940-53-4

Basic information

• Product Name: 2-hexylpiperidine
• CAS NO: 940-53-4
• Molecular Formula: C₁₁H₂₃N
• Molecular Weight: 169.307
• Mol File: 940-53-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 233.7°C at 760 mmHg
• Flash Point: 91.8°C
• Density: 0.821g/cm³
• Vapor Pressure: 0.055mmHg at 25°C
• Refractive Index: 1.439
• CAS DataBase Reference: 2-hexylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hexylpiperidine(940-53-4)
• EPA Substance Registry System: 2-hexylpiperidine(940-53-4)

Safety Data

• Hazardous Substances Data: 940-53-4(Hazardous Substances Data)

Usage

General Description

2-Hexylpiperidine, also known as capesirine, is a chemical compound with the molecular formula C11H23N. It is a piperidine derivative, which is a type of heterocyclic organic compound. 2-Hexylpiperidine is a colorless liquid with a strong and unpleasant odor. It is used as a solvent and as an intermediate in the production of various organic compounds. It is also used in the synthesis of pharmaceuticals and agrochemicals. Additionally, 2-hexylpiperidine has been studied for its potential use in the treatment of neurological disorders and as an insecticide. However, it is important to handle this compound with caution, as it is toxic if ingested or inhaled and can cause irritation to the skin and eyes.

Upstream product

• 110-89-4 piperidine 
• 592-41-6 1-hexene 
• 110-05-4 di-tert-butyl peroxide 
• 1129-69-7 2-hexylpyridine 
• 109-06-8 α-picoline 
• 2528-61-2 Heptanoic acid chloride 
• 35329-56-7 methyl (E)-undec-4-enoate 
• 21676-08-4 (E)-undec-4-en-1-ol 
• 21964-44-3 non-1-en-3-ol 
• 316147-57-6 (E)-1-azidoundec-4-ene 
• 60278-15-1 5-oxo-undecanenitrile 

Relevant articles and documents

Azidomercurations of alkenes: Mercury-promoted Schmidt reactions

Azides bearing a suitably disposed alkene, when treated with either mercuric perchlorate or mercuric trifluoromethanesulfonate, produce bicyclic iminium ions. This new version of the Schmidt reaction proceeds by capture of the mercuronium ion intermediate by the azide to produce an aminodiazonium ion, which suffers a 1,2-shift to give an iminium ion (e.g., 10 → 16 → 17 → 18). Reduction of the iminium ion may then be carried out to produce an amine. Compared to earlier work on the protic acid-promoted intramolecular Schmidt reaction of azido-alkenes, the mercury-promoted Schmidt reaction has several advantages. First, the acid-promoted Schmidt reaction of azido-alkenes requires that the intermediate carbocations be tertiary, allylic, benzylic, or propargylic. The mercury-promoted method has no such limitation; thus even 1,2-disubstituted alkenes may be used. Second, the mercury-promoted method is milder, allowing the presence of acid-sensitive functionality. The protic version, typically employing trifluoromethanesulfonic acid, is limited in its functional group tolerance. Third, whereas carbocation rearrangement is often observed prior to cyclization/rearrangement in the acid-promoted Schmidt reaction, the mercury-promoted method avoids this problem. Fourth, the presence of the mercurio group during the rearrangment may alter the regioselectivity of the 1,2-migration. Finally, the mercury-bearing iminium ions that are the result of the Schmidt reaction were found to be sensitive to protodemercuration, precluding their use in other transformations.