Phospholane

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Phospholane
C4H8PH.png
Names
Preferred IUPAC name
Phospholane [1]
Identifiers
3D model (JSmol)
605298
ChEBI
ChemSpider
ECHA InfoCard 100.020.383 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 222-420-5
323930
PubChem CID
UNII
  • InChI=1S/C4H9P/c1-2-4-5-3-1/h5H,1-4H2
    Key: GWLJTAJEHRYMCA-UHFFFAOYSA-N
  • C1CPCC1
Properties
C4H9P
Molar mass 88.090 g·mol−1
Appearancecolorless liquid
Boiling point 100–103 °C (212–217 °F; 373–376 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phospholane is the organophosphorus compound with the formula (CH2)4PH. This colorless liquid is the parent member of a family of five-membered, saturated rings containing phosphorus. Although phospholane itself is only of minor academic interest, the class of C- and P-substituted phospholanes are valued ligands in asymmetric hydrogenation and related areas of homogeneous catalysis. [2] Phospholane is prepared by reduction of 1-chlorophospholane, which in turn is obtained by the reaction of 1-phenylphospholane and phosphorus trichloride. [3]

DuPhos is one of several phospholane ligands. DuPhos ligands.svg
DuPhos is one of several phospholane ligands.

Related Research Articles

Phosphorus Chemical element, symbol P and atomic number 15

Phosphorus is a chemical element with the symbol P and atomic number 15. Elemental phosphorus exists in two major forms, white phosphorus and red phosphorus, but because it is highly reactive, phosphorus is never found as a free element on Earth. It has a concentration in the Earth's crust of about one gram per kilogram. In minerals, phosphorus generally occurs as phosphate.

Phosphine Chemical compound hydrogen phosphide

Phosphine is a colorless, flammable, highly toxic compound with the chemical formula PH3, classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane. With traces of P2H4 present, PH3 is spontaneously flammable in air (pyrophoric), burning with a luminous flame. Phosphine is a highly toxic respiratory poison, and is immediately dangerous to life or health at 50 ppm. Phosphine has a trigonal pyramidal structure.

Thionyl chloride Chemical compound

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 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 Chemical compound

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 Chemical compound

Phosphorus trichloride is a 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.

Phosphorus trifluoride (formula PF3), is a colorless and odorless gas. It is highly toxic and reacts slowly with water. Its main use is as a ligand in metal complexes. As a ligand, it parallels carbon monoxide in metal carbonyls, and indeed its toxicity is due to its binding with the iron in blood hemoglobin in a similar way to carbon monoxide.

Phosphorous acid (or phosphonic acid (singular)) is the compound described by the formula H3PO3. This acid is diprotic (readily ionizes two protons), not triprotic as might be suggested by this formula. Phosphorous acid is an intermediate in the preparation of other phosphorus compounds. Organic derivatives of phosphorous acid, compounds with the formula RPO3H2, are called phosphonic acids.

Phosphorus pentoxide Chemical compound

Phosphorus pentoxide is a chemical compound with molecular formula P4O10 (with its common name derived from its empirical formula, P2O5). This white crystalline solid is the anhydride of phosphoric acid. It is a powerful desiccant and dehydrating agent.

Phosphoryl chloride Chemical compound

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.

Phosphorus sulfides

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".

Phosphorus pentasulfide Chemical compound

Phosphorus pentasulfide is the inorganic compound with the formula P2S5 or dimer P4S10. 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.

Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective insecticides, although some are extremely toxic to humans, including sarin and VX nerve agents.

Molecular solid Solid consisting of discrete molecules

A molecular solid is a solid consisting of discrete molecules. The cohesive forces that bind the molecules together are van der Waals forces, dipole-dipole interactions, quadrupole interactions, π-π interactions, hydrogen bonding, halogen bonding, London dispersion forces, and in some molecular solids, coulombic interactions. Van der Waals, dipole interactions, quadrupole interactions, π-π interactions, hydrogen bonding, and halogen bonding are typically much weaker than the forces holding together other solids: metallic, ionic, and network solids. Intermolecular interactions, typically do not involve delocalized electrons, unlike metallic and certain covalent bonds. Exceptions are charge-transfer complexes such as the tetrathiafulvane-tetracyanoquinodimethane (TTF-TCNQ), a radical ion salt. These differences in the strength of force and electronic characteristics from other types of solids give rise to the unique mechanical, electronic, and thermal properties of molecular solids.

Trimethylolpropane phosphite Chemical compound

Trimethylolpropane phosphite, C2H5C(CH2O)3P, is a phosphite ester used as a ligand in organometallic chemistry. Trimethylolpropane phosphite is sometimes abbreviated to EtCage. It is a white solid that is soluble in organic solvents. It is also highly toxic.

Allotropes of phosphorus Solid forms of the element phosphorus

Elemental phosphorus can exist in several allotropes, the most common of which are white and red solids. Solid violet and black allotropes are also known. Gaseous phosphorus exists as diphosphorus and atomic phosphorus.

Thiophosphates are chemical compounds and anions with the general chemical formula PS
4−x
O3−
x
and related derivatives where organic groups are attached to one or more O or S. Thiophosphates feature tetrahedral phosphorus(V) centers.

DuPhos

DuPhos is a class of organophosphorus compound that are used ligands for asymmetric synthesis. The name DuPhos is derived from (1) the chemical company that sponsored the research leading to this ligand's invention, DuPont and (2) the compound is a diphosphine ligand type. Specifically it is classified as a C2-symmetric ligand, consisting of two phospholanes rings affixed to a benzene ring.

Triphosphorus pentanitride Chemical compound

Triphosphorus pentanitride is an inorganic compound with the chemical formula P3N5. Containing only phosphorus and nitrogen, this material is classified as a binary nitride. While it has been investigated for various applications this has not led to any significant industrial uses. It is a white solid, although samples often appear colored owing to impurities.

Methylfluorophosphonylcholine Chemical compound

Methylfluorophosphonylcholine (MFPCh) is an extremely toxic chemical compound related to the G-series nerve agents. It is an extremely potent acetylcholinesterase inhibitor which is around 100 times more potent than sarin at inhibiting acetylcholinesterase in vitro, and around 10 times more potent in vivo, depending on route of administration and animal species tested. MFPCh is resistant to oxime reactivators, meaning the acetylcholinesterase inhibited by MFPCh can't be reactivated by oxime reactivators. MFPCh also acts directly on the acetylcholine receptors. However, despite its high toxicity, methylfluorophosphonylcholine is a relatively unstable compound and degrades rapidly in storage, so it was not deemed suitable to be weaponised for military use.

Phosphorus monoxide Chemical compound

Phosphorus monoxide is an unstable radical inorganic compound with molecular formula PO.

References

  1. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 392, 599. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. Clark, Thomas; Landis, Clark (2004). "Recent developments in chiral phospholane chemistry". Tetrahedron: Asymmetry. 15: 2123–2137. doi:10.1016/j.tetasy.2004.06.025.
  3. K. Sommer (1970). "Zur Spaltung tertiärer Phosphine. II". Zeitschrift für Anorganische und Allgemeine Chemie. 379: 56–62. doi:10.1002/zaac.19703790110.