Details
Factory Supply industrial standard Ferrocenecarboxaldehyde 12093-10-6 In Stock
- Molecular Formula: C11H10FeO
- Molecular Weight: 214.047
- Appearance/Colour: crystalline solid
- Vapor Pressure: 5.03mmHg at 25°C
- Melting Point: 118-120 °C(lit.)
- Refractive Index: 1.623
- Boiling Point: 213.6 °C at 760 mmHg
- Flash Point: 98.8 °C
- PSA： 17.07000
- Density: 1.149g/cm3
- LogP: 1.60960
Ferrocenecarboxaldehyde(Cas 12093-10-6) Usage
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Purification Methods |
It forms red crystals from heptane/CH2Cl2, EtOH or pet ether and sublimes at 70o/1mm. The cyanohydrin has m 104o (from *C6H6/EtOH). The semicarbazone has m 217-219o(dec) after recrystallisation from aqueous EtOH. The oxime provides two isomers from pet ether viz m 96-99o and m 155o. The O-acetyloxime has m 80-81o after recrystallisation from hexane [Lindsay & Hauser J Org Chem 22 355 1957]. The 2,4-dinitrophenylhydrazone has m 248o(dec). [Beilstein 16 IV 1798, Graham et al. J Am Chem Soc 79 3416 1957, Broadhead et al. J Chem Soc 650 1958.] |
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General Description |
Ferrocenecarboxaldehyde, also known as formylferrocene, is an organometallic compound featuring a ferrocene core with a formyl (–CHO) substituent. It exhibits structural versatility, as demonstrated by its orthorhombic crystal and plastic phases, with molecular motion along the *a*-axis contributing to phase transitions. Ferrocenecarboxaldehyde's redox-active ferrocene moiety makes it valuable in applications such as liquid crystalline materials, self-assembling systems, and redox-responsive sensors. Its derivatives, including β-ferrocenyl-β-amino alcohols and α-cyanoarylethene-linked compounds, are used in asymmetric synthesis and functional materials. Additionally, ferrocenecarboxaldehyde-based probes enable multichannel detection of reactive oxygen species like H2 O2 in biological systems, highlighting its utility in electrochemical and fluorescent sensing. |
InChI:InChI=1/C6H6O/c7-5-6-3-1-2-4-6/h1-6H
12093-10-6 Relevant articles
PLASTIC PHASE OF FORMYLFERROCENE STUDIED BY X-RAY DIFFRACTION AND MOSSBAUER SPECTROSCOPY.
Sato,Iwai,Sano,Konno
, p. 634 - 638 (1984)
The structures of both the crystal and t...
α-Cyanoarylethene ferrocene based rod-shaped compounds, synthesis, self-assembly and redox-responsive properties
Tao, Yuan,Chang, Qing,Ding, Wei,Sun, Yue-Yu,Ma, Tao,Cheng, Xiao-Hong
, (2021)
A series of novel α-cyanoarylethene ferr...
β-Ferrocenyl-β-amino alcohols: a new class of central chiral ferrocene derivatives
Catasús, Mònica,Bueno, Agustí,Moyano, Albert,Maestro, Miguel A,Mahía, José
, p. 212 - 226 (2002)
An efficient procedure for the enantiose...
Chromogenic, Fluorescent, and Redox Sensors for Multichannel Imaging and Detection of Hydrogen Peroxide in Living Cell Systems
Ni, Yue,Liu, Hong,Dai, Di,Mu, Xiqiong,Xu, Jian,Shao, Shijun
, p. 10152 - 10158 (2018)
Hydrogen peroxide (H2O2) is an important...
A DFT-Elucidated comparison of the solution-phase and SAM electrochemical properties of short-chain mercaptoalkylferrocenes: Synthetic and spectroscopic aspects, and the structure of Fc- CH2CH2-S-S-CH2CH2-Fc
Lewtak, Jan P,Landman, Marilé,Fernández, Israel,Swarts, Jannie C
, p. 2584 - 2596 (2016)
Facile synthetic procedures to synthesiz...
Synthesis, characterization, and electronic properties of novel Fc-DCM conjugated system; Experimental and computational studies
Teimuri-Mofrad, Reza,Rahimpour, Keshvar,Ghadari, Rahim
, p. 14 - 19 (2016)
Novel Fc-DCM conjugated compound, 2-(2-f...
New synthesis of ferrocene monocarboxylic acid and systematic studies on the preparation of related key-intermediates
Neto, Alberto Federman,Miller, Joseph,De Andrade, Vania Faria,Fujimoto, Susana Yumi,De Freitas Afonso, Marcia Maisa,Archanjo, Fernando Costa,Darin, Vitor Andre,Andrade E Silva, Marcio Luis,Borges, Aurea Donizete Lanchote,Del Ponte, Gino
, p. 209 - 216 (2002)
An improved technique for the preparatio...
Site-selective cation-π interaction as a way of selective recognition of the caesium cation using sumanene-functionalized ferrocenes
Kasprzak, Artur,Sakurai, Hidehiro
, p. 17147 - 17152 (2019)
The first sumanene-ferrocene probes for ...
Simultaneous Construction of Planar and Central Chiralities as Well as Unprecedented Axial Chirality on and around a Ferrocene Backbone
Li, Hongjie,Jia, Peijing,Qian, Naixin,Li, Shasha,Jiao, Peng
, p. 2817 - 2828 (2019)
Simultaneous generation of planar, centr...
Light-Triggered Metal Coordination Dynamics in Photoswitchable Dithienylethene-Ferrocene System
Adarsh, Nayarassery N.,Karmakar, Manisha,Mondal, Bijan,Pal, Adwitiya,Thakur, Arunabha
, p. 6086 - 6098 (2021)
The C2-symmetric photochromic molecule 3...
Enantiopure Ferrocene-Based Planar-Chiral Iridacycles: Stereospecific Control of Iridium-Centred Chirality
Arthurs, Ross A.,Ismail, Muhammad,Prior, Christopher C.,Oganesyan, Vasily S.,Horton, Peter N.,Coles, Simon J.,Richards, Christopher J.
, p. 3065 - 3072 (2016)
Reaction of [IrCp?Cl2]2 with ferrocenyli...
Nano islet formation of formyl- and carboxyferrocene, -ruthenocene, -osmocene and cobaltocenium on amine-functionalized silicon wafers highlighted by crystallographic, AFM and XPS studies
Trzebiatowska-Gusowska, Monika,Ga?gor, Anna,Coetsee, Elizabeth,Erasmus, Elizabeth,Swart, Hendrik C.,Swarts, Jannie C.
, p. 393 - 403 (2013)
Surface-hydroxylated silicon wafers, 8, ...
Synthesis and Anti-Biofilm Activity of New Ferrocene Schiff Bases
G?ver, T.,Sevgi, F.,Taner, B.
, p. 907 - 910 (2020)
Abstract: Four new Schiff bases have bee...
Flash vacuum pyrolysis study of iron cyclopentadienyl complexes and the crystal structure of O-acetyl-N-(1-ferrocenylpropylidene)hydroxylamine
Barnes, John C.,Bell, William,Glidewell, Christopher,Howie, R. Alan
, p. 343 - 351 (1992)
Under flash vacuum pyrolysis (FVP) condi...
Enantiospecific alkylations of alanine
Alonso, Francisco,Davies, Stephen G.,Elend, Almut S.,Haggitt, Jane L.
, p. 257 - 264 (1998)
Reaction of ferrocenecarbaldehyde 3 with...
Multifunctional geometrical isomers of ferrocene-benzo[1,2-b:4,5-b′]difuran-2,6-(3H,7H)-dione adducts: second-order nonlinear optical behaviour and charge transport in thin film OFET devices
Singla, Priya,Van Steerteghem, Nick,Kaur, Navdeep,Ashar,Kaur, Paramjit,Clays, Koen,Narayan,Singh, Kamaljit
, p. 697 - 708 (2017)
Geometrical isomers of a set of new ferr...
A simple synthesis of metallocene aldehydes from lithiometallocenes and N,N-dimethylformamide: ferrocene and ruthenocene aldehydes and 1,1'-dialdehydes
Mueller-Westerhoff, Ulrich T.,Yang, Zheng,Ingram, Georg
, p. 163 - 168 (1993)
Lithioferrocene, 1,1'-dilithioferrocene,...
The reactions of α-phenyl- and α-ferrocenylcarbinols with diiron nonacarbonyl
Bankston, D.
, p. 129 - 138 (1989)
Diiron nonacarbonyl oxidized a series of...
Cis and Trans Isomers of 1-Hydroxyiminoalkylferrocenes and Their Antioxidant Activity
Sun, Xiqing,Zhang, Jian,Jin, Longfei
, p. 170 - 174 (2013)
Condensation reactions of acylferrocene ...
A convenient method for synthesis of novel alkylferrocene derivatives with various functional groups: synthesis, characterization and electrochemical investigation
Teimuri-Mofrad, Reza,Aghaiepour, Alireza,Rahimpour, Keshvar
, p. 2449 - 2462 (2020)
Abstract: In this research, new ferrocen...
Ferrocenylethenyl-substituted 1,3,4-oxadiazolyl-1,2,4-oxadiazoles: Synthesis, characterization and DNA-binding assays
Mayer, Jo?o C.P.,Sauer, André C.,Iglesias, Bernardo A.,Acunha, Thiago V.,Back, Davi F.,Rodrigues, Oscar E.D.,Dornelles, Luciano
, p. 1 - 11 (2017)
This article describes the synthesis, ch...
Chiral platinum(II) compounds containing ferrocenyl Schiff bases acting as (N), (N,O)-, [C(sp2,ferrocene),N]- or [C(sp2,ferrocene),N,O]2- ligands
Lopez, Concepcion,Caubet, Amparo,Perez, Sonia,Solans, Xavier,Font-Bardia, Merce,Molins, Elies
, p. 3974 - 3984 (2006)
A study of the reactions of the followin...
Synthesis and characterization of new ferrocene-containing ionic liquids
Gharib, Bhasem,Hirsch, Andreas
, p. 4123 - 4136 (2014)
A series of several new families of ferr...
Fluorescent and electrochemical detection of Cu (II) ions in aqueous environment by a novel, simple and readily available AIE probe
Gunduz, Simay,Karaku?, Erman,Liv, Lokman,Ozturk, Turan
, (2020)
We have devised a novel and fluorescent ...
Picolinamide as a Directing Group on Metal Sandwich Compounds: sp2 C-H Bond Activation and sp3 C-H Bond Oxidation
Hazra, Susanta,Deb, Mayukh,Singh, Jatinder,Elias, Anil J.
, p. 1784 - 1794 (2017)
Palladium catalyzed bis-arylations, -alk...
Conditions for manifestation of approachment and orientation effect at the oxidation of ferrocenylacetic acid and its methyl ester by molecular oxygen in organic Solvents
Fomin,Shirokov
, p. 81 - 90 (2011)
By comparison of reactivity of the ferro...
The first colorimetric receptor for the B4O72- anion based on nitro substituted phenanthroimidazole ferrocene derivatives
Wu, Pei,Wang, Guo,Zhou, Lu,Lu, Jing,Wang, Jianchun
, p. 3782 - 3788 (2018)
Four phenanthroimidazole ferrocene deriv...
On the radical chain mechanism of oxidation of a series of ferrocene derivatives with molecular oxygen
Fomin,Shirokov,Polyakova,Smirnov
, p. 652 - 653 (2007)
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Synthesis and third-order optical nonlinearities of ferrocenyl Schiff base
Jia, Jian-Hong,Tao, Xiao-Min,Li, Yu-Jin,Sheng, Wei-Jian,Han, Liang,Gao, Jian-Rong,Zheng, Yu-Fen
, p. 114 - 118 (2011)
Four ferrocenyl Schiff bases were synthe...
Conformationally rigid chiral ferrocene derivative: Synthesis, resolution and stereochemical assignment
Achari, Kamsali Murali Mohan,Ramanathan, Chinnasamy Ramaraj
, p. 830 - 836 (2017)
A conformationally rigid chiral molecule...
Ferrocenylmethyl azide
Bublitz
, p. 225 - 228 (1970)
The preparation of ferrocenylmethyl azid...
Selective anion receptor for fluoride detection using ferrocenyl-boronate derivative
Su, Zhi-Ming,Lin, Cai-Xia,Zhou, Yun-Tao,Xie, Li-Li,Yuan, Yao-Feng
, p. 17 - 26 (2015)
The reaction of ferrocenecarboxaldehyde ...
Organometalloidal derivatives of the transition metals XXVII. Chemical and structural investigations on (ferrocenylacyl)germanes
Sharma, Hemant K.,Cervantes-Lee, Francisco,Pannell, Keith H.
, p. 321 - 330 (1991)
(Ferrocenylacyl)germanes, (η5-C5H5)Fe(η5...
Ferrocene-based porous organic polymer derived high-performance electrocatalysts for oxygen reduction
Zhou, Baolong,Liu, Liangzhen,Cai, Pingwei,Zeng, Guang,Li, Xiaoqiang,Wen, Zhenhai,Chen, Long
, p. 22163 - 22169 (2017)
Two nitrogen-rich porous organic polymer...
Features of the oxidation of certain hydroxy derivatives of ferrocene with molecular oxygen in organic solvents
Fomin,Shirokov,Polyakova
, p. 1361 - 1370 (2008)
Features of the oxidation of hydroxymeth...
A hexaferrocenyl cluster based on a cyclotriphosphazene core: Synthesis and electrochemistry
Sengupta, Saumitra
, p. 1237 - 1240 (2003)
Sixfold substitution reaction of hexachl...
Novel meso-substituted ferrocene-appended porphyrins: Synthesis, characterization, and electrochemical evaluation
Payami, Elmira,Neshad, Saeed,Aghaiepour, Alireza,Teimuri-Mofrad, Reza
, (2021/09/08)
This paper focuses on the synthesis of t...
Planar binuclear ferrocene derivative as well as synthesis method and application thereof
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Paragraph 0011; 0047-0048; 0057-0059; 0068-0070; 0079-0081, (2021/11/27)
The invention discloses a planar binucle...
12093-10-6 Process route
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102-54-5,55404-68-7
ferrocene
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68-12-2,33513-42-7
N,N-dimethyl-formamide
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-
12093-10-6
ferrocenecarboxaldehyde
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-
1271-48-3
1,1'-ferrocenyldicarboxaldehyde
| Conditions | Yield |
|---|---|
|
With
tert.-butyl lithium;
In
tetrahydrofuran; n-heptane;
under N2; tBuLi in hexane is added to ferrocene in THF at -20°C, stirred for 30 min, DMF is added at -10°C, HCl is added; extd. with CH2Cl2, chromd. (SiO2, CH2Cl2);
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91%
1% |
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With
potassium tert-butylate; tert.-butyl lithium;
In
tetrahydrofuran;
N2-atmosphere; dropwise addn. of t-BuLi to mixt. of ferrocene and t-BuOKat -74 to -70°C, stirring at -74°C for 1 h, addn. of exce ss DMF, warming to -40°C over 20 min; water addn., solvent removal (reduced pressure), extn. into CH2Cl2, drying (MgSO4), chromy. (SiO2, hexane, then CH2Cl2, then CH2Cl2/Et2O=1:1);
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90.7%
4.9% |
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ferrocene;
With
n-butyllithium; N,N,N,N,-tetramethylethylenediamine;
In
hexane;
at -80 - 0 ℃;
for 0.25h;
N,N-dimethyl-formamide;
In
n-heptane;
at -80 ℃;
for 2h;
|
71%
20% |
|
With
sec.-butyllithium;
In
tetrahydrofuran;
N2-atmosphere; treatment of ferrocene with of 1.6 equiv. s-BuLi (-10°C, 15 min), DMF addn.; chromy.;
|
|
|
With
potassium tert-butylate; tert.-butyl lithium;
In
tetrahydrofuran;
N2-atmosphere; treatment of ferrocene with varying amts. of bases (-74°C, 60 min), DMF addn.; chromy.; product ratio and total conversion depending on ratio of bases;
|
|
|
With
tert.-butyl lithium;
In
tetrahydrofuran;
N2-atmosphere; treatment of ferrocene with 1.5 or 2 equiv. t-BuLi (-20°C, 30-195 min), DMF addn.; chromy.; product ratio and total conversion depending on educt ratio;
|
-
-
102-54-5,55404-68-7
ferrocene
-
-
93-61-8
N-methyl-N-phenylformamide
-
-
12093-10-6
ferrocenecarboxaldehyde
-
-
1271-48-3
1,1'-ferrocenyldicarboxaldehyde
| Conditions | Yield |
|---|---|
|
With
trichlorophosphate;
In
not given;
Vilsmeyer formylation;;
|
0%
|
12093-10-6 Upstream products
-
1273-86-5
1-ferrocenylmethanol
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116693-42-6
ferrocenyl-pentacarbonylmanganese
-
75-05-8
acetonitrile
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63511-14-8
ferrocenoyl-pentacarbonylmanganese
12093-10-6 Downstream products
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334992-59-5
(1-ferrocenyl)imino-benzyldiethylphosphonate
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12094-24-5
1-ferrocenyl-2-phenylethylene
-
903899-95-6
[α-(N,N-dibenzylamino)-γ-phenylpropynyl]ferrocene
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903899-94-5
[α-(N,N-diallylamino)-γ-phenylpropynyl]ferrocene
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