Bis(eta-cyclopentadienyl) iron

HCID 7611CAS 102-54-5

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

CCRIS 3195HSDB 2878EINECS 203-039-3UNII-U96PKG90JQAI3-23119FERROCENE [MI]FERROCENE [HSDB]EC 203-039-3SCHEMBL29681ferrous;cyclopenta-1,3-dieneBis(eta-cyclopentadienyl) ironFe(C5H5)2
Show more names
ermaotieFERROCENBIS(CYCLOPENTADIENYL)IRONBIS(CYCLOPENTADIEN)IRONcataneFerrotsenOxolan-3-olDICYCLOPENTADIENYLIRONIRON DICYCLOPENTADIENYLFERROCENE
DTXCID105326Bis( cyclopentadienyl)eisen(II)Tox21_202514NCGC00091936-01NCGC00260063-01CAS-102-54-5Q/TY.J08.19-2022NS00041498

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

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

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

Chemistry & industry

Applications · 3 items

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)

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Additional notes · 1 item

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

104 records

Linked notes

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