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Basic Information

Molecular Structure:
CAS No.:	137349-65-6
Name:	Bis(dicyclohexylphosphino)methane
Article Data:	7

Formula:	C₂₅H₄₆P₂
Molecular Weight:	408.588
Synonyms:	Methylenebis(dicyclohexylphosphine);Bis(dicyclohexylphosphino)methane;Phosphine,methylenebis[dicyclohexyl- (9CI);
Melting Point:	95-102 °C(lit.)
Boiling Point:	511.2 °C at 760 mmHg
Flash Point:	279.4 °C
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
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

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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