent odor. Yellows upon standing. |
Density | 1.67 g cm−3 (20 °C) |
Melting point | −54.1 °C (−65.4 °F; 219.1 K) |
Boiling point | 69.4 °C (156.9 °F; 342.5 K) |
hydrolyzes | |
Solubility | miscible with benzene, toluene, chloroform, CCl4, glacial acetic acid |
Refractive index (nD) | 1.4437 (20 °C) [1] |
Hazards | |
GHS labelling: | |
Danger | |
H314, H335 | |
P260, P261, P264, P271, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | Not flammable |
Related compounds | |
Related sulfuryl halides | Sulfuryl fluoride |
Related compounds | Thionyl chloride Chlorosulfonic acid Sulfuric acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Sulfuryl chloride is an inorganic compound with the formula SO2Cl2. At room temperature, it is a colorless liquid with a pungent odor. Sulfuryl chloride is not found in nature, as can be inferred from its rapid hydrolysis.
Sulfuryl chloride is commonly confused with thionyl chloride, SOCl2. 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. An alternative IUPAC name is sulfuryl dichloride.
Sulfur is tetrahedral in SO2Cl2 and the oxidation state of the sulfur atom is +6, as in sulfuric acid.
SO2Cl2 is prepared by the reaction of sulfur dioxide and chlorine in the presence of a catalyst, such as activated carbon. [2]
The product can be purified by fractional distillation.
Sulfuryl chloride was first prepared in 1838 by the French chemist Henri Victor Regnault. [3]
Older routes include oxidation of thionyl chloride:
Sulfuryl chloride reacts with water, releasing hydrogen chloride gas and sulfuric acid:
For sulfuryl chloride, this happens at room temperature, but the related sulfuryl fluoride does not hydrolyse at temperatures up to 150 °C.
SO2Cl2 will also decompose when heated to or above 100 °C, about 30 °C above its boiling point.
Upon standing, SO2Cl2 decomposes to sulfur dioxide and chlorine, which gives the older samples a slightly yellowish color. [2]
SO2Cl2 can be used as a source of chlorine in alkane chlorination, initiated by chemicals (usually a peroxide) or light: [4]
Sulfuryl chloride is used as a source of Cl2. Because it is a pourable liquid, it is considered more convenient than Cl2 to dispense.
Sulfuryl chloride is used in the conversion of C−H to C−Cl adjacent to activating substituents such as carbonyls and sulfoxides: [5] [6]
It also chlorinates alkanes, alkenes, alkynes, aromatics, ethers (such as tetrahydrofuran) and epoxides. Such reactions occur under free radical conditions using an initiator such as AIBN. It convert thiols or disulfides into the corresponding sulfenyl chlorides: [7]
Occassionally, sulfinyl chlorides result from such reactions. [8] SO2Cl2 can also convert alcohols to alkyl chlorides. In industry, sulfuryl chloride is most used in producing pesticides. Phosphorus pentachloride is prepared by the reaction of white phosphorus with sulfuryl chloride.
Sulfuryl chloride can also be used to treat wool to prevent shrinking.
Sulfuryl chloride is toxic, corrosive, and acts as a lachrymator. It releases hydrogen chloride upon contact with water, as well as donor solvents such as dimethyl sulfoxide and dimethylformamide.
In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.
Manganese(II) chloride is the dichloride salt of manganese, MnCl2. This inorganic chemical exists in the anhydrous form, as well as the dihydrate (MnCl2·2H2O) and tetrahydrate (MnCl2·4H2O), with the tetrahydrate being the most common form. Like many Mn(II) species, these salts are pink, with the paleness of the color being characteristic of transition metal complexes with high spin d5 configurations.
Iron(II) chloride, also known as ferrous chloride, is the chemical compound of formula FeCl2. It is a paramagnetic solid with a high melting point. The compound is white, but typical samples are often off-white. FeCl2 crystallizes from water as the greenish tetrahydrate, which is the form that is most commonly encountered in commerce and the laboratory. There is also a dihydrate. The compound is highly soluble in water, giving pale green solutions.
Acetyl chloride is an acyl chloride derived from acetic acid. It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl.
Thionyl chloride is an inorganic compound with the chemical formula SOCl2. 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 per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons.
Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.
Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides/oxychlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.
Sulfur compounds are chemical compounds formed the element sulfur (S). Common oxidation states of sulfur range from −2 to +6. Sulfur forms stable compounds with all elements except the noble gases.
Tellurium tetrachloride is the inorganic compound with the empirical formula TeCl4. The compound is volatile, subliming at 200 °C at 0.1 mmHg. Molten TeCl4 is ionic, dissociating into TeCl3+ and Te2Cl102−.
Sulfur tetrafluoride is a chemical compound with the formula SF4. It is a colorless corrosive gas that releases dangerous hydrogen fluoride gas upon exposure to water or moisture. Sulfur tetrafluoride is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries.
Arsenic trichloride is an inorganic compound with the formula AsCl3, also known as arsenous chloride or butter of arsenic. This poisonous oil is colourless, although impure samples may appear yellow. It is an intermediate in the manufacture of organoarsenic compounds.
Thionyl bromide is the chemical compound SOBr2. It is less stable and less widely used than its chloride analogue, thionyl chloride, but engages in similar reactions.
In inorganic chemistry, sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula RSO2X, where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series.
Nitrosyl chloride is the chemical compound with the formula NOCl. It is a yellow gas that is commonly encountered as a component of aqua regia, a mixture of 3 parts concentrated hydrochloric acid and 1 part of concentrated nitric acid. It is a strong electrophile and oxidizing agent. It is sometimes called Tilden's reagent, after William A. Tilden, who was the first to produce it as a pure compound.
Sulfuryl chloride fluoride is a chemical compound with the formula SO2ClF. It is a colorless, easily condensed gas. It is a tetrahedral molecule.
Thiophosphoryl chloride is an inorganic compound with the chemical formula PSCl3. It is a colorless pungent smelling liquid that fumes in air. It is synthesized from phosphorus chloride and used to thiophosphorylate organic compounds, such as to produce insecticides.
In organosulfur chemistry, a sulfenyl chloride is a functional group with the connectivity R−S−Cl, where R is alkyl or aryl. Sulfenyl chlorides are reactive compounds that behave as sources of RS+. They are used in the formation of RS−N and RS−O bonds. According to IUPAC nomenclature they are named as alkyl thiohypochlorites, i.e. esters of thiohypochlorous acid.
Sulfur tetrachloride is an inorganic compound with chemical formula SCl4. It has only been obtained as an unstable pale yellow solid. The corresponding SF4 is a stable, useful reagent.
In chemistry, molecular oxohalides (oxyhalides) are a group of chemical compounds in which both oxygen and halogen atoms are attached to another chemical element A in a single molecule. They have the general formula AOmXn, where X is a halogen. Known oxohalides have fluorine (F), chlorine (Cl), bromine (Br), and/or iodine (I) in their molecules. The element A may be a main group element, a transition element, a rare earth element or an actinide. The term oxohalide, or oxyhalide, may also refer to minerals and other crystalline substances with the same overall chemical formula, but having an ionic structure.
Methylphosphonyl dichloride (DC) or dichloro is an organophosphorus compound. It has commercial application in oligonucleotide synthesis, but is most notable as being a precursor to several chemical weapons agents. It is a white crystalline solid that melts slightly above room temperature.