Bis(dicyclohexylphosphino)methane supplier

Name
Bis(dicyclohexylphosphino)methane
EINECS
CAS No. 137349-65-6
Article Data7
CAS DataBase
Density
Solubility
Melting Point 95-102 °C(lit.)
Formula C₂₅H₄₆P₂
Boiling Point 511.2 °C at 760 mmHg
Molecular Weight 408.588
Flash Point 279.4 °C
Transport Information
Appearance
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Methylenebis(dicyclohexylphosphine);Bis(dicyclohexylphosphino)methane;Phosphine,methylenebis[dicyclohexyl- (9CI);
PSA 27.18000
LogP 9.23850

Synthetic route

: 2071-20-7
bis-diphenylphosphinomethane

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
With Nb(OC6H3Ph2-2,6)2(CH2C6H4-4Me)3; hydrogen In cyclohexane at 100℃; under 62057.8 Torr; for 96h;	96%
With hydrogen In cyclohexane; water	96%

: 75-09-2
dichloromethane

: Cd(2+)*2C12H22P(1-)

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
at 70℃; for 12h;	95%

: 829-84-5
dicyclohexylphosphane

: 74-95-3
1,2-dibromomethane

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
Stage #1: dicyclohexylphosphane With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: 1,2-dibromomethane In N,N-dimethyl-formamide at 20℃; for 38h; Inert atmosphere; Molecular sieve;	85%

: 16523-54-9
chlorodicyclohexylphosphane

: 563539-93-5
C13H24LiP

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃;	83%

: Cy2PCH2SnPh3

: 16523-54-9
chlorodicyclohexylphosphane

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
at 240℃; for 0.333333h; Substitution;	80%

: 2071-20-7
bis-diphenylphosphinomethane

A: 137349-65-6
bis(dicyclohexylphosphino)methane

B: {Cyclohexyl-[(dicyclohexylphosphanyl)-methyl]-phosphanyl}-benzene

C: 83291-39-8
CyPCH2PPh2

D: C25H28P2

E: C25H34P2

Conditions

Conditions	Yield
With n-butyllithium; hydrogen; tris(2,6-diisopropylphenoxy) dichloroniobium(V) In hexane; benzene at 60℃; under 62057.8 Torr; Kinetics;

...Expand

: 542-18-7
cyclohexyl chloride

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Mg / diethyl ether / 2.5 h / Heating 2: PCl3 / diethyl ether 3: diethyl ether; pentane 4: tert-BuLi / heptane 5: 83 percent / tetrahydrofuran / -78 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: Mg / diethyl ether / 2.5 h / Heating 2: PCl3 / diethyl ether 3: 83 percent / tetrahydrofuran / -78 - 20 °C View Scheme

: 50420-46-7
dicyclohexylmethylphosphine

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tert-BuLi / heptane 2: 83 percent / tetrahydrofuran / -78 - 20 °C View Scheme

: 931-51-1
cyclohexylmagnesiumchloride

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: PCl3 / diethyl ether 2: diethyl ether; pentane 3: tert-BuLi / heptane 4: 83 percent / tetrahydrofuran / -78 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: PCl3 / diethyl ether 2: 83 percent / tetrahydrofuran / -78 - 20 °C View Scheme

: 16523-54-9
chlorodicyclohexylphosphane

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether; pentane 2: tert-BuLi / heptane 3: 83 percent / tetrahydrofuran / -78 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2: ethylmagnesium bromide / tetrahydrofuran / 0 - 20 °C 3: 12 h / 70 °C View Scheme

: 65768-05-0
diethyl-dicyclohexylphosphino-amine

: 137349-65-6
bis(dicyclohexylphosphino)methane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethylmagnesium bromide / tetrahydrofuran / 0 - 20 °C 2: 12 h / 70 °C View Scheme

: cobalt(II) chloride hexahydrate

: 75-09-2
dichloromethane

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [CoCl3(Cy2PCH2Cy2PH)]*0.5CH2Cl2

Conditions

Conditions	Yield
In methanol; toluene to a methanol-soln. of CoCl2*6H2O was added a toluene-soln. of diphosphine, the soln. was stirred for 12 h; stripped to dryness, dissolved in degased CH2Cl2, placed in a freezer; elem. anal.;	99.2%

...Expand

: 224195-09-9
(dimethyl sulfoxide)(2,6-diphenylpyridinate(2-))platinum(II)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 350045-85-1
[Pt2((C6H4)2C5H3N)2(μ-bis(dicyclohexylphosphino)methane)]

Conditions

Conditions	Yield
In chloroform mixt. stirred for 12 h under N2 at room temp.; soln. evapd. to dryness; purifn. by chromy. (Al, CH2Cl2 as eluent); elem. anal.;	99%

: PdCl2(COD)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 295325-16-5
Pd(dcpm)Cl2

Conditions

Conditions	Yield
In toluene (N2); addn. of phosphine to palladium complex in toluene, stirring at 20 °C for 5 min; decantation, washing with petroleum ether, drying under vac.;	98%

: trans[iodobis(triphenylphosphine)phenylpalladium(II)]

: 75-09-2
dichloromethane

: 137349-65-6
bis(dicyclohexylphosphino)methane

: C6H5PdI((C6H11)2PCH2P(C6H11)2)*CH2Cl2

Conditions

Conditions	Yield
In toluene (N2); addn. of phosphine soln. in toluene to a soln. of palladium complex in toluene, stirring for 12 h at room temp.; filtration, washing with petroleum ether, recrystn. (CH2Cl2-ether) at -25 °C; elem. anal.;	96%

...Expand

: 7681-65-4
copper(l) iodide

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [(copper(I))2(μ-bis(dicyclohexylphosphanyl)methane)2]I2

Conditions

Conditions	Yield
In acetone mixt. of Cu and P compds. in acetone stirred for 2 h at room temp.; filtered, recrystd. from CH2Cl2/Et2O, elem. anal.;	95%

: ammonium hexafluorophosphate

: [(AuCl)2{μ-(N-butylimidazol-N-yl-2-ylidene)2(CH2)}]

: 137349-65-6
bis(dicyclohexylphosphino)methane

: C40H70Au2N4P2(2+)*2F6P(1-)

Conditions

Conditions	Yield
Stage #1: [(AuCl)2{μ-(N-butylimidazol-N-yl-2-ylidene)2(CH2)}]; bis(dicyclohexylphosphino)methane In dichloromethane at 20℃; for 3h; Stage #2: ammonium hexafluorophosphate In dichloromethane; acetonitrile at 20℃; for 0.5h;	95%

...Expand

: nickel(II) chloride hexahydrate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [bis(dicyclohexylphosphino)methaneNiCl2] * C7H8

Conditions

Conditions	Yield
In methanol; toluene stirred, 12 h; elem. anal.;	94%

: dichlorotetrakis(dimethylsulfoxide)ruthenium(II)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: trans-RuCl2(bis(dicyclohexylphosphino)methane)2

Conditions

Conditions	Yield
In ethanol Ar-atmosphere; refluxing for 1 h; evapn., recrystn. (hot EtOH/PhCl=1:1, slow cooling, then standing overnight; two crops), collection (filtration), washing (cold EtOH), drying (vac.);	94%

: trans-[(Cy3P)2PtCl(InCl2)]

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [(Cy3P)(dcpm)Pt→InI3]

Conditions

Conditions	Yield
With ortho-difluorobenzene In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube;	94%

: 404573-66-6
bis(cycloocta-1,5-diene)rhodium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]-borate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [Rh(Cy2PCH2PCy2)(cyclooctadiene)] [BArF4]

Conditions

Conditions	Yield
In dichloromethane at -78 - 20℃; for 16h; Glovebox; Inert atmosphere; Schlenk technique;	93%

: (1,5-cyclooctadiene)Rh(η3-CH2Ph)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: (dcypm)Rh(η3-CH2Ph)

Conditions

Conditions	Yield
In hexane N2; equimolar amounts; 1h;; filtration; solvent concentration; crystn. at -40 ° C;;	92%

: 26042-63-7
silver(I) hexafluorophosphate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [Ag2(μ-bis(dicyclohexylphosphino)methane)](PF6)2

Conditions

Conditions	Yield
In dichloromethane soln. in CH2Cl2 was stirred at 40°C for 5 h; pptn. by Et2O, recrystn. by diffusion of Et2O into a CH2Cl2 soln.; elem. anal.;	92%

: 223596-54-1
[(η(5)-C5H5)Fe(CO)(μ-CN)2Cu(CH3CN)2]2

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [(η(5)-C5H5)Fe(CO)(CN)(μ-CN)Cu(bis(dicyclohexylphosphanyl)methane)]2

Conditions

Conditions	Yield
In dichloromethane; acetonitrile all manipulations under Ar atm.; soln. of org. compd. in CH2Cl2 slowly added to soln. of complex in MeCN, stirred for 30 min at ambient temp.; solvent removed in vac.;	92%

: 2923-28-6
silver trifluoromethanesulfonate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [Ag2(μ-bis(dicyclohexylphosphino)methane)](CF3SO3)2

Conditions

Conditions	Yield
In dichloromethane ssoln. in CH2Cl2 was stirred for 6 h; pptn. by Et2O, recrystn. by diffusion of Et2O into an acetonitrile soln.; elem. anal.;	90%

: 14515-95-8, 56083-13-7
cis-(tungsten tetracarbonyl bipiperidine)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 1001401-12-2
[W(CO)4(bis(dicyclohexylphosphino)methane)]

Conditions

Conditions	Yield
In dichloromethane (N2); reflux of PCy2CH2PCy2 and W(CO)4(NHC5H10)2 in CH2Cl2 for 4.5 h; cooling, filtration, addn. of MeOH; placing of mixt. in the freezer; removal of cryst., concn. of soln. on rotary evaporator; cooling in the freezer; crystn., elem. anal.;	90%

: cobalt(II) nitrate hexahydrate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 835605-09-9
((C6H11)2PCH2P(C6H11)2O)Co(NO3)2

Conditions

Conditions	Yield
In methanol; dichloromethane; toluene to a methanol soln. of Co-salt was added a toluene-soln. of diphosphine,CH2Cl2 was added to the soln., stirred for 12 h; stripped to dryness, dissolved in degased CH2Cl2, allowed to slow evapn.; elem. anal.;	89.4%

: 14057-91-1
tetrakis(acetonitrile)copper(I) perchlorate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [(copper(I))2(μ-bis(dicyclohexylphosphanyl)methane)2](ClO4)2

Conditions

Conditions	Yield
In acetone mixt. of Cu and P compds. in acetone stirred for 1 h at room temp.; solvent removed, Et2O added, recrystd. from CH2Cl2/Et2O, elem. anal.;	89%

: [Rh(cod)2]+[Al(OC(CF3)3)4]-

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [Rh(Cy2PCH2PCy2)(cyclooctadiene)][Al{OC(CF3)3}4]

Conditions

Conditions	Yield
In dichloromethane at -78 - 20℃; for 16h; Glovebox; Inert atmosphere; Schlenk technique;	89%

: 13869-38-0, 21264-32-4, 13869-42-6
bis(acetonitrile)dichloroplatinum(II)

: 75-09-2
dichloromethane

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [Pt(bis(dicyclohexylphosphino)methane)2]Cl2*0.5CH2Cl2

Conditions

Conditions	Yield
In dichloromethane stirring of CH2Cl2 soln. of Pt(NCMe)2Cl2 (1 equiv.) and PCy2CH2PCy2 (2 equiv.) for 48 h; concd., filtration, drying in vac., elem. anal.;	88%

...Expand

: 39929-21-0
(tetrahydrothiophene)gold(I) chloride

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 180333-95-3
[Au2(bis(dicyclohexylphosphanyl)methane)Cl2]

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;	87%
In tetrahydrofuran stoichiometric amounts of Au-complex and phosphine in THF; pptn. with pentane, vac.-filtered;

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [(copper(I))2(μ-bis(dicyclohexylphosphanyl)methane)2](PF6)2

Conditions

Conditions	Yield
In acetone mixt. of Cu and P compds. in acetone stirred for 1 h at room temp.; solvent removed, Et2O added, recrystd. from CH2Cl2/Et2O, elem. anal.;	86%

: 1,3-(μ-propanedithiolato)diironhexacarbonyl

: 75-09-2
dichloromethane

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 4[Fe2(CO)4(μ-SCH2CH2CH2S)(μ-bis(dicyclohexylphosphino)methane)]*2CH2Cl2

Conditions

Conditions	Yield
In toluene byproducts: CO; (N2); reflux of toluene soln. of Fe2(CO)6(SCH2CH2CH2S) and PCy2CH2PCy2 for 16 h; cooling to room temp., removal of volatiles by rotary evapn., washing with hexane; drying; dissolving in min. of CH2Cl2; chromy. on alumina; eluting with Et2O:hexane (1:9); elem. anal.;	84%

...Expand

: (hexafluoroacetylacetonato)(1,5-cyclooctadiene)rhodium(I)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 222017-64-3
(((C6H11)2P)2CH2)Rh(OC(CF3))2CH

: ((((C6H11)2P)2CH2)Rh)2((OC(CF3))2CH)2

Conditions

Conditions	Yield
In tetrahydrofuran Ar-atmosphere; slow phosphine soln. addn.; crystn.; elem. anal.;	A 82% B n/a

...Expand

: bis(bis(trimethylsilyl)amido)zinc(II)

: 128-39-2
2,6-di-tert-butylphenol

: 137349-65-6
bis(dicyclohexylphosphino)methane

: [Zn(2,6-di-tert-butylphenoxide)2]2(bisdicyclohexylphosphinomethane)

Conditions

Conditions	Yield
In toluene under Ar; toluene soln. of phosphine and substituted phenol (molar ratio 1:2) added to neat Zn compd.; stirred for 0.5 h; volatiles stripped away in vac.;	82%

...Expand

: (N,N,N',N'-tetramethylethylenediamine)dimethylpalladium(II)

: 137349-65-6
bis(dicyclohexylphosphino)methane

: 343987-35-9
(bis(dicyclohexylphosphino)methane)dimethylpalladium(II)

Conditions

Conditions	Yield
In benzene at room temp.; characterized spectroscopically and by single crystal X-ray diffraction;	82%

Bis(dicyclohexylphosphino)methane Specification

The Bis(dicyclohexylphosphino)methane, with CAS registry number 137349-65-6, has the systematic name of methanediylbis(dicyclohexylphosphane). Besides this, it is also called Bis(dicyclohexylphosphino)methane. And the chemical formula of this chemical is C₂₅H₄₆P₂.

Physical properties of Bis(dicyclohexylphosphino)methane: (1)ACD/LogP: 9.80; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 9.8; (4)ACD/LogD (pH 7.4): 9.8; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 5088476.5; (8)ACD/KOC (pH 7.4): 5088476.5; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 27.18 Å²; (13)Flash Point: 279.4 °C; (14)Enthalpy of Vaporization: 75.26 kJ/mol; (15)Boiling Point: 511.2 °C at 760 mmHg; (16)Vapour Pressure: 4.63E-10 mmHg at 25°C.

Preparation: this chemical can be prepared by tetra-P-phenyl-P,P'-methanediyl-bis-phosphane. This reaction will need reagents H₂, Nb(OC₆H₃Ph₂-2,6)₂(CH₂C₆H₄-4Me)₃ and solvent cyclohexane. The reaction time is 4 day(s) with reaction temperature of 100 ℃. The yield is about 96%.

When you are using this chemical, please be cautious about it as the following:
The Bis(dicyclohexylphosphino)methane 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: P(CP(C1CCCCC1)C2CCCCC2)(C3CCCCC3)C4CCCCC4
(2)InChI: InChI=1/C25H46P2/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25/h22-25H,1-21H2
(3)InChIKey: OWFLJHJHQKHZJR-UHFFFAOYAT
(4)Std. InChI: InChI=1S/C25H46P2/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25/h22-25H,1-21H2
(5)Std. InChIKey: OWFLJHJHQKHZJR-UHFFFAOYSA-N

Product Name

Bis(dicyclohexylphosphino)methane

Synthetic route

Bis(dicyclohexylphosphino)methane Specification

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