Conditions | Yield |
---|---|
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; zinc In N,N-dimethyl-formamide at 20℃; for 12h; Reagent/catalyst; Time; | 95% |
(cyclohexyl)diphenylphosphane oxide
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With copper(II) trifluoromethanesulfonate; 1,1,3,3-Tetramethyldisiloxane In toluene at 100℃; Inert atmosphere; | 86% |
With oxalyl dichloride; hydrogen In chloroform-d1 at 130℃; under 60006 Torr; for 18h; Reagent/catalyst; | 85% |
With copper(II) bis(trifluoromethanesulfonate); 1,1,3,3-tetramethyldisilazane In toluene at 80℃; | 82% |
cyclohexyl chloride
sodium diphenylphosphide
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
With 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene; N-ethyl-N,N-diisopropylamine In acetonitrile for 24h; Inert atmosphere; Glovebox; Sealed tube; Irradiation; | 73% |
Conditions | Yield |
---|---|
Stage #1: triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 1-bromocyclohexane In tetrahydrofuran for 0.166667h; Inert atmosphere; | 70% |
With ammonia; sodium 2.) irradiation, 30 min; Multistep reaction; |
ammonium hydroxide
cyclohexylmagnesiumchloride
Dichlorophenylphosphine
phenylmagnesium bromide
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With hydrogenchloride In water | 70% |
Conditions | Yield |
---|---|
With ammonia; sodium 2.) irradiation, 180 min; Multistep reaction; |
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; |
dicyclohexylzinc(II)
chloro-diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 1h; |
1-bromocyclohexane
chloro-diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With pyridine; tris-(trimethylsilyl)silane; 1,1'-azobis(1-cyanocyclohexanenitrile) In benzene for 20h; Heating; | |
Stage #1: 1-bromocyclohexane; chloro-diphenylphosphine With manganese; CpCr[(XylNCMe)2CH]; lead(II) bromide In tetrahydrofuran at 25℃; for 28h; Stage #2: | 92 %Spectr. |
1H-imidazole-1-carbothioic acid O-cyclohexyl ester
chloro-diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With tris-(trimethylsilyl)silane; triethylamine; 1,1'-azobis(1-cyanocyclohexanenitrile) In benzene for 18h; Heating; |
Conditions | Yield |
---|---|
In dichloromethane-d2 at 20℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane-d2 at 20℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane-d2 at 20℃; Equilibrium constant; |
Conditions | Yield |
---|---|
In dichloromethane-d2 at 20℃; Equilibrium constant; |
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-iodocyclohexane
(trimethylsilyl)diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With 1,1'-azobis(cyclohexane)-1-carbonitrile In n-heptane at 100℃; for 72h; |
1-iodocyclohexane
(trimethylstannyl)diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With 1,1'-azobis(cyclohexane)-1-carbonitrile In benzene at 80℃; for 16h; |
1H-imidazole-1-carbothioic acid O-cyclohexyl ester
(trimethylsilyl)diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With 1,1'-azobis(cyclohexane)-1-carbonitrile In n-heptane at 100℃; for 72h; |
1H-imidazole-1-carbothioic acid O-cyclohexyl ester
(trimethylstannyl)diphenylphosphine
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With 1,1'-azobis(cyclohexane)-1-carbonitrile In benzene at 80℃; for 16h; |
Conditions | Yield |
---|---|
With Ti(N[t-Bu](3,5-Me2C6H3))3 In benzene at 20℃; Inert atmosphere; | > 95 %Spectr. |
Stage #1: 1-bromocyclohexane; Tetraphenyldiphosphin With manganese; CpCr[DppNC(Me)CHC(Me)NTol]; lead(II) bromide In tetrahydrofuran at 25℃; for 28h; Stage #2: | 70 %Spectr. |
Conditions | Yield |
---|---|
Stage #1: cyclohexyl chloride; Tetraphenyldiphosphin With manganese; CpCr[(XylNCMe)2CH]; lead(II) bromide In tetrahydrofuran at 55℃; for 312h; Stage #2: | 81 %Spectr. |
CpCr[DppNC(Me)CHC(Me)NTol](Cy)
Tetraphenyldiphosphin
A
C29H36BrCrN2
B
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With 1-bromocyclohexane In benzene at 20℃; | A n/a B 96 %Spectr. |
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohexane; diphenylphosphane With manganese; CpCr[(XylNCMe)2CH]; lead(II) bromide In tetrahydrofuran at 25℃; for 28h; Stage #2: | 83 %Spectr. |
CpCr[DppNC(Me)CHC(Me)NTol](Cy)
diphenylphosphane
A
C29H36BrCrN2
B
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
With 1-bromocyclohexane In benzene at 20℃; | A n/a B 30 %Spectr. |
CpCr[DppNC(Me)CHC(Me)NTol](Cy)
chloro-diphenylphosphine
A
[(cyclopentadienyl)Cr(III)Cl(2,6-(Me2CH)2C6H3NC(Me)CH(Me)NC6H4Me)]
B
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In benzene at 20℃; | A n/a B 94 %Spectr. |
chloro-diphenylphosphine
cyclohexylmagnesium bromide
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran at 0 - 20℃; |
Conditions | Yield |
---|---|
With [κ5-N,N,N,N,C-(Me3SiNCH2CH2)2NCH2CH2NSiMe2CH2]Zr In benzene-d6 at 20℃; for 72h; UV-irradiation; | |
With C34H64N4Si4Sm In neat (no solvent) at 90℃; for 168h; Temperature; Inert atmosphere; Sealed tube; chemoselective reaction; |
cyclohexyldiphenylphosphine
(cyclohexyl)diphenylphosphane 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 1.33333h; Irradiation; | 99% |
With dihydrogen peroxide Yield given; |
[WI2(CO)(NCMe)(η(2)-MeC2Me)2]
cyclohexyldiphenylphosphine
bis(PPh2Cy)(η2-but-2-yne)carbonyldi-iodotungsten
Conditions | Yield |
---|---|
In dichloromethane N2 atmosphere; addn. of PPh2(C6H11) to soln. of W-complex (stirring), stirring (3 days), filtration; removal of solvent (vac.), recrystn. (CH2Cl2); elem. anal.; | 98% |
cyclohexyldiphenylphosphine
(diphenylcyclohexylphosphine)gold(I) chloride
Conditions | Yield |
---|---|
Stage #1: hydrogen tetrachloroaurate(III) tetrahydrate With propyl sulfide In ethanol at 40℃; for 0.166667h; Stage #2: cyclohexyldiphenylphosphine In ethanol at 40℃; for 1h; | 95% |
rac.-[Ru(η6:η1-2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl)Cl2]
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In dichloromethane byproducts: AgCl; under N2; CH2Cl2 added to mixt. of Ru complex, AgSbF6 and phosphine, mixt. stirred in the dark; monitoring by NMR; filtration through Celite, filtrate evapd. under vac., crystn. on slow diffusion of Et2O into CH2Cl2 soln.; elem. anal.; | 94% |
Conditions | Yield |
---|---|
With copper(l) iodide In dichloromethane; acetonitrile | 94% |
Conditions | Yield |
---|---|
In 1,4-dioxane at 100℃; | 93% |
cyclohexyldiphenylphosphine
bis(cyclohexyldiphenylphosphine)nickel(II) chloride
Conditions | Yield |
---|---|
In ethanol at 80℃; for 1h; Sealed tube; Inert atmosphere; | 92% |
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1.5h; | 90.6% |
dimethylsulfide borane complex
cyclohexyldiphenylphosphine
diphenylcyclohexylphosphine-borane complex
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 20h; Inert atmosphere; Schlenk technique; | 90% |
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane; water at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h; | 90% |
1-bromo-butane
cyclohexyldiphenylphosphine
n-butyl cyclohexyl phenyl phosphine
Conditions | Yield |
---|---|
Stage #1: cyclohexyldiphenylphosphine In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; Stage #2: 1-bromo-butane In tetrahydrofuran for 0.5h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
Stage #1: silver perchlorate; thiosemicarbazide; acetone In acetonitrile at 50℃; for 1h; Stage #2: cyclohexyldiphenylphosphine In chloroform; acetonitrile for 0.5h; | 88% |
cyclohexyldiphenylphosphine
cobalt(II) chloride
[CoCl2(cyclohexyldiphenylphosphine)2]
Conditions | Yield |
---|---|
In ethanol soln. of phosphine in ethanol was added to soln. of CoCl2 in ethanol; mixt. was stirred for 24 h; filtered; washed (ethanol, pentane); dried in vac.; extd. (Soxhlet, boiling pentane, several d); soln. removed; residue dried (vac.); elem. anal.; | 87% |
cyclohexyldiphenylphosphine
[Pt2(P(C6H11)Ph2)2(μ-Cl)2Cl2]
Conditions | Yield |
---|---|
In further solvent(s) stoich. amts., refluxing and stirring in Cl2CHCHCl2 for 60 min; cooling to room temp., solvent removal (vac.), dissoln. in CHCl3, filtration, hexane addn., crystn. (-30°C); elem. anal.; | 86% |
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In methanol; acetonitrile at 65℃; for 24h; | 85% |
Conditions | Yield |
---|---|
In acetonitrile for 16h; Reflux; | 84% |
Conditions | Yield |
---|---|
In water byproducts: KCl; reduction of HAuCl4 with thiodiglycol at 0°C, followed by the phosphine addition; intermediate complex was washed several times with EtOH and then reacted with KCN; elem. anal.; | 82% |
Conditions | Yield |
---|---|
In methanol at 70℃; | 82% |
Conditions | Yield |
---|---|
With pyridine In acetonitrile for 2.5h; Reflux; | 81% |
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In dichloromethane React. of W-compd. with 4 equiv of PPh2Cy (CH2Cl2, dry N2, room temp.).; Elem. anal.; | 80% |
[Pd(3,5-dichloro-2,4,6-trifluorophenyl)2(1,5-cyclooctadiene)]
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In tetrahydrofuran to a stirred soln. of complex in THF was added phosphine, 30 min; concd., n-hexane was added, evapd.; elem. anal.; | 80% |
bis(1,5-cyclooctadiene)nickel (0)
N,N-Dimethyl-1-cyanoformamide
triphenylborane
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In benzene stoich. reaction of nickel compd., phosphine deriv., nitrile deriv. and borane deriv. in benzene at room temp.; evapn., washing with hexane; | 80% |
bis(4-bromomethylphenyl)methanone
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 100℃; for 72h; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
In methanol; water; acetonitrile at 20℃; for 3h; Darkness; | 80% |
Conditions | Yield |
---|---|
Stage #1: palladium diacetate; saccharin In water; acetonitrile at 20℃; for 0.5h; Stage #2: cyclohexyldiphenylphosphine In methanol; water; acetonitrile Reflux; | 80% |
methanol
[RhCl(1,5-cyclooctadiene)(tris(hydroxymethyl)phosphine)]
hydrogen
cyclohexyldiphenylphosphine
Conditions | Yield |
---|---|
In methanol; [(2)H6]acetone 2 equiv. of PMePh2 in acetone-d4 added to soln. of Rh complex in CH3OH at room temp.(Ar) in NMR tube, filled with H2, shaked; crystd. for 12 h, filtered, washed (Et2O), dried (vac.) overnight; | 79% |
Conditions | Yield |
---|---|
In water; isopropyl alcohol; acetonitrile at 20℃; for 1h; | 79% |
Molecular Structure of Cyclohexyldiphenylphosphine (CAS NO.6372-42-5):
IUPAC Name: Cyclohexyl(diphenyl)phosphane
Molecular Formula: C18H21P
Molecular Weight: 268.34
EINECS: 228-904-2
XLogP3-AA: 4.9
H-Bond Donor: 0
H-Bond Acceptor: 0
Melting Point: 58-62 °C(lit.)
Flash Point: 189.4 °C
Enthalpy of Vaporization: 59.7 kJ/mol
Boiling Point: 374 °C at 760 mmHg
Vapour Pressure: 1.85E-05 mmHg at 25 °C
Water Solubility: insoluble
Sensitive: Air Sensitive
Appearance: white to light yellow crystal powder
Canonical SMILES: C1CCC(CC1)P(C2=CC=CC=C2)C3=CC=CC=C3
InChI: InChI=1S/C18H21P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-2,4-7,10-13,18H,3,8-9,14-15H2
InChIKey: ZXKWUYWWVSKKQZ-UHFFFAOYSA-N
Product Categories: Ligand; Phosphine Ligands; Synthetic Organic Chemistry; Basic Phosphine LigandsCatalysis and Inorganic Chemistry; Catalysis and Inorganic Chemistry; Cross-Coupling; Phosphine Ligands; Phosphorus Compounds
Safety Information of Cyclohexyldiphenylphosphine (CAS NO.6372-42-5):
Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
RTECS: SY8387500
Cyclohexyldiphenylphosphine (CAS NO.6372-42-5), its Synonyms are Diphenylcyclohexylphosphine ; Phosphine, cyclohexyldiphenyl- ; Cyclohexyldiphenyl-phosphin ; Cyclohexyl diphenyl phosphine .
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