• Name

  1,1'-Bis(diphenylphosphino)ferrocene

• EINECS 430-420-3
• CAS No. 12150-46-8
• Article Data13
• CAS DataBase
• Density
• Solubility Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
• Melting Point 181-182 °C (dec.)(lit.)
• Formula C₃₄H₂₈FeP₂
• Boiling Point 363.8oC at 760mmHg
• Molecular Weight 556.407
• Flash Point 182.8oC
• Transport Information
• Appearance deep yellow crystalline powder
• Safety 22-24/25-45-28A-36-26
• Risk Codes 25-36/37/38-20/21/22
• Molecular Structure
• Hazard Symbols T,Xn,Xi
• Synonyms 1,1`-Bis(diphenylphosphino)errocene;Phosphine,1,1'-ferrocenediylbis[diphenyl- (8CI);Phosphine, cyclopentadienyldiphenyl-,iron deriv. (7CI);1,1'-Ferrocendiylbis(diphenylphosphine);DPPF;NSC 238923;1,1'-Bis(diphenylphosphino)ferrocene(DPPF);
• PSA 27.18000
• LogP 6.38890

Synthetic route

405164-68-3

[Fe(η5-C5H4P(OPh)2)2]

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
With tributylphosphine; iodine In tetrahydrofuran; acetonitrile at 20℃; for 0.166667h; Inert atmosphere;	94%

1,1'-bis(diphenylphosphino)ferrocene tetrafluoroborate

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
In methanol for 8h; Reflux;	92%

83272-80-4

lithium diphenylphosphinocyclopentadienyl

iron(II) chloride

1,2-bis(diphenylphosphanyl)-4-tert-butylcyclopentadienyl lithium

A

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

B

403815-19-0

1,1′,2,2′-tetrakis(diphenylphosphino)-4,4′-di-tert-butylferrocene

C

878190-65-9

1,1',2'-tris(diphenylphosphino)-4-tert-butylferrocene

Conditions

Conditions	Yield
In tetrahydrofuran (Ar); dropwise addn. of a soln. of trisubstituted lithium compd. in THF to a suspn. of iron salt in THF at -40°C, stirring for 2 h at room temp., addn. of a soln. of monosubstituted lithium salt in THF at -40°C; evapn., reflux in toluene for 3 h, cooling, filtration, column chromy. (SiO2, toluene/hexane 4:1); elem. anal.;	A n/a B n/a C 84%

...Expand

32660-24-5

bis(2-(diphenylphosphoryl)cyclopenta-2,4-dien-1-yl)iron

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
With Bis(p-nitrophenyl) phosphate; 1,3-diphenyl-disiloxane In ethyl acetate at 23℃; for 48h; Sealed tube; chemoselective reaction;	83%
With bis(2-chlorophenyl)borinic acid; phenylsilane In toluene at 80℃; for 18h; Inert atmosphere;	71%
With [AlH3(triethylamine)] In hexane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;	93 %Chromat.

1,1'-(ferrocenediyl)phenylphosphine

591-51-5

phenyllithium

1079-66-9

chloro-diphenylphosphine

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
In not given Fe complex was added to large excess of Li compd.; elem. anal.;	79%
In diethyl ether (N2); flask charged with excess of C6H5Li and Et2O, complex soln. addeddropwise at room temp. over 30 min, stirred for 30 min at room temp., (C6H5)2PCl soln. added dropwise for 10 min, stirred for 10 min at room temp.; chromd. (CH2Cl2/pentane), evapd. (vac.), recrystd. (C6H6/hexane) at -10°C;	79%

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102-54-5

ferrocene

1079-66-9

chloro-diphenylphosphine

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
Stage #1: ferrocene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane at 20℃; Inert atmosphere; Stage #2: chloro-diphenylphosphine In tetrahydrofuran; dichloromethane at -78 - 20℃; for 3h; Inert atmosphere;	73%

717901-49-0

[(η6-hexamethylbenzene)Ru(1,1'-bis(diphenylphosphino)ferrocene)(NCS)]PF6

540-72-7

sodium thiocyanide

A

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

B

[(η6-hexamethylbenzene)Ru(NCS)2]2(μ-1,1'-bis(diphenylphosphino)ferrocene)

Conditions

Conditions	Yield
In acetonitrile (N2); stirring a mixt. of ruthenium complex and NaNCS in acetonitrile for 2 d; filtration, concn., addn. of ether, cooling to 0°C for 3 h; elem.anal.;	A n/a B 70%

...Expand

chloro(η5-cyclopentadienyl)(1,1'-bis(diphenylphosphino)ferrocene)ruthenium(II)

75-09-2

dichloromethane

148-18-5

sodium N,N-diethyldithiocarbamate

A

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

B

[(η5-cyclopentadienyl)Ru(diethyldithiocarbamato)]2(μ-1,1'-bis(diphenylphosphino)ferrocene)*CH2Cl2

Conditions

Conditions	Yield
In methanol (N2); refluxing a suspn. of ruthenium complex and ligand in MeOH for 10 h; filtration, washing with methanol, ether, drying in vac., recrystn. (CH2Cl2/hexane, 0°C, 1 h); elem. anal.;	A n/a B 60%

...Expand

201543-21-7

[(η(6)-hexamethylbenzene)RuCl(1,1'-bis(diphenylphosphino)ferrocene-P,P')]PF6

672-66-2

Dimethyl(phenyl)phosphine

A

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

B

717901-65-0

[(η6-hexamethylbenzene)Ru(PMe2Ph)2Cl]PF6

Conditions

Conditions	Yield
In acetonitrile (N2); addn. of phosphine to a soln. of ruthenium complex in acetonitrile, stirring for 8 h; filtration, concn.; elem. anal.;	A n/a B 60%

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[Ni(1,1'-bis(diphenylphosphino)ferrocene)2]PF6

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
With [Fe(C5H5)2]PF6 In tetrahydrofuran Fe(C5H5)2PF6 added to a soln. of Ni complex; not isolated, detected by NMR;
In 2-methyltetrahydrofuran studied by ESR; not isolated;

33272-09-2

1,1'-dilithioferrocene

14311-22-9

phenylthiodiphenylphosphine

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
In hexane; benzene under N2; dropwise addn. of PhSPPh2 in benzene to hexane soln. of complex over 30 min with stirring at -50°C, stirred at room temp. overnight; addn. of H2O, ppt. filtered off, washed (H2O, hexane), recrystd. (CH2Cl2);

Co(1,1'-bis(diphenylphosphino)ferrocene)2

A

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

B

7440-48-4

cobalt

Conditions

Conditions	Yield
In tetrahydrofuran Kinetics; (N2); decompn. in soln. at 22°C;

12098-17-8

(diphenylphosphin)ferrocene

1079-66-9

chloro-diphenylphosphine

A

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

B

1,2,1'-tris-diphenylphosphinoferrocene

C

1,3,1'-tris-diphenylphosphinoferrocene

Conditions

Conditions	Yield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydrogencarbonate In diethyl ether; hexane Ar-atmosphere; addn. of BuLi (2.1 equivs.) to ferrocene derivative, addn. of TMEDA, stirring (>=20 h), addn. of ClPPh2, stirring (room temp., 10 h); addn. of aq. NaHCO3, extn. (CH2Cl2), solvent removal, chromy. (Al2O3, hexanes/Et2O=8:2); elem. anal.;

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105019-26-9

Fe(C5H3(PPh2)PPh-1,3)(C5H4)

591-51-5

phenyllithium

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions

Conditions	Yield
In diethyl ether Ar-atmosphere; excess PhLi; mixing at -70°C, warming to room temp.; H2O addn. (cooling), drying of Et2O layer (MgSO4), partial evapn. (vac.), crystn. (hexanes);	>80

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

29892-37-3

chloro(dimethylsulfide) gold(I)

122092-52-8

1,1'-bis[chlorogold(I)diphenylphosphino]ferrocene

Conditions

Conditions	Yield
In dichloromethane	100%
In tetrahydrofuran a soln. of dppf is added slowly to a rapidly stirred soln. of the Au-compd. at room temp., mixt. is stirred for 30 min (Ar); ppt. is collected by filtn., redissolved in CH2Cl2, filtered and recrystd. from hexane, soln. is kept overnight at -20°C, crystals are collected and identified by spectroscopy;	87%

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

tetrakis(acetonitrile)copper(I)tetrafluoroborate

[Cu2(1,1′-bis(diphenylphosphino)ferrocene)(1,1′-bis(diphenylphosphino)ferrocene)2](BF4)2

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1h; Inert atmosphere;	100%

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

1295-35-8

bis(1,5-cyclooctadiene)nickel (0)

107-05-1

3-chloroprop-1-ene

[(η3-allyl)Ni(dppf)Cl]

Conditions

Conditions	Yield
In toluene at 20℃; for 12h; Inert atmosphere;	100%

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12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

64519-62-6, 16842-03-8

cobalt tetracarbonyl hydride

CoH(1,1'-bis(diphenylphosphanyl)ferrocene)(CO)2

Conditions

Conditions	Yield
In hexane; dichloromethane at 0℃; for 0.5h;	100%

7647-01-0

hydrogenchloride

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

7440-05-3

palladium

72287-26-4, 95464-05-4

(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride

Conditions

Conditions	Yield
In tetrahydrofuran; ethanol; water at 55 - 60℃; for 3h; Solvent; Temperature; Inert atmosphere;	99.7%

...Expand

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

864439-66-7, 864439-72-5, 864515-21-9

C18H22Cl2N4O2Pd2

C80H64Cl2Fe2N2P4Pd2

Conditions

Conditions	Yield
In acetone at 20℃; for 72h; Sealed tube;	99.5%

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

1469538-67-7

C19H24Cl2N4O3Pd2

1569542-91-1

C47H38Cl2FeN2OP2Pd2

Conditions

Conditions	Yield
In acetone at 20℃; for 72h; Sealed tube;	99.2%

1,1'-Bis(diphenylphosphino)ferrocene Specification