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3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.013.858 |
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CompTox Dashboard (EPA) | |
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Properties | |
P2S5 (monomer) P4S10 (dimer) | |
Molar mass | 222.25 g/mol (monomer) 444.50 g/mol (dimer) |
Appearance | Yellow solid |
Odor | Rotten eggs [1] |
Density | 2.09 g/cm3 |
Melting point | 288 °C (550 °F; 561 K) |
Boiling point | 514 °C (957 °F; 787 K) |
Hydrolyses | |
Solubility in other solvents |
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Vapor pressure | 1 mmHg (300°C) [1] |
Structure | |
triclinic, aP28 | |
P1 (No. 2) | |
Td | |
Hazards | |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) | 389 mg/kg (oral, rat) [2] |
NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 1 mg/m3 [1] |
REL (Recommended) | TWA 1 mg/m3 ST 3 mg/m3 [1] |
IDLH (Immediate danger) | 250 mg/m3 [1] |
Related compounds | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Phosphorus pentasulfide is the inorganic compound with the formula P2S5 (monomer) or P 4 S 10 (dimer). This yellow solid is the one of two phosphorus sulfides of commercial value. Samples often appear greenish-gray due to impurities. It is soluble in carbon disulfide but reacts with many other solvents such as alcohols, DMSO, and DMF. [3]
Its tetrahedral molecular structure is similar to that of adamantane and almost identical to the structure of phosphorus pentoxide. [4]
Phosphorus pentasulfide is obtained by the reaction of liquid white phosphorus (P4) with sulfur above 300 °C. The first synthesis of P4S10 by Berzelius in 1843 [5] [6] was by this method. Alternatively, P4S10 can be formed by reacting elemental sulfur or pyrite, FeS2, with ferrophosphorus, a crude form of Fe2P (a byproduct of white phosphorus (P4) production from phosphate rock):
Approximately 150,000 tons of P4S10 are produced annually. The compound is mainly converted to other derivatives for use as lubrication additives such as zinc dithiophosphates. It is widely used in the production of sodium dithiophosphate for applications as a flotation agent in the concentration of molybdenite minerals. It is also used in the production of pesticides such as Parathion and Malathion. [7] It is also a component of some amorphous solid electrolytes (e.g. Li2S-P2S5) for some types of lithium batteries.
Phosphorus pentasulfide is a dual-use material, for the production of early insecticides such as Amiton and also for the manufacture of the related VX nerve agents.
Due to hydrolysis by atmospheric moisture, P4S10 evolves hydrogen sulfide H2S, thus P4S10 is associated with a rotten egg odour. Aside from H2S, hydrolysis of P4S10 eventually gives phosphoric acid:
Other mild nucleophiles react with P4S10, including alcohols and amines. Aromatic compounds such as anisole, ferrocene and 1-methoxynaphthalene react to form 1,3,2,4-dithiadiphosphetane 2,4-disulfides such as Lawesson's reagent.
P4S10 is used as a thionation reagent. Reactions of this type require refluxing solvents such as benzene, dioxane, or acetonitrile with P4S10 dissociating into P2S5. Some ketones, esters, and imides are converted to the corresponding thiocarbonyls. Amides give thioamides. With 1,4-diketones the reagent forms thiophenes. It is also used to deoxygenate sulfoxides. The use of P4S10 has been displaced by the aforementioned Lawesson's reagent. [8]
P2S5 reacts with pyridine to form the complex P2S5(pyridine)2. [9]
In organic chemistry, an ethyl group is an alkyl substituent with the formula −CH2CH3, derived from ethane. Ethyl is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated two-carbon moiety in a molecule, while the prefix "eth-" is used to indicate the presence of two carbon atoms in the molecule.
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.
Phosphorus pentachloride is the chemical compound with the formula PCl5. It is one of the most important phosphorus chlorides, others being PCl3 and POCl3. PCl5 finds use as a chlorinating reagent. It is a colourless, water-sensitive and moisture-sensitive solid, although commercial samples can be yellowish and contaminated with hydrogen chloride.
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic and reacts readily with water to release hydrogen chloride.
Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is widely used in the synthesis of organic and organometallic compounds. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.
A thioamide is a functional group with the general structure R–CS–NR′R″, where R, R′, and R″ are organic groups. They are analogous to amides but they exhibit greater multiple bond character along the C-N bond, resulting in a larger rotational barrier. One of the best-known thioamides is thioacetamide, which is used as a source of the sulfide ion and is a building block in heterocyclic chemistry.
Sodium dithiophosphate is the salt with the formula Na3PS2O2. It is usually supplied as the hydrated solid or as an aqueous solution together with other thiophosphates such as sodium monothiophosphate and sodium trithiophosphate. It is a colorless compound, but commercial samples can appear dark owing to the presence of impurities. It is used to facilitate the isolation of molybdenum from its ores.
Lawesson's reagent (LR) is a chemical compound used in organic synthesis as a thiation agent. Lawesson's reagent was first made popular by Sven-Olov Lawesson, who did not, however, invent it. Lawesson's reagent was first made in 1956 during a systematic study of the reactions of arenes with P4S10.
Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.
Phosphoryl chloride is a colourless liquid with the formula POCl3. It hydrolyses in moist air releasing phosphoric acid and fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate.
1,3,2,4-Dithiadiphosphetane 2,4-disulfides are a class of organophosphorus, four-membered ring compounds which contain a P2S2 ring, many of these compounds are able to act as sources of the dithiophosphine ylides. The most well known example of this class of compound is Lawesson's reagent.
Phosphorus sulfides comprise a family of inorganic compounds containing only phosphorus and sulfur. These compounds have the formula P4Sx with x ≤ 10. Two are of commercial significance, phosphorus pentasulfide (P4S10), which is made on a kiloton scale for the production of other organosulfur compounds, and phosphorus sesquisulfide (P4S3), used in the production of "strike anywhere matches".
The Barton–Kellogg reaction is a coupling reaction between a diazo compound and a thioketone, giving an alkene by way of an episulfide intermediate. The Barton–Kellogg reaction is also known as Barton–Kellogg olefination and Barton olefin synthesis.
Boron sulfide is the chemical compound with the formula B2S3. This polymeric material that has been of interest as a component of "high-tech" glasses and as a reagent for preparing organosulfur compounds. Like the sulfides of silicon and phosphorus, B2S3 reacts with water, including atmospheric moisture to release H2S. Thus, samples must be handled under anhydrous conditions.
The Paal–Knorr Synthesis in organic chemistry is a reaction that generates either furans, pyrroles, or thiophenes from 1,4-diketones. It is a synthetically valuable method for obtaining substituted furans and pyrroles, common structural components of many natural products. It was initially reported independently by German chemists Carl Paal and Ludwig Knorr in 1884 as a method for the preparation of furans, and has been adapted for pyrroles and thiophenes. Although the Paal–Knorr synthesis has seen widespread use, the mechanism wasn't fully understood until it was elucidated by V. Amarnath et al. in the 1990s.
Thiophosphoryl chloride is an inorganic compound with the 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.
Antimony pentasulfide is an inorganic compound of antimony and sulfur, also known as antimony red. It is a nonstoichiometric compound with a variable composition. Its structure is unknown. Commercial samples are usually contaminated with sulfur, which may be removed by washing with carbon disulfide in a Soxhlet extractor.
Triphenylborane, often abbreviated to BPh3 where Ph is the phenyl group C6H5-, is a chemical compound with the formula B(C6H5)3. It is a white crystalline solid and is both air and moisture sensitive, slowly forming benzene and triphenylboroxine. It is soluble in aromatic solvents.
The Abramov reaction is the related conversions of trialkyl to α-hydroxy phosphonates by the addition to carbonyl compounds. In terms of mechanism, the reaction involves attack of the nucleophilic phosphorus atom on the carbonyl carbon. It was named after the Russian chemist Vasilii Semenovich Abramov (1904–1968) in 1957.
Diethyl dithiophosphoric acid, sometimes mistakenly called diethyl dithiophosphate, is the organophosphorus compound with the formula (C2H5O)2PS2H. It is the processor for production of the organophosphate insecticide Terbufos. Although samples can appear dark, it is a colorless liquid.