121045-73-6

Basic information

• Product Name: (S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE
• Synonyms: (S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE
• CAS NO: 121045-73-6
• Molecular Formula: C14H17N
• Molecular Weight: 199.29
• Product Categories: Amines;Chiral Building Blocks;Organic Building Blocks
• Mol File: 121045-73-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 212 °C(lit.)
• Flash Point: 113 °C
• Appearance: /
• Density: 1.006 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00321mmHg at 25°C
• Refractive Index: n20/D 1.591(lit.)
• CAS DataBase Reference: (S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE(121045-73-6)
• EPA Substance Registry System: (S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE(121045-73-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 121045-73-6(Hazardous Substances Data)

Usage

Description

(S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE, also known as (-)-N,N-DMNE, is a chiral amine with the molecular formula C14H15N. It possesses a unique spatial arrangement of atoms, resulting in two distinct mirror image forms. (S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE is widely recognized for its utility in organic synthesis, particularly in the production of pharmaceuticals and fine chemicals, due to its ability to facilitate a variety of chemical reactions. Additionally, (-)-N,N-DMNE serves as a ligand in asymmetric synthesis and contributes to the development of new materials for electronic devices, highlighting its significance in organic chemistry and its broad spectrum of industrial and research applications.

Uses

Used in Pharmaceutical and Fine Chemicals Production:
(S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE is used as a reagent in the synthesis of pharmaceuticals and other fine chemicals for its ability to enable numerous chemical reactions, contributing to the development of a wide range of products.
Used in Asymmetric Synthesis:
In the field of organic chemistry, (-)-N,N-DMNE is utilized as a ligand in asymmetric synthesis, playing a crucial role in the production of various compounds with specific stereochemistry.
Used in Electronic Device Material Development:
(S)-(-)-N,N-DIMETHYL-1-(1-NAPHTHYL)ETHYLAMINE is also employed in the development of new materials for use in electronic devices, showcasing its versatility and importance in advancing technology.

InChI:InChI=1/C14H17N/c1-11(15(2)3)13-10-6-8-12-7-4-5-9-14(12)13/h4-11H,1-3H3/t11-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 86926-16-1 N,N-dimethyl[1-(1-naphthyl)ethyl]amine 
• 42882-31-5 (RS)-1-(1-naphthyl)ethylamine 
• 74-88-4 methyl iodide 

Downstream Products

• 119392-95-9 (R_c)-1-(1'-N,N-dimethylaminoethyl)naphthalene 
• 1416982-06-3 (S)-1-(1-p-tolylethyl)naphthalene 
• 941-98-0 1'-naphthacetophenone 
• 80145-77-3 bis(μ-chloro)bis[(R)-2-[1-(dimethylamino)ethyl]-naphthyl-C,N]dipalladium(II) 
• 1269772-84-0 (1-(naphthalen-1-yl)ethyl)(p-tolyl)sulfane 

Relevant articles and documents

Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates

A new protocol for the synthesis of (enantioenriched) benzylic sulfones via the Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).

Asymmetric induction in the arenethiolatocopper(I)-catalyzed substitution reaction of Grignard reagents with allylic substrates

The influence of some experimental parameters on the regio- and enantioselectivity in the 'γ-selective substitution reaction of Grignard reagents RMgX with acyclic allylic acetates catalyzed by the arenethiolatocopper(I) complex (S)-1 was studied. When more bulky arenethiolatocopper(I) complexes than (S)-1 were employed in a reaction of allylic acetate 3 with n-BuMgI, the enantioselectivities observed for the γ- product were lower. With an arenethiolatocopper(I) catalyst prepared in situ, several Grignard reagents were studied in a substitution reaction with acetate 2. Compared to n-BuMgI, more bulky Grignard reagents gave no improvement of the enantioselectivity in the formation of the γ-product. (C) 2000 Elsevier Science Ltd.

PHOSPHORORGANISCHE VERBINDUNGEN 102. TERTIAERE PHOSPHINE MIT o-DIALKYLAMINOPHENYL- UND ORTHO-DIALKYLAMINOBENZYLGRUPPEN

N,N-dialkylarylamines and N,N-dialkylbenzylamines are lithiated with n-butyllithium (n-BuLi) under the assistance of tetramethylethylenediamine (TMEDA) in the ortho-position.According the Eqs. (1) and (4) triarylphosphines (30-50percent) are obtained. 1-(N,N-dimethylamino)-naphthalene and N,N-dimethyl-1-(1-naphthyl)-ethylamine 18 are lithiated in the 8-position.In N,N-dimethyl-1-(2-naphthyl)-ethylamine 19 the 1- and 3-position is lithiated in nearly equal amount.Experiments to introduce lithium twice into the model compounds 28-30 are without success.