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102-54-5

Basic Information
CAS No.: 102-54-5
Name: Ferrocene
Article Data: 542
Cas Database
Molecular Structure:
Molecular Structure of 102-54-5 (Ferrocene)
Formula: C10H10Fe
Molecular Weight: 186.036
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%
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    Product Name: Ferrocene CAS: 102-54-5 MF: C10H10Fe MW: 186.03 EINECS: 203-039-3 Mol File: 102-54-5.mol Ferrocene Structure Ferrocene Chemical Properties Melting point 172-174 °C (lit.) Boiling point 249 °C (lit.) d

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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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