Name: 1,1'-Bis(diphenylphosphino)ferrocene
SKU: 12150-46-8

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Basic Information

Molecular Structure:
CAS No.:	12150-46-8
Name:	1,1'-Bis(diphenylphosphino)ferrocene
Article Data:	13

Formula:	C₃₄H₂₈FeP₂
Molecular Weight:	556.407
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
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:	T,Xn,Xi
Risk Codes:	25-36/37/38-20/21/22
Safety:	22-24/25-45-28A-36-26
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%

...Expand

: 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%

...Expand

: [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;

Raw Materials

591-51-5

672-66-2

102-54-5

1079-66-9

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

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