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| CAS No.: | 102-54-5 |
|---|---|
| Name: | Ferrocene |
| Molecular Structure: | |
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| 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: |
 F, Xn, N
|
| Risk Codes: | 11-22-51/53 |
| Safety: | 61-22 |
| Transport Information: | UN 1325 4.1/PG 2 |
| PSA: | 0.00000 |
| LogP: | 2.63090 |
ferrocene
| Conditions | Yield |
|---|---|
| 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;; |
ferrocenium(III) tetrafluoroborate
dicarbonyl(η5-cyclopentadienyl)(η1-7-methoxy-1-cycloheptenyl)iron
A
ferrocene
B
dicarbonyl(η5-cyclopentadienyl)(η1-7-methoxycycloheptene-1-carbonyl)iron
| Conditions | Yield |
|---|---|
| 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% |
ferrocenium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate
A
ferrocene
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With C26H46ClO3Ru2S2(1+)*CF3O3S(1-); hydrogen In dichloromethane at 20℃; under 760.051 Torr; for 11h; Catalytic behavior; Inert atmosphere; | A 99% B 98% |
| Conditions | Yield |
|---|---|
| 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% |
A
ferrocene
| Conditions | Yield |
|---|---|
| In acetonitrile byproducts: CH4, C2H6; inert atmosphere; | A 92% B 98% |
| In tetrahydrofuran byproducts: CH4, C2H6; inert atmosphere; | A 94% B 95% |
| Conditions | Yield |
|---|---|
| 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% |
A
ferrocene
B
1,2-bis-(4-chlorophenoxy)benzene
| Conditions | Yield |
|---|---|
| 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% |
[C6H5S(O)CH2](1-)*Li(1+)=[C6H5S(O)CH2]Li
(C5H5)Fe[P(OC6H5)3]2Cl
A
ferrocene
B
bis(phenylthio)methane
C
1,2-bis(phenylthio)ethane
D
diphenyldisulfane
| Conditions | Yield |
|---|---|
| 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% |
tetrabutylammonium dimethylaurate(I)
A
ferrocene
| Conditions | Yield |
|---|---|
| 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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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.
Reported in EPA TSCA Inventory.
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. |
