| Identification | More | [Name]
Ferrocene | [CAS]
102-54-5 | [Synonyms]
BIS(CYCLOPENTADIEN)IRON
BIS(CYCLOPENTADIENYL)IRON
BIS(CYCLOPENTADIENYL)IRON(+2)
di-2,4-cyclopentadien-1-yliron
DICYCLOPENTADIENYLIRON
DICYCLOPENTADIENYLIRON(II)
FERROCENE
IRON DICYCLOPENTADIENYL
Bis(eta-cyclopentadienyl) iron
biscyclopentadienyliron[qr]
catane
Di(pi-cyclopentadienyl)iron
di-2,4-cyclopentadien-1-yliron[qr]
dicyclopentadienyl
dicyclopentadienyliron[qr]
di-pi-cyclopentadienyliron[qr]
Ferrotsen
ferrotsen[qr]
Iron bis(cyclopentadienide)
Iron, bis(eta(sup5)-2,4-cyclopentadien-1-yl)- | [EINECS(EC#)]
203-039-3 | [Molecular Formula]
C10H10Fe | [MDL Number]
MFCD00001427 | [Molecular Weight]
186.03 | [MOL File]
102-54-5.mol |
| Chemical Properties | Back Directory | [Definition]
A coordination compound of ferrous iron and two molecules of
cyclopentadiene in which the organic portions have
typically aromatic chemical properties. Its activity is intermediate between phenol and anisole.
The first compound shown to have the “sandwich | [Appearance]
Ferrocene, a metallocene, is a bright orange
salt-like crystals from alcohol. Camphor odor. | [Melting point ]
172-174 °C (lit.) | [Boiling point ]
249 °C (lit.) | [bulk density]
500kg/m3 | [density ]
1.490 | [vapor pressure ]
0.03 mm Hg ( 40 °C)
| [Fp ]
100°C | [storage temp. ]
Flammables area | [solubility ]
insoluble in H2O; soluble in ethanol, ethyl ether,benzene, dilute HNO
3 | [form ]
crystal | [color ]
orange | [Stability:]
Stable at room temperature. Incompatible with strong oxidizing agents. Highly flammable. | [Water Solubility ]
practically insoluble | [Sensitive ]
Air & Moisture Sensitive | [λmax]
358 nm | [Merck ]
14,4037 | [Sublimation ]
100 ºC | [Exposure limits]
ACGIH: TWA 10 mg/m3; TWA 1 mg/m3
OSHA: TWA 15 mg/m3; TWA 5 mg/m3
NIOSH: TWA 10 mg/m3; TWA 5 mg/m3; TWA 1 mg/m3 | [InChI]
1S/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H; | [InChIKey]
DFRHTHSZMBROSH-UHFFFAOYSA-N | [SMILES]
[Fe].[CH]1[CH][CH][CH][CH]1.[CH]2[CH][CH][CH][CH]2 | [LogP]
3.711 at 22℃ | [CAS DataBase Reference]
102-54-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Ferrocene(102-54-5) | [EPA Substance Registry System]
102-54-5(EPA Substance) |
| Questions And Answer | Back Directory | [Discovery]
Ferrocene (Fc), which was discovered in 1951, is one of themost stable organometallic compounds. The interesting charac-teristic features of ferrocenes depend on reversible redoxproperties and a sandwich-shaped structure with two rotatorycoplanar cyclopentadienyl (Cp) rings. Another Intriguing structural feature of ferrocene is that theinter-ring distance between the two rotatory Cp rings is about 3.3 Å, which is appropriate for hydrogen bonding betweenattached peptide chains on two Cp rings. Secondary structuressuch as α- helices, β-sheets, and β-turns are formed dependingon the hydrogen bonds, which play key factors in proteinfoldings to fulfill unique functions as observed in enzymes,receptors, etc[1]. | [Organic transition metal]
Ferrocene is an organic transition metal compound that has aromatic properties and is also known as dicyclopentadienyl iron. Its molecular structure contains a divalent iron cation and two cyclopentadienyl anions. It is used as a raw material in the production of ferrocenecarboxylic acid and was first successfully produced in the 1950s by reacting cyclopentadienyl magnesium bromide with anhydrous ferric chloride. Ferrocene is a non-polar compound that appears as an orange needle crystal powder with a camphor-like smell at room temperature. It is soluble in many organic solvents, including methanol, ethanol, ethyl ether, petroleum ether, gasoline, kerosene, diesel oil, methylene chloride, benzene, toluene, and xylene. Ferrocene has a molecule with polarity, high thermal stability, chemical stability, and radiation resistance, making it useful in industry, agriculture, medicine, aerospace, energy, environmental protection, and other fields. | [Uses]
Ferrocene and its derivatives have various applications in different fields. It can be used as additives in rocket fuel, antiknock agent in gasoline, curing agent in rubber and silicone resin, and ultraviolet absorber. It can also be used in the production of metal-containing polymers and as a coating material for spacecraft. Ferrocene has a smoke abatement and combustion facilitating effect, which can reduce smoke production and increase power efficiency in fuel. It can also be used as an iron fertilizer for plants and as a pesticide. Ferrocene derivatives have applications as antioxidants, stabilizers, catalysts, and promoting agents in different industrial and organic synthesis processes. Addition of ferrocene to fuels such as diesel, gasoline, heavy oil, and coal can decrease the fuel consumption rate and reduce smoke production. Overall, ferrocene has unique characteristics that make it suitable for various applications in different fields. | [Category]
toxic substances
| [Toxicity grading]
poisoning
| [Acute toxicity]
Oral-rat LD50: 1320 mg/kg; Oral-Mouse LD50: 832 mg/kg.
| [Flammability and hazard characteristics]
flammable with the combustion generating iron-containing acrid smoke
| [Storage properties]
warehouse: ventilated, low temperature and dry; Store it separately from oxidants.
| [Extinguishing agent]
Water, carbon dioxide, dry, sandy soil.
| [Professional standards]
TWA 10 mg/m³; STEL 20 mg/m3 |
| Safety Data | Back Directory | [Symbol(GHS) ]
   
GHS02,GHS07,GHS08,GHS09 | [Signal word ]
Danger | [Hazard statements ]
H228-H302+H332-H360FD-H373-H410 | [Precautionary statements ]
P202-P210-P273-P301+P312-P304+P340+P312-P308+P313 | [Hazard Codes ]
F,Xn,N | [Risk Statements ]
R11:Highly Flammable.
R22:Harmful if swallowed.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S22:Do not breathe dust . | [OEB]
B | [OEL]
TWA: 10 mg/m3 (total) | [RIDADR ]
UN 1325 4.1/PG 2
| [WGK Germany ]
2
| [RTECS ]
LK0700000
| [Autoignition Temperature]
>150 °C | [TSCA ]
Yes | [REACH Registrations]
Active | [HazardClass ]
4.1 | [PackingGroup ]
II | [HS Code ]
29310095 | [Storage Class]
4.1B - Flammable solid hazardous materials | [Hazard Classifications]
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Aquatic Chronic 1
Flam. Sol. 1
Repr. 1B
STOT RE 2 Inhalation | [Safety Profile]
Poison by
intraperitoneal and intravenous routes.
Moderately toxic by ingestion. Questionable
carcinogen with experimental tumorigenic
data. Mutation data reported. Flammable;
reacts violently with NH4ClO4. When heated
to decomposition it emits acrid smoke and
irritating fumes. | [Hazardous Substances Data]
102-54-5(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 1320 mg/kg LD50 dermal Rat > 3000 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sodium hydroxide-->Tetrahydrofuran-->Diethylamine-->Pentane-->1,3-Cyclopentadiene-->Ferrous chloride-->CYCLOHEXANE-D12-->ANHYDROUS FERRIC CHLORIDE | [Preparation Products]
1,1'-DIMETHYLFERROCENE-->1,1'-Bis (di-t-butylphosphino)ferrocene palladium dichloride,-->1,1'-Bis(di-tert-butylphosphino)ferrocene-->1,1'-Bis(diphenylphosphino)ferrocene-->1-DIPHENYLPHOSPHINO-1'-(DI-TERT-BUTYLPH&-->1 1'-BIS(DIPHENYLPHOSPHINO)FERROCENE-->1,1'-FERROCENEDICARBOXALDEHYDE-->1,1'-Bis(diisopropylphosphino)ferrocene-->1,1'-DI-N-BUTYLFERROCENE-->Butylferrocene-->Benzoylferrocene-->1,1'-Diacetylferrocene-->dibuty cebacate with ferric chloride-->Chlorocarbonyl ferrocene-->1,1'-DIETHYLFERROCENE-->Methylcyclopentadienyl manganese tricarbonyl-->FERROCENEBORONIC ACID-->1,1'-binaphthalene-2,2'-diyl diacetate-->Acetylferrocene-->ferroceron |
| Hazard Information | Back Directory | [General Description]
Orange crystalline solid or orange-yellow powder. Sublimes above 212°F. Camphor odor. | [Reactivity Profile]
FERROCENE(102-54-5) reacts violently with tetranitromethane. . Contact of tetranitromethane with FERROCENE(102-54-5) under various conditions leads to violent explosion, [Trans. Met. Chem., 1979, 4, 207-208]. | [Air & Water Reactions]
Sensitive to prolonged exposure to air and may be sensitive to light. Insoluble in water. | [Hazard]
Moderate fire risk. Evolves toxic products
on decomposition and heating. | [Potential Exposure]
Used as additive in fuel oil; antiknock
agent in gasoline fuel; used in making rubber, silicone
resins, high-temperature polymers and lubricants; interme diate for high-temperature polymers; as a smoke suppres sant and catalyst | [Fire Hazard]
Flash point data for this chemical are not available. FERROCENE is probably combustible. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ ing resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medi cal attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit. | [Shipping]
UN1325 Flammable solids, organic, n.o.s.,
Hazard Class: 4.1; Labels: 4.1-Flammable solid. | [Incompatibilities]
Violent reaction with ammonium per chlorate, tetranitromethane, mercury(II) nitrate. Incompa tible with oxidizers (chlorates, nitrates, peroxides, perman ganates, perchlorates, chlorine, bromine, fluorine, etc.);
contact may cause fires or explosions. Keep away from
alkaline materials, strong bases, strong acids, oxoacids,
epoxides.
Peroxomonosulfuric acid. Decomposes @≧465 ℃. | [Description]
Ferrocene, a metallocene, is a bright orangesalt-like crystals from alcohol with a camphor odor.Molecular weight = 186.05; Boiling point = 249 C (sublimes); Freezing/Melting point = 173 C. Decomposes at465 C. Hazard Identification (based on NFPA-704 MRating System): Health 2, Flammability 2, Reactivity 1.Insoluble in water. | [Chemical Properties]
Ferrocene, a metallocene, appears as bright orange salt-like crystals when crystallized from alcohol. It has a camphor-like odor and forms an orange crystalline solid. The compound is insoluble in water but soluble in benzene, ether, and alcohol, with an iron content of 29.4–30.6%.
 | [Physical properties]
Orange crystals; camphor-like odor; melts at 172.5°C; vaporizes at 249°C; sublimes above 100°C; thermally stable above 500°C; insoluble in water; soluble in alcohol, ether and benzene; also soluble in dilute nitric acid and concentrated sulfuric acid forming a deep red solution that fluoresces. | [Application]
Ferrocene, the most well-known cyclopentadienyl sandwich compound, contains up to 30% iron. It is primarily used as an organometallic framework and is widely applied in fields such as aerospace, petroleum, chemical engineering and biomedicine. For example:
(1) Biomedicine: Research has revealed that ferrocene and its derivatives possess a wide range of pharmacological activities, such as anti-anaemic, antibacterial, anti-proliferative, anti-malarial, anti-tubercular and antiviral properties. Consequently, it can be utilised in the development of drug candidates for the treatment of iron-deficiency anaemia, cancer (e.g. tamoxifen, a drug used to treat hormone-dependent breast cancer) and malaria (e.g. chloroquine) [2].
(2) Aerospace sector: Among various catalysts for combustion rates, ferrocene and its derivatives demonstrate excellent catalytic performance. Currently, ferrocene-based catalysts for the oxidation of solid rocket propellants are in widespread use [3].
(3) Chemical Industry: Ferrocene is a well-known iron precursor molecule for depositing iron-containing films in processes such as chemical vapour deposition (CVD) and can be used to prepare iron nanoparticles. Ferrocene precursors are commonly used as suspension catalysts in the synthesis of carbon nanotubes (CNTs)[4]. Furthermore, it can serve as an iron source for the manufacture of low-cost catalyst supports used in fixed-bed CVD synthesis of carbon nanotubes.
(4) Petroleum sector: Ferrocene can be added to kerosene or diesel to enhance combustion efficiency and reduce carbon monoxide emissions, thereby achieving energy savings and reducing atmospheric pollution. | [Preparation]
Dicyclopentadienyliron may be obtained in a single-step synthetic route by heating cyclopentadiene with iron or iron pentacarbonyl at 300°C:
2C5H5 + Fe → (C5H5)2Fe
Also, it can be prepared by the reaction of iron(II) chloride with cyclopentadiene in the presence of an alkyl amine or a similar base.
Another convenient method of preparing this π-complex of iron is a twostep process in which the first step involves preparation of cyclopentadienyl Grignard reagent, such as 2,4-cyclopentadienylmagnesium bromide C5H5MgBr which may then be combined with ferric chloride to yield dicyclopentadienyl iron:
3C5H5MgBr + FeCl3 → (C5H5)2Fe + 3MgBrCl
Another general method of preparation involves the reaction of cyclopentadiene with sodium metal or sodium hydride in tetrahydrofuran (THF). Addition of iron(II) chloride to this solution forms the complex dicyclopentadienyliron:
2C5H6 + 2Na → 2C5H5ˉ + 2Na+ + H2
In 3:2 molar ratio of cyclopentadiene to sodium cyclopentene is obtained along with cyclopentadienidide (C5H5ˉ ) anion:
3C5H6 + 2Na → 2C5H5¯ + 2Na+ + C5H8
FeCl2 + 2C5H6Na → (C5H5)2Fe + 2NaCl
| [Production Methods]
Ferrocene is produced from the reaction of cyclopentadiene
with reduced iron in the presence of metal oxides. There is
also a two-stage production process in which produced iron
(II)oxide (stage 1) is reacted with cyclopentadiene. | [Health Hazard]
Dicyclopentadienyl iron causes
changes in blood parameters and hepatic
cirrhosis.
The toxicological properties of dicyclopentadienyl
iron have not been extensively
investigated. However, it has been used as a
preventive and therapeutic iron deficiency
drug, and its utilization is listed as tolerable. | [Flammability and Explosibility]
Highlyflammable | [reaction suitability]
core: iron
reagent type: catalyst | [Carcinogenicity]
Ferrocene was administered by
intramuscular injection at a dose of 5175 mg/kg/2 years.
By the criterion established by the Registry of Toxic Effects
of Chemical Substances (RTECS), ferrocene was an equivocal
tumorigenic agent and tumors were most evident at the
site of multiple injections. | [storage]
Color Code—Red: Flammability Hazard: Store ina flammable materials storage area. Prior to working withthis chemical you should be trained on its proper handlingand storage. Store in tightly closed containers in a cool,well-ventilated area away from oxidizers, ammonium perchlorate, tetranitromethane, mercury(II) nitrate, and heat.Sources of ignition, such as smoking and open flames, areprohibited where this chemical is used, handled, or stored ina manner that could create a potential fire or explosionhazard. | [Purification Methods]
Purify it by crystallisation from pentane or cyclohexane (also *C6H6 or MeOH can be used). It is moderately soluble in Et2O and sublimes readily above 100o. Crystallisation from EtOH gave material m 172.5-173o. [Wilkinson Org Synth Coll Vol IV 473 1963, Miller J Chem Soc 632 1952.] It has also been crystallised from methanol and sublimed in vacuo. [Saltiel et al. J Am Chem Soc 109 1209 1987, Beilstein 16 IV 1783.] | [Structure and conformation]
X-ray diffraction studies show that in crystalline ferrocene (and in its
substituted derivatives) the iron atom is "sandwiched" between the two cyclopentadienyl
rings, these rings having the staggered configuration relative to each other (Fig. 16). The
rings are parallel plane regular pentagons, all the C-C and Fe-C distances being equal.
Electron diffraction studies show, however, that ferrocene has the eclipsed configuration
in the vapour state.
 | [References]
[1] Moriuchi, Prof. T. (2021). Helical Chirality of Ferrocene Moieties in Cyclic Ferrocene-Peptide Conjugates. European Journal of Inorganic Chemistry, 2022 5. https://doi.org/10.1002/ejic.202100902
[2] Snegur, L. (2022). Modern Trends in Bio-Organometallic Ferrocene Chemistry. Inorganics. https://doi.org/10.3390/inorganics10120226
[3] Weidong Zhou. (2016). Progress on the synthesis and catalytic and anti-migration properties of ferrocene-based burning rate catalysts. Applied Organometallic Chemistry, 30 9, 796–805. https://doi.org/10.1002/aoc.3502
[4] Martin Lubej, Igor P. (2014). Theoretical and experimental study of iron catalyst preparation by chemical vapor deposition of ferrocene in air. Chemical Engineering Journal, 242, Pages 306-312. https://doi.org/10.1016/j.cej.2013.12.038 |
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