methanol
methylenebis(diphenylphosphane)-borane(1:2)
A
Trimethyl borate
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In toluene at 100℃; Inert atmosphere; | A n/a B 100% |
Conditions | Yield |
---|---|
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 16h; | 95% |
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 16h; | 95% |
Stage #1: diphenylphosphane 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 16h; Inert atmosphere; Molecular sieve; | 95% |
ethanol
methylenebis(diphenylphosphane)-borane(1:2)
A
triethyl borate
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Inert atmosphere; Reflux; | A n/a B 91% |
Conditions | Yield |
---|---|
Stage #1: tetraphenyldiphosphine oxide; Cp2Ti=CH2 In benzene at 50℃; Stage #2: at 80℃; | 66% |
Conditions | Yield |
---|---|
With tris(dimethylamino)(methylimino)phosphorane In tetrahydrofuran; diethyl ether for 24h; Ambient temperature; | 50% |
With potassium hydroxide; potassium carbonate 1.) HMPT, 20 deg C, 2.) 40 - 45 deg C, 1 h; Yield given. Multistep reaction; | |
With potassium hydroxide; potassium carbonate 1) HMPA, 20 deg C, 2) HMPA, 40-45 deg C, 1 h; Yield given. Multistep reaction; |
chloroform
potassium diphenylphosphine
A
Tetraphenyldiphosphin
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In ammonia at -50℃; | A n/a B 45% |
In ammonia at -50℃; Product distribution; Mechanism; another solvent; | A n/a B 45% |
Conditions | Yield |
---|---|
With sodium und Umsetzung mit CH2Cl2; |
(diphenylphosphinomethyl)diphenylphosphine sulphide
A
bis(diphenylthiophosphoryl)methane
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
at 150℃; vacuum; | |
at 150℃; vacuum sublimation; |
Lithium-bis(diphenylphosphanyl)methanid
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In tetrahydrofuran for 0.25h; Ambient temperature; |
C25H21CsP2
cyclohexylamine
A
Caesium-cyclohexylamid
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Equilibrium constant; pK; |
Conditions | Yield |
---|---|
With Pd2(bis(diphenylphosphino)methane)3 Quantum yield; Irradiation; |
Conditions | Yield |
---|---|
With phosphazene base-P4-tert-butyl In tetrahydrofuran; diethyl ether for 24h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at 0℃; for 0.5h; |
PdPtCoI(CO)3(dppm)2
A
{Pd(η2-dppm)(DMSO)2}I2
B
{Pt(η2-dppm)(DMSO)2}I2
C
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide To a soln. of PdPtCoI(CO)3(dppm)2 in DMSO was added I2. This resulted in an immediate color change from deep red to red-orange.; Not isolated. Detected by (31)P-NMR.; |
A
Co2(CO)4(μ-CO)2(μ-bis(diphenylphosphino)methane)
C
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With CO In not given in presence of CO; not isolated; detected by NMR; |
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In not given equilibrium in soln.; (31)P NMR data; |
Pt((C6H5)2PCH2P(C6H5)2)2(C6F5)2
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In not given equilibrium in soln.; (31)P NMR data; |
A
(μ2-CH2)(Cl)2(bis(diphenylphosphino)methane)2dipalladium
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With dichloromethane In dichloromethane Irradiation (UV/VIS); |
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane warming the soln. to ambient temp.; |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Zn / acetonitrile 2: CO / not given View Scheme |
Co2(CO)4(μ-CO)2(μ-bis(diphenylphosphino)methane)
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: I2 / tetrahydrofuran 2: Zn / acetonitrile 3: CO / not given View Scheme |
B
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: not given 2: not given View Scheme |
diphenyl(trimethylsilylmethyl)phosphane
A
bis[{(trimethylsilyl)methyl}phenylphosphino]methane
B
<(Diphenylarsino)methyl>diphenylphosphan
E
Diphenylphosphine oxide
F
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With arsenic trichloride In neat (no solvent) at 90 - 100℃; Solvent; |
dichlorophenylarsine
diphenyl(trimethylsilylmethyl)phosphane
A
dpma
B
<(Diphenylarsino)methyl>diphenylphosphan
C
bis(diphenylphosphino)methane monooxide
E
diphenyl(methyl)phosphine
F
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In neat (no solvent) at 90 - 100℃; Inert atmosphere; |
mer,cis-(Mn(CO)2(dppm-PP')(dppm-P)Br)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With sodium methylate In methanol for 72h; Guerbet Reaction; Glovebox; |
Conditions | Yield |
---|---|
With HOF* CH3CN In dichloromethane at 0℃; for 0.0833333h; | 100% |
With dihydrogen peroxide In dichloromethane; water for 0.0833333h; | 93% |
With dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 2h; | 90% |
{(carbonyl)3cobalt(μ-hexafluorobut-2-yne)cobalt(carbonyl)3}
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With benzophenone ketyl In not given inert gas; 293 K; a small amount benzophenone ketyl was added to a solution of the metal complex and the P-compound; solvent was removed; chromatographed; | 100% |
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)
bis-diphenylphosphinomethane
A
tetracarbonyl-bis(diphenylphosphino)methane-molybdenum(0)
B
bicyclo[2.2.1]hepta-2,5-diene
Conditions | Yield |
---|---|
In tetrahydrofuran reaction in a calorimeter under argon; | A 100% B n/a |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In toluene (N2 or Ar); complex added to ligand soln., suspn. stirred at 80°C for 15 h; filtered off, washed with toluene and Et2O; | 100% |
In toluene at 80℃; for 12h; |
trichlorotris(tetrahydrofuran)molybdenum(III)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
Mo(III) complex and excess diphosphine heating to melting point of the diphosphine for 10 min, on cooling the solid washing with hot toluene; identified by elem. anal., and IR spectrum; | 100% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In acetone PtCl2 was reacted with ligand in boiling acetone for 5 h; | 100% |
pentacarbonyl-(μ-di-tert-butylphosphido)-(μ-dicyclohexylphosphido)diiron
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In tetrahydrofuran (Ar); stirring (25°C, 2 h); solvent removal (vac.), extracting (pentane), filtn., solvent redn. (vac.), crystn. (-30°C); elem. anal.; | 100% |
Conditions | Yield |
---|---|
for 0.0833333h; Sonication; | A 100% B n/a |
trichlorotris(tetrahydrofuran)chromium(III)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In not given ligand reacted with Cr complex (A.Bollmann, K.Blann, J.T.Dixon, F.M.Hess, E.Killian et al. J. Am. Chem. Soc. 126 (2004) 14712); elem. anal.; | 99% |
[(PPh3)ClPd(μ-[C=C(H)-N=CPh2])PdCl(PPh3)2]*toluene
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane byproducts: PPh3; all manipulations under purified N2; org. compd. added to soln. of Pd complex, stirred for 10 min; solvent removed in vac., residue rinsed with Et2O, dried, elem. anal.; | 99% |
[MoCl(SnCl3)(CO)3(NCCH3)2]
bis-diphenylphosphinomethane
MoCl(SnCl3)(CO)3((C6H5)2P(CH2)P(C6H5)2)
Conditions | Yield |
---|---|
In acetone stirring 30 min, under dry nitrogen stream; removal of solvent in vacuo, elem anal.; | 99% |
cis-dirhenium diacetate tetrachloride dihydrate
bis-diphenylphosphinomethane
[Re2Cl4(μ-bis(diphenylphosphino)methane)2]
Conditions | Yield |
---|---|
In ethanol by refluxing ethanol soln. contg. cis-Re2(μ-O2CCH3)2Cl4(H2O)2 and bis(diphenylphosphino)methane for 18 h under N2; | 99% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane byproducts: cyclooctadiene; under Ar; to a soln. of the Pt complex and the phosphine in CH2Cl2 was added NH4PF6, stirred for 3 h; solvent was removed, washed with pentane, redissolved in CH2Cl2, passed through an alumina column, evapd. to dryness, washed with pentane, dried in vac.; elem. anal.; | 99% |
[Mo2(η5-cyclopentadienyl)2(μ-H)(μ-PCy2)(CO)2]
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In toluene (N2); stirring molybdenum compd. and phosphine deriv. in toluene at roomtemp. for 2 h; | 99% |
1,4-pyrazine
methanol
bis-diphenylphosphinomethane
copper(I) bromide
Conditions | Yield |
---|---|
In dichloromethane mixt. of CuBr, C4H4N2 and (Ph2P)2CH2 (1:2:1 molar ratio) in CH2Cl2 stirred (6 h, ambient temp.); elem. anal.; | 99% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
heating; | 99% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
heating; | 99% |
silver trifluoromethanesulfonate
mercuric triflate
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
In dichloromethane | 99% |
Conditions | Yield |
---|---|
With Et3N In acetonitrile byproducts: [Et3NH]NO3; alcohol-comp. then excess of Et3N were added to 3 equiv. of AgNO3 in MeCN, stirring for 3 h, 3 equiv. of solid P-compd. was added, stirring for 18 h; soln. was filtered through Celite, evapd. to dryness, solid was washed with H2O, Et2O and dried, recrystn. from CH2Cl2/hexane; | 99% |
2,4,6-trimethylbenzylbromide
bis-diphenylphosphinomethane
[(diphenylphosphino)methyl]diphenyl[(2,4,6-trimethylphenyl)methyl]phosphonium bromide
Conditions | Yield |
---|---|
In toluene at 80℃; for 48h; Inert atmosphere; | 99% |
bis-diphenylphosphinomethane
(diphenylphosphinomethyl)(ferrocenylmethyl)diphenylphosphoniumiodide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide byproducts: N(CH3)3; (N2), mixture stirred for 5 hat 120°C, cooled to 20°C; solvent removed in vacuo, residue washed with toluene and pentane, dried in vacuo; | 98.5% |
p-methylazidobenzene
bis-diphenylphosphinomethane
bis(N-p-tolyliminodiphenylphosphoranyl)methane
Conditions | Yield |
---|---|
In benzene at 60℃; for 4h; | 98% |
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With bromine In dichloromethane | 98% |
With bromine In dichloromethane at -78 - 20℃; | 100 % Spectr. |
dodecacarbonyl-triangulo-triruthenium
bis-diphenylphosphinomethane
(Ru3(CO)11)2((C6H5)2PCH2P(C6H5)2)
Conditions | Yield |
---|---|
With sodium diphenylketyl In tetrahydrofuran a THF soln. of Ph2CONa was added dropwise under N2 to a soln. of Ru3(CO)12 and dppm in 2:1 molar ratio in THF, reaction was monitored by IR spectroscopy; THF was pumped off under vac., residue recrystd.; elem. anal.; | 98% |
Conditions | Yield |
---|---|
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.; | 98% |
potassium tetrachloroplatinate(II)
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With NaBH4 In acetonitrile (N2); stirring (12 h); filtn., washing (pentane), drying; | 98% |
bis-diphenylphosphinomethane
Co4(CO)7(H2C(P(C6H5)2)2)(HC(P(C6H5)2)3)
Conditions | Yield |
---|---|
In tetrahydrofuran refluxed in THF for 2 h; filtered through silica gel, evapd. to dryness; washed with diethylether; | 98% |
silver(I) hexafluorophosphate
bis-diphenylphosphinomethane
Conditions | Yield |
---|---|
With n-hexane In dichloromethane; acetone ligand was added to soln. of Rh-complewx in dichloromethane, followed by soln. of AgPF6 in acetone, soln. stirred for 5 min; Et2O added, soln. filtered, filtrate evapd. to dryness under reduced pressure, residue triturated with Et2O, filtered off, washed with Et2O anddried in vacuo over P2O5, product recrystd. from acetone-n-hexane; elem. anal.; | 98% |
carbonylchlorohydridotris(triphenylphosphine)ruthenium(II)
bis-diphenylphosphinomethane
[RuHCl(CO)(PPh3)2(dppm)]
Conditions | Yield |
---|---|
In toluene in an oxygen-free environment; a suspn. of the Ru complex in toluene was treated with the phosphine, refluxed for 30 min; cooled to room temp., concd. in vac., slow addn. of pentane, filtered, washed with pentane and Et2O, dried in vac. (mixt. of cis- and trans-isomers); elem. anal.; | 98% |
In dichloromethane under N2 or Ar; addn. of phosphine to a CH2Cl2 soln. of the Ru complex,mixt. stirred (23°C, 72 h); mixt. cooled (-15°C), crystals filtered off, washed (Et2O); the mixt. of isomers could not be sepd.; | 70% |
The Methylenebis(diphenylphosphine), with the CAS registry number 2071-20-7, is also known as Bis(diphenylphosphino)methane. It belongs to the product categories of Phosphines; Ligand; Phosphine Ligands; Synthetic Organic Chemistry. Its EINECS registry number is 218-194-2. This chemical's molecular formula is C25H22P2 and molecular weight is 384.39. Its IUPAC name is called diphenylphosphanylmethyl(diphenyl)phosphane. What's more, this chemical is white to light yellow crystal powder, which is used in inorganic and organometallic chemistry as a ligand. It is more specifically a chelating ligand because it is a ligand that is attached to the central metals (the phosphorus) by bonds from two or more donor atoms.
Physical properties of Methylenebis(diphenylphosphine): (1)ACD/LogP: 8.57; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 8.57; (4)ACD/LogD (pH 7.4): 8.57; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 1090949.38; (8)ACD/KOC (pH 7.4): 1090949.38; (9)#Freely Rotating Bonds: 6; (10)Flash Point: 270.2 °C; (11)Enthalpy of Vaporization: 73.61 kJ/mol; (12)Boiling Point: 497.2 °C at 760 mmHg; (13)Vapour Pressure: 1.55E-09 mmHg at 25°C.
Preparation: this chemical can be prepared by diphenylphosphane and dichloromethane. This reaction will need reagent (Me2N)3P=NMe and solvents diethyl ether, tetrahydrofuran. The reaction time is 24 hours at ambient temperature. The yield is about 50%.
Uses of Methylenebis(diphenylphosphine): it can be used to produce 1,1,3,3-tetraphenyl-[1,3]diphosphinanediium; dibromide. This reaction will need solvent dimethylformamide.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)P(CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
(2)InChI: InChI=1S/C25H22P2/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/h1-20H,21H2
(3)InChIKey: XGCDBGRZEKYHNV-UHFFFAOYSA-N
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View