1486-28-8

Basic information

• Product Name: METHYLDIPHENYLPHOSPHINE
• Synonyms: METHYLDIPHENYLPHOSPHINE;DIPHENYLMETHYLPHOSPHINE;Methyldiphenylphsphine;Methyldiphenylphosphine,99%;Diphenylphosphinomethane;Methyldiphenylphosphine 99%;Methyldiphenylphosphine, 99% 25GR;Methyldiphenylphosphine, 99% 5GR
• CAS NO: 1486-28-8
• Molecular Formula: C₁₃H₁₃P
• Molecular Weight: 200.22
• EINECS: 216-065-5
• Product Categories: Ligand;Phosphine Ligands;Synthetic Organic Chemistry;organophosphorus ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 1486-28-8.mol
• Article Data: 59

Chemical Properties

• Melting Point: 117-118 °C
• Boiling Point: 120-122 °C1.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.076 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00127mmHg at 25°C
• Refractive Index: n20/D 1.625(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 743075
• CAS DataBase Reference: METHYLDIPHENYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYLDIPHENYLPHOSPHINE(1486-28-8)
• EPA Substance Registry System: METHYLDIPHENYLPHOSPHINE(1486-28-8)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 17-23-24/25-36/37/39-26
• WGK Germany: 3
• F: 1-10
• TSCA: No
• Hazardous Substances Data: 1486-28-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Methyldiphenylphosphine, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.

InChI:InChI=1/C13H13P/c1-14(12-8-4-2-5-9-12)13-10-6-3-7-11-13/h2-11H,1H3

Synthetic route

{Cp(PMePh2)2molybdenum(III) dichloride} + trimethylphosphane (594-09-2) → cyclopentadienylmolybdenum(III)(PMe3)2Cl2 + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In toluene mixing of the Mo compd. with the free phosphine (molar ratio 2.1:1) in toluene;;	A 100% B n/a

{Cp(PMePh2)2molybdenum(III) dichloride} + triethylphosphine (554-70-1) → {Cp(PEt3)2molybdenum(III) dichloride} + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In toluene mixing of the Mo compd. with the free phosphine (molar ratio 2.0:1) in toluene;;	A 100% B n/a

{Cp(PMePh2)2molybdenum(III) dichloride} + Dimethyl(phenyl)phosphine (672-66-2) → {Cp(PMe2Ph)2molybdenum(III) dichloride} + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In toluene mixing of the Mo compd. with the free phosphine (molar ratio 2.0:1) in toluene;;	A 100% B n/a

{Cp(PMePh2)2molybdenum(III) dichloride} + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → cyclopentadienylmolybdenum(III)(bis(diphenylphosphino)ethane)Cl2 + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 1.1:1) inCH2Cl2;;	A 100% B n/a

diphenyl(methyl)phosphine oxide (2129-89-7) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With lithium aluminium tetrahydride; cerium(III) chloride In tetrahydrofuran at 40℃; for 0.5h;	98%
With aluminium hydride*tetrahydrofuran In tetrahydrofuran for 0.5h; Heating;	96%
Stage #1: diphenyl(methyl)phosphine oxide With trityl tetrakis(pentafluorophenyl)borate In (2)H8-toluene at 20℃; Glovebox; Inert atmosphere; Stage #2: With phenylsilane In (2)H8-toluene at 80℃; for 1.5h; Glovebox; Inert atmosphere; Sealed tube;	93%

Diphenylphosphonigsaeure-trimethylsilylester (13683-01-7) + methyllithium (917-54-4) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 2h;	96%

Ph2PCH2NHPh + methyl iodide (74-88-4) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
Stage #1: Ph2PCH2NHPh With methyllithium In toluene at -78 - 20℃; Inert atmosphere; Stage #2: methyl iodide In toluene at -78℃; Inert atmosphere;	95%

n-butyl magnesium bromide (693-03-8) + methylmagnesium bromide (75-16-1) + cis-2,10-dimethyl-<1,2,3>benzothiadiphospholo<2,3-b><1,2,3>benzothiadiphosphole (119841-34-8, 127780-84-1) + phenylmagnesium bromide → dibutyl-methyl-phosphine (33374-48-0) + n-Butyl-methyl-phenyl-phosphin (36050-91-6, 36850-51-8, 36850-52-9) + diphenyl(methyl)phosphine (1486-28-8) + 4-methyl-2-[(5-methyl-2-sulfanylphenyl)phosphanyl]benzenethiol (736137-64-7)

Conditions	Yield
Stage #1: n-butyl magnesium bromide; cis-2,10-dimethyl-<1,2,3>benzothiadiphospholo<2,3-b><1,2,3>benzothiadiphosphole; phenylmagnesium bromide In tetrahydrofuran for 0.0833333h; Stage #2: methylmagnesium bromide In tetrahydrofuran Title compound not separated from byproducts;	A n/a B n/a C n/a D 90%

methylmagnesium bromide (75-16-1) + ethylmagnesium bromide (925-90-6) + cis-2,10-dimethyl-<1,2,3>benzothiadiphospholo<2,3-b><1,2,3>benzothiadiphosphole (119841-34-8, 127780-84-1) + phenylmagnesium bromide → diethylmethylphosphine (1605-58-9) + ethylmethylphenylphosphine (15849-84-0, 52119-19-4, 72974-35-7) + diphenyl(methyl)phosphine (1486-28-8) + 4-methyl-2-[(5-methyl-2-sulfanylphenyl)phosphanyl]benzenethiol (736137-64-7)

Conditions	Yield
Stage #1: ethylmagnesium bromide; cis-2,10-dimethyl-<1,2,3>benzothiadiphospholo<2,3-b><1,2,3>benzothiadiphosphole; phenylmagnesium bromide In tetrahydrofuran for 0.0833333h; Stage #2: methylmagnesium bromide In tetrahydrofuran Title compound not separated from byproducts;	A n/a B n/a C n/a D 90%

Ph2PCH2NH(t-Bu) (126140-10-1) + methyl iodide (74-88-4) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
Stage #1: Ph2PCH2NH(t-Bu) With methyllithium In toluene at -78 - 20℃; Inert atmosphere; Stage #2: methyl iodide In toluene at -78℃; Inert atmosphere;	89%

trimethylsulphonium iodide (2181-42-2) + (trimethylsilyl)diphenylphosphine (17154-34-6) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
Stage #1: trimethylsulphonium iodide With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.166667h; Stage #2: (trimethylsilyl)diphenylphosphine In tetrahydrofuran; hexane at -70 - 20℃; for 0.5h;	88%

phenylsilane (694-53-1) + Methylenetriphenylphosphorane (19493-09-5) → triphenyl<(phenylsilyl)methylene>phosphorane + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With bis(trimethylsilyl)amide yttrium(III) In benzene-d6 at 25℃; for 0.5h; Catalytic behavior; Reagent/catalyst;	A 88% B n/a

Na(1+)*P(CH3)C6H5(1-)=NaP(CH3)C6H5 + chlorobenzene (108-90-7) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With 15-crown-5 In tetrahydrofuran at 25℃; for 6h; Inert atmosphere;	88%

1-methoxy-2-trimethylsilylethyne (24082-05-1) + (trimethylsilyl)diphenylphosphine (17154-34-6) → bis(trimethylsilyl)ketene (19061-00-8) + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In acetonitrile for 48h; Ambient temperature;	A 65% B 82%

methyl-triphenylphosphonium iodide (2065-66-9) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With lithium aluminium tetrahydride; water In 1,4-dioxane for 0.25h; Heating;	79%
With tetrakis(triphenylphosphine) palladium(0); hydrogen; triethylamine In 1,4-dioxane at 130℃; under 76000 Torr; Product distribution; other quaternary phosphonium salts;

6,6'-dimethyl fulvene (2175-91-9) + (lithiomethyl)diphenylphosphane (62263-69-8) → lithium (1-methylethenyl)cyclopentadiene (77060-52-7) + dilithium salt of 2,4-bis(1,3-cyclopentadienyl)-4-methyl-1-pentene (77060-51-6) + dilithium salt of 6-(1,3-cyclopentadienyl)-6,8,8-trimethylbicyclo<3.3.0>octa-1,3-diene (77060-48-1) + lithium <1,1-dimethyl-2-(diphenylphosphino)ethyl>cyclopentadienide (77061-27-9) + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In Petroleum ether at 27℃; for 168h; Product distribution;	A 5% B 30% C 25% D 12% E 78%

6,6'-dimethyl fulvene (2175-91-9) + (lithiomethyl)diphenylphosphane (62263-69-8) → dilithium salt of 2,4-bis(1,3-cyclopentadienyl)-4-methyl-1-pentene (77060-51-6) + dilithium salt of 6-(1,3-cyclopentadienyl)-6,8,8-trimethylbicyclo<3.3.0>octa-1,3-diene (77060-48-1) + lithium <1,1-dimethyl-2-(diphenylphosphino)ethyl>cyclopentadienide (77061-27-9) + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In Petroleum ether at 27℃; for 168h;	A n/a B n/a C 12% D 78%

N-phenyl methyldiphenyl-λ5-phosphazene (57901-20-9) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 6h; Ambient temperature;	78%

phenylsilane (694-53-1) + Methylenetriphenylphosphorane (19493-09-5) → Diphenyl-phenylsilanylmethyl-phosphane (86934-57-8) + triphenyl<(phenylsilyl)methylene>phosphorane + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With C31H52N2PSi4Y In benzene-d6 at 25℃; for 3.5h;	A n/a B 77% C n/a

[Li(THF)1.5][(CO)4W(μ-PPh2)2Os(CO)2(CHO)(PMePh2)] (88904-52-3) → Li[(CO)4W(μ-PPh2)2Os(H)(CO)2(PMePh2)] (91740-00-0) + Li[(CO)4W(μ-PPh2)2Os(H)(CO)3] (91739-99-0) + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In dimethylsulfoxide-d6 under N2, soln. of educt in (CD3)2SO heated at 100°C for 11 h; identified by NMR;	A 25% B 75% C n/a

triphenylphosphine (603-35-0) + methyl iodide (74-88-4) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
Stage #1: triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran for 0.166667h; Inert atmosphere;	75%

methyl magnesium iodide (917-64-6) + chloro-diphenylphosphine (1079-66-9) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In diethyl ether at -35℃; Inert atmosphere;	74%

methyl(phenyl)(trimethylsilyl)phosphine (59877-21-3) + chlorobenzene (108-90-7) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With bis(triphenylphosphine)nickel(II) chloride; potassium tert-butylate In 1,4-dioxane at 90℃; for 12h; Inert atmosphere;	69%

Lithiumdiphenylphosphinoformiat + methyl iodide (74-88-4) → diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In pentane at -30 - 20℃; for 16h;	60%

Cp2Zr(Cl)CH2PPh2 → ((η5-cyclopentadienyl)2ZrCl)2(OCC(H)PPh2) + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
With CO In tetrahydrofuran treatment with CO; addn. of pentane;	A 60% B n/a

borane-THF (14044-65-6) + diphenyl(methyl)phosphine oxide (2129-89-7) → diphenyl(methyl)phosphine (1486-28-8) + diphenylmethylphosphine-borane complex (54067-17-3)

Conditions	Yield
With titanium(IV) isopropylate In tetrahydrofuran; toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere;	A 57% B 20%
With titanium(IV) isopropylate In tetrahydrofuran; toluene at 80℃; for 24h; Schlenk technique; Inert atmosphere;	A 40% B 45%

5-lithiomethyl-5H-dibenzophosphole (98753-65-2) → 5-methyl-5H-dibenzophosphole (16546-79-5) + diphenyl(methyl)phosphine (1486-28-8) + benzene (71-43-2)

Conditions	Yield
by hydrolysis;	A 43% B 10% C n/a

cis-{PdMe2(PMePh2)2} + 2-dimethylsilyl-1-diphenylphosphinoethane (86934-58-9) → (Si(CH3)2C2H4P(C6H5)2)2Pd + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In diethyl ether byproducts: CH4; (N2), dried solvents, -40°C, dropwise addn. of educts, 4 h, evapn. in vac. (same temp.), addn. of petroleum ether yield yellow pptn., cooled down to -78°C; filtration ppt., washing (pentane), dried (high vac.), elem. anal.;	A 42% B n/a

[{((2,6-dimethylphenyl)NC(methyl))2CH}AlH2] (1357931-84-0) + Methylenetriphenylphosphorane (19493-09-5) → C27H31AlN2 + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In benzene at 60℃; for 2h; Glovebox; Heating;	A 21% B n/a

diethyl ether (60-29-7) + sodium methylate (124-41-4) + chloro-diphenylphosphine (1079-66-9) → diphenyl(methyl)phosphine (1486-28-8) + diphenyl(methyl)phosphine oxide (2129-89-7)

diphenyl(methyl)phosphine (1486-28-8) → diphenyl(methyl)phosphine oxide (2129-89-7)

Conditions	Yield
With polymeric complex of oxodiperoxochromium(VI) compound and pyrazine (Pyz-CrO5)n In dichloromethane for 0.1h; Ambient temperature;	100%
With dihydrogen peroxide In dichloromethane; water at 20℃; for 3h; Glovebox; Inert atmosphere;	100%
With α-azohydroperoxides In benzene-d6 at 32℃;	95%

Phenyl azide (622-37-7) + diphenyl(methyl)phosphine (1486-28-8) → N-phenyl methyldiphenyl-λ5-phosphazene (57901-20-9)

Conditions	Yield
In dichloromethane at 25℃; for 4h; Staudinger reaction;	100%

diphenyl(methyl)phosphine (1486-28-8) → methyldiphenylphosphine borane complex

Conditions	Yield
With borane-THF In tetrahydrofuran at -78 - 20℃;	100%
With dimethylsulfide borane complex In tetrahydrofuran at 25℃; for 1h;	91%
With dimethylsulfide borane complex complexation;

diphenyl(methyl)phosphine (1486-28-8) → C13H13IP(1+)*I3(1-)

Conditions	Yield
With iodine In diethyl ether at 20℃; for 48h; Addition;	100%

diphenyl(methyl)phosphine (1486-28-8) + C16H31PSi → C29H44P2Si

Conditions	Yield
In pentane at 0℃; Addition;	100%

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0) (12146-37-1, 124717-04-0) + diphenyl(methyl)phosphine (1486-28-8) → cis-{molybdenum(0)(carbonyl)4(P(phenyl)2(methyl))2} (37438-49-6, 81938-99-0) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0)

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

PPh4{PtW(μ-CC6H3Me2-2,6)(CO)2(cod)(η5-C2B9H9Me2)} + diphenyl(methyl)phosphine (1486-28-8) → PPh4{PtW(μ-CC6H3Me2-2,6)(CO)2(PMePh2)2(η5-C2B9H9Me2)}

Conditions	Yield
With PMePh2 In dichloromethane; dichloromethane-d2 shaken for 1 min; evapn., not isolated, identified by NMR-spectroscopy;;	100%

{(Rh(η5-pentamethylcyclopentadienyl)Br2)2} + diphenyl(methyl)phosphine (1486-28-8) → (η5-C5Me5)Rh{PMePh2}Br2

Conditions	Yield
In dichloromethane N2 atmosphere; addn. of phosphine to Rh complex, stirring (30 min., room temp.); evapn. (vac.), recrystn. (CH2Cl2/hexane); elem. anal.;	100%

[Rh(η(5)-pentamethylcyclopentadienyl)(μ-I)I]2 + diphenyl(methyl)phosphine (1486-28-8) → (η5-C5Me5)Rh{PMePh2}I2

Conditions	Yield
In dichloromethane N2 atmosphere; addn. of phosphine to Rh complex, stirring (30 min., room temp.); evapn. (vac.), recrystn. (CH2Cl2/hexane);	100%

HRh{(P(OCH3)2O)2H}2(CO) + diphenyl(methyl)phosphine (1486-28-8) → HRh{(P(OCH3)2O)2H}2(P(C6H5)2CH3)

Conditions	Yield
In chloroform-d1 byproducts: CO; (N2); stirring at ambiente temp.; react. followed by (1)H NMR; completed after 20 h; evapn. to dryness; recrystn. from pure hexane; elem. anal.; (31)P-, (1)H-, (13)C-NMR; IR;	100%

exo-nido-[Rh(PhS(CH3)C2B9H10)(PPh3)2] + diphenyl(methyl)phosphine (1486-28-8) → Rh(P(C6H5)2CH3)4(1+)*CH3(SC6H5)C2B9H10(1-)=[Rh(P(C6H5)2CH3)4][CH3(SC6H5)C2B9H10]

Conditions	Yield
In not given	100%

(Z)-methyl 2-azido-3-phenylacrylate (81777-11-9) + diphenyl(methyl)phosphine (1486-28-8) → 3-methoxycarbonyl-1-methyl-1,1,4-triphenyl-2-aza-1λ5-phosphabuta-1,3-diene (129990-86-9)

Conditions	Yield
In diethyl ether Ambient temperature;	99%

[ReOCl3(PPh3)2] + diphenyl(methyl)phosphine (1486-28-8) → Re(PMe2Ph)3Cl3 (15613-32-8)

Conditions	Yield
In not given Re-complex reacted with ligand according to Chatt, J; Leigh, G. J; Mingos, D. M. P.; Paske, R. J. J. Chem. Soc. A 1968, 2636;	99%

borane tetrahydrofuran + diphenyl(methyl)phosphine (1486-28-8) → diphenylmethylphosphine-borane complex (54067-17-3)

Conditions	Yield
In tetrahydrofuran under N2, Schlenk techniques; soln. of P compd. (1.35 mmol) added to soln. of B compd. (1.30 mmol) at -78°C with stirring, warmed to roomtemp. overnight; evapd.;	99%

[((triphenylphosphane)2Pd)2(P2C(=N(iPr)2))](BF4) + diphenyl(methyl)phosphine (1486-28-8) → [((diphenylmethylphosphane)2Pd)2(P2C(=N(iPr)2))](BF4) (174092-69-4)

Conditions	Yield
In dichloromethane 4 equivs. of phosphine, stirring for 30 min at room temp.; evapn., washing (MePh, ether); NMR spectroscopy;	99%

fac-[(Ph2PC6H4CHOCH2C5H4N-κ(3)P,C,N)Rh(H)(Cl)(PPh3)] + diphenyl(methyl)phosphine (1486-28-8) → fac-[(Ph2PC6H4CHOCH2C5H4N-κ(3)P,C,N)Rh(H)(Cl)(PPh2Me)]

Conditions	Yield
In toluene (Ar); std. Schlenk technique; soln. of P ligand in toluene was added dropwise to stirred soln. of Rh complex in toluene; soln. was stirred at room temp. for 20 h; solvent removed (vac.);	99%

chlorobis(cyclooctene)-iridium(I) dimer + o-Ph2PC6H4CH2OCH2C5H4N-2 (146583-33-7) + diphenyl(methyl)phosphine (1486-28-8) → mer-[(Ph2PC6H4CHOCH2C5H4N-κ(3)P,C,N)Ir(H)(Cl)(PMePh2)] (921195-66-6, 920742-68-3)

Conditions	Yield
In toluene (Ar); std. Schlenk technique; soln. of P ligand in toluene was added dropwise to stirred soln. of Ir complex (0.5 equiv.) and P-N ligand (1 equiv.) in toluene; soln. was stirred at room temp. for 12 h; solvent removed (vac.);	99%

dichloromethane (75-09-2) + water (7732-18-5) + diphenyl(methyl)phosphine (1486-28-8) + cobalt(II) chloride (7646-79-9) + zinc (7440-66-6) → ZnCl4(2-)*2(C6H5)2(CH3)2P(1+)=[(C6H5)2(CH3)2P]2[ZnCl4] + cobalt (7440-48-4) + zinc(II) chloride (7646-85-7) + zinc(II) hydroxide

Conditions	Yield
In dichloromethane	A n/a B 99% C n/a D n/a

...Expand

nickel(II) chloride hexahydrate + diphenyl(methyl)phosphine (1486-28-8) → bis(methyldiphenylphosphine)nickel(II) chloride (28665-20-5, 15683-37-1)

Conditions	Yield
In ethanol at 80℃; for 0.5h; Sealed tube; Inert atmosphere;	99%

1-ferrocenylphenylmethanol + trifluorormethanesulfonic acid (1493-13-6) + diphenyl(methyl)phosphine (1486-28-8) → [phenyl(ferrocenyl)methyl]methyldiphenylphosphonium triflate

Conditions	Yield
In chloroform Inert atmosphere;	99%

diphenyl(methyl)phosphine (1486-28-8) + azidoformiate de methyle (1516-56-9) → P,P-diphenyl-P-(methyl)(N-methoxycabonyl)phosphazene (127802-81-7)

Conditions	Yield
In diethyl ether Staudinger reaction;	98%

N-[5-(bromomethyl)-4-(4-fluorophenyl)-6-(propan-2-yl)pyrimidin-2-yl]-N-methylmethanesulfonamide (799842-07-2) + diphenyl(methyl)phosphine (1486-28-8) → ({4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-5-pyrimidinyl}methyl)-methyldiphenylphosphonium bromide

Conditions	Yield
In tetrahydrofuran at 50℃; for 0.25h;	98%

iron pentacarbonyl (13463-40-6) + diphenyl(methyl)phosphine (1486-28-8) → Fe(CO)4PPh2Me (37410-36-9, 41206-81-9)

Conditions	Yield
cyclopentadienyl iron(II) dicarbonyl dimer In toluene to boiling soln. of Fe(CO)5 and catalyst added ligand, heated for 1.75 h; evapd. in vac., chromd., recrystd.;	98%
[(η(5)-C5H4Me)Fe(CO)2]2 In toluene to boiling soln. of Fe(CO)5 and catalyst added ligand, heated for 1.25 h; evapd. in vac., chromd., recrystd.;	98%
cobalt(II) chloride dihydrate In toluene ligand and catalyst added to toluene, stirred soln. brought to reflux, Fe(CO)5 added to this soln., reflux continued for 1 h under N2; catalyst and excess ligand removed by chromy., solvent and excess Fe(CO)5 removed by evapn.;	98%
pentamethylcyclopentadienyliron(III) dicarbonyl dimer In toluene to boiling soln. of Fe(CO)5 and catalyst added ligand, heated for 1.25 h; evapd. in vac., chromd., recrystd.;	96%
cobalt(II)-iodide * 4 H2O In toluene ligand and catalyst added to toluene, stirred soln. brought to reflux, Fe(CO)5 added to this soln., reflux continued for 1.5 h under N2; catalyst and excess ligand removed by chromy., solvent and excess Fe(CO)5 removed by evapn.;	78%

(N,N,N',N'-tetramethylethylenediamine)dimethylpalladium(II) + diphenyl(methyl)phosphine (1486-28-8) → cis-{PdMe2(PMePh2)2}

Conditions	Yield
In pentane; benzene react. of Pd complex with phosphine in benzene and addn. of pentane;	98%
In benzene addn. of pentane; cooling to -30°C; decanting;	90%

thallium(I) tetrafluoroborate (28625-02-7) + {bis(2,6-diisopropylphenylimido)pyridine(chloro)(methyldiphenylphosphine)tungsten} + diphenyl(methyl)phosphine (1486-28-8) → {bis(2,6-diisopropylphenylimido)bis(methyldiphenylphosphine)tungsten} tetrafluoroborate

Conditions	Yield
In tetrahydrofuran TlBF4 is added to a soln. of the starting complex and the phosphine in THF, stirred overnight; cooled to -40°C, filtered, the filtrate is evapd. to dryness, elem. anal.;	98%

Upstream product

• 60-29-7 diethyl ether 
• 124-41-4 sodium methylate 
• 1079-66-9 chloro-diphenylphosphine 
• 544-97-8 dimethyl zinc(II) 
• 603-32-7 triphenyl-arsane 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 74-88-4 methyl iodide 
• 24082-05-1 methoxy(trimethylsilyl)acetylene 
• 17154-34-6 (trimethylsilyl)diphenylphosphine 
• 74-83-9 methyl bromide 
• 65567-06-8 lithium diphenylphosphide 
• 1605-53-4 diethyl-phenyl-phosphine 
• 693-03-8 n-butyl magnesium bromide 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 1661-08-1 diphenylethylmethylphosphonium iodide 
• 106141-00-8 methylallyldiphenylphosphonium bromide 
• 55759-63-2 4-(methyl-phenyl-phosphanyl)-butan-1-ol 
• 21955-55-5 benzyl(methyl)diphenylphosphonium bromide 
• 29955-01-9 (+/-)-1-(Diphenylphosphino)-2-(methylphenylphosphino)ethane 
• 701-03-1 methylpropylphenylphosphine 
• 33077-98-4 N-benzoyl-P-methyldiphenyl-λ⁵-phosphazene 
• 266363-49-9 N-(3-benzo[b]thienyl)iminomethyldiphenylphosphorane 
• 2129-89-7 diphenyl(methyl)phosphine oxide 
• 18818-41-2 2-(4-methylphenyl)-4(3H)-quinazolinone 
• 1605-53-4 diethyl-phenyl-phosphine 
• 607-01-2 ethyl-diphenyl-phosphane 
• 6476-37-5 dicyclohexylphenylphosphine 
• 127802-81-7 P,P-diphenyl-P-(methyl)(N-methoxycabonyl)phosphazene 

Relevant articles and documents

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Palladium-Catalyzed Cleavage of P-C Bonds In Quaternary Phosphonium Salts and Its Applications to Organic Synthesis

Phosphonium salts, PPh4I and PMePh3I, oxidatively add to Pd(methyl acrylate)(PMePh2)2 to give trans- in moderate yields with cleavage of the P-phenyl bond.Conversely thermolysis of trans-PdPhIL2(L = PMePh2 and PPh3) reductively eliminates PMePh3I and PPh4I, respectively.Application of the P-C bond cleavage process in phosphonium salts to olefination, carbonylation and hydrogenation reactions has been explored.

Dimethylsulfonium methylide in methylation of silylphosphines

Selective monodesilylation of bissilylated alkyl- or arylphosphines under the action of dimethylsulfonium methylide and the subsequent methylation of the resulting silyl phosphides with the sulfonium salt offers a convenient route to difficultly accessible monosilylated secondary methylalkyl(aryl)phosphines.

The Trityl-Cation Mediated Phosphine Oxides Reduction

Reduction of phosphine oxides into the corresponding phosphines using PhSiH3 as a reducing agent and Ph3C+[B(C6F5)4]? as an initiator is described. The process is highly efficient, reducing a broad range of secondary and tertiary alkyl and arylphosphines, bearing various functional groups in generally good yields. The reaction is believed to proceed through the generation of a silyl cation, which reaction with the phosphine oxide provides a phosphonium salt, further reduced by the silane to afford the desired phosphine along with siloxanes. (Figure presented.).

Reductive conversion of phosphoryl P(O) compounds to trivalent organophosphines R3P

By introducing trimethylsilyl chloride (TMSCl), the pentavalent phosphoryl P(V) compounds such as triphenylphosphine oxides, secondary phosphine oxides etc., were readily converted to the corresponding R2P(OTMS) intermediates, that can further react efficiently with an electrophile R'X or with a nucleophile R'Li to produce the corresponding trivalent phosphines R2PR’. Chiral phosphines could also be obtained stereospecifically by this strategy.

Reduction of tertiary phosphine oxides to phosphine-boranes using Ti(Oi-Pr)4/BH3-THF

A new method for reduction of tertiary phosphine oxides leading to the formation of tertiary phosphine-boranes has been developed. The BH3-THF/Ti(Oi-Pr)4 reducing system enables conversion of triaryl, diarylalkyl and trialkylphosphine oxides directly to their borane analogues in good to high yields. In contrast to the previously reported protocols, the presence of activating groups in the structure of starting material is not necessary for the reaction to occur. The reaction is highly stereoselective and proceeds with predominant retention of configuration at the phosphorus atom. A plausible mechanism of reduction of the P[dbnd]O bond by BH3-THF/Ti(Oi-Pr)4 has been proposed.