54391-01-4

Basic information

• Product Name: N,N-diallylcyclohexylamine
• Synonyms: Cyclohexanamine, N,N-di-2-propen-1-yl-; Diallylcyclohexylamine; Cyclohexanamine, N,N-di-2-propenyl-; N,N-Diallylcyclohexylamine; N,N-di(prop-2-en-1-yl)cyclohexanamine
• CAS NO: 54391-01-4
• Molecular Formula: C₁₂H₂₁N
• Molecular Weight: 179.3018
• EINECS: 259-140-8
• Mol File: 54391-01-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 242.8°C at 760 mmHg
• Flash Point: 91.8°C
• Density: 0.87g/cm³
• Vapor Pressure: 0.0334mmHg at 25°C
• Refractive Index: 1.484
• CAS DataBase Reference: N,N-diallylcyclohexylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-diallylcyclohexylamine(54391-01-4)
• EPA Substance Registry System: N,N-diallylcyclohexylamine(54391-01-4)

Safety Data

• Hazardous Substances Data: 54391-01-4(Hazardous Substances Data)

Upstream product

• 6628-00-8 N-Allylcyclohexylamin 
• 106-95-6 allyl bromide 
• 557-40-4 Allyl ether 
• 19573-22-9 cyclohexyl azide 
• 591-87-7 Allyl acetate 
• 108-91-8 cyclohexylamine 
• 107-18-6 allyl alcohol 
• 874480-14-5 O-benzoyl-N,N-diallylhydroxylamine 
• 931-50-0 cyclohexylmagnesium bromide 

Downstream Products

• 70169-47-0 cyclohexyl-dipropenyl-amine 
• 65819-72-9 cyclohexyl-(2-methyl-pent-2-enyliden)-amine 
• 68109-75-1 1-cyclohexyl-2,5-dihydro-1H-pyrrole 
• 6628-00-8 N-Allylcyclohexylamin 
• 108-91-8 cyclohexylamine 

Relevant articles and documents

PRODUCTION METHOD FOR 2-ALKENYLAMINE COMPOUND

Provided is a method for producing a 2-alkenylamine compound efficiently and at low cost, using a primary or secondary amine compound and a 2-alkenyl compound as the starting materials therefor. The 2-alkenyleamine compound is produced by 2-alkenylating a primary or secondary amine compound, using a specified 2-alkenylating agent and in the presence of a catalyst comprising a complexing agent and a transition metal precursor stabilized by a monovalent anionic five-membered conjugated diene.

An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis

The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.

Mechanistic studies of the copper-catalyzed electrophilic amination of diorganozinc reagents and development of a zinc-free protocol

Equation Presented An SN2 mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxyamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.