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102-54-5

Basic Information
CAS No.: 102-54-5
Name: Ferrocene
Molecular Structure:
Molecular Structure of 102-54-5 (Ferrocene)
Formula: C10H10Fe
Molecular Weight: 186.03
Synonyms: Bis(cyclopentadienyl)iron;Ferrotsen;Biscyclopentadienyl iron;Iron dicyclopentadienyl;Iron bis (cyclopentadiene);bis(eta(5)-cyclopentadienyl)iron(II);[Fe(eta(5)-C5H5)2];cyclopenta-1,3-diene; iron;Iron, bis(.eta.5-2,4-cyclopentadien-1-yl)-;Bis(.eta.-cyclopentadienyl) iron;Catane TM;bis(eta(5)-cyclopentadienyl)iron;Di(.pi.-cyclopentadienyl)iron;cyclopenta-1,3-diene; iron(+2) cation;Dicyclopentadienyl Iron;Bis-(Cyclopentadienyl)iron;Ferrocene 99.9% Pureness;Ferrocene;bis(cyclopentadienyl) iron;Di-2, 4-cyclopentadien-1-yliron;
EINECS: 203-039-3
Density: 1.107 g/cm3(0 ºC)
Melting Point: 172-174 ºC
Boiling Point: 41.5 ºC at 760 mmHg
Flash Point: 100 ºC
Solubility: practically insoluble in water
Appearance: Orange crystalline solid or orange-yellow powder
Hazard Symbols: FlammableF,HarmfulXn,DangerousN
Risk Codes: 11-22-51/53
Safety: 61-22
Transport Information: UN 1325 4.1/PG 2
PSA: 0.00000
LogP: 2.63090
Synthetic route

ferrocenyl(triphenylphosphine)gold

102-54-5

ferrocene

Conditions
ConditionsYield
With potassium cyanide In chloroform; water byproducts: P(C6H5)3; (Ar); shaking a soln. of the Au complex in CHCl3 with aq. KCN, 8 h; sepn. of the org. layer, drying over K2CO3, evapn. to dryness; products determined by thin-layer chromy. and 1H-NMR;100%
In not given with electrophilic reacgents;;
1282-37-7

ferrocenium(III) tetrafluoroborate

95865-41-1

dicarbonyl(η5-cyclopentadienyl)(η1-7-methoxy-1-cycloheptenyl)iron

A

102-54-5

ferrocene

B

95865-47-7

dicarbonyl(η5-cyclopentadienyl)(η1-7-methoxycycloheptene-1-carbonyl)iron

Conditions
ConditionsYield
With `CO In dichloromethane Addn. of Cp2FeBF4 to iron-compd. (methylene chloride, 55 psiCO, 1h).; Removal of solvent (vacuo), elution with hexane (alumina column) gives yellow band of ferrocene, elution with CH2Cl2 gives yellow band of dicarbonyl complex, elem. anal.;A n/a
B 99%
156301-37-0

ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate

([3,5-(2,4,6-i-Pr3C6H2)2C6H3NCH2CH2]3N)Mo(η2-C2H2)

A

102-54-5

ferrocene

[([3,5-(2,4,6-i-Pr3C6H2)2C6H3NCH2CH2]3N)Mo(C2H2)][B(3,5-(CF3)2C6H3)4]

Conditions
ConditionsYield
In benzene under N2 atm. to soln. Mo complex in benzene (Cp2Fe)(BAr'4) was added and stirred for 30 min; volatiles were removed in vacuo, residue was dissolved in heptane, ppt. was dried in high vac.; elem. anal.;A n/a
B 99%

ferrocenium trifluoromethanesulfonate

6163-58-2

tris-(o-tolyl)phosphine

A

102-54-5

ferrocene

B

tri(o-tolyl)phosphonium trifluoromethanesulfonate salt

Conditions
ConditionsYield
With C26H46ClO3Ru2S2(1+)*CF3O3S(1-); hydrogen In dichloromethane at 20℃; under 760.051 Torr; for 11h; Catalytic behavior; Inert atmosphere;A 99%
B 98%
542-92-7

cyclopenta-1,3-diene

iron(II) bromide

102-54-5

ferrocene

Conditions
ConditionsYield
With iron; diethylamine In further solvent(s) further solvents: mixt. of HN(C2H5)2, CH3OH, DME and (C6H5CH2N(CH3)3)OH; amine method; FeBr2 and Fe from Fe and Br2, Fe excess;;98%
With diethylamine In 1,2-dimethoxyethane; diethylamine amine method; FeBr2 from Fe and Br2;;85%
With diethylamine In 1,2-dimethoxyethane; diethylamine amine method; FeBr2 from Fe and Br2;;85%
With diethylamine In diethylamine byproducts: HBr;4%

ferrocenium hexafluorophosphate

tetra-n-butylammonium tetramethylaurate(III)

A

102-54-5

ferrocene

Conditions
ConditionsYield
In acetonitrile byproducts: CH4, C2H6; inert atmosphere;A 92%
B 98%
In tetrahydrofuran byproducts: CH4, C2H6; inert atmosphere;A 94%
B 95%

ferrocenium hexafluorophosphate

tetra-n-butylammonium tetramethylaurate(III)

603-35-0

triphenylphosphine

A

102-54-5

ferrocene

trimethyl(triphenylphosphine)gold(III)

Conditions
ConditionsYield
In tetrahydrofuran byproducts: CH4; He-atmosphere; -196°C, addn. of Cp2FePF6 to soln. of aurate and PPh3; not sepd., NMR-spectroscopy;A 98%
B 98%
In diethyl ether byproducts: CH4, C2H6; inert atmosphere;A 95%
B 94%
In acetonitrile byproducts: CH4; inert atmosphere; -40°C;A 94%
B 89%

1,2-bis((η6-4-chlorophenoxy-η5-cyclopentadienyl)iron)benzene hexafluorophosphate

A

102-54-5

ferrocene

B

153288-01-8

1,2-bis-(4-chlorophenoxy)benzene

Conditions
ConditionsYield
In dichloromethane; acetonitrile Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. by evapn. under reduced pressure, column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;A n/a
B 98%
59501-96-1

[C6H5S(O)CH2](1-)*Li(1+)=[C6H5S(O)CH2]Li

84430-52-4

(C5H5)Fe[P(OC6H5)3]2Cl

A

102-54-5

ferrocene

B

3561-67-9

bis(phenylthio)methane

C

622-20-8

1,2-bis(phenylthio)ethane

D

882-33-7

diphenyldisulfane

E

lithium chloride

Conditions
ConditionsYield
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;A 27%
B 27%
C 38%
D 25%
E 98%

ferrocenium hexafluorophosphate

228118-52-3

tetrabutylammonium dimethylaurate(I)

A

102-54-5

ferrocene

Conditions
ConditionsYield
In tetrahydrofuran byproducts: CH4, C2H6; He-atmosphere; addn. of 1 equiv. of Cp2FePF6 to soln. of aurate at -196°C, warming to room temp.;A 94%
B 97%
In acetonitrile byproducts: CH4, C2H6; He-atmosphere; addn. of 1 equiv. of Cp2FePF6 to soln. of aurate at -196°C, warming to room temp.;A 96%
B 96%

[(η6-p-xylene)(η5-cyclopentadienyl)iron(II)](hexafluorophosphate)

75-05-8

acetonitrile

102-54-5

ferrocene

Conditions
ConditionsYield
In acetonitrile byproducts: Fe(II), p-xylene; Irradiation (UV/VIS); a CH3CN soln. of Fe-compd. was degassed by bubbling with N2 for 10 min and irradiated with sunlight for 3 h 25 min at room temp.;; evapn. of the solvent and extn. the residue with cyclohexane; detected by NMR-expt.;;97%
In acetonitrile byproducts: Fe(II), p-xylene; Irradiation (UV/VIS); a CH3CN soln. of Fe-compd. was degassed by bubbling with N2 for 10 min and irradiated with an Oriel lamp for 3 h 25 min at room temp.;; evapn. of the solvent and extn. the residue with cyclohexane; detected by NMR-expt.;;93%
135348-57-1

ferrocenium tetrakis(pentafluorophenyl)borate

Ti(N[tBu](3,5-Me2C6H3))3

A

102-54-5

ferrocene

B

[Ti(N[tBu](3,5-Me2C6H3))3][B(C6F5)4]

Conditions
ConditionsYield
In diethyl ether for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;A 80%
B 97%
34822-90-7

cyclopentadienylthallium

7705-08-0

iron(III) chloride

102-54-5

ferrocene

Conditions
ConditionsYield
In tetrahydrofuran anhyd. FeCl3, boiling abs. THF, under exclusion of air; preparation of small amts.;;96%
1271-15-4

lithiumferrocene

lead(II) chloride

B

102-54-5

ferrocene

Conditions
ConditionsYield
In diethyl ether byproducts: LiCl; Ar; to a suspn. of PbCl2 added a suspn. of FcLi, stirred for 2 h; ppt. (Pb) filtered, washed (H2O), dried, analyzed; Fc not isolated, detected by NMR;A 96%
B n/a

4,4'-bis((η6-phenoxy-η5-cyclopentadienyl)iron)biphenyl hexafluorophosphate

A

102-54-5

ferrocene

B

2519-16-6

4,4'-diphenoxy-1,1'-biphenyl

Conditions
ConditionsYield
In dichloromethane; acetonitrile Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. by evapn. under reduced pressure, column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;A n/a
B 96%

1,2-bis((η6-4-methylphenoxy-η5-cyclopentadienyl)iron)benzene hexafluorophosphate

A

102-54-5

ferrocene

B

153287-98-0

1,2-bis-(4-methylphenoxy)benzene

Conditions
ConditionsYield
In dichloromethane; acetonitrile Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. by evapn. under reduced pressure, column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;A n/a
B 96%
1282-37-7

ferrocenium(III) tetrafluoroborate

122711-31-3

(triphenylphosphane)gold(I) tert-butylthiolate

A

102-54-5

ferrocene

B

tetrakis(triphenylphosphane)bis(tert-butylthiolate)tetragold(I) tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane byproducts: (SC(CH3)3)2; N2, Fe:Au=0.136:0.276 molar ratio, Fe compd. added to a soln. of Au compd., stirred for 30 min; solvent evapd., residue washed (diethyl ether, benzene), dried (vac.), recrystd. (CH2Cl2, -5°C), org. phases evapd. to dryness, ferrocenesublimied (40°C, high vac.); elem. anal.;A n/a
B 96%

ferrocenium hexafluorophosphate

C6H3(C(CH2CH2CH2Si(CH3)2CH2OC6H4C(CH2CH2CH2Si(CH3)2CH2N3C2HC5H4FeC5H4C5H4FeC5H5)3)3)3

A

102-54-5

ferrocene

B

C6H3(C(CH2CH2CH2Si(CH3)2CH2OC6H4C(CH2CH2CH2Si(CH3)2CH2N3C2HC5H4FeC5H4C5H4FeC5H5)3)3)3(27+)*27PF6(1-)

Conditions
ConditionsYield
In dichloromethane byproducts: ferrocene; 27 equivs. of (C5H5)Fe(C5H5)(PF6) in CH2Cl2 added to dendrimer complex in CH2Cl2 at room temp.; allowed to stir under N2 for 1 h at room temp.; Et2O added dropwise; filtered under N2 on Celite; dried in vac.; elem. anal.;A 96%
B 66.3%

{fc-P(C6H5)2CH2C6H5}OH

A

102-54-5

ferrocene

B

(diphenylphosphinoyl)ferrocene

C

fc-PO(C6H5)(CH2C6H5)

D

108-88-3

toluene

E

71-43-2

benzene

Conditions
ConditionsYield
With potassium chloride In 1,2-dimethoxyethane; water ratio H2O:(CH2OCH3)2 = 50:50 %, 0.4 M KCl, boiling; not isolated;A n/a
B 35.9%
C n/a
D 95.3%
E 3.9%
With KCl In 1,2-dimethoxyethane; water ratio H2O:(CH2OCH3)2 = 50:50 %, 0.4 M KCl, boiling; not isolated;A n/a
B 35.9%
C n/a
D 95.3%
E 3.9%

ferrocenium hexafluorophosphate

126572-58-5

di(t-butylimido)di(2,4,6-trimethylphenyl)rhenium(VI)

A

102-54-5

ferrocene

B

di(t-butylimido)di(2,4,6-trimethylphenyl)rhenium(VII) hexafluorophosphate

Conditions
ConditionsYield
In tetrahydrofuran absence of air; stirring (1 h); solvent removal (vac.), washing (hexane), crystn. (THF/Et2O); elem. anal.;A n/a
B 95%

1,2-bis((η6-phenoxy-η5-cyclopentadienyl)iron)benzene hexafluorophosphate

A

102-54-5

ferrocene

B

3379-37-1

1,2-diphenoxybenzene

Conditions
ConditionsYield
In dichloromethane; acetonitrile Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. (vac.), column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;A n/a
B 95%
1282-37-7

ferrocenium(III) tetrafluoroborate

223424-75-7

bis[(1,2-bis(dimethylphosphino)ethane)(η(5)-methylcyclopentadienyl)manganese(I)](μ-2,3-diphenylbutadien-1,4-diylidene)

A

102-54-5

ferrocene

B

bis[(1,2-bis(dimethylphopshino)ethane)(η(5)-methylcyclopentadienyl)manganese(III)](μ-2,3-diphenylbut-2-en-1,4-diylidyne) bis(tetrafluoroborate)

Conditions
ConditionsYield
In dichloromethane N2-atmosphere; filtering, concg., pptn. on Et2O addn.; collecting, washing (Et2O), drying (vac.), repptn., recrystn. (CH2Cl2, room temp.); elem. anal.;A n/a
B 95%
209473-49-4

(η(5)-2-cyclopentadienyl-2-indenyl-propane)Rh(1,5-cyclooctadiene)

232282-91-6

[(cyclopentadienyl)Fe(fluorene)]PF6

A

102-54-5

ferrocene

B

329985-01-5, 912572-47-5

[Rh(cyclooctadiene)(η5-cyclopentadienyl)C(CH3)2(η5-indenyl)Fe(η5-cyclopentadienyl)]

Conditions
ConditionsYield
With BuLi In tetrahydrofuran byproducts: fluorene; (N2); (COD)Rh(Cp)C(CH3)2(C9H6) deprotonated with BuLi in THF; soln. prepared from (CpFe(fluorene))PF6 and BuLi added at 0 °C after 1 h; refluxed for 16 h; solvend removed; extracted by pentane/diethyl ether (1:1); chromy.(pentane/diethyl ether); elem. anal.;A n/a
B 95%
1282-37-7

ferrocenium(III) tetrafluoroborate

1002113-69-0

(methyldiphenylphosphane)gold(I) tetr-butylthiolate

A

102-54-5

ferrocene

B

tetrakis(methyldiphenylphosphane)bis(tert-butylthiolate)tetragold(I) tetrafluoroborate

Conditions
ConditionsYield
In dichloromethane byproducts: (SC(CH3)3)2; N2, Fe:Au=0.136:0.276 molar ratio, Fe compd. added to a soln. of Au compd., stirred for 30 min; solvent evapd., residue washed (diethyl ether, benzene), dried (vac.), recrystd. (CH2Cl2, -5°C), org. phases evapd. to dryness, ferrocenesublimied (40°C, high vac.); elem. anal.;A n/a
B 95%

ferrocenium hexafluorophosphate

W6S8(P(C2H5)3)6

A

102-54-5

ferrocene

B

W6S8(P(C2H5)3)6(1+)*PF6(1-)=W6S8(P(C2H5)3)6PF6

Conditions
ConditionsYield
In benzene W-cluster was dissolved in benzene in Schlenk flask, soln. of Fe-complexwas added, stirred for 1 h; after 2 d filtered, washed with Et2O, dried;A n/a
B 95%
In dichloromethane W-cluster was dissolved in CH2Cl2 in Schlenk flask, soln. of Fe-complex in CH2Cl2 was added, stirred for 30 min; solvent was removed under vac. washed with benzene and Et2O;A n/a
B 85%
1293-65-8

1,1'-dibromoferrocene

A

102-54-5

ferrocene

B

1273-73-0

bromoferrocene

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran under N2; n-BuLi in THF added dropwise at -35°C to soln. of Fe complex in THF; stirred at -35°C for 1 h; H2O added dropwise; warmed to room temp. over 1 h; extd. with Et2O; org. layer collected; washed with H2O; dried (Na2SO4); solvent removed under reduced pressure; bromoferrocene contaminated withferrocene (10%);A n/a
B 95%

ferrocenium trifluoromethanesulfonate

A

102-54-5

ferrocene

B

1493-13-6

trifluorormethanesulfonic acid

Conditions
ConditionsYield
With C26H46ClO3Ru2S2(1+)*CF3O3S(1-); hydrogen In water at 20℃; under 760.051 Torr; for 1.2h; Catalytic behavior; Temperature; Reagent/catalyst; Inert atmosphere; Schlenk technique;A 95%
B n/a
With [(pentamethylcyclopentadienyl)Ru{PhP(C6H4-o-S)2}Ru(pentamethylcyclopentadienyl)](OTf)2; hydrogen In water at 20℃; under 760.051 Torr; for 20h;A 87%
B 86%
With [η5-C5Me5Ru(μ-SiPr)2Ru(OH2)-η5-C5Me5](OTf)2; hydrogen In methanol at 20℃; under 760.051 Torr; for 1.4h; Temperature; Reagent/catalyst; Solvent; Pressure; Schlenk technique;

ferrocenium hexafluorophosphate

102-54-5

ferrocene

Conditions
ConditionsYield
With tetramethylpiperidine; H2; Cp*Ru(dppf)H In acetone (Ar);; concn., extn. (hexanes);94%
With 1,7-dilithio-m-carborane In cyclohexane byproducts: LiPF6, m-carborane; (N2 or Ar); heated at 80°C for 24 h; quenched with wet n-hexane, passed through silica gel, washed (ether), the org. portions combined, evapd. (vac.), flash-chromd. (silica gel, n-hexane);49%
With sodium benzotriazolide In tetrahydrofuran at 20°C;
1282-37-7

ferrocenium(III) tetrafluoroborate

Cp2Ta{(μ-CH2)2}CoCp

A

102-54-5

ferrocene

B

{Cp2Ta(μ-CH2)2Co(CH3CN)Cp}(1+)BF4(1-)*CH3CN

Conditions
ConditionsYield
In acetonitrile 20 °C; variable temp. NMR;A n/a
B 94%

1,3-bis((η6-phenoxy-η5-cyclopentadienyl)iron)benzene hexafluorophosphate

A

102-54-5

ferrocene

B

3379-38-2

1,3-diphenoxybenzene

Conditions
ConditionsYield
In dichloromethane; acetonitrile Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. by evapn. under reduced pressure, column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;A n/a
B 94%
102-54-5

ferrocene

103-71-9

phenyl isocyanate

N-phenylferrocenecarboxamide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid at 25℃; for 8h; Reagent/catalyst; Temperature; Inert atmosphere;100%
With aluminium trichloride25%
With AlCl325%
aluminium trichloride In carbon disulfide
102-54-5

ferrocene

ferricinium chloroferrate

Conditions
ConditionsYield
With hydrogenchloride; oxygen; iron(III) chloride In diethyl ether passing O2 through mixt. of ferrocene in ether and FeCl3 in aq. HCl;;100%
With FeCl3; O2; HCl In diethyl ether passing O2 through mixt. of ferrocene in ether and FeCl3 in aq. HCl;;100%
With sulfuryl dichloride In benzene in boiling benzene, equimolar amt. of ferrocene and SO2Cl2;;97%
102-54-5

ferrocene

β-cyclodextrin decahydrate

ferrocene, β-cyclodextrin complex

Conditions
ConditionsYield
In water molar ratio cyclodextrin : ferrocene = 1:4, addn. of crystals of ferrocene to an aq. soln. of cyclodextrin at 60°C with stirring; washed with water, dried in vac., washed with THF, recrystn. from water or aq. alcohol; elem. anal.;100%
In ethanol; water molar ratio cyclodextrin : ferrocene = 2:1, an aq. alcohol soln. of cyclodextrin (40% ethanol) was mixed with an aq. alcohol soln. of ferrocene (60% ethanol); addn. of water and/or partial removal of ethanol by evapn.; elem. anal.;85%
In ethanol; water molar ratio cyclodextrin : ferrocene = 1:1, addn. of aq. soln. of cyclodextrin to an alcohol soln. of ferrocene with stirring and heating; elem. anal.;56%
In ethanol; water molar ratio cyclodextrin : ferrocene = 1:1, addn. of aq. soln. of cyclodextrin to an alcohol soln. of ferrocene with stirring and heating; elem. anal.;36%
102-54-5

ferrocene

[Cu((NCH2CH2)3(CH(CH3)2)2(CH2C6H2(O)(C(CH3)3)2))OSO2CF3](1+)

A

12125-80-3

ferrocenium

B

[Cu((NCH2CH2)3(CH(CH3)2)2(CH2C6H2(O)(C(CH3)3)2))OSO2CF3]

Conditions
ConditionsYield
In not given stoichiometric amt.;A n/a
B 100%
102-54-5

ferrocene

2-ferrocenyl-6-methyl-pyridin-4-yl nonaflate

152602-97-6

2-methyl-4,6-bisferrocenyl pyridine

Conditions
ConditionsYield
Stage #1: ferrocene With potassium tert-butylate In tetrahydrofuran Inert atmosphere; Schlenk technique;
Stage #2: With tert.-butyl lithium In tetrahydrofuran; pentane at -30℃; for 1h; Inert atmosphere;
Stage #3: 2-ferrocenyl-6-methyl-pyridin-4-yl nonaflate Further stages;
100%
102-54-5

ferrocene

3-diazonium-o-carborane tetrafluoroborate

C12H20B10Fe

Conditions
ConditionsYield
With eosin In acetonitrile at 20℃; for 2h; Inert atmosphere; Schlenk technique; Irradiation; regioselective reaction;100%
102-54-5

ferrocene

7664-39-3

hydrogen fluoride

7647-19-0, 874483-74-6

phosphorus pentafluoride

C10H11Fe(1+)*F6P(1-)

Conditions
ConditionsYield
at -196 - 20℃; Sealed tube;100%
102-54-5

ferrocene

693-98-1

2-methylimidazole

[iron(II)(2-methylimidazolate)2]

Conditions
ConditionsYield
With 4,4'-bipyridine at 150℃; for 48h; Reagent/catalyst;100%
102-54-5

ferrocene

18734-63-9

perfluoro-o-phenylenemercury trimer

2(HgC6F4)3*Fe(C5H5)2

Conditions
ConditionsYield
In dichloromethane soln. of (HgC6F5)3 (0.096 mol) in CH2Cl2 mixed with soln. ferrocene (0.538 mol) in CH2Cl2; crystd. by slow evapn. of solvent; crystals washed (hexane); elem. anal.;99%
In dichloromethane no react. in CH2Cl2 soln.; (199)Hg NMR;0%

hexafluorophosphoric acid

102-54-5

ferrocene

700-12-9

pentamethylbenzene,

112596-54-0

{(Cp)iron(II)(η6-pentamethylbenzene)}(PF6)

Conditions
ConditionsYield
With aluminium trichloride; aluminium In neat (no solvent) ferrocene, Al-powder and AlCl3 are ground in a mortar, the arene is added and mixt. is reground, rapidly transferred to a microwave app. (react. time 3 min) and heated; complex is isolated by adding water and pptg. with HPF6 from the aq. soln.;99%
With aluminium trichloride; water; aluminium In not given treatment of ferrocene with benzene deriv. in presence of aluminium, AlCl3 and 1 equiv. of water at 100°C; Hamon J.R., Astruc D., MichaudP., J. Am. Chem. Soc., 1981, 103, 758-766; treatment with aq. ammonia, treatment with HPF6;
135348-57-1

ferricenium tetrakis(pentafluorophenyl)borate

Ti(N[tBu](3,5-Me2C6H3))3

A

102-54-5

ferrocene

B

[Ti(N[tBu](3,5-Me2C6H3))3][B(C6F5)4]

Conditions
ConditionsYield
In diethyl ether for 0.5h; Inert atmosphere; Schlenk technique; Glovebox;A 80%
B 97%
102-54-5

ferrocene

100-52-7

benzaldehyde

Ferrocenyl(phenyl)carbenium perchlorate

Conditions
ConditionsYield
With trichlorophosphate In perchloric acid; diethyl ether aq. HClO4 addn. to ferrocene, carbonyl compd. and POCl3 (room temp., over 2 h), addn. of ether, standing (15 h), pptn.; collection (filtration), washing (ether); elem. anal.;99%
102-54-5

ferrocene

98-88-4

benzoyl chloride

12180-80-2, 32983-90-7

1,1’-dibenzoylferrocene

Conditions
ConditionsYield
With aluminium chloride In dichloromethane ferrocene (1.0 equiv.) added to a stirred suspension of benzoyl chloride(2.2 equiv.) and aluminium chloride (2.2 equiv.) in dichloromethane, st irred at room temp. overnight (16 h); washed with water, organic layer passed through a plug of alumina, washed with chloroform, washings concentrated in vacuo, crude product purified by flash column chromy. on silica gel (TLC Rf 0.26 (1:1 ether-hexane)), elem. anal.;99%
With aluminium trichloride In dichloromethane to suspn. of AlCl3 in CH2Cl2 ligand was added, soln. of Fe-complex in CH2Cl2 was added, stirred for 3 ds at room temp. under Ar; aq. soln. of NaHCO3 was added, extd. with CH2Cl2, washed with aq. NaHCO3, dried over MgSO4, concd. under reduced pressure, column chromy. on silica gel with pentane-Et2O; elem. anal.;87%
With aluminium trichloride; benzoyl chloride In dichloromethane soln. of C6H5COCl and AlCl3 in dry CH2Cl2 was added dropwise over a period of 1 h to a stirred soln. of ferrocene in dry CH2Cl2; soln. was refluxed for 30 min, hydrolized with 0.1 M HCl, product worked up; solid chromd. on alumina using benzene, following by ether ewluant;86%
With aluminum (III) chloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere; Schlenk technique;75%
With AlCl3 In dichloromethane
487-89-8

Indole-3-carboxaldehyde

102-54-5

ferrocene

(C5H5FeC5H4CHC8H5NH)(1+)*ClO4(1-)=(C5H5FeC5H4CHC8H5NH)ClO4

Conditions
ConditionsYield
With trichlorophosphate In perchloric acid; diethyl ether aq. HClO4 addn. to ferrocene, carbonyl compd. and POCl3 (room temp., over 1 h), addn. of ether, standing (15 h), pptn.; collection (filtration), washing (ether); elem. anal.;99%

ammonium hexafluorophosphate

102-54-5

ferrocene

13821-31-3

<33>(1,3,5)-cyclophane

bis(η(5)-cyclopentadienyl)(η(6),η(6)-[3(3)](1,3,5)cyclophane)diiron(II,II) bis(hexafluorophosphate)

Conditions
ConditionsYield
With aluminium trichloride; aluminium In decalin Ar-atmosphere; heating cyclophane with excess of Fe-complex, AlCl3 and Al (160°C, 2 h), cooling in ice bath, washing aq. layer (Et2O), filtration, addn. of excess of aq. NH4PF6 (pptn.); filtration, drying (vac., room temp.); elem. anal.;99%
102-54-5

ferrocene

Co(C27H34N4O4)

212846-49-6

(C5H5)2Fe(1+)*Co(C27H34N4O4)(1-)=[(C5H5)2Fe][Co(C27H34N4O4)]

Conditions
ConditionsYield
In cyclohexane excess Cp2Fe (pptn.); centrifugation;99%
102-54-5

ferrocene

Co(C27H32Cl2N4O4)

212846-59-8

(C5H5)2Fe(1+)*Co(C27H32Cl2N4O4)(1-)=[(C5H5)2Fe][Co(C27H32Cl2N4O4)]

Conditions
ConditionsYield
In cyclohexane excess Cp2Fe (pptn.); centrifugation;99%
102-54-5

ferrocene

[Fe(η5-cyclopentadienyl)(η-benzene)]

(η-C5H5)Fe(μ-η:η-C5H5)Fe(η-C5H5)

Conditions
ConditionsYield
In dichloromethane Irradiation (UV/VIS); irradiation (visible light, 250 W luminescence lamp), 0°C, 1 h, intense stirring; soln. concentrating in vacuum, residue washing repeatedly by petroleum ether, vacuum drying; elem. anal.;99%
102-54-5

ferrocene

15873-63-9, 20464-21-5

mercury(II) trichloroacetate

7647-14-5

sodium chloride

decakis(chloridomercury(II))ferrocene

Conditions
ConditionsYield
In methanol; diethyl ether; water addn. of soln. of ferocene (in Et2O) to soln. of Hg-salt (in MeOH), stirring (ambient temp., 15 - 30 min), pouring into ice H2O, satd. with NaCl, stirring (2 h); filtration, washing, (15 % aq. KI, satd. aq. NaCl, H2O, EtOH and ether),drying; elem. anal.;99%
In methanol; water 50°C; addn. of soln. of ferocene (in Et2O) to soln. of Hg-salt (in MeOH), stirring (ambient temp., 15 - 30 min), pouring into ice H2O, satd. with NaCl, stirring (2 h); filtration, washing, (15 % aq. KI, satd. aq. NaCl, H2O, EtOH and ether),drying; elem. anal.;99%
In methanol; water addn. of ferocene to soln. of Hg-salt (in MeOH), stirring (ambient temp., 15 - 30 min), pouring into ice H2O, satd. with NaCl, stirring (2 h); filtration, washing, (15 % aq. KI, satd. aq. NaCl, H2O, EtOH and ether),drying;99%
102-54-5

ferrocene

132278-01-4

(E)-4,4-dimethyl-2-pentenoyl chloride

E-1-ferrocenyl-4,4-dimethylpent-2-ene-1-one

Conditions
ConditionsYield
With AlCl3 In dichloromethane under N2; CH2Cl2 added with stirring to mixt. of Fe complex and AlCl3 (molar ratio 1:1); cooled to -78°C; soln. of t-BuCHCHC(O)Cl (1 equiv.) in CH2Cl2 added dropwise over 30 min; warmed slowly to room temp. over 20 min; quenched by dropwise addition of satd. aq. soln. of Na2S2O4; org. layer sepd.; washed with water and satd. aq. NaCl in air; dried (MgSO4); soln.filtered; volatiles removed in vac.; recrystd. from satd. soln. in hexa ne-Et2O at -30°C; elem. anal.;99%
102-54-5

ferrocene

609-67-6

2-Iodobenzoyl chloride

109800-02-4

(o-Iodobenzoyl)ferrocene

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 0.25h; Friedel-Crafts Acylation; Inert atmosphere; Schlenk technique;99%
With aluminum (III) chloride In dichloromethane at 20℃; for 3h; Inert atmosphere;0.243 g
Friedel-Crafts Acylation;
102-54-5

ferrocene

26842-85-3

bis(nonafluoro-tert-butyl) peroxide

ferrocenium nonafluoro-tert-butoxide

Conditions
ConditionsYield
at 20℃; Schlenk technique;99%
Schlenk technique; Inert atmosphere;99%
102-54-5

ferrocene

93-61-8

N-methyl-N-phenylformamide

12093-10-6

ferrocenecarboxaldehyde

Conditions
ConditionsYield
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 0℃; for 0.25h;
Stage #2: ferrocene at 20℃; Inert atmosphere;
98%
With phosphorus oxychloride In neat (no solvent) anilide and P-compd. stirring at room temp. for 30 min, Fe-compd. addn.,mixt. stirring at room temp. for 3 d, quenching by pouring onto ice, aq . layer extn. after 2 h with Et2O, org. layer drying (MgSO4), vac. concn.; residue flash column chromy. (SiO2, petrol/E2O 7:3 to 5:5), recrystn. (hot petroleum);87%
With trichlorophosphate In neat (no solvent) Vilsmeyer formylation; double mol amt. of formylation mixt., few days at ambient temp.;;81%
102-54-5

ferrocene

123-62-6

propionic acid anhydride

propionylferrocene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane ferrocene and 2 equivs. of acid anhydride suspended in CH2Cl2 and cooledto 0°C, boron trifluoride etherate added over 10 min, stirred at room temp. for 3 h; poured into ice H2O, sepd., the org. layer washed (satd. NaHCO3 soln.), dried (MgSO4), solvent-removed, flash-chromd. (SiO2, cyclohexane/EtOAc);98%
With aluminum (III) chloride In chloroform at 4 - 40℃; for 1h; Friedel-Crafts Acylation;87%
With polyphosphoric acid In propionic acid anhydride Ar-atmosphere; addn. of excess of anhydride to Fe-complex soln., addn. of polyphosphoric acid, heating to 100°C for 15 min; pouring into ice water, neutralization (aq. Na2CO3), extn. into ether, washing of org. phase (H2O), drying (MgSO4), filtration, concn. (vac.), chromy. (SiO2, ether/pentane=1:3);80%
106-31-0

butanoic acid anhydride

102-54-5

ferrocene

1-butanoylferrocene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane ferrocene and 2 equivs. of acid anhydride suspended in CH2Cl2 and cooledto 0°C, boron trifluoride etherate added over 10 min, stirred at room temp. for 3 h; poured into ice H2O, sepd., the org. layer washed (satd. NaHCO3 soln.), dried (MgSO4), solvent-removed, flash-chromd. (SiO2, cyclohexane/EtOAc);obtained as oil;98%
With aluminum (III) chloride In chloroform at 4 - 40℃; for 1h; Friedel-Crafts Acylation;84%
With aluminum oxide In dichloromethane stirring (30 min); extraction (water, Et2O), chromy.;60%
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History

 Ferrocene was first prepared unintentionally. In 1951, Pauson and Kealy at Duquesne University reported the reaction of cyclopentadienyl magnesium bromide and ferric chloride with the goal of oxidatively coupling the diene to prepare fulvalene. Instead, they obtained a light orange powder of "remarkable stability."[3] This stability was accorded to the aromatic character of the negative charged cyclopentadienyls, but the sandwich structure of the η5 (pentahapto) compound was not recognized by them. Robert Burns Woodward and Geoffrey Wilkinson deduced the structure based on its reactivity.[4] Independently Ernst Otto Fischer also came to the conclusion of the sandwich structure and started to synthesize other metallocenes such as nickelocene and cobaltocene. Ferrocene's structure was confirmed by NMR spectroscopy and X-ray crystallography Its distinctive "sandwich" structure led to an explosion of interest in compounds of d-block metals with hydrocarbons, and invigorated the development of the flourishing study of organometallic chemistry. In 1973 Fischer of the Technische Universität München and Wilkinson of Imperial College London shared a Nobel Prize for their work on metallocenes and other aspects of organometallic chemistry.

Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of Ferrocene is cyclopenta-1,3-diene; iron(2+). With the CAS registry number 102-54-5, it is also named as AI3-23119; Biscyclopentadienyliron; CCRIS 3195; Catane; Di(pi-cyclopentadienyl)iron; Di-2,4-cyclopentadien-1-yliron; Iron bis(cyclopentadiene); Iron, bis(eta5-2,4-cyclopentadien-1-yl)-. The product's categories are organometallics, classes of metal compounds, Fe (Iron) compounds, ferrocenes, metallocenes and transition metal compounds.

The Ferrocene is orange crystalline solid or orange-yellow powder which is stable at room temperature and incompatible with strong oxidizing agents. It is soluble in dilute nitric acid, sulfuric acid, benzene, ethyl ether, petroleum ether, and tetrahydrofuran. It is sensitive to prolonged exposure to air and may be sensitive to light. Ferrocene reacts violently with tetranitromethane. Contact of tetranitromethane with Ferrocene under various conditions leads to violent explosion. Thic chemical can be used as antiknock additive for gasoline, catalyst and pharmaceutical intermediates. 

The Ferrocene is highly flammable. It is harmful if swallowed. And it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. So people should not breathe dust and avoid release to the environment. So the storage environment should be ventilate, low-temperature and dry. Keep Ferrocene separate from oxidant.

The Ferrocene can be obtained by the reaction of Sodium cyclopentadienide with Anhydrous iron(II) chloride in ethereal solvents:
2 NaC5H5 + FeCl2 → Fe(C5H5)2 + 2 NaCl

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.79; (4)ACD/LogD (pH 7.4): 1.79; (5)ACD/BCF (pH 5.5): 13.44; (6)ACD/BCF (pH 7.4): 13.44; (7)ACD/KOC (pH 5.5): 223.49; (8)ACD/KOC (pH 7.4): 223.49; (9)Enthalpy of Vaporization: 27.4 kJ/mol; (10)Vapour Pressure: 418 mmHg at 25°C; (11)Exact Mass: 186.013192; (12)MonoIsotopic Mass: 186.013192; (13)Heavy Atom Count: 11; (14)Complexity: 11.6.

People can use the following data to convert to the molecule structure. SMILES: [Fe+2].[c-]1cccc1.c1[c-]ccc1; InChI: InChI=1/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2; InChIKey: KTWOOEGAPBSYNW-UHFFFAOYAZ. Ferrocene has many suppliers, such as A-Chem Technologies Co., Ltd., Chem-Base (Nantong) Laboratories Co., Ltd., Jiangsu International Economic-Technical Cooperation Corp. and Jingtan Qingcheng Environmental Technologies Co., Ltd..

The following is the toxicity data which has been tested.  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LC inhalation > 21700ug/m3 (21.7mg/m3)   "Spravochnik po Toksikologii i Gigienicheskim Normativam Vol. -, Pg. 228, 1999.
mouse LD50 intraperitoneal 335mg/kg (335mg/kg)   Progress Report for Contract No. PH-43-64-886, Submitted to the National Cancer Institute by The Institute of Chemical Biology, University of San Francisco. Vol. PH43-64-886,
mouse LD50 intravenous 178mg/kg (178mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02382,
mouse LD50 oral 832mg/kg (832mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 24, Pg. 352, 1965.
 
rat LD50 intraperitoneal 500mg/kg (500mg/kg)   Progress Report for Contract No. PH-43-64-886, Submitted to the National Cancer Institute by The Institute of Chemical Biology, University of San Francisco. Vol. PH43-64-886,
rat LD50 oral 1320mg/kg (1320mg/kg)   Shell Chemical Company. Unpublished Report. Vol. -, Pg. 5, 1961.

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