Ferrocene

 Ferrocene was first prepared unintentionally. In 1951, Pauson and Kealy at Duquesne University reported the reaction of cyclopentadienyl magnesium bromide and ferric chloride with the goal of oxidatively coupling the diene to prepare fulvalene. Instead, they obtained a light orange powder of "remarkable stability."[3] This stability was accorded to the aromatic character of the negative charged cyclopentadienyls, but the sandwich structure of the η5 (pentahapto) compound was not recognized by them. Robert Burns Woodward and Geoffrey Wilkinson deduced the structure based on its reactivity.[4] Independently Ernst Otto Fischer also came to the conclusion of the sandwich structure and started to synthesize other metallocenes such as nickelocene and cobaltocene. Ferrocene's structure was confirmed by NMR spectroscopy and X-ray crystallography Its distinctive "sandwich" structure led to an explosion of interest in compounds of d-block metals with hydrocarbons, and invigorated the development of the flourishing study of organometallic chemistry. In 1973 Fischer of the Technische Universität München and Wilkinson of Imperial College London shared a Nobel Prize for their work on metallocenes and other aspects of organometallic chemistry.

Reported in EPA TSCA Inventory.

The IUPAC name of Ferrocene is cyclopenta-1,3-diene; iron(2+). With the CAS registry number 102-54-5, it is also named as AI3-23119; Biscyclopentadienyliron; CCRIS 3195; Catane; Di(pi-cyclopentadienyl)iron; Di-2,4-cyclopentadien-1-yliron; Iron bis(cyclopentadiene); Iron, bis(eta5-2,4-cyclopentadien-1-yl)-. The product's categories are organometallics, classes of metal compounds, Fe (Iron) compounds, ferrocenes, metallocenes and transition metal compounds.

The Ferrocene is orange crystalline solid or orange-yellow powder which is stable at room temperature and incompatible with strong oxidizing agents. It is soluble in dilute nitric acid, sulfuric acid, benzene, ethyl ether, petroleum ether, and tetrahydrofuran. It is sensitive to prolonged exposure to air and may be sensitive to light. Ferrocene reacts violently with tetranitromethane. Contact of tetranitromethane with Ferrocene under various conditions leads to violent explosion. Thic chemical can be used as antiknock additive for gasoline, catalyst and pharmaceutical intermediates. 

The Ferrocene is highly flammable. It is harmful if swallowed. And it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. So people should not breathe dust and avoid release to the environment. So the storage environment should be ventilate, low-temperature and dry. Keep Ferrocene separate from oxidant.

The Ferrocene can be obtained by the reaction of Sodium cyclopentadienide with Anhydrous iron(II) chloride in ethereal solvents:
2 NaC₅H₅ + FeCl₂ → Fe(C₅H₅)₂ + 2 NaCl

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.79; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.79; (4)ACD/LogD (pH 7.4): 1.79; (5)ACD/BCF (pH 5.5): 13.44; (6)ACD/BCF (pH 7.4): 13.44; (7)ACD/KOC (pH 5.5): 223.49; (8)ACD/KOC (pH 7.4): 223.49; (9)Enthalpy of Vaporization: 27.4 kJ/mol; (10)Vapour Pressure: 418 mmHg at 25°C; (11)Exact Mass: 186.013192; (12)MonoIsotopic Mass: 186.013192; (13)Heavy Atom Count: 11; (14)Complexity: 11.6.

People can use the following data to convert to the molecule structure. SMILES: [Fe+2].[c-]1cccc1.c1[c-]ccc1; InChI: InChI=1/2C5H5.Fe/c2*1-2-4-5-3-1;/h2*1-5H;/q2*-1;+2; InChIKey: KTWOOEGAPBSYNW-UHFFFAOYAZ. Ferrocene has many suppliers, such as A-Chem Technologies Co., Ltd., Chem-Base (Nantong) Laboratories Co., Ltd., Jiangsu International Economic-Technical Cooperation Corp. and Jingtan Qingcheng Environmental Technologies Co., Ltd..

The following is the toxicity data which has been tested.