1271-86-9

Basic information

• Product Name: N,N-Dimethylaminomethylferrocene
• Synonyms: Ferrocenemethylamine;N,N-Dimethylferrocenylmethylamine;N,N-Dimethylaminomethylferrocene;FERROCENYLMETHYLDIMETHYLAMINE;DIMETHYLAMINOMETHYLFERROCENCE;(DIMETHYLAMINOMETHYL)FERROCENE;CYCLOPENTADIENYL(DIMETHYLAMINOMETHYL)CYCLOPENTADLENYL IRON;N,N-DIMETHYLAMINOMETHYLFERROCENE
• CAS NO: 1271-86-9
• Molecular Formula: C₁₃H₁₇FeN
• Molecular Weight: 243.13
• EINECS: 215-044-8
• Product Categories: Other Metal;Industrial/Fine Chemicals;Ferrocene series;Classes of Metal Compounds;Fe (Iron) Compounds;Ferrocenes;Metallocenes;Transition Metal Compounds;Catalysis and Inorganic Chemistry;Chemical Synthesis;metallocene
• Mol File: 1271-86-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 65 °C
• Boiling Point: 124-128 °C2.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: amber/liquid
• Density: 1.228 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.42mmHg at 25°C
• Refractive Index: n20/D 1.59(lit.)
• Solubility: Difficult to mix.
• CAS DataBase Reference: N,N-Dimethylaminomethylferrocene(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Dimethylaminomethylferrocene(1271-86-9)
• EPA Substance Registry System: N,N-Dimethylaminomethylferrocene(1271-86-9)

Safety Data

• Statements: R36/38:Irritating to eyes and skin.
• Safety Statements: 23-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1271-86-9(Hazardous Substances Data)

Usage

Chemical Properties

Brown to dark brown liquid

Uses

(Dimethylaminomethyl)ferrocene is used as an active pharmaceutical ingredient.

InChI:InChI=1/C8H13N/c1-9(2)7-8-5-3-4-6-8/h3-6,8H,7H2,1-2H3/p+1

Upstream product

• 264191-78-8 [Fe(η5-C5H5)(η5-C5H3(CH2NMe2)-2)-C,N]2Pb 
• 102-54-5 ferrocene 
• 51-80-9 bis-(dimethylamino)methane 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 
• 12093-10-6 ferrocenecarboxaldehyde 
• 506-59-2 N,N-dimethylammonium chloride 
• 56553-60-7 sodium tris(acetoxy)borohydride 
• 13292-87-0 dimethyl sulfide borane 
• 1273-86-5 1-ferrocenylmethanol 
• 69661-83-2 bis(ferrocenylmethyl)ether 
• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 

Downstream Products

• 16733-97-4 cyclopentadienyllithium 
• 1271-42-7 ferrocenecarboxylic acid 
• 12093-10-6 ferrocenecarboxaldehyde 
• 17632-84-7 Cr(II)(2,2'-bipyridine)3 

Relevant articles and documents

Ionic liquids as precursors for efficient mesoporous iron-nitrogen-doped oxygen reduction electrocatalysts

A ferrocene-based ionic liquid (Fe-IL) is used as a metal-containing feedstock with a nitrogen-enriched ionic liquid (N-IL) as a compatible nitrogen content modulator to prepare a novel type of non-precious-metal-nitrogen-carbon (M-N-C) catalysts, which feature ordered mesoporous structure consisting of uniform iron oxide nanoparticles embedded into N-enriched carbons. The catalyst Fesup10/sup@NOMC exhibits comparable catalytic activity but superior long-term stability to 20 wt% Pt/C for ORR with four-electron transfer pathway under alkaline conditions. Such outstanding catalytic performance is ascribed to the populated Fe (Feinf3/infOinf4/inf) and N (N2) active sites with synergetic chemical coupling as well as the ordered mesoporous structure and high surface area endowed by both the versatile precursors and the synthetic strategy, which also open new avenues for the development of M-N-C catalytic materials.

Controlled Reduction of Carboxamides to Alcohols or Amines by Zinc Hydrides

New protocols for controlled reduction of carboxamides to either alcohols or amines were established using a combination of sodium hydride (NaH) and zinc halides (ZnX2). Use of a different halide on ZnX2 dictates the selectivity, wherein the NaH-ZnI2 system delivers alcohols and NaH-ZnCl2 gives amines. Extensive mechanistic studies by experimental and theoretical approaches imply that polymeric zinc hydride (ZnH2)∞ is responsible for alcohol formation, whereas dimeric zinc chloride hydride (H?Zn?Cl)2 is the key species for the production of amines.

Synthesis of versatile intermediates of the ferrocene series: Reductive amination of ferrocenecarbaldehyde

Reductive amination of ferrocenecarbaldehyde with several primary and secondary amines in the presence of sodium triacetoxyborohydride was studied. This method was used for the synthesis of new ferrocenylmethylamines, viz., N-(ferrocenylmethyl)isoleucine methyl ester, N,N-bis(ferrocenylmethyl)glycine ethyl ester, and N-(3,5-dibenzyloxybenzyl)-N-(ferrocenylmethyl)methylamine. The latter is a potential precursor of a dendrimer with the chiral ferrocenyl plane in the core.