39713-71-8

Basic information

• Product Name: (2S)-2β,5α-Dimethylpyrrolidine
• Synonyms: (2S)-2β,5α-Dimethylpyrrolidine;(2R)-2α,5α-Dimethylpyrrolidine;(2R,5S)-2,5-Dimethylpyrrolidine;cis-2,5-Dimethylpyrrolidine;(2R,5R)-2,5-Dimethylpyrrolidine
• CAS NO: 39713-71-8
• Molecular Formula: C₆H₁₃N
• Molecular Weight: 99.17
• Mol File: 39713-71-8.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 145.71°C (rough estimate)
• Appearance: /
• Density: 0.8205
• Refractive Index: 1.4299
• PKA: 11.36±0.10(Predicted)
• CAS DataBase Reference: (2S)-2β,5α-Dimethylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2β,5α-Dimethylpyrrolidine(39713-71-8)
• EPA Substance Registry System: (2S)-2β,5α-Dimethylpyrrolidine(39713-71-8)

Safety Data

• Hazardous Substances Data: 39713-71-8(Hazardous Substances Data)

Usage

General Description

The chemical compound (2S)-2β,5α-Dimethylpyrrolidine is an organic compound with a pyrrolidine ring structure. It is also known as (+)-nicotine, a naturally occurring alkaloid found in tobacco plants. (2S)-2β,5α-Dimethylpyrrolidine has a molecular formula of C10H14N2 and a molar mass of 162.23 g/mol. Its IUPAC name is (S)-3-(1-methyl-2-pyrrolidinyl)pyridine, and it is a colorless to pale yellow liquid at room temperature. Nicotine is a highly addictive substance that affects the central nervous system, and it is commonly associated with tobacco use. It is used in various applications such as insecticides, pharmaceuticals, and research purposes.

Upstream product

• 7380-76-9 2-aminohex-5-ene 
• 62564-43-6 (+/-)-2r,5t-dimethyl-pyrrolidinoamine 
• 55556-86-0 (+/-)-2r,5t-dimethyl-1-nitroso-pyrrolidine 
• 625-84-3 2,5-Dimethylpyrrole 
• 10345-32-1 (+/-)-trans-2,5-dimethyl-2,5-dihydro-pyrrole 

Downstream Products

• 878021-25-1 2-[3-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2,5-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 
• 878021-32-0 C₁₉H₃₂NO₂Si 
• 31163-31-2 (+/-)-2r,5t-dimethyl-pyrrolidine-1-carboxylic acid anilide 
• 55556-86-0 (+/-)-2r,5t-dimethyl-1-nitroso-pyrrolidine 

Relevant articles and documents

Reactivity of functionalized indoles with rare-earth metal amides. Synthesis, characterization and catalytic activity of rare-earth metal complexes incorporating indolyl ligands

The reactivity of several functionalized indoles 2-(RNHCH2)C8H5NH (R = C6H5 (1), tBu (2), 2,6-iPr2C6H3 (3)) with rare-earth metal amides is described. Reactions of 1 or 2 with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 (RE = Eu, Yb) respectively produced the europium complexes [2-(C6H5NCH)C8H5N]2Eu[N(SiMe3)2] (4) and [2-(tBuNCH)C8H5N]Eu[N(SiMe3)2]2 (5), and the ytterbium complex [2-(tBuNCH)C8H5N]2Yb[N(SiMe3)2] (6), containing bidentate anionic indolyl ligands via dehydrogenation of the amine to the imine. In contrast, reactions of the more sterically bulky indole 3 with [(Me3Si)2N]3RE(μ-Cl)Li(THF)3 afforded complexes [2-(2,6-iPr2C6H3NCH2)C8H5N]RE[N(SiMe3)2](THF)2 (RE = Yb (7), Y (8), Er (9), Dy (10)) with the deprotonated indolyl ligand. While reactions of 3 with yttrium and ytterbium amides in refluxing toluene respectively gave the complexes [2-(2,6-iPr2C6H3NCH)C8H5N]3Y (11) and [2-(2,6-iPr2C6H3NCH)C8H5N]2YbII(THF)2 (12), along with transformation of the amino group to the imino group, and also with a reduction of Yb3+ to Yb2+ in the formation of 12. Reactions of 3 with samarium and neodymium amides provided novel dinuclear complexes {[μ-η5:η1:η1-2-(2,6-iPr2C6H3NCH2)C8H5N]RE[N(SiMe3)2]}2 (RE = Sm (13), Nd (14)) having indolyl ligands in μ-η5:η1:η1 hapticities. The pathway for the transformation of the amino group to the imino group is proposed on the basis of the experimental results. The new complexes displayed excellent activity in the intramolecular hydroamination of aminoalkenes.

Highly active and diastereoselective N,O- and N,N-yttrium complexes for intramolecular hydroamination

The intramolecular hydroamination of aminoalkynes and unactivated aminoalkenes catalyzed by yttrium N,O- and N,N-complexes has been investigated. The N,N-yttrium complexes are highly active, catalyzing the conversion of a wide range of terminal aminoalkenes at room temperature, and internal aminoalkenes at elevated temperature, to yield pyrrolidine and piperidine products in high yields. A high diastereoselectivity of up to 23:1 is observed at 0°C with 1-methyl-4-pentenylamine as substrate.

C2-symmetric zirconium Bis(Amidate) complexes with enhanced reactivity in aminoalkene hydroamination

Binaphthalenedicarboxamide zirconium complexes exhibit significantly enhanced catalytic activity in aminoalkene hydroamination reactions with respect to substrate scope (substrates without gem-dialkyl activation; cyclization of aminoheptenes), catalyst loading (as low as 0.5 mol %) and reaction temperatures (as low as 70 °C) compared to previous group 4 metal-based hydroamination catalyst systems.