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Phosphonium iodide information


Phosphonium iodide
Space-filling model of the crystal structure of phosphonium iodide
Names
IUPAC name
Phosphanium iodide
Other names
Iodine phosphide
Identifiers
CAS Number
  • 12125-09-6
3D model (JSmol)
  • Interactive image
ChemSpider
  • 145802
ECHA InfoCard 100.031.978 Edit this at Wikidata
EC Number
  • 235-189-0
PubChem CID
  • 166618
UNII
  • 70782D13AF
CompTox Dashboard (EPA)
  • DTXSID30923738 Edit this at Wikidata
InChI
  • InChI=1S/HI.H3P/h1H;1H3
    Key: LSMAIBOZUPTNBR-UHFFFAOYSA-N
SMILES
  • [PH4+].[I-]
Properties
Chemical formula
PH
4
I
Molar mass 161.910 g/mol
Boiling point 62 °C (144 °F; 335 K) Sublimes[1]
Solubility in water
decomposes
Structure
Crystal structure
Tetragonal (P4/nmm)
Lattice constant
a = 6.34 Å, c = 4.62 Å
Lattice volume (V)
185.7 Å3
Formula units (Z)
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Phosphonium iodide is a chemical compound with the formula PH
4
I
. It is an example of a salt containing an unsubstituted phosphonium cation (PH+
4
). Phosphonium iodide is commonly used as storage for phosphine[2] and as a reagent for substituting phosphorus into organic molecules.[3]

  1. ^ Smith, Alexander.; Calvert, Robert Peyton. (July 1914). "The Dissociation Pressures of Ammonium- and Tetramethylammonium Halides and of Phosphonium Iodide and Phosphorus Pentachloride". Journal of the American Chemical Society. 36 (7): 1363–1382. doi:10.1021/ja02184a003. Retrieved 6 October 2020.
  2. ^ Morrow, B. A.; McFarlane, Richard A. (July 1986). "Trimethylgallium adsorbed on silica and its reaction with phosphine, arsine, and hydrogen chloride: an infrared and Raman study". The Journal of Physical Chemistry. 90 (14): 3192–3197. doi:10.1021/j100405a029. ISSN 0022-3654.
  3. ^ Mei, Yanbo (2020). Complexes, Heterocycles, and Depolymerizable Polymers. Made from Building Blocks with Low-coordinated Phosphorus (Thesis). ETH Zurich. p. 18. doi:10.3929/ethz-b-000431853. hdl:20.500.11850/431853. Retrieved 6 October 2020.

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Phosphonium iodide

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Phosphonium iodide is a chemical compound with the formula PH 4I. It is an example of a salt containing an unsubstituted phosphonium cation (PH+ 4). Phosphonium...

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Phosphonium

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take the color of the anions. The parent phosphonium is PH+ 4 as found in the iodide salt, phosphonium iodide. Salts of the parent PH+ 4 are rarely encountered...

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Cyclohexane

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Kohlenwasserstoffe durch Jodphosphonium" [On the reduction of aromatic compound by phosphonium iodide [H4IP]]. Annalen der Chemie und Pharmacie. 55: 266–281. Bei der Reduction...

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Diphosphorus tetraiodide

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phosphorus trichloride and potassium iodide in anhydrous conditions. Another synthesis route involves combining phosphonium iodide with iodine in a solution of...

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Ammonium iodide

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Ammonium iodide is the inorganic compound with the formula NH4I. A white solid. It is an ionic compound, although impure samples appear yellow. This salt...

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Phosphine

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P2H4, may be prepared using the action of potassium hydroxide on phosphonium iodide: [PH4]I + KOH → PH3 + KI + H2O Phosphine is a worldwide constituent...

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Wittig reaction

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olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide called a Wittig reagent. Wittig reactions are most commonly used...

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Rudolph Schoenheimer

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Bergmann which demonstrated that with a mixture of hydrogen iodide and phosphonium iodide, p-toluenesulfonyl amino acids could be detosylated reductively...

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Methylcyclopentane

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Kohlenwasserstoffe durch Jodphosphonium" [On the reduction of aromatic compound by phosphonium iodide [H4IP]]. Annalen der Chemie und Pharmacie. 55: 266–281. Bei der Reduction...

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Wittig reagents

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to be sold commercially. Wittig reagents are usually prepared from a phosphonium salt, which is in turn prepared by the quaternization of triphenylphosphine...

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Ionic liquid

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the acid and base. Phosphonium cations (R4P+) are less common but offer some advantageous properties. Some examples of phosphonium cations are...

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Organophosphorus chemistry

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organophosphorus compounds. Compounds with the formula [PR4+]X− comprise the phosphonium salts. These species are tetrahedral phosphorus(V) compounds. From the...

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Sulfonyl halide

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sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides...

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Peroxide

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Methyl group

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that reacts by the SN2 pathway: CH3OH + H+ → [CH3OH2]+ Similarly, methyl iodide and methyl triflate are viewed as the equivalent of the methyl cation because...

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Appel reaction

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alkyl bromides, whereas using carbon tetraiodide, methyl iodide or iodine gives alkyl iodides. The reaction is credited to and named after Rolf Appel,...

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Phenyl group

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Discodermolide

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vinyl iodide/phosphonium salt. phosphonium salt could be readily obtained as the trisubstituted vinyl iodide is less reactive than alkyl iodide. A Wittig...

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Benzoyl group

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Haloalkane

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volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting...

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Organic sulfide

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readily alkylate to stable sulfonium salts, such as trimethylsulfonium iodide: S(CH3)2 + CH3I → [S(CH3)3]+I− Sulfides also oxidize easily to sulfoxides...

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Acyl group

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Carbene

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limits reaction rate. In Simmons-Smith cyclopropanation, the iodomethylzinc iodide typically complexes to any allylic hydroxy groups such that addition is...

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Oxime

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Dimethyl sulfoxide

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nucleophilic toward hard electrophiles. With methyl iodide it forms trimethylsulfoxonium iodide, [(CH3)3SO]I: (CH3)2SO + CH3I → [(CH3)3SO]I This salt...

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Ethyl group

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Acetal

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Propyl group

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Phosphonate Phosphite Phosphonous Phosphinate Phosphine oxide Phosphine Phosphonium Phosphaalkene Phosphaalkyne Phosphaallene Sulfur Thiol Sulfide Sulfonium...

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Onium ion

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ammonium (IUPAC name azanium), NH+4 (protonated ammonia (IUPAC name azane)) phosphonium, PH+4 (protonated phosphine) arsonium, AsH+4 (protonated arsine) stibonium...

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