1663-45-2

Basic information

• Product Name: 1,2-Bis(diphenylphosphino)ethane
• Synonyms: [2-(Diphenylphosphino)ethyl](diphenyl)phosphine;1,2-Ethanediylbis(diphenylphosphine);1,2-ethanediylbis[diphenyl-phosphin;bis(diphenylphosphine)ethane;P,P'-Ethylenebis(diphenylphosphine);Phosphine, 1,2-ethanediylbis*diphenyl-;Phosphine, ethylenebis*diphenyl-;Phosphine, ethylenebis[diphenyl-
• CAS NO: 1663-45-2
• Molecular Formula: C₂₆H₂₄P₂
• Molecular Weight: 398.42
• EINECS: 216-769-2
• Product Categories: Phosphines;Ligand;Phosphine Ligands;Synthetic Organic Chemistry;organophosphine ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 1663-45-2.mol
• Article Data: 46

Chemical Properties

• Melting Point: 137-142 °C(lit.)
• Boiling Point: 514.815 °C at 760 mmHg
• Flash Point: 281.728 °C
• Appearance: White to off-white/Crystalline Powder or Crystals
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in acetone, methanol and alcoholic hydrochloric acid.
• Sensitive: Air Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May be air-sensitive.
• BRN: 761261
• CAS DataBase Reference: 1,2-Bis(diphenylphosphino)ethane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(diphenylphosphino)ethane(1663-45-2)
• EPA Substance Registry System: 1,2-Bis(diphenylphosphino)ethane(1663-45-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26-36
• WGK Germany: 3
• F: 9
• TSCA: Yes
• Hazardous Substances Data: 1663-45-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 1663-45-2 differently. You can refer to the following data:
1. suzuki reaction
2. 1,2-Bis(diphenylphosphino)ethane is a bidendate ligand used in coordination chemistry to prepare metal complexes. It is involved in the metal-catalyzed allylic alkylation and decarboxylation of allylic esters. It is also used in 1,3-diene synthesis. Further, it is used in cycloaddition reactions and carbonylation reactions. In addition to this, it is used to prepare bis(dicyclohexylphosphino)ethane by hydrogenation.

Purification Methods

Recrystallise it from aqueous EtOH or *C6H6. The dimethiodide, when recrystallised from MeOH has m 305-307o, and the dioxide when recrystallised from toluene or DMF (needles), or *C6H6 (plates) has m 252-254o (276-278o) [Isslieb et al. Chem Ber 92 3175 1959, NMR: Aquiar et al. J Org Chem 29 1660 1964, B.ckvall et al. J Org Chem 52 5430 1987]. [Beilstein 16 IV 958.]

InChI:InChI=1/C26H24P2/c1-22(27(23-14-6-2-7-15-23)24-16-8-3-9-17-24)28(25-18-10-4-11-19-25)26-20-12-5-13-21-26/h2-22H,1H3

Synthetic route

(1,2-bis(diphenylphosphino)ethane)tetracarbonylmolybdenum (15444-66-3) + (1,2-bis(diphenylarsino)ethane)molybdenum tetracarbonyl (38536-63-9) → (1-diphenylphosphino-2-diphenylarsinoethane)molybdenum tetracarbonyl (53557-42-9) + 1,2-bis(diphenylarsino)ethane (4431-24-7) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
reaction in a calorimeter under argon;	A 100% B n/a C n/a

cyclopentadienylmolybdenum(III)(bis(diphenylphosphino)ethane)Cl2 + trimethylphosphane (594-09-2) → cyclopentadienylmolybdenum(III)(PMe3)2Cl2 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 2.3:1) in CH2Cl2;;	A 100% B n/a

diphenylphosphane (829-85-6) + acetylene (74-86-2) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With potassium hydroxide In water; dimethyl sulfoxide for 1h;	97%

1,2-bis(diphenylphosphinoyl)ethane (4141-50-8) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
Stage #1: 1,2-bis(diphenylphosphinoyl)ethane 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 13.5h; Glovebox; Inert atmosphere; Sealed tube;	97%
With 1,1,3,3-Tetramethyldisiloxane; titanium(IV) isopropylate In various solvent(s) at 100℃; for 7h;	95%
With titanium(IV) isopropylate; Triethoxysilane In tetrahydrofuran at 67℃;	90%

1,2-bis(diphenylphosphinothioyl)ethane (7615-76-1) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With Raney-Ni In ethanol; benzene at 20℃; for 3h; Inert atmosphere;	97%

1,2-bis(diphenylphosphanyl)ethane monoxide (984-43-0) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With diethoxymethylane; Bis(p-nitrophenyl) phosphate In toluene at 110℃; Inert atmosphere; chemoselective reaction;	96%
With Bis(p-nitrophenyl) phosphate; 1,3-diphenyl-disiloxane In ethyl acetate at 23℃; for 70h; Sealed tube; chemoselective reaction;	96%
Stage #1: 1,2-bis(diphenylphosphanyl)ethane monoxide 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 4h; Glovebox; Inert atmosphere; Sealed tube;	90%

/PBGRG362--165/ → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With sodium hydrogencarbonate; tetrafluoroboric acid dimethyl ether complex In dichloromethane 1.) a.) -5 up to 25 deg C; b.) 25 deg C, 12h; 2.) 0 deg C;	92%

diphenylphosphane (829-85-6) + Diphenylvinylphosphine (2155-96-6) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide at 20℃;	90%

[dppeP][Br] + diphenyldisulfane (882-33-7) → triphenyl thiophosphite (1095-04-1) + C32H29P2S(1+)*Br(1-) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In dichloromethane for 1h; Inert atmosphere;	A 90% B n/a C n/a

ethylene dibromide (106-93-4) + diphenylphosphane (829-85-6) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With cesium hydroxide; 4 Angstroem MS In N,N-dimethyl-formamide at 23℃; for 36h;	78%
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 36h;	78%
Stage #1: diphenylphosphane With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 1h; Molecular sieve; Inert atmosphere; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 20℃; for 36h; Inert atmosphere; Molecular sieve;	78%
With cesiumhydroxide monohydrate In N,N-dimethyl-formamide at 20℃; for 36h; Molecular sieve; Inert atmosphere;	78%
With tris(dimethylamino)(methylimino)phosphorane In tetrahydrofuran; diethyl ether for 24h; Ambient temperature;

1,2-dichloro-ethane (107-06-2) + triphenylphosphine (603-35-0) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With lithium In tetrahydrofuran at 0℃; for 0.5h;	70%
With lithium In tetrahydrofuran; water at 50℃; for 4.5h; Inert atmosphere;	18 g

chloro-diphenylphosphine (1079-66-9) + 1,2-dichloro-ethane (107-06-2) → Tetraphenyldiphosphin (1101-41-3) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; tetra-(n-butyl)ammonium iodide In various solvent(s) Ambient temperature; elektrochemical reaction, anode Mg bar, cathode stainless steel; var. solv.; Yields of byproduct given;	A n/a B 65%

chloro-diphenylphosphine (1079-66-9) + 1,2-dichloro-ethane (107-06-2) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; tetrabutylammonium tetrafluoroborate; tetra-(n-butyl)ammonium iodide Ambient temperature; electrolysis;	65%

bromobenzene (108-86-1) + C20H19P2(1-) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran -78 deg C, 10 min, RT, 30 min;	62%

chloro-diphenylphosphine (1079-66-9) + ethylene dibromide (106-93-4) → Tetraphenyldiphosphin (1101-41-3) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With tetrabutylammonium tetrafluoroborate; tetra-(n-butyl)ammonium iodide In various solvent(s) Ambient temperature; elektrochemical reaction, anode Mg bar, cathode stainless steel; var. solv.; Yields of byproduct given;	A n/a B 40%

chloro-diphenylphosphine (1079-66-9) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With sodium und Umsetzung mit 1,2-Dibrom-aethan;
Multi-step reaction with 3 steps 1: 75 percent / NEt3 / tetrahydrofuran / 2.5 h / 0 - 20 °C 2: 9.1 percent / 250 °C 3: 84 percent / HSiCl3 / toluene / 12 h / 145 °C View Scheme

1,2-dichloro-ethane (107-06-2) + diphenylphosphane (829-85-6) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With potassium hydroxide 1.) DMSO, 20 deg C, 2.) 50 deg C, 1 h; Yield given. Multistep reaction;
With potassium hydroxide; potassium carbonate 1) DMSO, 20 deg C, 2) DMSO, 50 deg C, 1 h; Yield given. Multistep reaction;

1,2-bis(diphenylphosphino)ethane bis(borane) (24456-27-7) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With sodium hydrogencarbonate; tetrafluoroboric acid dimethyl ether complex 1.) CH2Cl2, from -5 to -25 degC, 12h; 2.) water, 0 degC; Yield given. Multistep reaction;

1,2-bis(diphenylphosphanyloxy)ethane (85324-78-3) → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 9.1 percent / 250 °C 2: 84 percent / HSiCl3 / toluene / 12 h / 145 °C View Scheme

bis(diphenylphosphino)ethane diborane → 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With piperazinomethyl polystyrene resin In toluene at 60℃; for 16h;

{NiJ2-(1.2-Bis-diphenylphosphino-aethan)2} (19615-85-1, 16126-81-1, 19978-60-0, 66972-96-1) → {NiJ2-1.2-Bis-diphenylphosphino-aethan} (15629-91-1, 47671-01-2) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In not given dissocn. equilibrium in soln.;
In not given dissocn. equilibrium in soln.;

{Mn(CO)2(η2-DPPE)(η1-DPPE)}(1-) (115162-69-1) → Mn(CO)3(η1-DPPE) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With carbon monoxide In tetrahydrofuran 1 atm carbon monoxide, ca. 30 min;

bis(cyanotrihydroborato)N,N-dimethylformamide-1,2-bis(diphenylphosphino)ethanecobalt(II) + N,N-dimethyl acetamide (127-19-5) → bis(cyanotrihydroborato)tetrakis(N,N-dimethylformamide)cobalt(II) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In N,N-dimethyl-formamide Co(BH3CN)2(Diphos)(DMF) was dissolved in DMF.; Addn. of ether produced crystals of Co(BH3CN)2(DMF)4.;

{NiBr2-(1.2-Bis-diphenylphosphino-aethan)2} (19615-83-9, 19978-59-7, 14403-79-3, 66972-95-0, 1240788-71-9) → dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) (14647-21-3) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In not given dissocn. equilibrium in soln.;
In not given dissocn. equilibrium in soln.;

trans-Mo(NH)I(Ph2PCH2CH2PPh2)2(1+) → trans-bisdinitrogenbis(1,2-diphenylphosphinoethane)molybdenum(0) + ammonia (7664-41-7) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
With nitrogen In tetrahydrofuran Electrolysis; electrolysis of molybdenum imide at mercury pool cathode in THF containing 0.2 M (NBu4)BF4 and saturated with N2 (1 atm);; Mo-complex identified by (31)P NMR and cyclovoltammetry and IR; also unidentified compounds obtained;

FeH(C6H4PPhCH2CH2PPh2)(dppe) + iodine (7553-56-2) → Fe(2+)*(P(C6H5)2CH2CH2P(C6H5)2)*2I(1-)=Fe(P(C6H5)2CH2CH2P(C6H5)2)I2 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Fe(NO)2(CO)(tri-n-butylphosphine) → [1,2-bis(diphenylphosphino)ethane]dinitrosyliron + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In toluene Kinetics;
In toluene Kinetics;

cyclopentadienylmolybdenum(III)(bis(diphenylphosphino)ethane)Cl2 + triethylphosphine (554-70-1) → {Cp(PEt3)2molybdenum(III) dichloride} + 1,2-bis-(diphenylphosphino)ethane (1663-45-2)

Conditions	Yield
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 3.7:1) in CH2Cl2; a molar artio of 2.1:1 yields an equilibrium;;	A >99 B n/a

dichloro(1,5-cyclooctadiene)platinum(ll) (12080-32-9) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → [platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)] (83095-83-4, 14647-25-7)

Conditions	Yield
In dichloromethane dropwise addn. of 1 equiv. dppe to Pt-complex; crystn. on Et2O addn.;	100%
In chloroform-d1 Pt complex dissolved in CDCl3, org. compd. added as a asolid, mixture stirred for 30 min; product not isolated, detected by NMR;
In not given displacement of cyclooctadiene;

C5H5FeC8H12(1+)*Li{CH2N(CH3)2}2(1-)=FeLiC19H33N2 (69393-63-1) + benzyllithium (766-04-1) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → C5H5Fe{(C6H5)2PCH2}2(CH2C6H5) (64827-29-8)

Conditions	Yield
In benzene addn. of 1 equiv. PhCH2Li to equimolar soln. of {CpFe(COD)}{Li(TMEDA)} in benzene at 25°C;	100%

(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0) (12146-37-1, 124717-04-0) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (1,2-bis(diphenylphosphino)ethane)tetracarbonylmolybdenum (15444-66-3) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0)

Conditions	Yield
In tetrahydrofuran reaction in a calorimeter under argon;	A 100% B n/a

tungsten hexacarbonyl (14040-11-0) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → tetracarbonyl-1,2-bis(diphenylphosphino)ethane-tungsten(0) (29890-05-9) + {μ-bis(diphenylphosphino)ethane}-bis{pentacarbonyltungsten(0)} (15413-06-6)

Conditions	Yield
With trimethylamine-N-oxide In acetonitrile W(CO)6 and Me3NO stirred in MeCN (20°C, 30 min, under nitrogen), addn. of diphosphine (molar ratio W(CO)6 : phosphine = 2:1), heated (75°C, 16 h), soln. pumped to dryness; washed with hexane; 31P-NMR;	A 0% B 100%

{N(C2H5)4}(1+)*{FeCo3(CO)12}(1-)={N(C2H5)4}{FeCo3(CO)12} + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → HFeCo3*10CO*P(C6H5)2CH2CH2P(C6H5)2=HFeCo3(CO)10P(C6H5)2CH2CH2P(C6H5)2

Conditions	Yield
With HCl In dichloromethane; acetone reflux in acetone for 10 min, recrystn. of the N(C2H5)4-compd., protonation with concd. HCl in CH2Cl2;	100%

(C5H5)MoCl2(P(C6H5)3)2 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → cyclopentadienylmolybdenum(III)(bis(diphenylphosphino)ethane)Cl2

Conditions	Yield
In dichloromethane byproducts: P(C6H5)3; mixing of the Mo compd. with the free phosphine (molar ratio 1:1) in CH2Cl2;;	100%
In tetrahydrofuran byproducts: P(C6H5)3; mixing of the Mo compd. with an excess of free phosphine in THF;;	100%

{W(NN(C6H5)2)Cl4} + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → {WCl3(NN(C6H5)2)((C6H5)2PCH2)2}

Conditions	Yield
With Zn In dichloromethane (N2); stirring (0.5 h); zinc decantation, pptn. on pentane addn., filtn., washing (pentane), drying (vac.);	100%
With zinc

Pd2{(η6-C6H5)Cr(CO)3}2(μ-Cl)2(PPh3)2 (136827-07-1) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → cis-Pd{(η6-C6H5)Cr(CO)3}Cl(dppe) (136805-10-2)

Conditions	Yield
In benzene (Ar), stirred at room temp. for 30 min; precipitated by hexane, washed with hexane, dried in vac., recrystd. from CH2Cl2/hexane, elem. anal.;	100%

{Cp(PMePh2)2molybdenum(III) dichloride} + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → cyclopentadienylmolybdenum(III)(bis(diphenylphosphino)ethane)Cl2 + diphenyl(methyl)phosphine (1486-28-8)

Conditions	Yield
In dichloromethane mixing of the Mo compd. with the free phosphine (molar ratio 1.1:1) inCH2Cl2;;	A 100% B n/a

germanium(II) chloride dioxane + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-Ethandiylbis(diphenylphosphan)-dichlorgermylen (77495-41-1)

Conditions	Yield
In toluene byproducts: C4H8O2; equimolar amts. of educts, 1 h, toluene and dioxane removed; crystd. from toluene;	100%
In toluene byproducts: dioxane; calcd. amts. of educts stirred at room temp. for 1 h, under Ar; evapd., recrystd. from benzene or benzene/toluene, elem. anal.;	100%

RuH((C6H5)2PCH2CH2P(C6H5)2)(C8H12)(NCCHCOOC2H5)*0.5C6H6 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → RuH((C6H5)2PCH2CH2P(C6H5)2)2(NCCHCOOC2H5)*0.5C6H6

Conditions	Yield
In benzene-d6 byproducts: 1,5-cyclooctadiene; 50°C, 118 h; NMR monitoring;	100%

(4RS,5RS)-2,2-dimethyl-α,α,α′,α′-tetraphenyl-1,3-dioxolane-4,5-dimethanol (93222-42-5) + titanium tetrachloride (7550-45-0) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → TiCl2(α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolate)(1,2-bis(diphenylphosphino)ethane) (215033-86-6)

Conditions	Yield
In tetrahydrofuran; diethyl ether; dichloromethane N2-atmosphere; stirring (room temp., 30 min), THF addn., stirring (1 h),evapn., CH2Cl2 and dppe addn., stirring (1 h); filtering, crystn. (CH2Cl2, -25°C); elem. anal.;	100%

{platinum(II)(μ-chloride)(pentafluorophenyl)(tetrahydrothiophene)}2 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → cis-[Pt(II)Cl(pentafluorophenyl)(1,2-bis(diphenylphosphino)ethane)] (212498-15-2)

Conditions	Yield
In chloroform byproducts: C4H8S; (N2); Schlenk technique; P ligand (2 equiv.) was added to soln. of Pt complex in CHCl3 at room temp.; soln. was stirred for 2 h; concd.; treated with pentane; filtered; dried (vac.); elem. anal.;	100%

[Mo(NNPh2)Cl3] + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → MoCl3NN(C6H5)2((C6H5)2PCH2)2

Conditions	Yield
With Zn In dichloromethane (N2); stirring (0.5 h); zinc decantation, pptn. on pentane addn., filtn., washing (pentane), drying (vac.);	100%

hexafluoro-1,4-naphthoquinone (1024-60-8) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 3,3'-(ethane-1,2-diylbis(diphenylphosphonionediyl))bis(5,6,7,8-tetrafluoro-1,4-dioxo-1,4-dihydronaphthalen-2-olate)

Conditions	Yield
In water; dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere;	100%

1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphinoyl)ethane (4141-50-8)

Conditions	Yield
With dihydrogen peroxide In dichloromethane; water for 0.0833333h;	99%
With dihydrogen peroxide In dichloromethane; water at 23℃; for 0.166667h; Inert atmosphere;	99%
With dihydrogen peroxide In dichloromethane; water for 0.0833333h;	98%

tetrakis(acetonitrile)copper(I)tetrafluoroborate + 1,10-phenanthroline hydrate (5144-89-8) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (1,10-phenanthroline)(1,2-bis(diphenylphosphino)ethane)copper(I) tetrafluoroborate (498584-34-2)

Conditions	Yield
In dichloromethane (N2); Cu complex was reacted with P ligand in CH2Cl2; phenanthroline wasadded after dissolution; mixt. was stirred for 1 h; solvent removed (vac.); Et2O added; pptd.; washed (Et2O);	99%

trichlorotris(tetrahydrofuran)chromium(III) (10170-68-0, 16997-54-9) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → [(1,2-bis(diphenylphosphino)ethane)CrCl2(μ-Cl)]2 (1119091-66-5)

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%

[2,2]bipyridinyl (366-18-7) + silver perchlorate + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → [Ag2(2,2'-bipyridyl)2(dppe)(ClO4)2] (936008-41-2)

Conditions	Yield
In acetonitrile stoich. mixt. in CH3CN stirred for 12 h at room temp.; evapd., washed (Et2O), elem. anal.;	99%

dimanganese decacarbonyl (10170-69-1) + dichloromethane (75-09-2) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → fac-Mn(CO)3(chloro)(1,2-bis(diphenylphosphino)ethane) (49695-20-7)

Conditions	Yield
In dichloromethane autoclave (N2, 130°C, 2 h); solvent removal, recrystn. (CH2Cl2/hexane);	99%

carbonylgold(I) chloride (50960-82-2) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane digold(I) dichloride (18024-34-5)

Conditions	Yield
In benzene byproducts: CO; soln. of Ph2PCH2CH2PPh2 dropped to soln. of (OC)AuCl at room temp. under dry N2, stirred for 1 h (CO removed); filtered;	99%

tungsten hexacarbonyl (14040-11-0) + acetone (67-64-1) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → fac-[W(CO)3(1,2-bis(diphenylphosphino)ethane)(Me2CO)] (87900-84-3, 84411-66-5)

Conditions	Yield
In acetone Irradiation (UV/VIS); N2-atmosphere; irradn. (450 W Hg lamp, 10 h); evapn. (vac.), washing (hexane / Et2O = 3 : 1), drying (vac.);	99%

Pt(Sn(CH3)3)2(P(CH3C6H4)3)2 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → 1,2-bis(diphenylphosphino)ethane-bis-(trimethylstannyl)platinum(II) (32035-20-4)

Conditions	Yield
	99%

(N,N,N',N'-tetramethylethylenediamine)Pd(phenyl)I + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (1,2-bis(diphenylphosphino)ethane)2Pd(phenyl)I (60674-49-9)

Conditions	Yield
In toluene under N2 atm. mixt. Pd complex and ligand in toluene was stirred at roomtemp. for 3 h; ppt. was separated, washed with hexane, dried under vac., product was recrystd. from 1,2-dichloroethane-hexane at 5°C for 1.5 h, ppt. wasseparated, washed with hexane, dried under vac.;	99%
In chloroform equiv. amts.; stirring (5-10 min, room temp.); solvent removal; drying (vac., 4 h), recrystn. (CH2Cl2/n-pentane);	87%

{Ru(η5-C7H11)2H}BF4 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → (η5-2,4-dimethylpentadienyl)bis(diphenylphosphino)ethaneiodoruthenium(II)

Conditions	Yield
With KI In acetone (N2); Ru-compound added slowly to soln. of KI and DPPE at 195 K; stirred at 195 K for 1 h; warmed to room temperature; stirred for 5 h; solvent evapd.; extd. (toluene); filtered; partial evapd.; pentane added; cooled (250 K); elem. anal.;	99%

[PdCl(C6H9)]2 + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → Pd(C6H9)(C2H4(P(C6H5)2)2)(1+)*Cl(1-)=[Pd(C6H9)(C2H4(P(C6H5)2)2)]Cl (203798-18-9)

Conditions	Yield
org. ligand addn. to Pd-complex in THF or CDCl3;	99%
In chloroform-d1 solvent addn. to org. ligand and Pd-complex in NMR tube filled with N2;

[(μ2-pentamethylcyclopentadienylgallium)3(pentamethylcyclopentadienylgallium)diplatinum] + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → [platinum(0)bis(1,2-bis(diphenylphosphino)ethane)] (25398-76-9)

Conditions	Yield
In not given	99%

tetrakis(acetonitrile)copper(I)tetrafluoroborate + pentacarbonyl(1,3-diethylimidazolin-2-ylidene)tungsten(0) + carbon monoxide (201230-82-2) + 1,2-bis-(diphenylphosphino)ethane (1663-45-2) → tungsten hexacarbonyl (14040-11-0) + [ Cu(1,2-bis(diphenylphosphino)ethane)2]BF4 (147892-57-7)

Conditions	Yield
N2-atmosphere; 3 equiv. of phosphine;	A 60% B 99%

Upstream product

• 107-06-2 1,2-dichloro-ethane 
• 829-85-6 diphenylphosphane 
• 106-93-4 ethylene dibromide 
• 74-86-2 acetylene 
• 4141-50-8 1,2-bis(diphenylphosphinoyl)ethane 
• 108-86-1 bromobenzene 
• 603-35-0 triphenylphosphine 
• 2155-96-6 Diphenylvinylphosphine 
• 115162-69-1 {Mn(CO)2(η2-DPPE)(η1-DPPE)}(1-) 
• 127-19-5 N,N-dimethyl acetamide 
• 19615-83-9 {NiBr₂-(1.2-Bis-diphenylphosphino-aethan)2} 
• 672-66-2 Dimethyl(phenyl)phosphine 
• 624-73-7 1,2-Diiodoethane 
• 1079-66-9 chloro-diphenylphosphine 

Downstream Products

• 23054-00-4 Ethan-1,2-bis- 
• 33476-38-9 1,2-bis5-azenyl>ethane 
• 98170-72-0 C₂₆H₃₆P₂ 
• 135491-07-5 4,4,7,7-tetraphenyl-4,7-diphosphonia-1,10-decadioic acid dichloride 
• 113237-53-9 tetrachlorure d'octaphenyl-1,1,6,6,9,9,14,14 tetraphosphonia-1,6,9,14 cyclohexadecadiene-3,11 
• 66055-14-9 1,2-bis(N-cyanodiphenylphospha-λ⁵-azeno)ethane 
• 141973-92-4 C₃₀H₂₉NP₂⁽²⁺⁾*2I^(1-) 
• 141973-91-3 C₃₁H₃₂O₂P₂⁽²⁺⁾*2I^(1-) 
• 79731-24-1 C₃₀H₃₂N₈O₄P₂ 
• 141973-89-9 C₃₁H₃₂OP₂⁽²⁺⁾*2I^(1-) 
• 53380-83-9 bis-N(trimethylsilyl)-ethylenebis(diphenylphosphine)imine 
• 141973-90-2 C₃₆H₃₄OP₂⁽²⁺⁾*2I^(1-) 
• 4129-36-6 1,2-bis5-azenyl>ethane 
• 82220-50-6 <2-(diphenylphosphino)ethyl>(9-fluorenyl)diphenylphosphonium bromide 

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A zinc coordination polymer, [ZnI2{Ph2P(O)-CH2CH2-P(O)Ph2}]n (1), has been prepared, which features a one-dimensional concavo-convex chain with alternative ZnI2 and 1,2-bis(diphenylphosphino)ethane dioxide (dppeO2) moieties. The dppeO2 ligand adopts the bridging coordination mode between two zin...detailed

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A mild and efficient CsOH-promoted synthesis of ditertiary phosphines

A mild and efficient method for the synthesis of ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves, and DMF, various dihalides were coupled with diphenylphosphine at room temperature, and the results have demonstrated that this methodology offers a general synthetic procedure producing a variety of ditertiary phosphines in high yields.

A Mild One-Pot Reduction of Phosphine(V) Oxides Affording Phosphines(III) and Their Metal Catalysts

The metal-free reduction of a range of phosphine(V) oxides employing oxalyl chloride as an activating agent and hexachlorodisilane as reducing reagent has been achieved under mild reaction conditions. The method was successfully applied to the reduction of industrial waste byproduct triphenylphosphine(V) oxide, closing the phosphorus cycle to cleanly regenerate triphenylphosphine(III). Mechanistic studies and quantum chemical calculations support the attack of the dissociated chloride anion of intermediated phosphonium salt at the silicon of the disilane as the rate-limiting step for deprotection. The exquisite purity of the resultant phosphine(III) ligands after the simple removal of volatiles under reduced pressure circumvents laborious purification prior to metalation and has permitted the facile formation of important transition metal catalysts.

Preparation technology of bis(dibenzyl)phosphorane

The invention provides a preparation technology of bis(dibenzyl)phosphorane and belongs to the technical field of synthesis of organic matters. The technology comprises the following steps: taking metallic lithium, triphenylphosphine and water to react to generate dibenzylphosphorane; taking the dibenzylphosphorane to react with dihalogenohydrocarbon to generate the bis(dibenzyl)phosphorane. According to a production technology, an intermediate product and an intermediate byproduct do not need to be separated; the technology is simple in technological operation, low in raw material cost and high in yield and can be used for producing the low-cost and high-quality bis(dibenzyl)phosphorane.