ChemicalBook
Chinese Japanese Germany Korea

Ferrocene

A kind of organic transition metal compound with aromatic property Chemical Properties Uses Production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage properties Extinguishing agent Professional standards
Ferrocene
Ferrocene structure
CAS No.
102-54-5
Chemical Name:
Ferrocene
Synonyms
catane;FERROCEN;FERROCENE;Ferrotsen;Ferroceene;Oxolan-3-ol;ferrotsen[qr];Ferrocene,98%;Ferrocene ,99%;Ferrocene 98.5%
CBNumber:
CB1414721
Molecular Formula:
C10H10Fe
Formula Weight:
186.03
MOL File:
102-54-5.mol

Ferrocene Properties

Melting point:
172-174 °C(lit.)
Boiling point:
249 °C(lit.)
Density 
1.490
vapor pressure 
0.03 mm Hg ( 40 °C)
Flash point:
100°C
storage temp. 
Flammables area
form 
crystal
color 
orange
Water Solubility 
practically insoluble
Sensitive 
Air & Moisture Sensitive
Sublimation 
100 ºC
Merck 
14,4037
Stability:
Stable at room temperature. Incompatible with strong oxidizing agents. Highly flammable.
CAS DataBase Reference
102-54-5(CAS DataBase Reference)
NIST Chemistry Reference
Ferrocene(102-54-5)
EPA Substance Registry System
Ferrocene(102-54-5)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  F,Xn,N
Risk Statements  11-22-51/53-2017/11/22
Safety Statements  61-22-24/25
RIDADR  UN 1325 4.1/PG 2
WGK Germany  2
RTECS  LK0700000
Autoignition Temperature >150 °C
TSCA  Yes
HazardClass  4.1
PackingGroup  II
HS Code  29310095
Hazardous Substances Data 102-54-5(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: 1320 mg/kg LD50 dermal Rat > 3000 mg/kg
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H228 Flammable solid Flammable solids Category 1
Category 2
Danger
Warning
P210, P240,P241, P280, P370+P378
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H320 Causes eye irritation Serious eye damage/eye irritation Category 2B Warning P264, P305+P351+P338,P337+P313
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
H401 Toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 2 P273, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
H411 Toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 2
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P240 Ground/bond container and receiving equipment.
P241 Use explosion-proof electrical/ventilating/lighting/…/equipment.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P271 Use only outdoors or in a well-ventilated area.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P314 Get medical advice/attention if you feel unwell.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.
P501 Dispose of contents/container to..…

Ferrocene price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich F408 Ferrocene 98% 102-54-5 5g $22.3 2018-11-13 Buy
Sigma-Aldrich F408 Ferrocene 98% 102-54-5 100g $35.2 2018-11-13 Buy
TCI Chemical D0444 Ferrocene >98.0%(GC) 102-54-5 25g $16 2018-11-22 Buy
TCI Chemical D0444 Ferrocene >98.0%(GC) 102-54-5 100g $28 2018-11-22 Buy
Alfa Aesar 087202 Ferrocene, 99% 102-54-5 50g $26.1 2018-11-16 Buy

Ferrocene Chemical Properties,Uses,Production

A kind of organic transition metal compound with aromatic property

Ferrocene is a kind of organic transition metal compound with aromatic nature. It is also called as dicyclopentadienyl iron. It contains a divalent iron cation and two cyclopentadienyl anions in its molecular structure. It is also the raw materials for production of ferrocenecarboxylic acid. In 1950s of the last century, people had first successfully produced it with the reaction between cyclopentadienyl magnesium bromide and anhydrous ferric chloride. At room temperature, it is orange needle crystal powder with a similar smell as camphor and belongs to non-polar compound. It is soluble in many organic solvents such as methanol, ethanol, ethyl ether, petroleum ether, gasoline, kerosene, diesel oil, methylene chloride, benzene, toluene, and xylene, Because of the large polarity of ethanol polarity, it is usually recommended to dissolve it with toluene. It is insoluble in water but soluble in concentrated sulfuric acid. It is also insoluble and doesn’t decompose in boiling caustic soda solution and hydrochloric acid. It molecule exhibits polarity with higher thermal stability, chemical stability and radiation resistance. It has wide range of application in industry, agriculture, medicine, aerospace, energy, environmental protection and other industries. Main applications are described below:
(1)It can be used as the fuel saving smoke suppressants and anti-knock agent. For example, it can be used for the production of gasoline antiknock agent, the fuel catalyst of rocket propellant and also the solid fuels of aerospace.
(2) It can be used as the catalyst such as catalyst for the production of ammonia, as the curing agent of silicone rubber; it can prevent the degradation of polyethylene by light; when applied to agricultural mulch, it can break its natural degradation without affecting the cultivation and fertilization within a certain time.
(3) It can be used as a gasoline anti-knock agent. It can substitute gasoline toxic tetraethyl lead for being used as the anti-knock agent and for production of high-grade unleaded petrol in order to eliminate the contamination of the environment and poisoning to human body by discharge of fuel.
(4) It can be used as radiation absorbers, heat stabilizers, light stabilizers, and smoke-retardants.
(5) For the chemical properties, ferrocene is similar to aromatic compounds which is not prone to have addition reaction but prone to have electrophilic substitution reaction. It can also participate in metallization, acylation, alkylation, sulfonation, formylation and ligand exchange reaction, which can be used for production of derivative with a wide range of applications.
The above information is edited by the Chemicalbook of Dai Xiongfeng.

Chemical Properties

It is an orange needles like crystal with its melting point being 172.5-173 ℃. It undergoes sublimation at temperature higher than 100 ℃. Its boiling point is 249 ℃. It is soluble in dilute nitric acid, concentrated sulfuric acid, benzene, ether, petroleum ether and tetrahydrofuran. It can generate 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. In the boiling solution of these solvents, ferrocene is neither dissolved nor decomposed. It can be evaporated together with water vapor. It has a smell similar to camphor and is stable in air. It has a strong property of UV absorbing and has great thermostability which can withstand the heating at a temperature as high as 470 ℃.

Uses

Ferrocene can be used as the additives of rocket fuel, the antiknock agent of gasoline and the curing agent of rubber and silicone resin as well as the ultraviolet absorber. The Vinyl derivative of ferrocene can be subject to ethylenic polymerization to obtain the metal-containing polymers of carbon chain skeleton which can be used as the outer coating of spacecraft. It has been found early regarding the smoke abatement effect and combustion effect of ferrocene. No matter whether being supplied in solid fuel, liquid fuel or gas fuel, it can always exert this kind of effect and this effect is more significant especially for hydrocarbons with smoke upon burning. Supplement it into the gasoline has a very good anti-hunt effect. However, due to the deposition of the iron oxide in park plug which can negatively affect ignition, its application is limited, therefore, some people also apply de-iron mixture in order to reduce the deposition phenomenon of iron. Supplement of ferrocene to the kerosene or diesel oil, due to the absence of ignition device in the engine, will have fewer adverse effects on it. In addition to the smoke abatement and combustion facilitating effect in the combustion, it also has effect of promoting the conversion of carbon monoxide into carbon dioxide. In addition, it can improve the heat of combustion and increase power efficiency to achieve the effects of energy saving and air pollution reduction. Supplement of ferrocene to the boiler fuel oil can reduce tobacco production and nozzle deposition. Supplement of 0.1% ferrocene in diesel can remove smoke by 30-70%, save fuel by 10-14%, and increase the power by 10%. There are even many more reports regarding the application of ferrocene in solid fuel of rocket fuel. Moreover, there are even cases regarding supplying it in pulverized coal for smoke-reduction agent. Upon applying the polymer water as fuel, supplement of ferrocene can reduce the smoke by several times. It can also be used as the smoke-reducing additive. In addition to the above applications, ferrocene also has other applications. When used as iron fertilizer, it can facilitate the absorption of plants on iron and increase the iron content of crops. Moreover, its derivatives can be used as pesticides. Ferrocene also has a lot of applications in industry and organic synthesis. For example, its derivatives can be used as the antioxidant of rubber or polyethylene, the stabilizer of polyurea ester, the catalyst of isobutene spasm methylation, the decomposition catalyst of polymer peroxide, and for increasing the yield of para-chlorotoluene produced during the process of chlorination of toluene. In other areas, it can also be used as anti-load additive of lubricants as well as the promoting agent of abrasive materials.
It can be used as catalyst and the antiknock additive of gasoline as well as energy-saving additives for combustion promotion and smoke removal; it can be applied to various kinds of fuels such as diesel, gasoline, heavy oil and coal. Supplement of 0.1% ferrocene into diesel can save fuel by 10-14%, increase the efficiency by 10-13%, and reduce the degree of smoke in exhaust by 30-80 ‰. In addition, addition of 0.3 ‰ to the heavy oil and addition of 0.2% ferrocene to coal can both decrease the fuel consumption rate while the degree of smoke is also reduced by 30%.
Ferrocene is a kind of sandwich-containing metal compound. Ferrocene and its derivatives, because of their own characteristics such as hydrophobicity, bio-oxidability, aroma, stability, low resistance, biological activity, has a wide range of application such as catalyst, the antiknock additive of gasoline, high-temperature lubricant, the intermediates of high-temperature polymer and UV absorber.

Production method

It can be produced either by the heating reaction between iron powder and cyclopentadiene in nitrogen atmosphere of 300 ℃ or the reaction between anhydrous ferric chloride together with the sodium cyclopentadienyl in tetrahydrofuran. Alternatively, it can also produced by electrolytic synthesis method. Taking cyclopentadiene, ferrous chloride, and diethylamine as raw material for synthesis of ferrocene can operate according to the following protocol. Upon stirring, add anhydrous ferric chloride (FeCl3) in several times to the tetrahydrofuran solution; further add iron powder into it and have heating reflux for 4.5 h under the protection of nitrogen gas, resulting in ferrous chloride solution. Further remove tetrahydrofuran solvent by evaporation under reduced pressure to give nearly dry residue. Under ice-cooling condition, add the mixture of cyclopentadienyl and diethylamine and stir vigorously at room temperature for 6-8h; remove the excess amount of amine through evaporation under reduced pressure and extract the residue with petroleum ether under reflux. The extract is subject to immediate filtering; evaporate the solvent to obtain ferrocene crude product. Employ pentane or cyclohexane for recrystallization, or apply sublimation method for extract purified product with the yield of refined product being 73-84%.

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

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.

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

An orange crystalline solid. It is an example of a sandwich compound, in which an iron(II) ion is coordinated to two cyclopentadienyl ions. The bonding involves overlap of d orbitals on the iron with the pi electrons in the cyclopentadienyl ring. The compound melts at 173°C, is soluble in organic solvents, and can undergo substitution reactions on the rings. It can be oxidized to the blue cation (C5H5)2Fe+. The systematic name is di-π-cyclopentadienyl iron(II).

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).

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.

Fire Hazard

Flash point data for Ferrocene are not available. Ferrocene is probably combustible.

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 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.

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.]

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 ℃.

Ferrocene Preparation Products And Raw materials

Raw materials

Preparation Products


Ferrocene Suppliers

Global( 255)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Dalian Richfortune Chemicals Co., Ltd
86-411-84820922, 84821539
86-411-84821380 sales@richfortunechem.com China 360 57
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21954 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile; WhatsApp; Telegram)
+86-571-56059825 fandachem@gmail.com CHINA 2561 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 1730 55
Tianjin Zhongxin Chemtech Co., Ltd.
022-89880739
022-66880086 sales@tjzxchem.com CHINA 558 58
Xiamen AmoyChem Co., Ltd
+86 (0)592-605 1114
sales@amoychem.com CHINA 6374 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 24001 58
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20095 58

View Lastest Price from Ferrocene manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-21 Ferrocene
102-54-5
US $1.00 / kg 1g 99% 100KG career henan chemical co
2019-04-10 Ferrocene
102-54-5
US $1.00 / g 1g 99% 2000 Metric Ton/Metric Tons per Year uv absorber Cangzhou Wanyou New Material Technology Co.,Ltd

Ferrocene Spectrum


102-54-5(Ferrocene)Related Search:


Copyright 2017 © ChemicalBook. All rights reserved