Ferrocene TOP 1 in China

Ferrocene (Dicyclopentadieny Iron)

F errocene is an orange solid with a camphor-like odor, that sublimes above room temperature, and is soluble in most organic solvents but is insoluble in water. Melting point 172-174, boiling point 249. Ferrocene can be sublimated above 100 degrees. It does not react with acid, alkali and UV, and has stable chemical properties, and does not decompose within 400 degrees. Its molecules show polarity, high thermal stability, chemical stability and radiation resistance

Ferrocene has not been widely used in many fields. many kinds of derivatives can be synthesized by known methods, which greatly extends the application of ferrocene. It is widely used in industry, agriculture, medicine, aerospace, ene rgy saving, environmental protection and other industries.

Physical and chemical properties:

CAS:   102-54-5

Molecular formula: C10H10Fe

Molecular formula (current): Fe (C55)2

Molecular Weight: 186.03

Produ ct technical data ：

Application:

Ferrocene powder has been used as energy-saving antismoke agent, antiknock agent, radiation absorber, heat stabilizer, light stabilizer. It has been applied to synthesize ammonia catalyst and rubber curing agent. In addition, it was replaced of toxic antiknock agent to prepare high-grade unleaded gasoline.

(1) Fuel additives. Ferrocene and its derivatives are antiknock agents used in the fuel for petrol engines. They are safer than previously used tetraethyllead.

(2) Solid Rocket Propellant. Ferrocene and related derivatives are used as powerful burn rate catalysts in ammonium perchlorate composite propellant.
(3) As a ligand scaffold. Chiral ferrocenyl phosphines are employed as ligands for transition-metal catalyzed reactions. Some of them have found industrial applications in the synthesis of pharmaceuticals and agrochemicals.

(4) Used as radiation absorber, heat stabilizer, light stabilizer and smoke inhibitor.

(5) It can also be used to make ammonia synthesis catalyst and rubber curing agent.

Package:

Woven bag (lined with plastic bag), net weight: 25 kg/bag or drum, net weight: 25kg/drum.

Storage: 

Sealed preservation. Store at cool and ventilate condition. Prohibit heating and sun exposure.

Expiration date：  

24 months.

Ferrocene Usage And Synthesis

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.
Chemical Properties	Ferrocene is a crystal with orange needle-like structure that sublimates at temperatures higher than 100℃ and melts at 172.5-173℃. Its boiling point is 249℃. It is soluble in dilute nitric acid, concentrated sulfuric acid, benzene, ether, petroleum ether and tetrahydrofuran and generates bluish fluorescence-containing deep red solution in dilute nitric acid and concentrated sulfuric acid. It is insoluble in water, 10% sodium hydroxide and hot concentrated hydrochloric acid, and it remains stable in air. Ferrocene has a strong property of UV absorbing and great thermostability, withstanding heating up to 470℃. It has a camphor-like scent and can be evaporated with water vapor. Ferrocene is neither dissolved nor decomposed in boiling solutions of these solvents.
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
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	Orange, crystalline solid; camphor-like odor. Insoluble in water; soluble in benzene, ether, and alcohol. Iron content 29.4–30.6%.
Chemical Properties	Ferrocene, a metallocene, is a bright orange salt-like crystals from alcohol. Camphor odor.
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.
Uses	In ultraviolet stabilizers and smoke depressants for polymers; to increase the burn rate of rocket propellants; to prevent erosion of space capsule shields; to improve the viscosity of lubricants; to catalyze polymerization reactions; to catalyze combustion; some derivatives used as hematinic agents
Uses	Ferrocene is used as a catalyst for vulcanization, acceleration, and polymerization, as a chemical intermediate for polymeric compounds such as high temperature polymers, as an antiknock additive for gasoline, as a coating for missiles and satellites, and as a high-temperature lubricant.
Uses	Antiknock additive for gasoline; catalyst.
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
Definition	ferrocene: An orange-red crystallinesolid, Fe(C5H5)2; m.p. 173°C. Itcan be made by adding the ioniccompound Na+C5H5 - (cyclopentadienylsodium, made from sodium andcyclopentadiene) to iron(III) chloride.In ferrocene, the two rings are parallel,with the iron ion sandwiched betweenthem (hence the namesandwich compound: see formula).The bonding is between pi orbitalson the rings and d-orbitals on theFe2+ ion. The compound can undergoelectrophilic substitution on theC5H5rings (they have some aromatic character).It can also be oxidized to theblue ion (C5H5)2Fe+. Ferrocene is the first of a class of similar complexescalled sandwich compounds. Its systematicname is di-π-cyclopentadienyliron(II).
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.
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
General Description	Orange crystalline solid or orange-yellow powder. Sublimes above 212°F. Camphor odor.
Air & Water Reactions	Sensitive to prolonged exposure to air and may be sensitive to light. Insoluble in water.
Reactivity Profile	Ferrocene reacts violently with tetranitromethane. . Contact of tetranitromethane with Ferrocene under various conditions leads to violent explosion, [Trans. Met. Chem., 1979, 4, 207-208].
Hazard	Moderate fire risk. Evolves toxic products on decomposition and heating.
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.
Fire Hazard	Flash point data for Ferrocene are not available. Ferrocene is probably combustible.
Flammability and Explosibility	Highly flammable
reaction suitability	core: iron reagent type: catalyst
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.
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
First aid	If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.
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.
Shipping	UN1325 Flammable solids, organic, n.o.s., Hazard Class: 4.1; Labels: 4.1-Flammable solid.
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.
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 ℃.