((Dimethylamino)methyl)ferrocene

Base Information

• Chemical Name: ((Dimethylamino)methyl)ferrocene
• CAS No.: 1271-86-9
• Deprecated CAS: 12184-36-0,242805-52-3
• Molecular Formula: C13H17FeN
• Molecular Weight: 243.132
• Hs Code.: 29319090
• Mol file: 1271-86-9.mol

Synonyms:((Dimethylamino)methyl)ferrocene;cyclopenta-1,3-diene;1-cyclopenta-1,3-dien-1-yl-N,N-dimethylmethanamine;iron(2+);Ferrocenylmethyldimethylamine;2-(dimethylamino-methyl)ferrocene;NSC 3432;EINECS 215-044-8;SY056775;D1271;D89824

Chemical Property of ((Dimethylamino)methyl)ferrocene

Chemical Property:

• Appearance/Colour: Dark brown liquid
• Vapor Pressure: 3.42mmHg at 25°C
• Melting Point: 65 °C
• Refractive Index: n20/D 1.59(lit.)
• Boiling Point: 124-128 °C (2.5 mmHg)
• Flash Point: >110 °C
• PSA: 3.24000
• Density: 1.228 g/cm³
• LogP: 1.97230
• Solubility.: Difficult to mix.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 243.071035
• Heavy Atom Count: 15
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

N,N-Dimethylaminomethylferrocene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/38:Irritating to eyes and skin.
• Hazard Codes: R36/38:Irritating to eyes and skin.
• Statements: R36/38:Irritating to eyes and skin.
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CC1=CC=C[CH-]1.[CH-]1C=CC=C1.[Fe+2]
• Uses: (Dimethylaminomethyl)ferrocene is used as an active pharmaceutical ingredient.

Technology Process of ((Dimethylamino)methyl)ferrocene

There total 60 articles about ((Dimethylamino)methyl)ferrocene 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%

ferrocenecarboxaldehyde (12093-10-6) + N,N-dimethylammonium chloride (506-59-2) + sodium tris(acetoxy)borohydride (56553-60-7) → N,N-dimethylaminomethylferrocene (1271-86-9)

Guidance literature:

With triethylamine; In dichloromethane; Fe complex reacted with HNMe2*HCl and B compd. in presence of Et3N in CH2Cl2;

DOI:10.1023/B:RUCB.0000037851.47573.4b

Reference yield: 95.0%

N,N,N-(ferrocenylmethyl)trimethylammonium iodide → methyl ferrocene + N,N-dimethylaminomethylferrocene (1271-86-9)

Guidance literature:

With sodium amalgam; In water; byproducts: (CH3)N, CH4;

DOI:10.1016/S0022-328X(00)81496-5

Reference yield: 95.0%

N,N,N-(ferrocenylmethyl)trimethylammonium iodide + bis-(dimethylamino)methane (51-80-9) → N,N-dimethylaminomethylferrocene (1271-86-9)

Guidance literature:

In acetic acid; 95-98°C, in CH3COOH/85% H3PO4 soln.;

upstream raw materials:

[Fe(η5-C5H5)(η5-C5H3(CH2NMe2)-2)-C,N]2Pb

ferrocene

bis-(dimethylamino)methane

formaldehyd

Downstream raw materials:

cyclopentadienyllithium

Refernces

• 1、 Zagorevskii, D. V.,Loim, N. M.,Nekrasov, Yu. S.,Sizoi, V. F.,Sukharev, Yu. N.. "MASS SPECTROMETRY OF ?-COMPLEXES OF TRANSITION METALS XX. DIMETHYLAMINOALKYL DERIVATIVES OF FERROCENE AND CYMANTRENE; THE DETERMINATION OF THE DISTRIBUTION AND THE TOTAL CONTENT OF DEUTERIUM LABEL". . p. 201 - 210. Retrieved 1980.
• 2、 Danneuberg et al.. "". . p. 1575,1582. Retrieved 1973.
• 3、 Thiele, Karl-Heinz,Krueger, Christian,Bartik, Tamas,Dargatz, Manfred. "Darstellung und Charakterisierung von -Verbindungen des Titaniums, Zirconiums und Hafniums". . p. 115 - 124. Retrieved 1988.
• 4、 Krueger, Christian,Thiele, Karl-Heinz,Dargatz, Manfred,Bartik, Tamas. "-Verbindungen des Zinks, Cadmiums und Quecksilbers". . p. 147 - 154. Retrieved 1989.
• 5、 Tarasova, Ol'Ga A.,Tatarinova, Inna V.,Vakul'Skaya, Tamara I.,Khutsishvili, Spartak S.,Smirnov, Vladimir I.,Klyba, Lyudmila V.,Prozorova, Galina F.,Mikhaleva, Al'Bina I.,Trofimov, Boris A.. "Propargyloxy- and allenyloxymethylferrocenes: Synthesis and oligomerization". . p. 1 - 7. Retrieved 2013.
• 6、 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". supporting information. p. 3065 - 3072. Retrieved 2016/03/23.