(2-Bromophenyl)diphenylphosphine

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(2-Bromophenyl)diphenylphosphine
BrC6H4PPh2.png
(2-Bromophenyl)diphenylphosphine-3D-balls-by-AHRLS-2012.png
Names
Preferred IUPAC name
(2-Bromophenyl)di(phenyl)phosphane
Other names
(o-Bromophenyl)diphenylphosphine
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 263-515-1
PubChem CID
UNII
  • InChI=1S/C18H14BrP/c19-17-13-7-8-14-18(17)20(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H
    Key: XIONUQPOXCUMMB-UHFFFAOYSA-N
  • InChI=1/C18H14BrP/c19-17-13-7-8-14-18(17)20(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14H
    Key: XIONUQPOXCUMMB-UHFFFAOYAI
  • c1ccc(cc1)P(c2ccccc2)c3ccccc3Br
Properties
C18H14BrP
Molar mass 341.188 g·mol−1
AppearanceWhite solid
Melting point 115 °C (239 °F; 388 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

(2-Bromophenyl)diphenylphosphine is an organophosphorus compound with the formula (C6H4Br)P(C6H5)2. It is a white crystalline solid that is soluble in nonpolar organic solvents. The compound is used as a precursor to the 2-lithiated derivative of triphenylphosphine, [1] which in turn is a precursor to other phosphine ligands.

Preparation

The compound has been prepared by several methods. [1] An efficient route is the coupling reaction of diphenylphosphine and 2-bromoiodobenzene, which is catalyzed by palladium complexes (Ph = C6H5): [2]

C6H4Br(I) + HPPh2 + Et3N → Ph2P(C6H4Br) + [Et3NH]I

The compound is isomorphous with (2-tolyl)diphenylphosphine. [3]

Lithiation with butyl lithium gives o-lithiated triphenylphosphine. The bromide also forms a Grignard reagent. These metallated phosphines are versatile reagents. [4]

BrC6H4PPh2 + Mg → BrMgC6H4PPh2
2 BrMgC6H4PPh2 + PhPCl2 → PhP[C6H4PPh2]2 + 2 MgClBr

Related Research Articles

<span class="mw-page-title-main">Phosphorus trichloride</span> Chemical compound

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.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">Tetrakis(triphenylphosphine)palladium(0)</span> Chemical compound

Tetrakis(triphenylphosphine)palladium(0) (sometimes called quatrotriphenylphosphine palladium) is the chemical compound [Pd(P(C6H5)3)4], often abbreviated Pd(PPh3)4, or rarely PdP4. It is a bright yellow crystalline solid that becomes brown upon decomposition in air.

<span class="mw-page-title-main">Iron pentacarbonyl</span> Chemical compound

Iron pentacarbonyl, also known as iron carbonyl, is the compound with formula Fe(CO)5. Under standard conditions Fe(CO)5 is a free-flowing, straw-colored liquid with a pungent odour. Older samples appear darker. This compound is a common precursor to diverse iron compounds, including many that are useful in small scale organic synthesis.

Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which 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.

<span class="mw-page-title-main">1,2-Bis(diphenylphosphino)ethane</span> Chemical compound

1,2-Bis(diphenylphosphino)ethane (dppe) is an organophosphorus compound with the formula (Ph2PCH2)2 (Ph = phenyl). It is a common symmetrical bidentate ligand in coordination chemistry. It is a white solid that is soluble in organic solvents.

<span class="mw-page-title-main">Triphenylphosphine oxide</span> Chemical compound

Triphenylphosphine oxide (often abbreviated TPPO) is the organophosphorus compound with the formula OP(C6H5)3, also written as Ph3PO or PPh3O (Ph = C6H5). It is one of the more common phosphine oxides. This colourless crystalline compound is a common but potentially useful waste product in reactions involving triphenylphosphine. It is a popular reagent to induce the crystallizing of chemical compounds.

<span class="mw-page-title-main">Triphenylarsine</span> Chemical compound

Triphenylarsine is the chemical compound with the formula As(C6H5)3. This organoarsenic compound, often abbreviated AsPh3, is a colorless crystalline solid that is used as a ligand and a reagent in coordination chemistry and organic synthesis. The molecule is pyramidal with As-C distances of 1.942–1.956 Å and C-As-C angles of 99.6–100.5°.

Organophosphines are organophosphorus compounds with the formula PRnH3−n, where R is an organic substituent. These compounds can be classified according to the value of n: primary phosphines (n = 1), secondary phosphines (n = 2), tertiary phosphines (n = 3). All adopt pyramidal structures. Organophosphines are generally colorless, lipophilic liquids or solids. The parent of the organophosphines is phosphine (PH3).

<span class="mw-page-title-main">Diphosphine ligands</span>

Diphosphines, sometimes called bisphosphanes, are organophosphorus compounds most commonly used as bidentate phosphine ligands in inorganic and organometallic chemistry. They are identified by the presence of two phosphino groups linked by a backbone, and are usually chelating. A wide variety of diphosphines have been synthesized with different linkers and R-groups. Alteration of the linker and R-groups alters the electronic and steric properties of the ligands which can result in different coordination geometries and catalytic behavior in homogeneous catalysts.

<span class="mw-page-title-main">Diphenylphosphine</span> Chemical compound

Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (C6H5)2PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts.

<span class="mw-page-title-main">Chlorodiphenylphosphine</span> Chemical compound

Chlorodiphenylphosphine is an organophosphorus compound with the formula (C6H5)2PCl, abbreviated Ph2PCl. It is a colourless oily liquid with a pungent odor that is often described as being garlic-like and detectable even in the ppb range. It is useful reagent for introducing the Ph2P group into molecules, which includes many ligands. Like other halophosphines, Ph2PCl is reactive with many nucleophiles such as water and easily oxidized even by air.

Phenylphosphine is an organophosphorus compound with the chemical formula C6H5PH2. It is the phosphorus analog of aniline. Like other primary phosphines, phenylphosphine has an intense penetrating odor and is highly oxidizable. It is mainly used as a precursor to other organophosphorus compounds. It can function as a ligand in coordination chemistry.

<span class="mw-page-title-main">Organoruthenium chemistry</span>

Organoruthenium chemistry is the chemistry of organometallic compounds containing a carbon to ruthenium chemical bond. Several organoruthenium catalysts are of commercial interest and organoruthenium compounds have been considered for cancer therapy. The chemistry has some stoichiometric similarities with organoiron chemistry, as iron is directly above ruthenium in group 8 of the periodic table. The most important reagents for the introduction of ruthenium are ruthenium(III) chloride and triruthenium dodecacarbonyl.

<span class="mw-page-title-main">Dichlorobis(triphenylphosphine)nickel(II)</span> Chemical compound

Dichlorobis(triphenylphosphine)nickel(II) refers to a pair of metal phosphine complexes with the formula NiCl2[P(C6H5)3]2. The compound exists as two isomers, a paramagnetic dark blue solid and a diamagnetic red solid. These complexes function as catalysts for organic synthesis.

Hydrophosphination is the insertion of a carbon-carbon multiple bond into a phosphorus-hydrogen bond forming a new phosphorus-carbon bond. Like other hydrofunctionalizations, the rate and regiochemistry of the insertion reaction is influenced by the catalyst. Catalysts take many forms, but most prevalent are bases and free-radical initiators. Most hydrophosphinations involve reactions of phosphine (PH3).

<span class="mw-page-title-main">Diphenylphosphine oxide</span> Chemical compound

Diphenylphosphine oxide is an organophosphorus compound with the formula (C6H5)2P(O)H. It is a white solid that soluble in polar organic solvents.

<span class="mw-page-title-main">Lithium diphenylphosphide</span> Chemical compound

Lithium diphenylphosphide contains lithium and the organophosphorus anion with the formula (C6H5)2PLi. It is an air-sensitive solid that is used in the preparation of diphenylphosphino compounds. As an ether complex, the lithium salt is dark red.

<span class="mw-page-title-main">Bis(triphenylphosphine)rhodium carbonyl chloride</span> Chemical compound

Bis(triphenylphosphine)rhodium carbonyl chloride is the organorhodium complex with the formula [RhCl(CO)(PPh3)2]. This complex of rhodium(I) is a bright yellow, air-stable solid. It is the Rh analogue of Vaska's complex, the corresponding iridium complex. With regards to its structure, the complex is square planar with mutually trans triphenylphosphine (PPh3) ligands. The complex is a versatile homogeneous catalyst.

<span class="mw-page-title-main">Triphenylbismuthine</span> Chemical compound

Triphenylbismuthine is an organobismuth compound with the formula Bi(C6H5)3. It is a white, air-stable solid that is soluble in organic solvents. It is prepared by treatment of bismuth trichloride with phenylmagnesium bromide.

References

  1. 1 2 Bennett, Martin A.; Bhargava, Suresh K.; Hockless, David C. R.; Welling, Lee L.; Willis, Anthony C. (1996). "Dinuclear Cycloaurated Complexes Containing Bridging (2-Diphenylphosphino)phenylphosphine and (2-Diethylphosphino)phenylphosphine, C6H4PR2 (R = Ph, Et). Carbon−Carbon Bond Formation by Reductive Elimination at a Gold(II)−Gold(II) Center". Journal of the American Chemical Society. 118 (43): 10469. doi:10.1021/ja961511h.
  2. Zhang, Fushi; Wang, Liduo; Chang, Shih-Han; Huang, Kuan-Lin; Chi, Yun; Hung, Wen-Yi; Chen, Chih-Ming; Lee, Gene-Hsiang; Chou, Pi-Tai (2013). "Phosphorescent Ir(iii) complexes with both cyclometalate chromophores and phosphine-silanolate ancillary: Concurrent conversion of organosilane to silanolate". Dalton Transactions. 42 (19): 7111–9. doi:10.1039/c3dt32408g. PMID   23518610.
  3. Williams, Michael L.; Noack, Cassandra L.; Saverin, Rodney J.; Healy, Peter C. (2002). "(2-Bromophenyl)diphenylphosphine". Acta Crystallographica Section E. 58 (3): o306–o307. doi:10.1107/S1600536802002945. hdl: 10072/6976 .
  4. Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The preparation and complex-forming properties of one tritertiary and one tetratertiary phosphine", J. Chem. Soc. 1963, 3930. doi : 10.1039/JR9630003930