Product Name

  • Name

    TRIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE

  • EINECS
  • CAS No. 13406-29-6
  • Article Data20
  • CAS DataBase
  • Density
  • Solubility Insoluble in water.
  • Melting Point 70-75 °C
  • Formula C21H12F9P
  • Boiling Point 382.8 °C at 760 mmHg
  • Molecular Weight 466.286
  • Flash Point 185.3 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 13406-29-6 (TRIS(4-TRIFLUOROMETHYLPHENYL)PHOSPHINE)
  • Hazard Symbols IrritantXi
  • Synonyms Phosphine,tris(a,a,a-trifluoro-p-tolyl)- (7CI,8CI);Tris[4-(trifluoromethyl)phenyl]phosphine;Tris[p-(trifluoromethyl)phenyl]phosphine;
  • PSA 13.59000
  • LogP 6.50120

Synthetic route

tris(4-trifluoromethylphenyl)phosphine oxide
13406-27-4

tris(4-trifluoromethylphenyl)phosphine oxide

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
With diisobutylaluminium hydride In cyclohexane at 72℃; for 14h;93%
Stage #1: tris(4-trifluoromethylphenyl)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 6h; Glovebox; Inert atmosphere; Sealed tube;		92%
With [AlH3(triethylamine)] In hexane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;88 %Chromat.
With hexylsilane; trifluorormethanesulfonic acid In toluene at 70℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction;>= 99 %Spectr.
With 2,6-dimethylpyridine; oxalyl dichloride; hydrogen; tris(2,6-difluorophenyl)borane triethylphosphine oxide In (2)H8-toluene at 130℃; under 3000.3 Torr; for 48h; Reagent/catalyst;57 %Spectr.
p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
Stage #1: p-trifluoromethylphenyl bromide With magnesium dihydride In diethyl ether at 20℃; for 1h;
Stage #2: With phosphorus trichloride In diethyl ether at 20℃; for 1h;		72%
Stage #1: p-trifluoromethylphenyl bromide With magnesium In diethyl ether for 2h; Reflux; Schlenk technique; Inert atmosphere;
Stage #2: With phosphorus trichloride In diethyl ether at 0℃; for 1h; Reflux; Schlenk technique; Inert atmosphere;		63%
With phosphorus trichloride 2) Et2O, reflux, 1h; Yield given. Multistep reaction;
(4-(trifluoromethyl)phenyl)zinc(II) bromide
198345-82-3

(4-(trifluoromethyl)phenyl)zinc(II) bromide

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
With phosphorus trichloride In acetonitrile at 20℃; for 2h;53%
aqueous sodium chloride

aqueous sodium chloride

p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In diethyl ether; hexane; water35%
...Expand
4-(trifluoromethyl)phenylmagnesium bromide
402-51-7

4-(trifluoromethyl)phenylmagnesium bromide

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
With phosphorus trichloride
tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

tris(4-trifluoromethylphenyl)phosphine oxide
13406-27-4

tris(4-trifluoromethylphenyl)phosphine oxide

Conditions
ConditionsYield
With dihydrogen peroxide In dichloromethane; water at 20℃; for 3h; Glovebox; Inert atmosphere;100%
With gold(III) complex supported on cellulose extracted from Carthamus tinctorius immobilized on nanofibrous phosphosilicate; air at 20℃; for 1h; Irradiation;99%
With dihydrogen peroxide In dichloromethane; water for 0.75h; cooling;97%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C27H23BF9O2P

C27H23BF9O2P

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In benzene at 100℃; for 6h; Inert atmosphere; Sealed tube;100%
7-azido-4-methyl-2H-chromen-2-one

7-azido-4-methyl-2H-chromen-2-one

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

4 -methyl-7-((tris(4-(trifluoromethyl)phenyl)-λ5-phosphanylidene)amino)-2H-chromen-2-one

4 -methyl-7-((tris(4-(trifluoromethyl)phenyl)-λ5-phosphanylidene)amino)-2H-chromen-2-one

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;100%
dichloro(hydrotris(1-pyrazolyl)borate)(nitrido)osmium(IV)

dichloro(hydrotris(1-pyrazolyl)borate)(nitrido)osmium(IV)

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

(hydrotris(1-pyrazolyl)borate)Os[NP(p-CF3C6H4)3]Cl2

(hydrotris(1-pyrazolyl)borate)Os[NP(p-CF3C6H4)3]Cl2

Conditions
ConditionsYield
In dichloromethane under inert atm. soln. TpOs(N)Cl2 andphosphine ligand in CH2Cl2 was stirred for 1 h; soln. was concd., hexane was added, ppt. was washed with Et2O and recrystd. from CH2Cl2 and heptane; elem. anal.;97%
chloro(1,5-cyclooctadiene)rhodium(I) dimer

chloro(1,5-cyclooctadiene)rhodium(I) dimer

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
In acetone all manipulations under dry N2 atm.; 2 equiv. of P compd. added to soln.of Rh compd., stirred at room temp. (checked for completion by TLC); solvent removed in vac., isolated as crystalline solid; elem. anal.;97%
copper(l) iodide
7681-65-4

copper(l) iodide

2-(diphenylphosphaneyl)-4-methylpyridine
151131-87-2

2-(diphenylphosphaneyl)-4-methylpyridine

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; Darkness;97%
...Expand
copper(l) iodide

copper(l) iodide

2-(diphenylphosphino)pyridine
37943-90-1

2-(diphenylphosphino)pyridine

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

[(2-(diphenylphosphino)pyridine)(tris(4-trifluoromethylphenyl)phosphine)2Cu2I2]

[(2-(diphenylphosphino)pyridine)(tris(4-trifluoromethylphenyl)phosphine)2Cu2I2]

Conditions
ConditionsYield
In dichloromethane at 20℃; for 12h; Inert atmosphere; Schlenk technique; Darkness;96%
...Expand
carbon dioxide
124-38-9

carbon dioxide

2-(trimethylsilyl)phenyl trifluoromethanesulfonate
88284-48-4

2-(trimethylsilyl)phenyl trifluoromethanesulfonate

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

2-(tris(4-(trifluoromethyl)phenyl)phosphonio)benzoate

2-(tris(4-(trifluoromethyl)phenyl)phosphonio)benzoate

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 0 - 50℃; under 760.051 Torr; for 36h; Schlenk technique; Sealed tube;96%
...Expand
[RhCl(cis-cyclooctene)2]2
63902-12-5, 12279-09-3

[RhCl(cis-cyclooctene)2]2

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C84H48Cl2F36P4Rh2

C84H48Cl2F36P4Rh2

Conditions
ConditionsYield
In toluene at 20℃; Inert atmosphere;95.1%

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

oxotrichlorobis(tris(p-(trifluoromethyl)phenyl)phosphine)rhenium(V)

oxotrichlorobis(tris(p-(trifluoromethyl)phenyl)phosphine)rhenium(V)

Conditions
ConditionsYield
In dichloromethane stirring ReOCl3(As(C6H5)3)2 (0.33 mmol) and P(C6H4CF3)2 (0.66 mmol) in CH2Cl2 at room temp. for 27 h; concg. in vac.; addn. of heptane;; pptn.; filtering off, washing with heptane and drying in vac.; elem. anal.;;95%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

N-(1-methoxyethyl)phthalimide
22156-23-6

N-(1-methoxyethyl)phthalimide

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Conditions
ConditionsYield
Stage #1: tetrafluoroboric acid diethyl ether; tris(para-trifluoromethyl)phenyl phosphine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: N-(1-methoxyethyl)phthalimide With sodium bromide at 95℃; for 7h;		95%
...Expand
[osmium(II)dichloride(η6-p-cymene)]2

[osmium(II)dichloride(η6-p-cymene)]2

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

(p-cymene)OsCl2(P(p-CF3C6H4)3)
212556-61-1

(p-cymene)OsCl2(P(p-CF3C6H4)3)

Conditions
ConditionsYield
In dichloromethane inert atmosphere; stirring soln. of Os-complex with 2 equivs. of phosphine for 60 min at room temp.; evapn., washing (hexane), collection (filtration), drying (vac.); elem. anal.;92%
C12H20ClNOPtS

C12H20ClNOPtS

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C31H26ClF9NPPt

C31H26ClF9NPPt

Conditions
ConditionsYield
Inert atmosphere; Schlenk technique;92%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

cis-dichlorobis{tris(4-(trifluoromethyl)phenyl)phosphane}platinum(II)
92471-73-3, 92451-53-1

cis-dichlorobis{tris(4-(trifluoromethyl)phenyl)phosphane}platinum(II)

Conditions
ConditionsYield
In ethanol; water addn. of aq. soln. of K2(PtCl4) to hot ethanolic soln. of phosphane; stirring at room temp. for 25 h; filtering, washing with water, ethanol and ether, drying in vac. at room temp.;91%
tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

bis(4-trifluoromethylphenyl)phosphonium bromide

bis(4-trifluoromethylphenyl)phosphonium bromide

Conditions
ConditionsYield
With phosphorus tribromide; iron (III) bromide In tetrachloromethane at 0 - 80℃; for 10h;91%
chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II)
92390-26-6

chloro(1,5-cyclooctadiene)(pentamethylcyclopentadiene)ruthenium(II)

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

(η(5)-C5Me5)RuCl(P(p-CF3C6H4)3)2
172220-62-1

(η(5)-C5Me5)RuCl(P(p-CF3C6H4)3)2

Conditions
ConditionsYield
In tetrahydrofuran Ar or N2-atmosphere; 2 equivs. of phosphine, stirring overnight; evapn., addn. of hexane, stirring for 20 min, collection (filtration), washing (hexanes), drying (vac.); elem. anal.;90%
In tetrahydrofuran Ar or N2-atmosphere; 30°C; not sepd., enthalpy of reaction determined;
C18H22Cl2F2N2Pt2

C18H22Cl2F2N2Pt2

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C30H23ClF10NPPt

C30H23ClF10NPPt

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1.5h;90%
Fe2(CO)6[μ-SCCHCHC(CH3)CHCS]

Fe2(CO)6[μ-SCCHCHC(CH3)CHCS]

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C33H18F9Fe2O5PS2

C33H18F9Fe2O5PS2

Conditions
ConditionsYield
With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h;90%
iodobenzene
591-50-4

iodobenzene

[RhCl(cis-cyclooctene)2]2
63902-12-5, 12279-09-3

[RhCl(cis-cyclooctene)2]2

cesium pivalate

cesium pivalate

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

[(p-CF3-C6H4)3P]2 bis(pivalate) rhodium(I)Ph
851530-55-7

[(p-CF3-C6H4)3P]2 bis(pivalate) rhodium(I)Ph

Conditions
ConditionsYield
In 1,4-dioxane in dioxane at 120°C;89%
...Expand
1,1'-bis-(diphenylphosphino)ferrocene
12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

tetrakis(acetonitrile)palladium(II) tetrafluoroborate
21797-13-7

tetrakis(acetonitrile)palladium(II) tetrafluoroborate

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

[Pd(dppf)(P(p-C6H4CF3)3)][BF4]2

[Pd(dppf)(P(p-C6H4CF3)3)][BF4]2

Conditions
ConditionsYield
In acetone; benzene for 0.166667h; Inert atmosphere; Glovebox;88%
...Expand
(tetrahydrothiophene)gold(I) chloride
39929-21-0

(tetrahydrothiophene)gold(I) chloride

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

[tris(para(trifluoromethyl)phenyl)phosphine]gold(I) chloride
385815-83-8

[tris(para(trifluoromethyl)phenyl)phosphine]gold(I) chloride

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;87%
In dichloromethane
copper(l) iodide
7681-65-4

copper(l) iodide

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C84H48Cu4F36I4P4

C84H48Cu4F36I4P4

Conditions
ConditionsYield
In dichloromethane for 12h; Schlenk technique;87%
(cyclooctadienyl)(cyclopentadienyl)ruthenium chloride

(cyclooctadienyl)(cyclopentadienyl)ruthenium chloride

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

(η(5)-C5H5)RuCl(P(p-CF3C6H4)3)2
172220-60-9

(η(5)-C5H5)RuCl(P(p-CF3C6H4)3)2

Conditions
ConditionsYield
In tetrahydrofuran Ar or N2-atmosphere; 2 equivs. of phosphine, stirring overnight; evapn., addn. of hexane, stirring for 20 min, collection (filtration), washing (hexanes), drying (vac.); elem. anal.;86%
In tetrahydrofuran Ar or N2-atmosphere; 30°C; not sepd., enthalpy of reaction determined;
[(η(5)-C5H5)Re(NO)(CO)(MeCN)]BF4
92269-93-7

[(η(5)-C5H5)Re(NO)(CO)(MeCN)]BF4

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

[(μ5-C5H5)Re(NO)(CO)(P(4-C6H4CF3)3)]BF4
344800-64-2

[(μ5-C5H5)Re(NO)(CO)(P(4-C6H4CF3)3)]BF4

Conditions
ConditionsYield
In butanone all manipulations under dry N2 atm.; EtCOMe added to Re complex and the phosphane, refluxed for 46 h; allowed to cool, hexane added, filtered, washed with pentane, dried in vac., elem. anal.;85%
acetylacetonatodicarbonylrhodium(l)

acetylacetonatodicarbonylrhodium(l)

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

Rh(CO)((CH3CO)2CH)(P(C6H4CF3)3)
201140-99-0

Rh(CO)((CH3CO)2CH)(P(C6H4CF3)3)

Conditions
ConditionsYield
In dichloromethane byproducts: CO; Ar or N2-atmosphere, 30°C; elem. anal.;85%
hydrogen tetrachloroaurate(III) tetrahydrate

hydrogen tetrachloroaurate(III) tetrahydrate

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

[tris(para(trifluoromethyl)phenyl)phosphine]gold(I) chloride
385815-83-8

[tris(para(trifluoromethyl)phenyl)phosphine]gold(I) chloride

Conditions
ConditionsYield
With β-thiodiglucol In methanol; dichloromethane; water under N2 or Ar using Schlenk techniques; in the dark; soln. of HAuCl4*4H2O dissolved in H2O/MeOH; cooled; soln. of β-thiodiglucol in MeOH added with stirring; soln. of org. ligand in MeOH/CH2Cl2 added; mixt. stirred overnight; MeOH added; solvent removed (vac.); recrystd. (CH2Cl2/hexane); dried (vac.);85%
(1,5-cyclooctadiene)dimethylplatinum(II)

(1,5-cyclooctadiene)dimethylplatinum(II)

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

cis-[Me2Pt(P(p-CF3C6H4)3)2]
220556-61-6

cis-[Me2Pt(P(p-CF3C6H4)3)2]

Conditions
ConditionsYield
In not given byproducts: cyclooctadiene; 2 equiv. of phosphine; elem. anal.;84%
1-Iodo-perfluorodecane
423-62-1

1-Iodo-perfluorodecane

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

(perfluorodecyl)bis(4-(trifluoromethyl)phenyl)phosphine

(perfluorodecyl)bis(4-(trifluoromethyl)phenyl)phosphine

Conditions
ConditionsYield
In chloroform-d1 at 20℃; for 30h; Irradiation; Sealed tube; Inert atmosphere;84%
at 15 - 25℃; for 30h; Irradiation; Sealed tube; Inert atmosphere;61 %Spectr.
μ-(1,2-ethanedithilato)diironhexacarbonyl

μ-(1,2-ethanedithilato)diironhexacarbonyl

tris(para-trifluoromethyl)phenyl phosphine
13406-29-6

tris(para-trifluoromethyl)phenyl phosphine

C28H16F9Fe2O5PS2

C28H16F9Fe2O5PS2

Conditions
ConditionsYield
With trimethylamine-N-oxide In dichloromethane; acetonitrile at 20℃; for 1h;84%

Phosphine,tris[4-(trifluoromethyl)phenyl]- Specification

The Phosphine,tris[4-(trifluoromethyl)phenyl]-, with CAS registry number 13406-29-6, belongs to the following product category: Ligand. It has the systematic name of tris[4-(trifluoromethyl)phenyl]phosphane. This chemical is a kind of white to light yellow crystal powder. And the chemical formula of this chemical is C21H12F9P.

Physical properties of Phosphine,tris[4-(trifluoromethyl)phenyl]-: (1)ACD/LogP: 7.41; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.41; (4)ACD/LogD (pH 7.4): 7.41; (5)#H bond acceptors: 0; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 3; (8)Polar Surface Area: 13.59 Å2; (9)Flash Point: 185.3 °C; (10)Enthalpy of Vaporization: 60.66 kJ/mol; (11)Boiling Point: 382.8 °C at 760 mmHg; (12)Vapour Pressure: 1.01E-05 mmHg at 25°C.

Uses of Phosphine,tris[4-(trifluoromethyl)phenyl]-: it can be used to produce Difluortris(p-trifluormethylphenyl)phosphoran. This reaction will need reagent 10 % IF5 and solvent acetonitrile. The reaction temperature is 0 ℃. The yield is about 34.2%.

When you are using this chemical, please be cautious about it as the following:
The Phosphine,tris[4-(trifluoromethyl)phenyl]- irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(ccc1C(F)(F)F)P(c2ccc(cc2)C(F)(F)F)c3ccc(cc3)C(F)(F)F
(2)InChI: InChI=1/C21H12F9P/c22-19(23,24)13-1-7-16(8-2-13)31(17-9-3-14(4-10-17)20(25,26)27)18-11-5-15(6-12-18)21(28,29)30/h1-12H
(3)InChIKey: PXYCJKZSCDFXLR-UHFFFAOYAI
(4)Std. InChI: InChI=1S/C21H12F9P/c22-19(23,24)13-1-7-16(8-2-13)31(17-9-3-14(4-10-17)20(25,26)27)18-11-5-15(6-12-18)21(28,29)30/h1-12H
(5)Std. InChIKey: PXYCJKZSCDFXLR-UHFFFAOYSA-N

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