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12150-46-8

Basic Information
CAS No.: 12150-46-8
Name: 1,1'-Bis(diphenylphosphino)ferrocene
Molecular Structure:
Molecular Structure of 12150-46-8 (1,1'-Bis(diphenylphosphino)ferrocene)
Formula: C34H28FeP2
Molecular Weight: 554.39
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);
EINECS: 430-420-3
Density:
Melting Point: 181-182 °C (dec.)(lit.)
Boiling Point: 363.8oC at 760mmHg
Flash Point: 182.8oC
Solubility: Soluble in chloroform, dichloromethane, alcohol and pentane. Insoluble in water.
Appearance: deep yellow crystalline powder
Hazard Symbols: ToxicT,HarmfulXn,IrritantXi
Risk Codes: 25-36/37/38-20/21/22
Safety: 22-24/25-45-28A-36-26
Transport Information:
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
32660-24-5

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

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions
ConditionsYield
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
ConditionsYield
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%
102-54-5

ferrocene

1079-66-9

chloro-diphenylphosphine

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions
ConditionsYield
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
ConditionsYield
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%

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
ConditionsYield
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%
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
ConditionsYield
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%

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

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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.;
105019-26-9

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

591-51-5

phenyllithium

12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

Conditions
ConditionsYield
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
ConditionsYield
In dichloromethane100%
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
ConditionsYield
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
ConditionsYield
In toluene at 20℃; for 12h; Inert atmosphere;100%
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
ConditionsYield
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
ConditionsYield
In tetrahydrofuran; ethanol; water at 55 - 60℃; for 3h; Solvent; Temperature; Inert atmosphere;99.7%
12150-46-8

1,1'-bis-(diphenylphosphino)ferrocene

C80H64Cl2Fe2N2P4Pd2

Conditions
ConditionsYield
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
ConditionsYield
In acetone at 20℃; for 72h; Sealed tube;99.2%
Downstream Products
124268-93-5
72287-26-4
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Specification

The 1,1'-Bis(diphenylphosphino)ferrocene, with the CAS registry number 12150-46-8, is also known as 1,1'-Ferrocenediyl-bis(diphenylphosphine). It belongs to the product categories of Phosphines; Boron, Nitrile, Thio,& TM-Cpds; Miscellaneous; Pharmacetical; Ligand; Catalysts-Ligands; Classes of Metal Compounds; Fe (Iron) Compounds; Ferrocenes; Metallocenes; Phosphine Ligands; Synthetic Organic Chemistry; Transition Metal Compounds. Its EINECS registry number is 430-420-3. This chemical's molecular formula is C34H28FeP2 and molecular weight is 554.378642. Its IUPAC name is called cyclopentyl(diphenyl)phosphane; iron. What's more, the product should be sealed and stored in cool and dry place.

Physical properties of 1,1'-Bis(diphenylphosphino)ferrocene: (1)H-Bond Donor: 0; (2)H-Bond Acceptor: 0; (3)Rotatable Bond Count: 6; (4)Exact Mass: 554.101566; (5)MonoIsotopic Mass: 554.101566; (6)Topological Polar Surface Area: 0; (7)Heavy Atom Count: 37; (8)Formal Charge: 0; (9)Complexity: 214; (10)Isotope Atom Count: 0; (11)Defined Atom StereoCenter Count: 0; (12)Undefined Atom StereoCenter Count: 0; (13)Defined Bond StereoCenter Count: 0; (14)Undefined Bond StereoCenter Count: 0; (15)Covalently-Bonded Unit Count: 3.

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 clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.C1=CC=C(C=C1)P(C2=CC=CC=C2)[C]3[CH][CH][CH][CH]3.[Fe]
(2)InChI: InChI=1S/2C17H14P.Fe/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;/h2*1-14H
(3)InChIKey: HPXNTHKXCYMIJL-UHFFFAOYSA-N