719304-60-6

Basic information

• Product Name: (+/-)-dimethyl-[3-(2-phenylnaphthalen-1-yl)pyridin-4-yl]amine
• CAS NO: 719304-60-6
• Molecular Weight: 324.425
• Mol File: 719304-60-6.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-dimethyl-[3-(2-phenylnaphthalen-1-yl)pyridin-4-yl]amine(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-dimethyl-[3-(2-phenylnaphthalen-1-yl)pyridin-4-yl]amine(719304-60-6)
• EPA Substance Registry System: (+/-)-dimethyl-[3-(2-phenylnaphthalen-1-yl)pyridin-4-yl]amine(719304-60-6)

Safety Data

• Hazardous Substances Data: 719304-60-6(Hazardous Substances Data)

Upstream product

• 719304-59-3 trifluoromethanesulfonic acid 1-(4-dimethylaminopyridin-3-yl)naphthalen-2-yl ester 
• 13626-17-0 3,5-dibromo-4-chloro-pyridine 
• 719304-56-0 1-(4-dimethylaminopyridin-3-yl)naphthalen-2-ol 
• 719304-45-7 3,5-dibromo(pyridine-4-yl)dimethylamine 
• 612086-27-8 4-chloro-3-(2-phenyl-naphthalen-1-yl)pyridine 
• 89167-34-0 4-chloro-3-iodopyridine 
• 612086-25-6 4,4,5,5-tetramethyl-2-(2-phenyl-naphthalen-1-yl)-[1,3,2]dioxaborolane 

Relevant articles and documents

Energy barriers to rotation in axially chiral analogues of 4-(dimethylamino)pyridine

The barriers to enantiomerization of a series of axially chiral biaryl analogues of 4-(dimethylamino)-pyridine (DMAP) 1-10 were determined experimentally by means of dynamic HPLC measurements and racemization studies. The barriers to rotation in derivatives 1-6 (based on the bicyclic 5-azaindoline core) were lower than those in the corresponding derivatives 7-10 (based on the monocyclic DMAP core). Semiempirical (PM3), ab initio Hartree-Fock (HF/STO-3G), and density functional theory (DFT/B3LYP/6-31G*) calculations reveal that these differences in barriers to rotation are the result of differing degrees of hybridization of the non-pyridyl nitrogen in the enantiomerization transition states (TSs). The importance of heteroatom hybridization as a factor in determining nonsteric contributions to barriers to rotation in azabiaryls of this type is discussed.

Preparative-Scale Synthesis of Vedejs Chiral DMAP Catalysts

A scalable synthesis of chiral Vedejs-type DMAP catalysts is reported. The key step of the synthesis is amination of the enantiomerically pure 4-chloropyridine derivative using well-defined ZnCl2(amine)2 complexes. A series of Zn(II)-amine complexes have been synthesized to explore the scope of the ZnCl2-mediated amination of 4-halopyridines. Mechanistic studies support a Zn(II)-facilitated nucleophilic aromatic substitution as a plausible mechanism for the chlorine-to-amine exchange.

New atropisomeric biaryl derivatives of 4-aminopyridine - Identification of an improved nucleophilic catalyst for asymmetric acylation of sec-alcohols

The synthesis, CSP-HPLC resolution, and absolute configuration assignment of a series of 4-dialkylaminopyridine-based atropisomeric biaryls are described. Screening of these enantiomerically pure catalysts, which differ only in the nature of the 4-dialkylamino substituent, for the kinetic resolution of 1-(1-naphthyl)ethanol reveals the importance of this group on the selectivity of catalysis. The di-n-butylamino derivative displays the most favourable catalytic profile. The utility of this catalyst for the kinetic resolution of a selection of sec-alcohols, including a precursor for the synthesis of the antidepressant fluoxetine hydrochloride (Prozac) are reported. The possible role of the dialkylamino group in chirality transfer is discussed.