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1271-51-8

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1271-51-8 Usage

Chemical Properties

crystalline solid

Uses

Used in the synthesis of 2-aminomethylferrocenes from vinyl ferrocene and lithium amides.

Definition

ChEBI: Ferrocene substituted on one of the cyclopentadienyl rings by a vinyl group.

Purification Methods

Dissolve vinylferrocene in Et2O, wash it with H2O and brine, dry (Na2SO4), and evaporate to a small volume. Purify it through an Al2O3 (Spence grade H) column by eluting the yellow band with pet ether (b 40-60o). The low melting orange crystals can be sublimed. The tetracyanoethylene adduct crystallises from *C6H6/pentane and has m 137-139o(dec). [Horspool & Sutherland Can J Chem 46 3453 1968, Berger et al. J Org Chem 39 377 1974, Rauch & Siegel J Organomet Chem 11 317 1968, Beilstein 16 III 1787.]

Check Digit Verification of cas no

The CAS Registry Mumber 1271-51-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,2,7 and 1 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 1271-51:
(6*1)+(5*2)+(4*7)+(3*1)+(2*5)+(1*1)=58
58 % 10 = 8
So 1271-51-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H7.C5H5.Fe/c1-2-7-5-3-4-6-7;1-2-4-5-3-1;/h2-6H,1H2;1-5H;/q2*-1;+2

1271-51-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
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  • Detail
  • Alfa Aesar

  • (17450)  Vinylferrocene   

  • 1271-51-8

  • 1g

  • 1209.0CNY

  • Detail
  • Alfa Aesar

  • (17450)  Vinylferrocene   

  • 1271-51-8

  • 5g

  • 4006.0CNY

  • Detail

1271-51-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name vinylferrocene

1.2 Other means of identification

Product number -
Other names poly(vinyl-ferrocene)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1271-51-8 SDS

1271-51-8Related news

Biocompatible glucose sensor prepared by modifying protein and Vinylferrocene (cas 1271-51-8) monomer composite membrane08/14/2019

This paper proposes a very simple procedure for preparing a biocompatible sensor based on a protein (bovine serum albumin, BSA), enzyme and vinylferrocene (VF) composite membrane modified electrode. The membrane was prepared simply by first casting vinylferrocene and then coating it with BSA and...detailed

Synthesis, third-order nonlinear optical properties and theoretical analysis of Vinylferrocene (cas 1271-51-8) derivatives08/10/2019

A series of vinylferrocene derivatives were synthesized from the reaction of ferrocenecarboxaldehyde, alcohol, and triphenylphosphonium bromide in a one-pot, solid-state reaction. Their third-order nonlinear optical (NLO) properties were evaluated in N,N-dimethylformamide at 800 nm using femtose...detailed

1271-51-8Relevant articles and documents

Lednicer, D.,Hauser, C. R.

, p. 43 - 46 (1959)

A versatile electrochemical sensing receptor based on a molecularly imprinted polymer

Udomsap, Dutduan,Branger, Catherine,Culioli, Gérald,Dollet, Pascal,Brisset, Hugues

, p. 7488 - 7491 (2014)

Electrochemical molecularly imprinted polymers (e-MIPs) are reported for the first time. Their elaboration is based on the introduction of a redox tracer (vinylferrocene) inside the binding cavities of a cross-linked MIP. Determination of the analyte (benzo[a]pyrene) can be simply performed by measuring the redox tracer signal. the Partner Organisations 2014.

Goldberg, S. I.,Loeble, W. D.,Tidwell, T. T.

, p. 4070 - 4071 (1967)

Slocum, D. W.,Jones, W. E.,Ernst, C. R.

, p. 4278 - 4281 (1972)

Synthesis and Characterization of a Family of Air-Stable Ferrocene- and Ruthenocene-Containing Primary, Secondary, and Tertiary Phosphines

Kenaree, Amir Rabiee,Cuthbert, Tyler J.,Barbon, Stephanie M.,Boyle, Paul D.,Gillies, Elizabeth R.,Ragogna, Paul J.,Gilroy, Joe B.

, p. 4272 - 4280 (2015)

The synthesis and characterization of a family of air-stable primary, secondary, and tertiary phosphines containing all possible combinations of ethylferrocene and ethylruthenocene substituents are reported. Each phosphine was characterized by 1H, 13C, and 31P NMR spectroscopy, IR and UV-vis absorption spectroscopy, mass spectrometry, and elemental analysis. With the exception of primary ethylruthenocene phosphine 8a, all of the title compounds have been studied by single-crystal X-ray crystallography. Ferrocene-containing phosphines showed maximum absorption at wavelengths of ca. 440 nm and qualitatively reversible oxidation waves in their cyclic voltammograms with intensities scaling to the number of ferrocene units present. The average metal-cyclopentadienyl centroid distances observed for ferrocene-containing phosphines were shorter than those of ruthenocene-containing phosphines, which also had maximum absorption wavelengths of ca. 320 nm and underwent irreversible electrochemical oxidation. Phosphines containing both ethylferrocene and ethylruthenocene substituents displayed properties consistent with the presence of both metallocene types.

Synthesis, characterization and second-order nonlinear optical behaviour of ferrocene-diketopyrrolopyrrole dyads: The effect of alkene: Vs. alkyne linkers

Kaur, Sarbjeet,Van Steerteghem, Nick,Kaur, Paramjit,Clays, Koen,Singh, Kamaljit

, p. 9717 - 9726 (2016)

New, thermally stable dipolar ferrocene-diketopyrrolopyrrole (Fc-DPP) dyads with alkene as a linker exhibited structure dependent first hyperpolarizabilities, βHRS, recorded by a femtosecond HRS technique using a femtosecond (120 fs) pulsed laser light system at 900 nm at ambient temperature. On the basis of linear optical, electrochemical and TD-DFT studies, a good structure-polarization relationship has been established to account for the observed trends in first hyperpolarizabilities. The dyads exhibited fluctuating but matching solvatochromism. Nonlinear optical properties are modulated both by the strength of the acceptor as well as the length and nature of the π-conjugation bridge. βHRS of the dyads were compared with structurally related dyads in which the DPP core and the Fc donor are linked via an alkyne bridge. It is interesting to observe that the replacement of an alkyne link with alkene in these D-π-A chromophores does not necessarily furnish enhanced βHRS.

Synthesis, spectra and crystal structure of (E)-(CO)2(NO)Cr[(η5-C5H 4)-CH=CH(η5-C5H4)]Cr(CO) 2(NO)

Wang, Yu-Pin,Lui, Xen-Hum,Lin, Bi-Son,Tang, Wei-Der,Lin, Tso-Shen,Liaw, Jen-Hai,Wang, Yu,Liu, Yi-Hung

, p. 310 - 319 (1999)

Compounds 1,2-bis[(η5-cyclopentadienyl)dicarbonylnitrosylchromium]ethene (7) (hereafter called 1,2-dicynichrodenylethene) and 1,2-diferrocenylethene (10) were prepared from formylcynichrodene (3) and formylferrocene (9), respectively, via the McMurry's low-valent titanium coupling method. Compounds (η5-vinylcyclopentadienyl)dicarbonylnitrosylchromium (6) and vinylferrocene (11) were obtained by the dehydration of the corresponding alcohols. The structure of 7 was solved by an X-ray diffraction study: space group, P21/c; monoclinic; a=6.379(5), b=11.295(3) and c=11.9352(24); Z=2. It turns out that compound 7 adopts a transoid conformation at the ethenylene bridge and the two cyclopentadienyl rings are coplanar. The nitrosyl group in each cynichrodenyl moiety of 7 is located at the side towards the corresponding ethenylene carbon atom with a twist angle of 46.5°. The chemical shifts of H(2)-H(5) protons and C(2)-C(5) carbon atoms of a series of vinyl derivatives of compounds bearing cyclopentadienyl rings have been assigned using two-dimensional HetCOR-NMR spectroscopy. For the derivatives of cynichrodene (1) and ferrocene, it was found that the shielding of C(2,5) and C(3,4) carbon atoms is parallel to the shielding of the ortho- and para-carbon atoms of benzene derivatives. The electron density distribution in the cyclopentadienyl ring is discussed on the basis of 13C-NMR data. Surprisingly, the vinyl group donates electron density to the adjacent cynichrodene moieties rather than withdraws from them.

Mechtler,Schloegl

, p. 754 (1966)

Dixneuf, P.

, (1971)

Synthesis of ferrocenyl-bearing dendrimers with a resorcinarene core

Valderrama, M.I. Reyes,García, R.A. Vázquez,Klimova,Klimova,Ortiz-Frade,García, M. Martínez

, p. 1597 - 1605 (2008)

A series of ferrocenyl ended dendrons containing π-conjugated systems were obtained using Wittig and Heck reactions. The dendrons were attached to eight functionalized resorcinarenes via Williamson reaction obtaining high molecular weight dendrimers. No electronic communication between metal centers was observed by cyclic voltammetry. All the dendrimers were characterized by 1H, 13C NMR, FTIR, UV-Vis, MALDI-TOF, elemental analyses, and electrochemical studies.

First-and second-generation heterometallic dendrimers containing ferrocenyl-ruthenium(II)-arene motifs: Synthesis, structure, electrochemistry, and preliminary cell proliferation studies

Govender, Preshendren,Lemmerhirt, Heidi,Hutton, Alan T.,Therrien, Bruno,Bednarski, Patrick J.,Smith, Gregory S.

, p. 5535 - 5545 (2014)

Four first- and second-generation heterometallic ferrocenyl derived p-cymene-Ru(II) metallodendrimers, of general formula [DAB-PPI{(κ6-p-cymene)Ru((C7H5NO)-2-N,O)PTA(5-ferrocenylvinyl)}n][PF6/su

Schloegl, K.,Mohar, A.

, (1961)

Solvent-free synthesis of ferrocenylethene derivatives

Liu, Wan-Yi,Xu, Qi-Hai,Ma, Yong-Xiang,Liang, Yong-Min,Dong, Ning-Li,Guan, De-Peng

, p. 128 - 131 (2001)

Herein, we report a fast, mild, efficient and simple Wittig reaction in a dry state to get ferrocenylethene derivatives. The Z and E isomers can be separated by chromatography and many isomers are characterized for the first time.

Synthesis of ferrocenyl-containing silicone rubbers via platinum-catalyzed Si–H self-cross-linking

Deriabin, Konstantin V.,Lobanovskaia, Ekaterina K.,Kirichenko, Sergey O.,Barshutina, Marie N.,Musienko, Pavel E.,Islamova, Regina M.

, (2020)

Self-cross-linkable ferrocenyl-containing polymethylhydrosiloxanes were synthesized. Karstedt's catalyst and cis-[PtCl2(BnCN)2] were examined as cross-linking catalysts at room temperature for the reaction between Si–H groups of the ferrocenyl-containing polymethylhydrosiloxanes. Cis-[PtCl2(BnCN)2] is an effective catalyst that allows cross-linked ferrocenyl-containing silicones (silicone rubbers) to be obtained with no visible mechanical defects (bubbles or cracks) compared with Karstedt's catalyst. The ferrocene content of the ferrocenyl-containing silicone rubbers was found to be approximately 50?wt.% by energy-dispersive X-ray analysis. Compared with cross-linked non-modified polymethylhydrosiloxanes, the ferrocenyl-containing silicone rubbers exhibited improved tensile properties (the tensile strength increased from 0.47 to 0.75?MPa) and a 1.5–2.5 times lower cross-linking degree. The surface resistivity of the ferrocenyl-containing silicone rubbers (50?wt.% ferrocenyl units) was approximately 7 × 109?Ω/□, which was 10,000 times lower than that of pure polymethylhydrosiloxane. The obtained flexible electroactive ferrocenyl-containing silicone rubbers can potentially be applied as coatings for electronic and electrostatic-sensitive devices, interfaces, and sensors.

Synthesis of α-arylalkylferrocenes through cesium fluoride-promoted coupling of arylboronic acids with N-tosylhydrazones

Liu, Yueqiang,Ma, Xiaowei,Liu, Yan,Liu, Ping,Dai, Bin

, p. 921 - 928 (2018)

A cesium fluoride-promoted reductive coupling reaction of acylferrocene tosylhydrazones with arylboronic acids has been developed, producing highly substituted α-arylalkylferrocenes in moderate to excellent yields. The reaction employs anionic fluorine to facilitate the cleavage of C–B bond. The developed methodology demonstrates a wide substrate scope and high functional groups tolerance. Moreover, the α-arylalkylferrocenes compounds were also obtained on a multi-gram scale.

Synthesis and properties of optically active ferrocenylethylindazoles

Simenel,Kuzmenko, Yu. V.,Ilyin,Gumenyuk,Snegur,Nekrasov, Yu. S.

, p. 939 - 941 (2004)

The stereochemistry of two processes, viz., α-ferrocenylalkylation of indazole with optically active S-(+)-1-ferrocenylethanol and the thermal rearrangement of S-(+)-2-N-(ferrocenylethyl)indazole into S-(+)-1-N- (ferrocenylethyl)indazole, was studied. Bot

Wittig Olefination Using Phosphonium Ion-Pair Reagents Incorporating an Endogenous Base

Vetter, Anna C.,Gilheany, Declan G.,Nikitin, Kirill

supporting information, p. 1457 - 1462 (2021/03/08)

Despite common perception, the use of strong bases in Wittig chemistry is utterly unnecessary: we report a series of novel ion-pair phosphonium carboxylate reagents which are essentially "storable ylides". These reagents are straightforwardly prepared in excellent yields, and their fluxional nature permits clean olefination of a broad range of aldehydes and even hemiacetals.

Functionalization of Alkenyl C-H Bonds with D 2 O via Pd(0)/Carboxylic Acid Catalysis

Bigi, Franca,Camedda, Nicola,Cera, Gianpiero,Maestri, Giovanni,Maggi, Raimondo,Serafino, Andrea

supporting information, p. 1762 - 1772 (2020/06/08)

We report herein a simple catalytic method for the extensive labeling of alkenyl C-H bonds through the combination of a palladium(0) complex and a carboxylic acid in the presence of deuterium oxide. The reaction can be applied to a variety of terminal alkenes and the best results are obtained with aryl-substituted examples. This method represents a convenient approach for the preparation of extensively labeled chemicals from the cheapest and safest source of deuterium.

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