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inquiryTrimethylphosphine Chemical Properties Melting point -86 °C (lit.) Boiling point 38-40 °C (lit.) density 0.738 g/mL at 20 °C (lit.) vapor pressure 7.24 psi ( 20 °C) refractive index n20/D 1.428(lit.) Fp −
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Conditions | Yield |
---|---|
In acetone for 1 h; evapd. slowly under vacuo; | A 98% B n/a |
In [(2)H6]acetone at room temp. for 1 day; | |
In tetrahydrofuran Kinetics; monitored by UV; |
methyl isocyanate
B
trimethylphosphane
Conditions | Yield |
---|---|
In diethyl ether under Ar, reaction temp.: -78°C, warmed to room temp.; removal of solvent, extn. (pentane), brought to dryness in vac., stored at -78°C for 2 days; | A 95% B n/a |
methylene chloride
phosphan
A
methylphosphine
B
dimethylphosphane
C
chloro-tetramethyl-phosphorane
D
trimethylphosphane
Conditions | Yield |
---|---|
With potassium hydroxide; PTK In toluene at 15℃; for 18h; | A 4% B 92% C 4 g D 2% |
methylenetriphenylphosphorane-(4,5-diethyl-2,5-dihydro-2,2,3-trimethyl-1-phenyl-1,2,5-phosphasilaborole)
A
dimeric (P-B)(2)-4,5-diethyl-1,2,5,6-tetrahydro-2,2,3-trimethyl-1-phenyl-1,2,5-phosphasilaborine * toluene
B
trimethylphosphane
Conditions | Yield |
---|---|
With toluene In toluene Ar atmosphere, refluxing (3 h); sublimation of PMe3, recrystn. of B-complex (hot toluene), washing (toluene), drying (0.001 Torr); elem. anal.; | A 84% B 92% |
(η5-C5Me5)(PMe3)2Ru(CH2SiMe3)
Triethoxysilane
A
tetramethylsilane
C
trimethylphosphane
Conditions | Yield |
---|---|
In inert atmosphere, heating of Ru-complex with HSi(OEt)3 (80°C, 12 h, closed vessel), briefly pumping to remove PMe3, continued heating (80°C, 6 h).; Evapn. in vac. gives a waxy solid, recrystn. (acetone), elem. anal.; | A n/a B 92% C n/a |
(bis(diisopropylamino)phosphanyl)diazomethane, lithium salt
rhodium(trimethylphosphine)4Cl
5-bis(trimethylphosphine)rhoda-4-bis(diisopropylamino)phospha-1-n-butyl-Δ2-pyrazoline
B
trimethylphosphane
Conditions | Yield |
---|---|
With n-C4H9Li byproducts: LiCl; Excess of n-Buli.; | A 90% B n/a |
cis-HRh(COCH3)(P(CH3)3)3Cl
A
RhCl(CO)(PMe3)2
[Rh(trimethylphosphine)3]Cl
C
methane
D
acetaldehyde
E
trimethylphosphane
Conditions | Yield |
---|---|
Rh complex heated at 90°C for 2 h; collection of the volatile products under high vaccum; | A 13% B 80% C 13% D 87% E 19% |
In benzene-d6 soln. of Rh complex in benzene-d6 heated at 70°C for 2 h; | A 54% B 15% C 51% D 14% E 50% |
Conditions | Yield |
---|---|
In diethyl ether addn. of fumaric acid dimethylester to the Co compd. in ether under Ar and stirring at room temp. for 30 min; evapn. (vac.), chromy. on Al2O3, elution with ether-pentane, concn. (vac.), filtn., washing with pentane and drying (vac.); elem. anal.; | A 85% B n/a |
acrylic acid methyl ester
B
trimethylphosphane
Conditions | Yield |
---|---|
In hexane addn. of acrylic acid methylester to the Co compd. in hexane under Ar and stirring at room temp. for 30 min; evapn. (vac.), dissolving in ether, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with cold pentane and drying (vac.); elem. anal.; | A 85% B n/a |
In diethyl ether addn. of acrylic acid methylester to the Co compd. in ether under Ar and stirring at room temp. for 30 min; evapn. (vac.), dissolving in ether, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with cold pentane and drying (vac.); elem. anal.; | A 85% B n/a |
Benzyl isocyanide
B
trimethylphosphane
Conditions | Yield |
---|---|
In benzene under Ar, stirred for a few minutes at room temp.; removal of solvent in vac., extn. (pentane), cooling to -78°C; elem. anal.; | A 85% B n/a |
(η2-1,2-diphenyl-1-cyclopropene)(trimethylphosphane)zirconocene
A
1,1-bis(η5-cyclopentadienyl)-2,3-diphenyl-1-(trimethylphosphane)-1-zirconacyclobut-2-ene
B
1,1-bis(η5-cyclopentadienyl)-2,3-diphenyl-1-zirconacyclobut-2-ene
C
trimethylphosphane
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 (Ar), -100°C; (31)P-NMR; | A 84% B 0% C 16% |
acrylic acid methyl ester
B
trimethylphosphane
Conditions | Yield |
---|---|
In hexane addn. of acrylic acid methylester to the Co compd. in hexane under Ar and stirring at room temp. for 30 min; evapn. (vac.), dissolving in ether, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with cold pentane and drying (vac.); elem. anal.; | A 83% B n/a |
In diethyl ether addn. of acrylic acid methylester to the Co compd. in ether under Ar and stirring at room temp. for 30 min; evapn. (vac.), dissolving in ether, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with cold pentane and drying (vac.); elem. anal.; | A 83% B n/a |
tetrakis(trimethylphosphine)platinum(0)
Benzo[b]thiophene
[(CH3)3P]2PtC8SH6
B
trimethylphosphane
Conditions | Yield |
---|---|
In toluene reflux; elem. anal.; | A 83% B n/a |
carbon disulfide
tetrakis(trimethylphosphine)nickel(0)
B
trimethylphosphane
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; for 24h; Inert atmosphere; Schlenk technique; | A 81% B n/a |
B
trimethylphosphane
Conditions | Yield |
---|---|
In not given byproducts: NaCl; N2 atmosphere; react. of Ni-complex with excess of NaCp (1.5 equiv) at 20°C for 12 h; elem. anal.; | A 80% B n/a |
B
trimethylphosphane
Conditions | Yield |
---|---|
In not given byproducts: NaBr; N2 atmosphere; react. of Ni-complex with excess of NaCp (1.5 equiv) at 20°C for 12 h; elem. anal.; | A 80% B n/a |
Conditions | Yield |
---|---|
In diethyl ether addn. of fumaric acid dimethylester to the Co compd. in ether under Ar and stirring at room temp. for 30 min; evapn. (vac.), chromy. on Al2O3, elution with ether-pentane, concn. (vac.), filtn., washing with pentane and drying (vac.); elem. anal.; | A 80% B n/a |
Conditions | Yield |
---|---|
In diethyl ether addn. of fumaric acid dimethylester to the Co compd. in ether under Ar and stirring at room temp. for 30 min; evapn. (vac.), chromy. on Al2O3, elution with ether-pentane, concn. (vac.), filtn., washing with pentane and drying (vac.); elem. anal.; | A 78% B n/a |
(η5-C5Me5)(PMe3)2Ru(CH2SiMe3)
diphenylsilyl chloride
A
tetramethylsilane
C
trimethylphosphane
Conditions | Yield |
---|---|
In inert atmosphere, heating of Ru-complex with HSi(Ph2Cl)3 (110°C, 16 h, closed vessel, stirring), periodic pumping to remove PMe3.; Cooling to room temp., addn. of pentane, cooling (-78°C, 6 h), filtn. of pale yellow crystals, washing (pentane, -78°C), drying in vac, elem. anal.; | A n/a B 78% C n/a |
1,2-bis(dimethylphosphanyl)ethane
B
trimethylphosphane
Conditions | Yield |
---|---|
In toluene N2 or Ar atmosphere of vac.; stirring (1 h); filtn., concn. (vac.), cooling (-20°C); elem. anal.; | A 76% B n/a |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether inert atmosphere; -78°C, then room temp., stirring 15 min.; evapn. (vac.), drying, extn. (petroleum ether), partial evapn. of filtrate, crystn. (-78°C), collection (filtration), drying (vac.); elem. anal.; | A 76% B n/a |
trans-MoCl(NO)(PMe3)4
MoCl(η3-S2CPMe3)(NO)(PMe3)2
B
trimethylphosphane
Conditions | Yield |
---|---|
With CS2 In tetrahydrofuran Ar or N2 atmosphere; addn. of 1.4 equiv of CS2 to a soln. of Mo-complex, stirring (24 h at room temp.), pptn.; collection (filtration), washing (Et2O), crystn. (CHCl3), -30°C; | A 75% B n/a |
Conditions | Yield |
---|---|
In water heating an aq. soln. of the Ag compound with a concd. soln. of thiourea with N2 bubbling through the soln.; | 75% |
acrylic acid methyl ester
B
trimethylphosphane
Conditions | Yield |
---|---|
In hexane addn. of acrylic acid methylester to the Co compd. in hexane under Ar and stirring at room temp. for 30 min; evapn. (vac.), dissolving in ether, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with cold pentane and drying (vac.); elem. anal.; | A 73% B n/a |
In diethyl ether addn. of acrylic acid methylester to the Co compd. in ether under Ar and stirring at room temp. for 30 min; evapn. (vac.), dissolving in ether, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with cold pentane and drying (vac.); elem. anal.; | A 73% B n/a |
Conditions | Yield |
---|---|
In diethyl ether addn. of acrylonitrile to the Co compd. in ether under Ar and stirring at room temp. for 1 h; evapn. (vac.), dissolving in ether-hexane, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with pentane and drying (vac.); elem. anal.; exo-endo-mixture, identified by (1)H-NMR; | A 73% B n/a |
Conditions | Yield |
---|---|
In diethyl ether addn. of acrylonitrile to the Co compd. in ether under Ar and stirring at room temp. for 1 h; evapn. (vac.), dissolving in ether-hexane, chromy. on Al2O3, elution with ether-hexane, concn., cooling to -78°C, filtn., washing with pentane and drying (vac.); elem. anal.; exo-endo-mixture, identified by (1)H- and (13)C-NMR; | A 72% B n/a |
tetrakis(trimethylphosphine)nickel(0)
phenyl isothiocyanate
B
trimethylphosphane
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; for 24h; Inert atmosphere; Schlenk technique; | A 72% B n/a |
MoCl2(CO)2{P(CH3)3}3
potassium isopropylxanthate
A
Mo(η3-(S,S',C)S2CO-i-Pr)2(CO)(trimethylphosphine)2
B
trimethylphosphane
Conditions | Yield |
---|---|
In tetrahydrofuran byproducts: CO, KCl; N2 or Ar atmosphere; stirring (2 h, room temp.); evapn. (vac.), extn. (petroleum ether/Et2O 1:1), centrifugation and cooling (-35°C); elem. anal.; | A 70% B n/a |
Conditions | Yield |
---|---|
In benzene addn. of maleic anhydride to the Co compd. in benzene under Ar and stirring at room temp. for 30 min; evapn. (vac.), washing with hexane, recrystn. from acetone-hexane, filtn., washing with ether and pentane and drying (vac.); elem. anal.; | A 70% B n/a |
trans-{W(ethylene)2(P(CH3)3)4}
A
{WH(OOCCHCH2)(C2H4)(P(CH3)3)2}2*0.5(C2H5)2O
B
trimethylphosphane
Conditions | Yield |
---|---|
With CO2 In diethyl ether under N2; reacting ethene complex with CO2, 20°C, 1 atm, 30 min; filtering off ppt., 2nd crop from mother liquor by cooling to -20°C overnight; elem. anal.; | A 65% B n/a |
1 ,6-dibromohexane
trimethylphosphane
(6-Bromhexyl)trimethylphosphoniumbromid
Conditions | Yield |
---|---|
In toluene for 72h; Ambient temperature; | 100% |
allyl bromide
trimethylphosphane
trimethyl-2-propen-1-ylphosphonium bromide
Conditions | Yield |
---|---|
In tetrahydrofuran; dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere; | 100% |
In diethyl ether Ambient temperature; | |
In toluene at 20℃; Inert atmosphere; | |
In dichloromethane for 12h; Inert atmosphere; |
(bromomethyl)pentafluorobenzene
trimethylphosphane
Trimethyl<(pentafluorphenyl)methyl>phosphoniumbromid
Conditions | Yield |
---|---|
In diethyl ether at 0℃; for 1h; | 100% |
1,10-diiododecane
trimethylphosphane
(10-Iodo-decyl)-trimethyl-phosphonium; iodide
Conditions | Yield |
---|---|
In toluene for 72h; Ambient temperature; | 100% |
(2-chloroethyl)diphenylphosphane
trimethylphosphane
(2-Diphenylphosphanyl-ethyl)-trimethyl-phosphonium; chloride
Conditions | Yield |
---|---|
In toluene for 72h; Heating; | 100% |
3-(diphenylphosphino)propyl chloride
trimethylphosphane
(3-Diphenylphosphanyl-propyl)-trimethyl-phosphonium; chloride
Conditions | Yield |
---|---|
In toluene for 72h; Heating; | 100% |
Phosphoric acid (E)-2-chloro-1-chloromethyl-vinyl ester diethyl ester
trimethylphosphane
O,O-diethyl α-(trimethylphosphoniummethyl)-β-chlorovinyl phosphate chloride
Conditions | Yield |
---|---|
at 0℃; for 2h; | 100% |
In diethyl ether for 12h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
In pentane at 0℃; Addition; | 100% |
Conditions | Yield |
---|---|
In dichloromethane Irradiation (UV/VIS); | 100% |
In chloroform Irradiation (UV/VIS); | 100% |
In chloroform Irradiation (UV/VIS); addn. of PMe3 to the Mo compd. in CHCl3 and irradiation (Hanovia medium pressure mercury vapor lamp) for 30 min at room temp.; evapn. (vac.), dissolving in CH2Cl2 and pptn. with hexane; elem. anal.; | 60% |
trimethylphosphane
Conditions | Yield |
---|---|
In acetone cooled to -76°C, stirred at 23°C for 3h; filtered; NMR, IR, elem. anal.; | 100% |
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
trimethylphosphane
cis-bis(trimethylphosphine)tetracarbonylmolybdenum
B
bicyclo[2.2.1]hepta-2,5-diene
Conditions | Yield |
---|---|
In tetrahydrofuran reaction in a calorimeter under argon; | A 100% B n/a |
Conditions | Yield |
---|---|
With Mg In tetrahydrofuran addn. of Mg (177 mmol) and P(CH3)3 (200 mmol) to soln. of ((C5H5)2TiCl2) (40.2 mmol) in THF under Ar; stirring for 20 h;; evapg. solvent at 1E-2 bar; extg. residue with pentane; crystn. at -78°C; elem. anal.;; | 100% |
With n-C4H9Li In tetrahydrofuran byproducts: LiCl, C4H8, C4H10; (Ar); to soln. of Ti complex was dropped hexane soln. of BuLi at -78°C within 0,5 h and stirred for 0,5 h, then was added PMe3, soln. was allowed to warm up to room temp. within 8 h and volatiles were removed at 0,1 Torr; pentane soln. of residue was filtered and filtrate cooled to -20°C, black crystals pptd., which were filtered off and dried at 0,01 Torr; elem. anal.; | 90% |
With Na#Hg In diethyl ether byproducts: NaCl; (Ar); a suspn. of Ti complex in a soln. of ligand added slowly to Na amalgam, stirred for 12 h; filtered, evapd. (Ar); | 66% |
cis-bis{(trimethylsilyl)methyl}(1,5-cyclooctadiene)platinum(II)
trimethylphosphane
Conditions | Yield |
---|---|
In toluene under Ar, heated to 60°C for 14 days; removal of solvent in vacuo, addn. of n-hexane, cooled to -25°C; elem. anal.; | 100% |
trimethylphosphane
Conditions | Yield |
---|---|
In benzene (under N2 or Ar) addn. of P-compd. to Pt-complex in benzene at room temp., standing overnight (ambient temp.); solvent removal (vac.); elem. anal.; | 100% |
Conditions | Yield |
---|---|
In dichloromethane PMe3 was condensed into a flask with complex and CH2Cl2 at -196°C, the mixt. was warmed to 25°C and stirred for 10 min;; recrystd. from CH2Cl2-hexane;; | 100% |
{(η4-2-methyl-1,3-pentadiene)cobalt(carbonyl)3} tetrafluoroborate
trimethylphosphane
Conditions | Yield |
---|---|
In nitromethane addn. of the Co complex to CH3NO2 at 0°C, stirring to complete dissoln., dropwise addn. of PMe3 in CH3NO2 and react. for 10-15 min; addn. of Et2O, removing the solvent using cannula and drying (vac.); | 100% |
Conditions | Yield |
---|---|
In dichloromethane byproducts: P(C6H5)3; mixing of the Mo compd. with the free phosphine (molar ratio 2.6:1) in CH2Cl2;; | 100% |
Conditions | Yield |
---|---|
In pentane a solution of the alkyne-complex was cooled to -78°C; Me3P was added; standing over dry ice overnight; evaporation to dryness; dried in high vacuum; | 100% |
Conditions | Yield |
---|---|
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 2.3:1) in CH2Cl2;; | A 100% B n/a |
Conditions | Yield |
---|---|
In pentane a solution of the alkyne-complex was cooled to -78°C; Me3P was added; standing over dry ice overnight; evaporation to dryness; dried in high vacuum; | 100% |
Conditions | Yield |
---|---|
In pentane a solution of the alkyne-complex was cooled to -78°C; Me3P was added; standing over dry ice overnight; evaporation to dryness; dried in high vacuum; | 100% |
Conditions | Yield |
---|---|
In pentane a solution of the alkyne-complex was cooled to -78°C; Me3P was added; standing over dry ice overnight; evaporation to dryness; dried in high vacuum; | 100% |
Conditions | Yield |
---|---|
In pentane a solution of the alkyne-complex was cooled to -78°C; Me3P was added; standing over dry ice overnight; evaporation to dryness; dried in high vacuum; | 100% |
Conditions | Yield |
---|---|
In hexane evapd.; | 100% |
In benzene-d6 under N2, soln. of educts in C6D6 heated at 51°C for 30 min; not isolated; detected by NMR; | |
In [(2)H6]acetone in NMR tube at room temp.; |
3-(NNN'N'-tetramethylethylenediamine)-1,2-dicarba-3-palladadodecaborane
trimethylphosphane
3,3-bis(trimethylphosphine)-1,2-dicarba-3-palladadodecaborane
Conditions | Yield |
---|---|
In dichloromethane PMe3 passed into soln. of Pd complex in CH2Cl2; added hexane, filtered, washed with Et2O/acetone, dried in vac.; elem. anal.; | 100% |
trimethylphosphane
Conditions | Yield |
---|---|
In benzene-d6 under N2; to Ru compd. in C6D6 addn. of PMe3 at room temp.; monitored by NMR; evapn. of solvent; elem. anal.; | 100% |
Conditions | Yield |
---|---|
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 4.5:1) in CH2Cl2;; | A 100% B n/a |
In toluene mixing of the Mo compd. with the free phosphine (molar ratio 2.1:1) in toluene;; | A 100% B n/a |
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 |
Conditions | Yield |
---|---|
In toluene mixing of the Mo compd. with the free phosphine (molar ratio 2.2:1) in toluene;; | A 100% B n/a |
trimethylphosphane
tetra-iso-propoxy(phenylimido)trimethylphosphinetungsten(VI)
Conditions | Yield |
---|---|
In petroleum ether PMe3 is added to soln. of W(NPh)(NH2CMe3)(OCHMe2)4 in petroleum ether and mixt. is stirred for 3 h; soln. is filtered, solvent removed; | 100% |
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