12085-68-6

Basic information

• Product Name: (1-CHLORO-2-FORMYLVINYL)FERROCENE
• Synonyms: (1-Chloro-3-oxo-1-propenyl)ferrocene;[(1-Chloro-2-formylvinyl)cyclopentadienyl]cyclopentadienyliron;3-Ferrocenyl-3-chloropropenal;-Ferrocenyl--chloroacrolein
• CAS NO: 12085-68-6
• Molecular Formula: C₁₃H₁₁ClFeO
• Molecular Weight: 274.527
• Product Categories: Catalysis and Inorganic Chemistry;Chemical Synthesis
• Mol File: 12085-68-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 74-78 °C(lit.)
• Appearance: /
• CAS DataBase Reference: (1-CHLORO-2-FORMYLVINYL)FERROCENE(CAS DataBase Reference)
• NIST Chemistry Reference: (1-CHLORO-2-FORMYLVINYL)FERROCENE(12085-68-6)
• EPA Substance Registry System: (1-CHLORO-2-FORMYLVINYL)FERROCENE(12085-68-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 12085-68-6(Hazardous Substances Data)

Usage

General Description

(1-Chloro-2-formylvinyl)ferrocene is a chemical compound containing a ferrocene core with a vinyl group substituted with a formyl and a chloro group. It is often used in organic synthesis as a versatile reagent for various reactions, including carbo- and hetero-cyclization, cross-coupling, and cycloaddition reactions. The presence of the ferrocene moiety gives this compound unique redox properties, making it useful in electrochemical and catalytic applications. Additionally, it has been investigated for potential use in medicinal chemistry, particularly in the development of new anti-cancer agents. Overall, (1-chloro-2-formylvinyl)ferrocene is a versatile and valuable compound in various chemical and biological applications.

InChI:InChI=1/C8H6ClO.C5H5.Fe/c9-8(5-6-10)7-3-1-2-4-7;1-2-4-5-3-1;/h1-6H;1-5H;

Upstream product

• 1271-55-2 acetylferrocene 
• 68-12-2 N,N-dimethyl-formamide 
• 10025-87-3 trichlorophosphate 
• 92952-15-3 (3-chloro-3-ferrocenylallylidene)dimethylammonium phenylsulphonate 
• 63782-40-1 (3-chloro-3-ferrocenylallylidene)dimethylammonium perchlorate 
• 92952-14-2 (3-chloro-3-ferrocenylallylidene)dimethylammonium iodide 

Downstream Products

• 1207093-43-3 C₁₇H₁₂O 
• 1291-56-1 3⁽⁵⁾-ferrocenylpyrazole 
• 956103-49-4 (3-ferrocenylpyrazol-1-yl)(4-hydroxyphenyl)methanone 
• 956103-45-0 1-benzyl-5-ferrocenyl-1H-pyrazole 

Relevant articles and documents

Design, synthesis and fungicidal activity studies of 3-ferrocenyl-N-acryloylmorpholine

Ferrocene and its derivatives have been widely used in many fields and also used to modify and improve the performance. Particularly, their low toxicity also attract much attention in medical and pesticide fields. In order to get fungicides with higher biological activity, ferrocenyl groups were introduced into the skeleton of dimethomorph instead of phenyl groups and a series of 3-ferrocenyl-N-acryloylmorpholine were synthesized. The fungicidal bioassay results indicated that most of compounds showed moderate fungicidal activities against 14 kinds of agricultural pathogenic fungi and some compounds displayed higher fungicidal activities than that of dimethomorph. Intrestlingly, compounds 5(Z) exhibited better fungicidal activity against Sclerotinia sclerotiorum than that of compound 5(E).

New π-Conjugated Ferrocenyl-Substituted Heterocyclic Systems Containing Electron-Deficient Aromatic Nitrogen Heterocycles

A series of ferrocenyl-substituted methyl ketones and chalcones were synthesized and converted to unsymmetrical 4,6-disubstituted pyrimidin-2-amines and 2-(1H-pyrrol-1-yl)pyrimidines in which the ferrocene fragment is separated from the pyrimidine ring by

The synthesis, structural characterization and biological evaluation of novel N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters as anticancer agents

A series of N-{para-(ferrocenyl) ethynyl benzoyl} amino acid and dipeptide methyl and ethyl esters 4–18 were prepared by coupling para-(ferrocenyl) ethynyl benzoic acid 3 to the amino acids GABA(OMe), GABA(OEt) and the dipeptide esters GlyGly(OMe), GlyGly(OEt), Gly-L-Ala(OMe), Gly-L-Ala(OEt), Gly-D-Ala(OMe), Gly-D-Ala(OEt), Gly-L-Leu(OEt), Gly-L-Phe(OEt), SarGly(OMe), SarGly(OEt), Sar-L-Ala(OEt), L-ProGly(OEt) and L-Pro-L-Ala(OEt) using the standard N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (EDC), 1-hydroxybenzotriazole (HOBt) protocol. All the compounds were fully characterized using a combination of I.R., UV-Vis, 1H NMR, 13C NMR, DEPT-135, 1H-13C COSY (HMQC) spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Selected compounds 5, 7, 9, 11, 16, 17 and 18 showed micromolar activity in the H1299 NSCLC cell line, with IC50 values in the range of 3.8–8.3 μM.

Novel ferrocene-labeled propargyl amines via CuI multicomponent amination/alkynylation

An efficient synthesis of ferrocene-tagged propargyl amine derivatives via one-pot three-component domino amination/alkynylation in water is reported. The synthesis involves a single Cu(i) catalyst without addition of a ligand, has broad substrate applicability and gives excellent yields.

Colchicine metallocenyl bioconjugates showing high antiproliferative activities against cancer cell lines

A series of ferrocenyl and ruthenocenyl conjugates with colchicine bearing a 1,2,3-triazole moiety were synthesized and their anticancer properties were evaluated. We found that the most potent metallocenyl derivatives Rc4 and Rc5 are 6-7 times more cytotoxic toward HepG2 cells, while Fc4 and Fc5 are two times more cytotoxic toward HCT116 cells as colchicine. We also found that compounds Fc4, Fc5, Rc1 and Rc3-Rc5 are able to induce apoptosis, while compound Fc2 arrests mitosis.

Cationic (η6-Arene)tricarbonylmanganese Linked to Ferrocene Complexes

Palladium-catalyzed Sonogashira coupling reactions of the neutral [η 5(1-5)-(1-chloro-4-methoxycyclohexa-2,4-dienyl)] tricarbonylmanganese(I) (2) and 2-bromo-5-{[η 5(1-5)-(4-methoxycyclohexa-2,4-dienyl]tricarbonylmanganese(I)} thioph