Basic information
- Standard SMILES
[Fe+2].c1cc[cH-]c1.c1cc[cH-]c1- InChIKey
KTWOOEGAPBSYNW-UHFFFAOYSA-N- Molecular formula
- C10H10Fe
- Average molar mass
- 186.03 g/mol
- Monoisotopic mass
- 186.013186
Names & identifiers
- Preferred name
- Bis(eta-cyclopentadienyl) iron
- IUPAC
- bis(cyclopenta-1,3-diene);iron(2+)
- English name
- Ferrocene
- Molecular formula
- C10H10Fe
- Molecular weight
- 186.03
Names & synonyms
Show more names
Database identifiers
- CAS
102-54-5- PubChem CID
- 7611
- UNII
- U96PKG90JQ
Properties
Computed structural properties
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 11
Physicochemical properties
- Melting point
- 172 · 172-174 °C (lit.)
- Boiling point
- 249 °C · 249 °C (lit.)
- Density
- 1.49 · 1.490
- bulk density
- 500 kg/m3 · 500kg/m3
- vapor pressure
- 0.03 mm · 0.03 mm Hg ( 40 °C)
- Flash point
- 100 °C · 100°C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 2 O; · insoluble in H2O; soluble in ethanol, ethyl ether,benzene, dilute HNO 3
- form
- crystal
- color
- orange
- Water Solubility
- practically insoluble
- Sensitive
- Air & Moisture Sensitive
- λmax
- 358 nm · 358 nm
- Sublimation
- 100 · 100 ºC
- Merck
- 14 · 14,4037
- Exposure limits
- 10 mg/m3,as · ACGIH:TLV-TWA 10 mg/m3,as FeOSHA:PEL-TWA 15 mg/m3 (total dust),5 mg/m3 (respirable fraction)NIOSH:REL-TWA 10 mg/m3 (total dust),5 mg/m3 (respirable fraction)
- Stability
- Stable at room temperature. Incompatible with strong oxidizing agents. Highly flammable.
- 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 · 3.711 at 22℃
- CAS DataBase Reference
- 102 · 102-54-5(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 96 PKG90JQ · U96PKG90JQ
- NIST Chemistry Reference
- Ferrocene(102-54-5)
- EPA Substance Registry System
- Ferrocene (102-54-5)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 228 · H228-H302+H332-H360FD-H373-H410
- Precautionary statements
- 202 · P202-P210-P273-P301+P312-P304+P340+P312-P308+P313
- target organs
- Liver
- PPE
- 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- F,Xn,N
- Risk Statements
- 11 · 11-22-51/53-2017/11/22
- Safety Statements
- 61 · 61-22-24/25
- OEB
- B
- OEL
- 10 mg/m3 · TWA: 10 mg/m3 (total)
- RIDADR
- 1325 · UN 1325 4.1/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 700000 · LK0700000
- Autoignition Temperature
- 150 °C · >150 °C
- TSCA
- TSCA listed
- HazardClass
- 4.1 · 4.1
- PackingGroup
- II
- HS Code
- 29310095 · 29310095
- Storage Class
- 4.1 B · 4.1B - Flammable solid hazardous materials
- Hazard Classifications
- 4 InhalationAcute · Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 1Flam. Sol. 1Repr. 1BSTOT RE 2 Inhalation
- Hazardous Substances Data
- 102 · 102-54-5(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1320 mg/kg LD50 dermal Rat > 3000 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1.0 Kg (2.2 lbs)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
Safety data
- OEB
- B
- OEL
- TWA: 10 mg/m3 (total)
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- LK0700000
- ridadr
- UN 1325 4.1/PG 2
- hs_code
- 29310095
- Toxicity
- LD50 orally in Rabbit: 1320 mg/kg LD50 dermal Rat > 3000 mg/kg
- risk_code
- 11-22-51/53-2017/11/22
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07,GHS08,GHS09
- hazard_code
- F,Xn,N
- safety_code
- 61-22-24/25
- hazard_class
- 4.1
- Storage Class
- 4.1B - Flammable solid hazardous materials
- packing_group
- II
- target organs
- Liver
- Hazard statements
- H228-H302+H332-H360FD-H373-H410
- Limited Quantities
- 1.0 Kg (2.2 lbs)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralAquatic Chronic 1Flam. Sol. 1Repr. 1BSTOT RE 2 Inhalation
- Autoignition Temperature
- >150 °C
- Precautionary statements
- P202-P210-P273-P301+P312-P304+P340+P312-P308+P313
- Hazardous Substances Data
- 102-54-5(Hazardous Substances Data)
Chemistry & industry
Applications
UsesFerrocene 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.
UsesFerrocene 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.
General DescriptionFerrocene appears as orange crystalline solid or orange-yellow powder. Sublimes above 212 °F. Camphor odor. (NTP, 1992)
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
Definitionferrocene: 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).
Related reactions
Linked notes
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