123-13-7

Basic information

• Product Name: 1-hexylpyrrolidine
• Synonyms: 1-hexylpyrrolidine
• CAS NO: 123-13-7
• Molecular Formula: C₁₀H₂₁N
• Molecular Weight: 155.28044
• EINECS: 204-604-7
• Mol File: 123-13-7.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 195.7°Cat760mmHg
• Flash Point: 76.8°C
• Appearance: /
• Density: 0.846g/cm³
• Vapor Pressure: 0.413mmHg at 25°C
• Refractive Index: 1.456
• CAS DataBase Reference: 1-hexylpyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-hexylpyrrolidine(123-13-7)
• EPA Substance Registry System: 1-hexylpyrrolidine(123-13-7)

Safety Data

• Hazardous Substances Data: 123-13-7(Hazardous Substances Data)

Usage

Physical form

Clear, colorless to light yellow liquid

Compound type

Pyrrolidine derivative

Structure

Five-membered ring with four carbon atoms and one nitrogen atom

Uses

Production of pharmaceuticals, solvent in the synthesis of organic compounds, stabilizer in rubber and plastics, manufacture of pesticides, dyes, and other industrial chemicals

Toxicity

Low toxicity, not classified as a hazardous substance under normal handling and use.

InChI:InChI=1/C10H21N/c1-2-3-4-5-8-11-9-6-7-10-11/h2-10H2,1H3

Upstream product

• 75719-23-2 1-hexyl-2,5-pyrrolidinedione 
• 110-63-4 Butane-1,4-diol 
• 111-26-2 hexan-1-amine 
• 13325-10-5 4-Aminobutanol 
• 111-27-3 hexan-1-ol 
• 123-75-1 pyrrolidine 
• 111-25-1 1-bromo-hexane 
• 3389-56-8 1-(pyrrolidin-1-yl)hexan-1-one 
• 109-67-1 1-penten 
• 201230-82-2 carbon monoxide 
• 66-25-1 hexanal 

Downstream Products

• 1075198-40-1 1-hexylpyrrolidinium 4,4,4-trifluoro-1-phenyl-1,3-butanedionate 

Relevant articles and documents

Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines

A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding the formation of pyrrolidines, cyclic imides, and lactones.

Method for catalytically synthesizing 1-substituted pyrrolidine/piperidine derivative by using supported metal

The invention provides a method for catalytically synthesizing a 1-substituted pyrrolidine/piperidine derivative by using a supported metal. The method comprises: carrying out a reaction with ammoniato form a pyrrolidine ring/piperidine ring by using a supported metal as a catalyst, using 1,4-butanediol/1, 5-pentanediol as a cyclization raw material and using alcohol as an N-alkylation raw material, wherein the high-selectivity synthesis of the 1-substituted pyrrolidine/piperidine derivative is achieved through the one-step reaction, the active components of the supported metal catalyst are Cu, Ni and Pd/Ru, the total loading capacity of the active components Cu and Ni is 3-15 wt% of the carrier, and the loading capacity of Pd/Ru is 0-1 wt% of the carrier. According to the invention, themethod is simple, low in cost and environmentally friendly, the conversion rate of 1,4-butanediol/1,5-pentanediol is high, the selectivity of the pyrrolidine/piperidine derivatives is high, and the method is a production route with practical application value.

Synthesis of β-Chiral Amines by Dynamic Kinetic Resolution of α-Branched Aldehydes Applying Imine Reductases

Imine reductases (IREDs) allow the one-step preparation of optically active secondary and tertiary amines by reductive amination of ketones. Until now, mainly α-chiral amines have been prepared by this route. In this study, we explored the possibility of synthesizing β-chiral amines, a class of compounds which is also frequently found as structural motif in pharmaceuticals but much more challenging to prepare due to the following reasons: (i) The aldehyde substrate already contains the chiral center and needs to be racemized to enable full conversion. (ii) Because the intermediate imine bears the stereo center two carbon atoms remote to the imine nitrogen, it is more challenging to achieve high enantioselectivity compared to α-chiral amine synthesis. For investigating the proof of concept, we first confirmed that different IREDs are able to convert a variety of α-branched aldehydes when combined with five different amine substrates. The IRED from Streptomyces ipomoeae was a suitable enzyme facilitating the dynamic kinetic resolution of 2-phenylpropanal and a substituted 2-methyl-3-phenylpropanal: the corresponding N-methylated β-chiral amines were obtained with '95 % conversion and 78 and 95 %ee. Other amines were formed with low to moderate enantiomeric excess. This exemplifies the potential of IREDs for the one-step synthesis of secondary β-chiral amines, but also the challenge to identify highly selective enzymes for a desired amine product.