CID 233405

Base Information

• Chemical Name: CID 233405
• CAS No.: 1277-49-2
• Molecular Formula: C12H14FeO
• Molecular Weight: 230.09
• Hs Code.: 29319090
• NSC Number: 31904
• Mol file: 1277-49-2.mol

Synonyms:NSC31904;NSC-31904

Chemical Property of CID 233405

Chemical Property:

• Appearance/Colour: yellow to yellow-orange crystalline powder
• Melting Point: 76-79 °C
• Boiling Point: 184.6oC at 760mmHg
• Flash Point: >100 °C
• PSA: 20.23000
• Density: 1.016g/cm3
• LogP: 1.79150
• Storage Temp.: 2-8°C
• Solubility.: soluble in Benzene
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 230.039401
• Heavy Atom Count: 14
• Complexity: 124

Purity/Quality:

99% ^*data from raw suppliers

1-Hydroxyethylferrocene >95.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=C[CH-]C=C1)O.[CH-]1C=CC=C1.[Fe+2]
• Uses: Ligand in titanium-catalyzed intermolecular hydroamination of terminal alkynes (Markovnikov vs. anti-Markovnikov addition) . Reactant for: Single-electron transfer living radical polymerization reactions. Preparation of ferrocene-modified thiopyrimidines as anticancer agents. Preparation of rersible addition-fragmentation chain transfer (RAFT) agent for RAFT polymerization of styrene. Ligand in titanium-catalyzed intermolecular hydroamination of terminal alkynes (Markovnikov vs. anti-Markovnikov addition)Reactant for:Single-electron transfer living radical polymerization reactionsPreparation of ferrocene-modified thiopyrimidines as anticancer agentsPreparation of rersible addition-fragmentation chain transfer (RAFT) agent for RAFT polymerization of styrene

Technology Process of CID 233405

There total 36 articles about CID 233405 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: 99.0%

acetylferrocene (1271-55-2) → 1-ferrocenylethanol (1277-49-2)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C₃₉H₄₅FeN₂O₂PS; hydrogen; sodium methylate; In methanol; at 40 ℃; for 12h; Reagent/catalyst; Solvent; Autoclave; Large scale;

Reference yield: 93.0%

ferrocenecarboxaldehyde (12093-10-6) → 1-ferrocenylethanol (1277-49-2)

Guidance literature:

With LiAlH₄; In diethyl ether; Ar-atmosphere; addn. of acetylferrocene to excess LiAlH4 (15-20°C, stirring); addn. of satd. aq. NH4Cl (cooling to 0-5°C), washing of org. layer (water), drying (Na2SO4), solvent removal;

DOI:10.1016/S0022-328X(98)01097-3

Reference yield: 92.0%

acetylferrocene (1271-55-2) + water (7732-18-5) → 1-ferrocenylethanol (1277-49-2)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; N2-atmosphere; molar ratio SmI2:ferrocene derivative:water=2.6:1:11, 25°C, 10 min; addn. of ice water, filtration over SiO2, concn.;

DOI:10.1016/S0022-328X(99)00411-8

upstream raw materials:

acetylferrocene

water

lithium aluminium tetrahydride

aniline

Downstream raw materials:

acetylferrocene

vinyl ferrocene

N,N-dimethyl-1-ferrocenylethylamine

C₅H₅FeC₅H₄CH(CH₃)N(C₆H₅)2

Refernces

• 1、 Sheridan, Matthew V.,Lam, Kevin,Geiger, William E.. "An anodic method for covalent attachment of molecules to electrodes through an ethynyl linkage". . p. 2939 - 2942. Retrieved 2013.
• 2、 Ori, Aiichiro,Shinkai, Seiji. "Electrochemical Detection of Saccharides by the Redox Cycle of a Chiral Ferrocenylboronic Acid Derivative: a Novel Method for Sugar Sensing". . p. 1771 - 1772. Retrieved 1995.
• 3、 Snegur, Lubov' V.,Boev, Victor I.,Nekrasov, Yury S.,Ilyin, Mikhail M.,Davankov, Vadim A.,Starikova, Zoya A.,Yanovsky, Alexander I.,Kolomiets, Alexey F.,Babin, Valery N.. "Synthesis and structure of biologically active ferrocenylalkyl polyfluoro benzimidazoles". . p. 26 - 35. Retrieved 1999.
• 4、 Rodionov, Alexey N.,Gerasimova, Maria D.,Osipova, Elena Yu.,Korlyukov, Alexander A.,Peregudov, Alexander S.,Simenel, Alexander A.. "Synthesis of bis-ferrocenylpyrazoles via ferrocenylalkylation reaction". . p. 925 - 932. Retrieved 2017.
• 5、 Khozeimeh Sarbisheh, Elaheh,Esteban Flores, Jose,Zhu, Jianfeng,Müller, Jens. "Insight into the Thermal Ring-Opening Polymerization of Phospha[1]ferrocenophanes". . p. 16838 - 16849. Retrieved 2016.
• 6、 Deriabin, Konstantin V.,Lobanovskaia, Ekaterina K.,Kirichenko, Sergey O.,Barshutina, Marie N.,Musienko, Pavel E.,Islamova, Regina M.. "Synthesis of ferrocenyl-containing silicone rubbers via platinum-catalyzed Si–H self-cross-linking". . . Retrieved 2019/11/22.
• 7、 Johnson, Jahvon,Li, Sihan,Mo, Zixuan,Neary, Michelle C.,Zeng, Haisu,Zhang, Guoqi,Zheng, Shengping. "1-D manganese(ii)-terpyridine coordination polymers as precatalysts for hydrofunctionalisation of carbonyl compounds". supporting information. p. 2610 - 2615. Retrieved 2020/03/05.