31886-58-5

Basic information

• Product Name: (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
• Synonyms: (R)-(+)-N,N-DIMETHYLFERROCENYLETHYLAMINE;(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE;(R)-(+)-[1-(DIMETHYLAMINO)ETHYL]FERROCENE;(R)-alpha-(N,N-Dimethylamino)ethylferrocene,;Ferrocene, (1R)-1-(dimethylamino)ethyl-;(R)-(+)-1-(DIMETHYLAMINO)ETHYLFERROCENE 98+%;[(1R)-1-(Dimethylamino)ethyl]ferrocene;R-N,N-Dimethyl-1-ferrocenylethylae
• CAS NO: 31886-58-5
• Molecular Formula: C₁₄H₁₉FeN
• Molecular Weight: 257.15
• EINECS: -0
• Product Categories: Classes of Metal Compounds;Fe (Iron) Compounds;Ferrocenes;Metallocenes;Transition Metal Compounds
• Mol File: 31886-58-5.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 120-121 °C0.7 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: dark brown/
• Density: 1.222 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.589(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE(31886-58-5)
• EPA Substance Registry System: (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE(31886-58-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 31886-58-5(Hazardous Substances Data)

Usage

Description

(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE, also known as (R)-(+)-N,N-Dimethyl-1-ferrocenylethylamine, is a chiral compound with a unique structure that features a ferrocene group attached to an ethylamine moiety. (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE is characterized by its brown liquid appearance and is known for its potential applications in various chemical and pharmaceutical processes due to its distinctive chemical properties.

Uses

Used in Chiral Synthesis:
(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE is used as a reactant in the preparation of chiral N-phosphoryl y-aminoboronates. These chiral compounds are essential in the synthesis of various pharmaceuticals and biologically active molecules, as they can exhibit different biological activities depending on their stereochemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE is used as a key intermediate for the synthesis of chiral drugs. (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE's unique structure allows for the development of new drugs with improved efficacy and selectivity, making it a valuable asset in drug discovery and development.
Used in Chemical Research:
(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE is also utilized in chemical research as a starting material for the synthesis of various complex organic molecules. Its unique properties make it an attractive candidate for the development of new chemical reactions and methodologies.
Used in Material Science:
(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE's unique structure and properties also make it a potential candidate for applications in material science, where it could be used to develop new materials with specific properties, such as chiral catalysts or enantioselective sensors.

InChI:InChI=1/C9H13N.C5H4.Fe/c1-8(10(2)3)9-6-4-5-7-9;1-2-4-5-3-1;/h4-6,8H,1-3H3;1-4H;/q2*-1;+2/t8-;;/m1../s1/rC14H17FeN/c1-11(16(2)3)13-9-6-10-14(13)15-12-7-4-5-8-12/h4-11H,1-3H3/t11-/m1/s1

Upstream product

• 124-40-3 dimethyl amine 
• 16940-66-2 sodium tetrahydroborate 
• 1085568-96-2 1-ferrocenylethylamine 
• 1277-49-2 1-ferrocenylethanol 
• 51-80-9 bis-(dimethylamino)methane 
• 102-54-5 ferrocene 
• 123-63-7 paracetaldehyde 
• 75-07-0 acetaldehyde 
• 1271-55-2 acetylferrocene 
• 506-59-2 N,N-dimethylammonium chloride 
• 50-00-0 formaldehyd 

Downstream Products

• 1271-51-8 vinyl ferrocene 

Relevant articles and documents

One-pot α-ferrocenylalkylation of amines and alcohols with α-ferrocenyl substituted alcohols under acid-free conditions

One-pot reaction of FcCH(R)OH with equimolar quantities of BunLi and EtOCOCl followed by an excess of amine produces N-(α-ferrocenylalkyl)amines in up to 98% yields. Nitrogen heteroaryl amines undergo the α-ferrocenylalkylation at the amino group. The α-ferrocenylalkylation of alcohols and phenols (R'OH) leads to a formation of ethers FcCH(R)OR′ in lower yields. The reactions proceed via an intermediate formation of α-ferrocenylalkyl carbonates FcCH(R)OCOOEt. The side reactions associated with this protocol are discussed.

Process for preparing (S)-1-ferrocene ethyl dimethylamine

The invention discloses a process for preparing (S)-1-ferrocene ethyl dimethylamine. In the preparation process, acetylferrocene is used as a raw material, and a complex obtained by reacting a metal Ir complex with a chiral ferrocene tridentate ligand L* is used as a catalyst, (S)-1-ferrocenyl ethanol is prepared by asymmetric catalytic hydrogenation, and the(S)-1-ferrocene ethyl dimethylamine isprepared by acetylation and dimethylamine substitution reaction. Compared with a traditional chiral separation method for preparing the (S)-1-ferrocene ethyl dimethylamine, the process has main beneficial effects of mild reaction conditions, simple operation, good stereoselectivity, high yield, short production cycle, small amount of three wastes , easy industrialization, and large implementationvalue and social and economic benefits.

Rhodium-Catalyzed Asymmetric Allylation of Malononitriles as Masked Acyl Cyanide with Allenes: Efficient Access to β,γ-Unsaturated Carbonyls

A rhodium-catalyzed regio- and enantioselective intermolecular allylation of malononitriles as masked acyl cyanides (MAC) with terminal and symmetrical internal allenes is reported. A RhI/Josiphos catalytic system combined with subsequent oxidative degradation of the primary adducts enables a straightforward access to α-branched, β,γ-unsaturated carbonyl compounds. The present protocol exhibits perfect atom economy in the allylation step and is characterized by a great functional group compatibility. Furthermore, the use of α-substituted malononitriles allowed for the construction of all-carbon quaternary centers.