(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE - CAS 31886-58-5

Inquiry

(R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE (CAS# 31886-58-5 ) is a useful research chemical.

Catalog Number

31886-58-5

CAS

31886-58-5

IUPAC Name

cyclopenta-1,3-diene;(1R)-1-cyclopenta-1,3-dien-1-yl-N,N-dimethylethanamine;iron(2+)

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

Molecular Weight

257.15

Molecular Formula

C14H19FeN

Product Information

Canonical SMILES

CC(C1=CC=C[CH-]1)N(C)C.[CH-]1C=CC=C1.[Fe+2]

InChI

InChI=1S/C9H14N.C5H5.Fe/c1-8(10(2)3)9-6-4-5-7-9;1-2-4-5-3-1;/h4-8H,1-3H3;1-5H;/q2*-1;+2/t8-;;/m1../s1

InChI Key

UNMQCGHIBZALKM-YCBDHFTFSA-N

Purity

> 98.0 % (GC)

MDL

MFCD00066273

Physical State

Liquid

Appearance

Amber to dark brown liquid

Storage

Room temperature.

Boiling Point

93 °C / 0.1 mmHg

Flash Point

>110 °C(230 °F)

Density

1.222 g/cm³

Optical Activity

15° (c=1 in ethanol)

Refractive Index

1.59

TSCA

Safety Information

Precautionary Statement

P264b - P280 - P302+P352 - P305+P351+P338 - P332+P313 - P362 - X

Hazard Statements

H315 - H319

Reference Reading

1. P-chiral ferrocenephospholanes: synthesis, Reactivity, Metal complex chemistry and application in the asymmetric hydrogenation of olefins.

Andreas Bertogg, Benoît Pugin, Björn Gschwend, Andreas Pfaltz. Chemistry. 2009 Dec 7; 15(47): 12993-3007. DOI: 10.1002/chem.200902418. PMID: 19894235.

Starting from (R)-N,N-dimethyl-1-ferrocenylethylamine, a diastereoselective ortho-lithiation procedure and a stereoconvergent intramolecular hydrophosphination gave access to P-chiral ferrocenephospholanes. These mono- or bidentate ligands were converted to the corresponding rhodium and iridium complexes, including a chiral version of Crabtree's catalyst, and tested in the asymmetric hydrogenation of functionalized and unfunctionalized olefins. A significant reactivity difference between the rhodium-1,5-cyclooctadiene and the rhodium-norbornadiene complex was observed during catalyst activation.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass