Conditions | Yield |
---|---|
In benzene-d6 at 20℃; for 0.166667h; Inert atmosphere; Glovebox; | A 95% B n/a |
tricyclohexylphosphine
Conditions | Yield |
---|---|
With methanol; 4 A molecular sieve In 1,4-dioxane at 115℃; for 42h; | 92% |
tricyclohexylphosphine
Conditions | Yield |
---|---|
With sodium hydroxide In water Product distribution / selectivity; | 90% |
Conditions | Yield |
---|---|
With pyridine In benzene-d6 at 25℃; Inert atmosphere; Glovebox; | A 87% B 13% |
tricyclohexylphosphine oxide
tricyclohexylphosphine
Conditions | Yield |
---|---|
With Bis(p-nitrophenyl) phosphate; 1,3-diphenyl-disiloxane In ethyl acetate at 23℃; for 70h; Sealed tube; chemoselective reaction; | 84% |
Stage #1: tricyclohexylphosphine oxide With triphenyl phosphite; diphenyl hydrogen phosphite; iodine; triethylamine In tetrahydrofuran at 25℃; for 63h; Inert atmosphere; Schlenk technique; Stage #2: With sodium hydroxide In water for 0.5h; Glovebox; | 82% |
With bis(2-chlorophenyl)borinic acid; phenylsilane In toluene at 80℃; for 36h; Inert atmosphere; | 78% |
ICo(CO)2(P(C6H11)3)2
diphenylphosphane sulfide
N-ethyl-N,N-diisopropylamine
B
dicarbonyl(η2-diphenylthiophosphinito)(tricyclohexylphosphane)cobalt(I)
C
tricyclohexylphosphine
Conditions | Yield |
---|---|
In toluene under N2 or Ar, exclusion of oxygen and moisture, addn. of soln. of amine in toluene to a part of soln. of Co compound in toluene at 25°C, addn. of the rest of this soln. together with (C6H5)2HPS during 2 h, 15 h; decantation, evapn. of solvent in vac., residue dissolved in n-hexane, filtration of ((Et)(i-Pr)2NH)I and excess ICo(CO)2(P(C6H11)3)2, crystn. at -5°C, recrystn. from n-hexane at -5°C; elem. anal.; | A n/a B 71% C n/a |
bis(tricyclohexylphosphine)platinum(0)
A
[(OC)3Fe{μ-BN(SiMe3)2}(μ-BDur)Pt(PCy3)]
B
tricyclohexylphosphine
Conditions | Yield |
---|---|
In hexane Inert atmosphere; Schlenk technique; Glovebox; | A 71% B n/a |
diethylphosphine sulfide
ICo(CO)2(P(C6H11)3)2
N-ethyl-N,N-diisopropylamine
dicarbonyl(η2-diethylthiophosphinito)(tricyclohexylphosphane)cobalt(I)
C
tricyclohexylphosphine
Conditions | Yield |
---|---|
In toluene under N2 or Ar, exclusion of oxygen and moisture, addn. of soln. of amine in toluene to a part of soln. of Co compound in toluene at 25°C, addn. of the rest of this soln. together with (C2H5)2HPS during 2 h, 15 h; decantation, evapn. of solvent in vac., residue dissolved in n-hexane, filtration of ((Et)(i-Pr)2NH)I and excess ICo(CO)2(P(C6H11)3)2, crystn. at -5°C, recrystn. from n-hexane at -5°C; elem. anal.; | A n/a B 65% C n/a |
ICo(CO)2(P(C6H11)3)2
dimethylphosphine sulfide
N-ethyl-N,N-diisopropylamine
C
dicarbonyl(η2-dimethylthiophosphinito)(tricyclohexylphosphane)cobalt(I)
D
tricyclohexylphosphine
Conditions | Yield |
---|---|
In toluene under N2 or Ar, exclusion of oxygen and moisture, addn. of Me2HPS to a soln. of Co compound in toluene and dropwise addn. of (Et)(i-Pr)2N in toluene at 25°C during 2 h, 8 h; decantation, concd. in vac., addn. of n-hexane, decantation, cooled to -30°C, filtration of pptn., suspension in toluene, filtration (polymeric product), addn. of hexane to the filtrate, crystn. at -30°C; elem. anal.; | A n/a B n/a C 46% D n/a |
ICo(CO)2(P(C6H11)3)2
di(yclohexyl)phosphine sulfide
N-ethyl-N,N-diisopropylamine
B
dicarbonyl(η2-dicyclohexylthiophosphinito)(tricyclohexylphosphane)cobalt(I)
C
tricyclohexylphosphine
Conditions | Yield |
---|---|
In toluene under N2 or Ar, exclusion of oxygen and moisture, addn. of soln. of amine in toluene to a part of soln. of Co compound in toluene at 25°C, addn. of the rest of this soln. together with (C6H11)2HPS during 2 h, 15 h; decantation, evapn. of solvent in vac., residue dissolved in n-hexane, filtration of ((Et)(i-Pr)2NH)I and excess ICo(CO)2(P(C6H11)3)2, crystn. at -5°C, recrystn. from n-hexane at -5°C; elem. anal.; | A n/a B 37% C n/a |
1-benzyl-2,2-di(2-propenyl)pyrrolidine
A
styrene
B
dibenzyl ether
C
1-benzyl-10-azaspiro[4.4]non-7-ene
D
tricyclohexylphosphine
Conditions | Yield |
---|---|
In chloroform for 7h; Heating; | A 4% B 10% C 24% D 13% |
Conditions | Yield |
---|---|
With phosphorus trichloride |
Conditions | Yield |
---|---|
With phosphorus trichloride |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 25℃; Equilibrium constant; |
tricyclohexyl(dithiocarboxylato)phosphonium
tricyclohexylphosphine
Conditions | Yield |
---|---|
In ethanol Heating; |
Conditions | Yield |
---|---|
With Nb(OC6H3Ph2-2,6)2(CH2C6H4-4Me)3; hydrogen In cyclohexane at 80℃; under 62057.8 Torr; for 24h; |
triphenylphosphine
A
dicyclohexylphenylphosphine
B
cyclohexyldiphenylphosphine
C
tricyclohexylphosphine
Conditions | Yield |
---|---|
With n-butyllithium; hydrogen; bis(2,6-diisopropylphenoxy) trichloroniobium(V) In hexane; benzene at 60℃; under 62057.8 Torr; Kinetics; var. of catalyst; | |
With n-butyllithium; hydrogen; In hexane; benzene at 60℃; under 62057.8 Torr; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Equilibrium constant; |
tri-tert-butyl phosphine
B
tricyclohexylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Equilibrium constant; |
tri-tert-butyl phosphine
B
tricyclohexylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; Equilibrium constant; |
1H-imidazole-1-carbothioic acid O-cyclohexyl ester
chlorodicyclohexylphosphane
tricyclohexylphosphine
Conditions | Yield |
---|---|
With tris-(trimethylsilyl)silane; triethylamine; 1,1'-azobis(1-cyanocyclohexanenitrile) In benzene for 18h; Heating; |
Grubbs catalyst first generation
(2Z)-methyl 2-N-acetylaminopenta-2,4-dienoate
C
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane-d2 at 20℃; for 2h; Reactivity; NMR tube; |
tributylphosphine
A
tris[tert-butyl]phosphonium tetrafluoroborate
B
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane-d2 at 20℃; Equilibrium constant; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran / 72 h / 20 °C 2: Et3N; tris(trimethylsilyl)silane; 1,1'-azobis(cyclohexane-1-carbonitrile) / benzene / 18 h / Heating View Scheme |
(1,3-dimesityl-4,5-dihydroimidazol-2-ylidene)(PCy3)Cl2Ru=CHPh
2-(2-{2-[2-(pyridin-4-yloxy)-ethoxy]-ethoxy}-ethoxy)-ethanol
B
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane for 1h; |
Conditions | Yield |
---|---|
With carbon monoxide quick react.; | |
With CO quick react.; |
bis(1,3-bis-tert-butyl-imidazol-2-ylidene)palladium(0)
tricyclohexylphosphine
Conditions | Yield |
---|---|
In benzene-d6 at room temp. for < 15 min; | 100% |
(μ-H)Fe4(μ-η(2)-CH)(CO)12
tricyclohexylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane N2-atmosphere; room temp. (20 h); evapn. (vac.), washing (hexanes), drying (vac.); elem. anal.; | 100% |
In dichloromethane N2-atmosphere; room temp. (20 h); evapn. (vac.), washing (hexanes), drying (vac.); elem. anal.; |
tricyclohexylphosphine
dicyclohexylphosphine oxide
Conditions | Yield |
---|---|
With lithium hexafluorophosphate; air at 120℃; for 2h; | 100% |
bis(1,5-cyclooctadiene)nickel (0)
(E)-2-(2,4-pentadienyl)-2-(2-propynyl)malonic acid diethyl ester
tricyclohexylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran-d8 at -20 - 20℃; for 1h; | 100% |
bis(1,5-cyclooctadiene)nickel (0)
lithium bromide
tricyclohexylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 100% |
(furan-2-yl)ethylene
bis(1,5-cyclooctadiene)nickel (0)
phenyl isocyanate
tricyclohexylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran exclusion of air; addn. of org. compds. to soln. opf Ni-compd. in THF (-78°C), warming with stirring (-10°C, 2 d); partial evapn., addn. of pentane, filtration (-10°C), washing (cold pentane), drying (vac.); elem. anal.; | 99.9% |
tricyclohexylphosphine
tricyclohexylphosphine oxide
Conditions | Yield |
---|---|
With water; Selectfluor In acetonitrile at 20℃; for 0.166667h; | 99% |
With 4-phenylthioxanthone In methanol at 20℃; under 760.051 Torr; for 1h; Irradiation; | 98% |
Stage #1: tricyclohexylphosphine With water; dihydrogen peroxide In toluene at 0 - 20℃; for 12h; Inert atmosphere; Stage #2: In toluene at 20℃; for 4h; Molecular sieve; | 91% |
rhodium(III)chloride
tricyclohexylphosphine
HRhCl2(tricyclohexylphosphine)2
Conditions | Yield |
---|---|
In water; isopropyl alcohol bubbled N2 through a stirred soln. of RhCl3; added tricyclohexylphosphine; refluxed for 18 h under stirring; filtered; washed with ethanol; dried in vacuo; | 99% |
Pt2(CH3)2(CH3SOCH3)2C15H9N3
tricyclohexylphosphine
Pt2(CH3)2(P(C6H11)3)2C15H9N3
Conditions | Yield |
---|---|
In dichloromethane stoichiometric amounts of phosphine, CH2Cl2, room temp., Ar; elem. anal.; | 99% |
diphenyl ketene
tricyclohexylphosphine
trans-chlorobis(tricyclohexylphosphine)(η2-C,O-diphenylketene)rhodium
Conditions | Yield |
---|---|
2 equiv. of Ph2CCO and 4 equiv. of P(i-Pr)3; | 99% |
In benzene-d6 to suspn. ((μ-Cl)Rh(cyclooctene)2)2 in C6D6 were added Ph2C=C=O and P(Cy)3 and kept at room temp. for 24 h; mixt. was concd. under vac., product was crystd. from hexane; elem. anal.; | 96% |
tris(triphenylphosphine)ruthenium(II) chloride
phenyldiazomethane
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane (Ar); stirring (-78 to -60°C, 5-10 min, room temp., 10 min); pptn. (MeOH); | 99% |
tricyclohexylphosphine
(η(5)-cyclopentadienyl)W(CO)2(PCy3)I
Conditions | Yield |
---|---|
With Me3NO In tetrahydrofuran Ar-atmosphere; 1 equiv. of Me3NO, 1 equiv. of ligand, stirring for 15 min; evapn., extn. (CH2Cl2), chromy. (TLC, CH2Cl2:hexane 1:2), recrystn. (CH2Cl2:hexane, -20°C); | 99% |
In tetrahydrofuran Ar-atmosphere; addn. of slight excess of phosphine to W-complex soln., heating to 50°C; filtration, evapn. (reduced pressure), extn. into CH2Cl2, TLC (CH2Cl2/hexane=1:2); mixt. of isomers (cis/trans=95:5) not sepd.; elem. anal.; |
tricyclohexylphosphine
[(cyclopentadienyl)bis(acetonitrile)(tricyclohexylphosphine)ruthenium(II)] hexafluorophosphate
Conditions | Yield |
---|---|
1 equiv. of phosphine; | 99% |
In dichloromethane Ar-atmosphere; stirring (room temp., 2 h); evapn., filtering, washing (Et2O), drying (vac.); elem. anal.; | 94% |
tricyclohexylphosphine
Conditions | Yield |
---|---|
In toluene equimol.; | 99% |
Conditions | Yield |
---|---|
In n-heptane; dichloromethane Ar-atmosphere; in CH2Cl2/heptane=1:10 v/v, equimolar amts., room temp. (UV-control); vol. reduction (Ar-stream), crystn. (-15°C); | 99% |
C6(CH3)3(CH2OC6H4CCH)3
tricyclohexylphosphine
Conditions | Yield |
---|---|
In toluene the suspn. in toluene was stirred for 24 h at 80°C (Ar); the solvent was removed in vac., the residue was washed with dry methanol; elem. anal.; | 99% |
[Ru(η5-C5H4CH2CH(Ph)-κ1P-PPh2)(acetonitrile)2]BF4
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane Ru-complex in CH2Cl2 was mixed with ligand, stirred at room temp. under N2; concd., Et2O was added dropwise, filtered; elem. anal.; | 99% |
tricyclohexylphosphine
tricyclohexylphosphinepalladium cinnamyl chloride
Conditions | Yield |
---|---|
In dichloromethane at 292 K; ligand added to a soln. of Pd complex, stirred for 30 min; evapd.; | 99% |
In dichloromethane (Ar); std. Schlenk technique; soln. of P ligand (1.03 equiv.) in CH2Cl2 was canulated over 5 min to soln. of Pd complex (0.5 equiv.) in CH2Cl2; stirred for 30 min; evapd. (vac.); triturated with hexane; rinsed with hexane; | 75% |
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane 4 equivs. of phosphine, stirring for 30 min at room temp.; evapn., washing (MePh, ether); NMR spectroscopy; | 99% |
bis(1,5-cyclooctadiene)nickel (0)
trimethylsilyl trifluoromethanesulfonate
benzaldehyde
tricyclohexylphosphine
[(η1:η1-Me3SiOCH(Ph)Ni(PCy3)OTf]
Conditions | Yield |
---|---|
In benzene-d6 C6D6, room temp., 5 min; | 99% |
bis(1,5-cyclooctadiene)nickel (0)
N-benzylidenephenylsulfonamide
diphenyl acetylene
tricyclohexylphosphine
[Ni(P(C6H11)3)(OS(C6H5)(O)NCH(C6H5)C2(C6H5)2)]
Conditions | Yield |
---|---|
In benzene-d6 at room temp., 10 min; elem. anal.; | 99% |
di[(2,4-bis-tert-butyl-1-methoxy-3-neopentylcyclopentadienyl)dichlororuthenium(III)]
[RuCl2(η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl)]2
tricyclohexylphosphine
(2,4-bis-tert-butyl-1-methoxy-3-neopentylcyclopentadienyl)(tricyclohexylphosphine)chlororuthenium(III)
Conditions | Yield |
---|---|
With zinc In tetrahydrofuran byproducts: ZnCl2; (N2); addn. of PCy3 and excess Zn dust to soln. of (RuCl2(C5H(OMe)(CMe3)2(CH2CMe3)))2 in THF; stirring at ambient temp. for 12 h; filtration, removal of solvent under high vac., addn. of hexane; removalof solvent under vac., extn. with hexane; removal of hexane under vac., elem. anal.; | 99% |
tricyclohexylphosphine
Conditions | Yield |
---|---|
In dichloromethane (N2); phosphine was added to soln. of Pd complex in CH2Cl2; mixt. was stirred at room temp. for 2 h; solvent evapd.; recrystd. (CH2Cl2/ether); elem. anal.; | 99% |
[Pd(Cl)(κ2N,C-(2,6-dimethylphenyl)(2,4,6-trimethylbenzylidene)amine(-1H))]2
tricyclohexylphosphine
[PdCl(κ2N,C-(2,6-dimethylphenyl)(2,4,6-trimethylbenzylidene)amine(-1H))(PCy3)]
Conditions | Yield |
---|---|
In dichloromethane (N2); phosphine was added to soln. of Pd complex in CH2Cl2; mixt. was stirred at room temp. for 2 h; solvent evapd.; recrystd. (CH2Cl2/ether); elem. anal.; | 99% |
[Pd(Cl)(kappa.2N,C-(2,6-diisopropylphenyl)(2,4,6-trimethylbenzylidene)amine(-1H))]2
tricyclohexylphosphine
[PdCl(κ2N,C-(2,6-diisopropylphenyl)(2,4,6-trimethylbenzylidene)amine(-1H))(PCy3)]
Conditions | Yield |
---|---|
In dichloromethane (N2); phosphine was added to soln. of Pd complex in CH2Cl2; mixt. was stirred at room temp. for 2 h; solvent evapd.; recrystd. (CH2Cl2/ether); elem. anal.; | 99% |
tricyclohexylphosphine
Conditions | Yield |
---|---|
In benzene | 99% |
tris(2,3,5,6-tetrafluorophenyl)borane triethylphosphine oxide
hydrogen
tricyclohexylphosphine
[Cy3PH][HB(p-C6F4H)3]
Conditions | Yield |
---|---|
In not given | 99% |
In hexane High Pressure; (N2); mixing hexane soln. of phosphine deriv. and borane deriv. in C6H5Br, freezing at -196°C, exposure to H2, warming to room temp., stirring overnight; pressure of H2 after warming to room temp. was 4 atm; evapn., recrystn. by addn. of hexanes to concd. CH2Cl2 soln. and keepingat -35°C for wk, elem. anal.; | 72% |
Conditions | Yield |
---|---|
In toluene to suspn. AcOAg in toluene soln. Cy3P in toluene was added dropwise, stirred for 8 h; soln. was filtered through Celite and concd. in vacuo, pentane was added, ppt. was collected and dried; elem. anal.; | 99% |
Conditions | Yield |
---|---|
In benzene-d6 (under N2, Schlenk); Re-complex and ligand mixed in benzene-d6, kept at 75°C for 30 min; monitored by NMR; | 99% |
The Tricyclohexyl phosphine, with the CAS registry number 2622-14-2,is also known as Phosphine,tricyclohexyl-. It belongs to the product categories of organophosphorus ligand;organophosphine ligand.Its EINECS number is 220-069-2. This chemical's molecular formula is C18H33P and molecular weight is 280.43. What's more,Its systematic name is Tricyclohexyl phosphine.It is a clear colorless to pale yellow solution.
Physical properties about Tricyclohexyl phosphine are:
(1)ACD/LogP: 6.352; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.35; (4)ACD/LogD (pH 7.4): 6.35; (5)ACD/BCF (pH 5.5): 39568.81; (6)ACD/BCF (pH 7.4): 39568.81; (7)ACD/KOC (pH 5.5): 67978.00; (8)ACD/KOC (pH 7.4): 67978.00; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Flash Point: 195.609 °C; (13)Enthalpy of Vaporization: 60.723 kJ/mol; (14)Boiling Point: 383.434 °C at 760 mmHg; (15)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:C1CCC(CC1)P(C2CCCCC2)C3CCCCC3;
(2)Std. InChI:InChI=1S/C18H33P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h16-18H,1-15H2;
(3)Std. InChIKey:WLPUWLXVBWGYMZ-UHFFFAOYSA-N.
Safety Information of Tricyclohexyl phosphine:
The Tricyclohexyl phosphine is Irritating to eyes, respiratory system and skin. It May form explosive peroxides and its Vapours may cause drowsiness and dizziness.And it may cause lung damage if swallowed. There is possible risk of harm to the unborn child.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it ,wear suitable protective clothing, gloves and eye/face protection. If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. Take precautionary measures against static discharges. This chemical is highly flammable,keep away from sources of ignition.
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