1,1'-Diacetylferrocene

Base Information

• Chemical Name: 1,1'-Diacetylferrocene
• CAS No.: 1273-94-5
• Molecular Formula: C14H14FeO2
• Molecular Weight: 310.947
• Hs Code.: 29319090
• Mol file: 1273-94-5.mol

Synonyms:Iron,bis(cyclopentadienyl methyl ketone)- (6CI,7CI);Bis(h5-acetylcyclopentadienyl)iron;DAF;Diacetylferrocene;NSC 16677;NSC 511707;

Chemical Property of 1,1'-Diacetylferrocene

Chemical Property:

• Appearance/Colour: dark orange to dark red powder
• Melting Point: 125-127 °C(lit.)
• Boiling Point: 166.6oC at 760 mmHg
• Flash Point: 53.1oC
• PSA: 34.14000
• LogP: 2.54930
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Insoluble

Purity/Quality:

98% ^*data from raw suppliers

1,1-Diacetylferrocene,97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of 1,1'-Diacetylferrocene

There total 11 articles about 1,1'-Diacetylferrocene 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: 100.0%

1,1'-bisferrocenedicarboxylic acid → 1,1'-ferrocenyldicarbonyl chloride (1273-94-5)

Guidance literature:

With thionyl chloride;

DOI:10.1134/S107036321706010X

Reference yield: 98.0%

ferrocene (102-54-5,55404-68-7) + acetyl chloride (75-36-5) → 1,1'-diacetylferrocene (1273-94-5)

Guidance literature:

With aluminium chloride; In dichloromethane; ferrocene (1.0 equiv.) added to a stirred suspension of acetyl chloride (2.2 equiv.) and aluminium chloride (2.2 equiv.) in dichloromethane, stirred at room temp. overnight (16 h); washed with water, organic layer passed through a plug of alumina, washed with chloroform, washings concentrated in vacuo, crude product purified by flash column chromy. on silica gel (TLC Rf 0.24 (1:3 acetone-hexane)), elem. anal.;

DOI:10.1039/b000833h

Reference yield: 97.0%

oxalyl dichloride (79-37-8) + 1,1'-bisferrocenedicarboxylic acid → 1,1'-ferrocenyldicarbonyl chloride (1273-94-5)

Guidance literature:

With pyridine; for 3h; Reflux; Inert atmosphere;

DOI:10.1016/j.jorganchem.2021.121945

upstream raw materials:

succinic acid anhydride

ferrocene

acetyl chloride

acetic anhydride

Downstream raw materials:

1,1'-diethylferrocene

Refernces

• 1、 Kletskov,Kolesnik,Dikusar,Zhukovskaya,Potkin. "Synthesis of new ferrocene derivatives with a 4,5-dichloroisothiazole fragment". . p. 1167 - 1171. Retrieved 2017.
• 2、 Rosenblum, M.,Woodward, R. B.. "". . p. 5443 - 5449. Retrieved 1958.
• 3、 Liu, Xiaoju,Xiang, Yulin,Ma, Xiangrong,Ren, Guoyu,Gao, Liguo. "Ferrocene Macrocyclic Schiff Base Complex: Synthesis, Structure and Recognition Properties for Dual Hg2+ and Cu2+". . p. 2986 - 2988. Retrieved 2017.
• 4、 Reiter, Christoph,Fr?hlich, Tony,Zeino, Maen,Marschall, Manfred,Bahsi, Hanife,Leidenberger, Maria,Friedrich, Oliver,Kappes, Barbara,Hampel, Frank,Efferth, Thomas,Tsogoeva, Svetlana B.. "New efficient artemisinin derived agents against human leukemia cells, human cytomegalovirus and Plasmodium falciparum: 2nd generation 1,2,4-trioxane-ferrocene hybrids". . p. 164 - 172. Retrieved 2015.
• 5、 Gonsalves, Kenneth,Zhan-ru, Lin,Rausch, Marvin D.. "". . p. 3862 - 3863. Retrieved 1984.
• 6、 Fahad, Shah,Khan, Amin,Lemenovskiy, Dmitry A.,Naveed, Kaleem-ur-Rehman,Nazir, Ahsan,Usman, Muhammad,Wang, Li,Yu, Haojie,Zarubin, Dmitry N.,Zhizhko, Pavel A.. "Synthesis of ferrocenylated-aminopyridines and ferrocenylated-aminothiazoles and their anti-migration and burning rate catalytic properties". . . Retrieved 2020.
• 7、 Pérez, Wanda I.,Soto, Yarelys,Ortíz, Carmen,Matta, Jaime,Meléndez, Enrique. "Ferrocenes as potential chemotherapeutic drugs: Synthesis, cytotoxic activity, reactive oxygen species production and micronucleus assay". . p. 471 - 479. Retrieved 2015.
• 8、 Hua, Chunxia,Dou, Shuliang,Xu, Hongbo,Hou, Shuai,Zhang, Hangchuan,Zhang, Panpan,Gan, Yang,Zhao, Jiupeng,Li, Yao. "A nanostructured Fc(COCH3)2 film prepared using silica monolayer colloidal crystal templates and its electrochromic properties". . p. 30756 - 30761. Retrieved 2017.
• 9、 . "Synthesis and characterization of a redox-active ion channel supporting cation flux in lipid bilayers". . p. 3862 - 3870. Retrieved 2009.
• 10、 Liu, Xiaoju,Ren, Guoyu,Ma, Xiangruo,Yan, Long,Jiao, Yurong,Ma, Yajun,Yang, Bingqin. "Synthesis and characterization of novel ferrocenyl heterocyclic compounds". . p. 144 - 147. Retrieved 2015.