6906-32-7

Basic information

• Product Name: N,N,2-TRIMETHYLPROPENYLAMINE
• Synonyms: Isobutenyl amine, n,n-dimethyl-;N,N,2-TRIMETHYLPROPENYLAMINE;N,N-DIMETHYLISOBUTENYLAMINE;1-(N,N-Dimethylamino)-2-methyl-1-propene
• CAS NO: 6906-32-7
• Molecular Formula: C₆H₁₃N
• Molecular Weight: 99.17
• Product Categories: monomer
• Mol File: 6906-32-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 113°C at 760 mmHg
• Flash Point: 13.2°C
• Appearance: /
• Density: 0.773g/cm³
• Vapor Pressure: 21.2mmHg at 25°C
• Refractive Index: 1.435
• CAS DataBase Reference: N,N,2-TRIMETHYLPROPENYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,2-TRIMETHYLPROPENYLAMINE(6906-32-7)
• EPA Substance Registry System: N,N,2-TRIMETHYLPROPENYLAMINE(6906-32-7)

Safety Data

• Hazardous Substances Data: 6906-32-7(Hazardous Substances Data)

Usage

General Description

N,N,2-trimethylpropenylamine is a chemical compound with the formula C6H13N. It is a flammable liquid with a strong, ammonia-like odor. N,N,2-trimethylpropenylamine is commonly used as a monomer in the production of polymers, particularly in the synthesis of polymeric quaternary ammonium compounds. It is also used as a reagent in organic synthesis and as an intermediate in the production of pharmaceuticals and agrochemicals. Additionally, it can be used as a chemical intermediate in the manufacturing of rubber accelerators and as a corrosion inhibitor in water treatment. However, it is important to handle N,N,2-trimethylpropenylamine with care as it is a hazardous chemical and should be used in accordance with proper safety precautions.

InChI:InChI=1/C6H13N/c1-6(2)5-7(3)4/h5H,1-4H3

Upstream product

• 51439-17-9 2-isopropyl-3-methyl-1,3-oxazolidine 
• 53742-70-4 diethyldimethylaminostibine 
• 53742-76-0 β,β-Dimethylvinyloxydiethylstibin 
• 21678-37-5 N,N,2-trimethylpropionamide 
• 13222-51-0 (E)-1-N,N-dimethylamino-1-propene 
• 6000-82-4 N,N-dimethyl-2-methylprop-2-enylamine 
• 124-40-3 dimethyl amine 
• 78-84-2 isobutyraldehyde 

Downstream Products

• 91693-53-7 Dimethyl-<1-isopropyl-3-butyl-2-propin-1-yl>-amin 
• 86220-41-9 1,4-diisopropyl-tetra-N-methyl-but-2-ynediyldiamine 
• 87065-05-2 N,N-Dimethyl-1-isopropyl-2-propinylamin 
• 15451-14-6 3-dimethylamino-2,2-dimethylpropanal 
• 76503-80-5 7-Dimethylamino-4,6,6-trimethylhexahydro-1,4-oxazepin 
• 76503-82-7 3,4,6,6-Tetramethyl-7-dimethylamino-2-phenylhexahydro-1,4-oxazepin 
• 1041847-87-3 [NMe₂(5-methyl-2-hexynyl)(CH=C(CH₃)2)][OTS] 
• 1041847-71-5 [NMe₂(2-propynyl)(CH=C(CH₃)2)][OTS] 
• 1041847-93-1 [NMe₂(3-phenyl-2-propynyl)(CH=C(CH₃)2)][OTS] 
• 1041847-74-8 [NMe₂(2-butynyl)(CH=C(CH₃)2)][OTS] 
• 1041848-36-5 [NMe₂(2-octynyl)(CH=C(CH₃)2)][OTS] 
• 1041847-77-1 [NMe₂(2-pentynyl)(CH=C(CH₃)2)][OTS] 
• 1041847-91-9 [NMe₂(4,4-dimethyl-2-pentynyl)(CH=C(CH₃)2)][OTS] 
• 1041847-83-9 [NMe₂(4-methyl-2-pentynyl)(CH=C(CH₃)2)][OTS] 

Relevant articles and documents

Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis

An unprecedented tandem N-alkylation-ionic aza-Cope (or Claisen) rearrangement-hydrolysis reaction of readily available indolyl bromides with enamines is described. Due to the complicated nature of the two processes, an operationally simple N-alkylation and subsequent microwave-irradiated ionic aza-Cope rearrangement-hydrolysis process has been uncovered. The tandem reaction serves as a powerful approach to the preparation of synthetically and biologically important, but challenging, 2-reverse quaternary-centered prenylated indoles with high efficiency. Notably, unusual nonaromatic 3-methylene-2,3-dihydro-1H-indole architectures, instead of aromatic indoles, are produced. Furthermore, the aza-Cope rearrangement reaction proceeds highly regioselectively to give the quaternary-centered reverse prenyl functionality, which often produces a mixture of two regioisomers by reported methods. The synthetic value of the resulting nonaromatic 3-methylene-2,3-dihydro-1Hindole architectures has been demonstrated as versatile building blocks in the efficient synthesis of structurally diverse 2-reverse prenylated indoles, such as indolines, indolefused sultams and lactams, and the natural product bruceolline D.

Supramolecular catalysis of unimolecular rearrangements: Substrate scope and mechanistic insights

A cavity-containing metal-ligand assembly is employed as a catalytic host for the 3-aza Cope rearrangement of allyl enammonium cations. Upon binding, the rates of rearrangement are accelerated for all substrates studied, up to 850-fold. Activation parameters were measured for three enammonium cations in order to understand the origins of acceleration. Those parameters reveal that the supramolecular structure is able to reduce both the entropic and enthalpic barriers for rearrangement and is highly sensitive to small structural changes of the substrate. The space-restrictive cavity preferentially binds closely packed, preorganized substrate conformations, which resemble the conformations of the transition states. This hypothesis is also supported by quantitative NOE studies of two encapsulated substrates, which place the two reacting carbon atoms in close proximity. The capsule can act as a true catalyst, since release and hydrolysis facilitate catalytic turnover. The question of product hydrolysis was addressed through detailed kinetic studies. We conclude that the iminium product must dissociate from the cavity interior and the assembly exterior before hydroxide-mediated hydrolysis, and propose the intermediacy of a tight ion pair of the polyanionic host with the exiting product.

Flash vacuum thermolysis of 2-isopropyl oxazolidines. Mechanism of the tautomerism between azomethine ylid, aziridine and enamine

Depending on the nature of the substitution of 2-isopropyl oxazolidines and the Flash Vacuum Thermolysis conditions, aziridines and/or enamines are recovered through the azomethine ylid formed in situ Studies with deuterium labelled molecules give arguments for a concerted process in the gas phase.