(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE Chemical Properties

Boiling point:

120-121 °C/0.7 mmHg (lit.)

Density 

1.222 g/mL at 20 °C (lit.)

refractive index 

1.5890

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid to cloudy liquid

color 

dark brown

optical activity

[α]20/D 14±1°, c = 1.5% in ethanol

InChI

InChI=1/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;/t8-;;/s3

InChIKey

ISOLNZQTVMCEOI-FGWUPGIONA-N

SMILES

[C]1([CH][CH][CH][CH]1)[C@H](C)N(C)C.[CH]1[CH][CH][CH][CH]1.[Fe] |&1:5,r,^1:0,1,2,3,4,10,11,12,13,14|

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

3

F 

10

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE Usage And Synthesis

Uses

(S)-(?)-N,N-Dimethyl-1-ferrocenylethylamine can be used:

• As a starting material in the synthesis of chiral diferrocenylphosphine-diamines applicable in catalysis.
• As a model chiral probe in the study of enantiodiscrimination ability of chiral ionic liquids using cyclic voltammetry.

Synthesis

General procedure for the synthesis of N,N-dimethylamino-1-ferrocenylethylamine from 1-(2-hydroxyethyl)ferrocene and dimethylamine: (3) (S)-1-ferrocenylethanol (1.03 kg, 4.47 mol), dichloromethane (3.0 L), and triethylamine (902.9 g, 8.94 mol) prepared above were added to the reaction vessel sequentially. Acetic anhydride (683.4 g, 6.70 mol) was slowly added dropwise at room temperature and the reaction was stirred for 3 hours. Subsequently, 33% aqueous dimethylamine solution (4.31 kg) was slowly added and stirring was continued for 5 hours. Upon completion of the reaction, the layers were left to separate and the organic phase was concentrated to recover the dichloromethane. The residue was purified by reduced pressure distillation and the fraction at 110 °C (0.07 kPa) was collected to give (S)-N,N-dimethyl-1-ferrocenylethylamine (1.02 kg) as a dark red oily liquid in 89% yield, 98% HPLC purity and 96% ee value.

References

[1] Patent: CN108409802, 2018, A. Location in patent: Paragraph 0050; 0053
[2] Canadian Journal of Chemistry, 1983, vol. 61, p. 2354 - 2358
[3] Bulletin de la Societe Chimique de France, 1972, p. 2847 - 2854
[4] Tetrahedron Letters, 1971, p. 1561 - 1563
[5] , Gmelin Handbook: Fe: Org.Verb.A4, 5.1.4.1.3.3, page 52 - 55,

(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE(31886-57-4)Related Product Information

• (S)-N,N-DIMETHYL-1-[(R)-1',2-BIS(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE
• (S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPHINO)FERROCENYL]ETHYLAMINE
• (S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
• (n)-n,n-dimethyl-1-ferrocenylethylamine,(+/-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
• (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
• (R)-(-)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate
• Ethylferrocene
• (S)-(+)-[(R)-2-DIPHENYLPHOSPHINOFERROCENYL](N,N-DIMETHYLAMINO)(2-DIPHENYLPHOSPHINOPHENYL)METHANE
• (S)-(+)-[(R)-2-DICYCLOHEXYLPHOSPHINOFERROCENYL](N,N-DIMETHYLAMINO)(2-DICYCLOHEXYLPHOSPHINOPHENYL)METHANE
• DICHLORO[(S)-N,N-DIMETHYL-1-[(R)-2-(DIPHENYLPHOSPINO)FERROCENYL]ETHYL-AMINE]PALLADIUM(II)
• (ALPHAS,ALPHAS)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]FERROCENE
• (R)-(+)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
• (S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
• (ALPHAS,ALPHAS)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS[BIS(2-METHYLPHENYL)PHOSPHINO]FERROCENE
• (S)-(+)-N,N-Dimethyl-1-ferrocenylethylamine (L)-tartrate
• (ALPHAS,ALPHAS)-1,1'-BIS-[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS[BIS(4-METHOXY-3,5-DIMETHYLPHENYL)PHOSPHINO]FERROCENE
• (ALPHAS,ALPHAS)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS(DICYCLOHEXYLPHOSPHINO)FERROCENE
• (ALPHAS,ALPHAS)-1,1'-BIS[ALPHA-(DIMETHYLAMINO)BENZYL]-(R,R)-2,2'-BIS(DIPHENYLPHOSPHINO)FERROCENE