Iron;1,2,3,4,5-pentamethylcyclopentane

Base Information

• Chemical Name: Iron;1,2,3,4,5-pentamethylcyclopentane
• CAS No.: 12126-50-0
• Molecular Formula: C20H30Fe
• Molecular Weight: 326.305
• Hs Code.: 29319090
• DSSTox Substance ID: DTXSID80923743
• Mol file: 12126-50-0.mol

Synonyms:

Chemical Property of Iron;1,2,3,4,5-pentamethylcyclopentane

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 1.97mmHg at 25°C
• Melting Point: 277 °C (dec.)(lit.)
• Boiling Point: 170.2 °C at 760 mmHg
• Flash Point: 44.4 °C
• PSA: 0.00000
• LogP: 5.94150
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 336.247937
• Heavy Atom Count: 21
• Complexity: 72.4

Purity/Quality:

98% ^*data from raw suppliers

1,1'',2,2'',3,3'',4,4'',5,5''-Decamethylferrocene ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C1C)C)C)C.CC1C(C(C(C1C)C)C)C.[Fe]
• Uses: Decamethylferrocene is used as a superior internal reference redox standard to ferrocene in voltammetric and amperometric titrations. It is used as photocathode for the detection of barium fluoride scintillation light. Bis(pentamethylcyclopentadienyl)iron(II)(Me10FeCp2, DecMFc) was used as an electron donor to functionalize high purity graphene with metallic palladium via a redox reaction.

Technology Process of Iron;1,2,3,4,5-pentamethylcyclopentane

There total 53 articles about Iron;1,2,3,4,5-pentamethylcyclopentane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

tetrabutylammonium dimethylaurate(I) (228118-52-3) + bis(pentamethylcyclopentadienyl)iron(III) hexafluorophosphate → bis(pentamethylcyclopentadienyl)iron(II) (12126-50-0) + gold (7440-57-5,457905-15-6)

Guidance literature:

In tetrahydrofuran; byproducts: CH4, C2H6; He-atmosphere; addn. of 1 equiv. of Cp*2FePF6 to soln. of aurate at -196°C, warming to room temp.;

DOI:10.1021/om990043s

Reference yield: 92.0%

1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) + iron(II) chloride → bis(pentamethylcyclopentadienyl)iron(II) (12126-50-0)

Guidance literature:

With Fe; n-BuLi; In 1,2-dimethoxyethane; hexane; N2, addn. of n-BuLi in hexane to C5Me5H in 1,2-dimethoxyethane at -78°C; warming to room temp.; addn. of FeCl2/reduced iron powder; refluxing overnight; extn. with hot cyclohexane, filtn., evapn., recrystn. from cyclohexane or Et2O, sublimation (0.06 torr, 110°C);

Reference yield: 73.0%

decamethylferrocenium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate (220517-48-6) + [(1,2-bis(dimethylphosphino)ethane)4Cr2(C2Si(i-Pr)3)2(μ-N2)] → bis(pentamethylcyclopentadienyl)iron(II) (12126-50-0) + [(1,2-bis(dimethylphosphino)ethane)4Cr2(C2Si(i-Pr)3)2(μ-N2)][tetrakis(3,5-bis(trifluoromethylphenyl)borate]2

Guidance literature:

In diethyl ether; (N2); Schlenk technique; soln. of Fe complex in Et2O was added to stirred soln. of Cr complex in Et2O; stirred for 5 min; filtered through Celite; pentane added; filtered; washed (pentane); elem. anal.;

DOI:10.1021/ic101528d

upstream raw materials:

tetrabutylammonium dimethylaurate(I)

ferrocene

methylene chloride

potassium tert-butylate

Downstream raw materials:

cumyl hydroperoxide anion

dihydrogen peroxide

decamethylferrocenium tetrakis(pentafluorophenyl)borate

Refernces

• 1、 Hoffert, Wesley A.,Rappe, Anthony K.,Shores, Matthew P.. "Unusual electronic effects imparted by bridging dinitrogen: An experimental and theoretical investigation". . p. 9497 - 9507. Retrieved 2010.
• 2、 Simons, L. H.,Lagowski, J. J.. "ORGANOMETALLIC DERIVATIVES OF THE TRANSITION ELEMENTS IV. FERROCENES VIA THE REACTION OF IRON ATOMS WITH ALKYNES". . p. 195 - 204. Retrieved 1983.
• 3、 Nielson, Roger M.,McManis, George E.,Golovin, Neal M.,Weaver, Michael J.. "Solvent Dynamical Effects in Electron Transfer: Comparisons of Self-Exchange Kinetics for Cobaltocenium-Cobaltocene and Related Redox Couples with Theoretical Predictions". . p. 3441 - 3450. Retrieved 1988.
• 4、 Fabrizio, Kevin,Lazarou, Konstantinos A.,Payne, Lillian I.,Twight, Liam P.,Golledge, Stephen,Hendon, Christopher H.,Brozek, Carl K.. "Tunable Band Gaps in MUV-10(M): A Family of Photoredox-Active MOFs with Earth-Abundant Open Metal Sites". . p. 12609 - 12621. Retrieved 2021.
• 5、 Hilbig, Harald,Hudeczek, Peter,K?hler, Frank H.,Xie, Xiulan,Bergerat, Pierre,Kahn, Olivier. "Ferro and Antiferromagnetic Exchange in Decamethylbimetallocenes". . p. 4246 - 4257. Retrieved 1998.
• 6、 Malischewski, Moritz,Seppelt, Konrad,Sutter, J?rg,Munz, Dominik,Meyer, Karsten. "A Ferrocene-Based Dicationic Iron(IV) Carbonyl Complex". . p. 14597 - 14601. Retrieved 2018.
• 7、 Novikova, Lyudmila N.,Zagorevskii, Dmitrii V.,Ustynyuk, Nikolai A.. "Deprotonation of decamethylferrocenium cation - new approach to alkyl group functionalization in transition metal complexes". . p. C6 - C7. Retrieved 1993.
• 8、 Effertz, Ulrike,Englert, Ulli,Podewils, Frank,Salzer, Albrecht,Wagner, Trixie,Kaupp, Martin. "Reaction of pentadienyl complexes with metal carbonyls: Synthetic, structural, and theoretical studies of metallabenzene π-complexes". . p. 264 - 274. Retrieved 2003.
• 9、 Ruiz, Jaime,Ogliaro, Fran?ois,Saillard, Jean-Yves,Halet, Jean-Fran?ois,Varret, Fran?ois,Astruc, Didier. "First 17-18-19-electron triads of stable isostructural organometallic complexes. The 17-electron complexes [Fe(C5R5)(arene)]2+ (R = H or Me), a novel family of strong oxidants: Isolation, characterization, electronic structure, and redox properties". . p. 11693 - 11705. Retrieved 1998.