Ferrocene, formyl-

Base Information

• Chemical Name: Ferrocene, formyl-
• CAS No.: 12093-10-6
• Molecular Formula: C11H10FeO
• Molecular Weight: 214.047
• Hs Code.: 29319090
• Mol file: 12093-10-6.mol

Synonyms:Ferrocene, formyl-;Ferrocenecarboxaldehyde (8CI);cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-ylidenemethanolate;iron(2+);ferrocene-aldehyde;MQHZGUNMWQBVDK-UHFFFAOYSA-N;EINECS 235-158-1;AS-17287;J-004413;Iron, pi-cyclopentadienyl(formyl-pi-cyclopentadienyl)-

Chemical Property of Ferrocene, formyl-

Chemical Property:

• 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
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Water Solubility.: INSOLUBLE
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 214.008100
• Heavy Atom Count: 13
• Complexity: 138

Purity/Quality:

99% ^*data from raw suppliers

Ferrocenecarboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [CH-]1C=CC=C1.C1=CC(=C[O-])C=C1.[Fe+2]
• Uses: Ferrocenecarboxaldehyde, is used to prepare chiral ferrocene aziridinylmethanols for selective azomethine ylide cycloaddtion. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals.

Technology Process of Ferrocene, formyl-

There total 147 articles about Ferrocene, formyl- 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: 98.0%

ferrocene (102-54-5,55404-68-7) + N-methyl-N-phenylformamide (93-61-8) → ferrocenecarboxaldehyde (12093-10-6)

Guidance literature:

N-methyl-N-phenylformamide; With trichlorophosphate; at 0 ℃; for 0.25h;

ferrocene; at 20 ℃; Inert atmosphere;

DOI:10.1039/c6tc03876j

Reference yield: 92.0%

1-ferrocenylmethanol (1273-86-5) → ferrocenecarboxaldehyde (12093-10-6)

Guidance literature:

With ferrocene-labeled Merrifield resin-supported ionic liquid ([FemDMMerA]RuO₄); In tetrahydrofuran; for 4h; Reflux; Green chemistry;

DOI:10.1007/s11164-016-2563-2

Reference yield: 91.0%

ferrocene (102-54-5,55404-68-7) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → ferrocenecarboxaldehyde (12093-10-6) + 1,1'-ferrocenyldicarboxaldehyde (1271-48-3)

Guidance literature:

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);

DOI:10.1016/0022-328X(93)83414-Q

upstream raw materials:

1-ferrocenylmethanol

ferrocenyl-pentacarbonylmanganese

acetonitrile

ferrocenoyl-pentacarbonylmanganese

Downstream raw materials:

[α-(N,N-dibenzylamino)-γ-phenylpropynyl]ferrocene

[α-(N,N-diallylamino)-γ-phenylpropynyl]ferrocene

1,1'-ferrocenyldicarboxaldehyde

(S)-α-(diphenylphosphino)ferrocenecarboxaldehyde

Refernces

• 1、 Tao, Yuan,Chang, Qing,Ding, Wei,Sun, Yue-Yu,Ma, Tao,Cheng, Xiao-Hong. "α-Cyanoarylethene ferrocene based rod-shaped compounds, synthesis, self-assembly and redox-responsive properties". . . Retrieved 2021.
• 2、 Ni, Yue,Liu, Hong,Dai, Di,Mu, Xiqiong,Xu, Jian,Shao, Shijun. "Chromogenic, Fluorescent, and Redox Sensors for Multichannel Imaging and Detection of Hydrogen Peroxide in Living Cell Systems". . p. 10152 - 10158. Retrieved 2018.
• 3、 Teimuri-Mofrad, Reza,Rahimpour, Keshvar,Ghadari, Rahim. "Synthesis, characterization, and electronic properties of novel Fc-DCM conjugated system; Experimental and computational studies". . p. 14 - 19. Retrieved 2016.
• 4、 Kasprzak, Artur,Sakurai, Hidehiro. "Site-selective cation-π interaction as a way of selective recognition of the caesium cation using sumanene-functionalized ferrocenes". . p. 17147 - 17152. Retrieved 2019.
• 5、 Li, Hongjie,Jia, Peijing,Qian, Naixin,Li, Shasha,Jiao, Peng. "Simultaneous Construction of Planar and Central Chiralities as Well as Unprecedented Axial Chirality on and around a Ferrocene Backbone". . p. 2817 - 2828. Retrieved 2019.
• 6、 Rinehart, K. L.,Ellis, A. F.,Michejda, C. J.,Kittle, P. A.. "". . p. 4112 - 4113. Retrieved 1960.
• 7、 Arthurs, Ross A.,Ismail, Muhammad,Prior, Christopher C.,Oganesyan, Vasily S.,Horton, Peter N.,Coles, Simon J.,Richards, Christopher J.. "Enantiopure Ferrocene-Based Planar-Chiral Iridacycles: Stereospecific Control of Iridium-Centred Chirality". . p. 3065 - 3072. Retrieved 2016.
• 8、 Trzebiatowska-Gusowska, Monika,Ga?gor, Anna,Coetsee, Elizabeth,Erasmus, Elizabeth,Swart, Hendrik C.,Swarts, Jannie C.. "Nano islet formation of formyl- and carboxyferrocene, -ruthenocene, -osmocene and cobaltocenium on amine-functionalized silicon wafers highlighted by crystallographic, AFM and XPS studies". . p. 393 - 403. Retrieved 2013.
• 9、 Barnes, John C.,Bell, William,Glidewell, Christopher,Howie, R. Alan. "Flash vacuum pyrolysis study of iron cyclopentadienyl complexes and the crystal structure of O-acetyl-N-(1-ferrocenylpropylidene)hydroxylamine". . p. 343 - 351. Retrieved 1992.
• 10、 Singla, Priya,Van Steerteghem, Nick,Kaur, Navdeep,Ashar,Kaur, Paramjit,Clays, Koen,Narayan,Singh, Kamaljit. "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". . p. 697 - 708. Retrieved 2017.