Cyclopenta-1,3-diene;cyclopenta-1,3-diene-1-carboxylic acid;iron(2+)

Base Information

• Chemical Name: Cyclopenta-1,3-diene;cyclopenta-1,3-diene-1-carboxylic acid;iron(2+)
• CAS No.: 1271-42-7
• Molecular Formula: C11H10FeO2
• Molecular Weight: 230.046
• Hs Code.: 29319090
• Mol file: 1271-42-7.mol

Synonyms:AKOS005439473;F0165

Chemical Property of Cyclopenta-1,3-diene;cyclopenta-1,3-diene-1-carboxylic acid;iron(2+)

Chemical Property:

• Appearance/Colour: dark brown powder
• Vapor Pressure: 0.016mmHg at 25°C
• Melting Point: 210 °C (dec.)(lit.)
• Boiling Point: 236.7oC at 760 mmHg
• Flash Point: 104.2oC
• PSA: 37.30000
• LogP: 1.49530
• Storage Temp.: Flammables area
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 230.003015
• Heavy Atom Count: 14
• Complexity: 155

Purity/Quality:

98%, ^*data from raw suppliers

Ferrocenecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [CH-]1C=CC=C1.[CH-]1C=CC=C1C(=O)O.[Fe+2]
• Uses: Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS. Ferrocenecarboxylic acid is used to esterify complex mixtures of phenols and alcohols for analysis by GCMS. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Technology Process of Cyclopenta-1,3-diene;cyclopenta-1,3-diene-1-carboxylic acid;iron(2+)

There total 51 articles about Cyclopenta-1,3-diene;cyclopenta-1,3-diene-1-carboxylic acid;iron(2+) 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: 97.0%

ferrocene (102-54-5,55404-68-7) + carbon dioxide (124-38-9,18923-20-1) + tert.-butyl lithium (594-19-4) → ferrocenecarboxylic acid (1271-42-7) + 1,1'-bisferrocenedicarboxylic acid

Guidance literature:

With potassium tert-butoxide; In tetrahydrofuran; diethyl ether; pentane; Ar-atmosphere; dissoln. of ferrocene and KO(t)Bu in THF, cooling (-78°C), dropwise addn. of (t)BuLi (pentane), stirring for 60 min at -78°C, pouring into dry ice:Et2O mixture, warming to room temp.; extn. (0.75M NaOH, 2x), neutralization (HCl, to pH>4, pptn.), extn. (Et2O), filtration, drying (MgSO4), concn., addn. of hexanes, concn. (pptn.), collection (filtration); NMR-spectroscopy;

DOI:10.1021/om990083w

Reference yield: 95.0%

acetylferrocene (1271-55-2) → ferrocenecarboxylic acid (1271-42-7)

Guidance literature:

With bromine; sodium hydroxide; In 1,4-dioxane; water; at 10 ℃; for 1h; Acidic conditions;

DOI:10.1021/om400339t

Reference yield: 94.0%

ferrocene (102-54-5,55404-68-7) + carbon dioxide (124-38-9,18923-20-1) → ferrocenecarboxylic acid (1271-42-7)

Guidance literature:

ferrocene; With potassium tert-butylate; tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere; Schlenk technique;

carbon dioxide; In tetrahydrofuran; at -78 - -15 ℃; Schlenk technique;

DOI:10.1055/s-0039-1689917

upstream raw materials:

ferrocene

chloroform

Bromotrichloromethane

water

Downstream raw materials:

ferrocenoyl chloride

Cr(II)(2,2'-bipyridine)3

(C₅H₅)Fe(C₅H₄CONHCH(CH₂C₆H₅)COOCH₃)

Ru(P(C₆H₅)3)2(CO)(Cl)((O₂CC₅H₄)Fe(C₅H₅))

Refernces

• 1、 Tazi, Mehdi,Erb, William,Halauko, Yury S.,Ivashkevich, Oleg A.,Matulis, Vadim E.,Roisnel, Thierry,Dorcet, Vincent,Mongin, Florence. "From 2- to 3-Substituted Ferrocene Carboxamides or How to Apply Halogen dance to the Ferrocene Series". . p. 4770 - 4778. Retrieved 2017.
• 2、 Nishibayashi, Yoshiaki,Segawa, Kyohei,Arikawa, Yasuyoshi,Ohe, Kouichi,Hidai, Masanobu,Uemura, Sakae. "Synthesis and structure of novel chiral oxazolinylferrocenes and oxazolinylferrocenylphosphines, and their rhodium(I) -complexes". . p. 381 - 398. Retrieved 1997.
• 3、 Batsanov, Andrei S.,Herault, Damien,Howard, Judith A. K.,Patrick, Leonard G. F.,Probert, Michael R.,Whiting, Andrew. "Synthesis and Structure of Planar Chiral, Bifunctional Aminoboronic Acid Ferrocene Derivatives". . p. 2414 - 2419. Retrieved 2007.
• 4、 Conradie, Jeanet,Swarts, Pieter J.. "Synthesis, spectroscopy, electrochemistry and DFT of electron-rich ferrocenylsubphthalocyanines". . . Retrieved 2020.
• 5、 Little, W. F.,Eisenthal, R.. "". . p. 1577 - 1580. Retrieved 1960.
• 6、 Roemer, Max,Wild, Duncan A.,Sobolev, Alexandre N.,Skelton, Brian W.,Nealon, Gareth L.,Piggott, Matthew J.,Koutsantonis, George A.. "Carbon-Rich Trinuclear Octamethylferrocenophanes". . p. 3789 - 3799. Retrieved 2019.
• 7、 Dorcet, Vincent,Erb, William,Roisnel, Thierry. "Practical Chromatography-Free Synthesis of 2-Iodo- N, N -diiso propylferrocenecarboxamide and Further Transformations". . p. 3205 - 3213. Retrieved 2019.
• 8、 Peng, Xiaoqian,He, Hanping,Xia, Jingping,Lou, Zhaowen,Chang, Gang,Zhang, Xiuhua,Wang, Shengfu. "Visual detection and removal of mercury ions by a ferrocene derivative". . p. 3541 - 3544. Retrieved 2014.