14465-46-4

Basic information

• Product Name: N-(3-methylpent-1-yn-3-yl)aniline
• Synonyms: Benzenamine, N-(1-ethyl-1-methyl-2-propyn-1-yl)-
• CAS NO: 14465-46-4
• Molecular Formula: C₁₂H₁₅N
• Molecular Weight: 173.2542
• Mol File: 14465-46-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 36-37 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 279.6°C at 760 mmHg
• Flash Point: 124.9°C
• Density: 0.988g/cm³
• Vapor Pressure: 0.00398mmHg at 25°C
• Refractive Index: 1.561
• PKA: 4.00±0.50(Predicted)
• CAS DataBase Reference: N-(3-methylpent-1-yn-3-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-methylpent-1-yn-3-yl)aniline(14465-46-4)
• EPA Substance Registry System: N-(3-methylpent-1-yn-3-yl)aniline(14465-46-4)

Safety Data

• Hazardous Substances Data: 14465-46-4(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 14179-94-3 3-chloro-3-methylpent-1-yne 
• 1185-96-2 3-acetoxy-3-ethylbutyne 
• 17889-27-9 1-trimethylsilyl-3-methyl-3-chloropent-1-yne 
• 77-75-8 meparfynol 
• 40296-03-5 N²-phenyl-2-butanimine 
• 74-86-2 acetylene 
• 17889-43-9 3-Hydroxy-3-methyl-1-trimethylsilyl-pentin-⁽¹⁾ 
• 10575-70-9 1-bromo-3-methyl-1,2-pentadiene 

Downstream Products

• 351523-44-9 (1-ethyl-1-methyl-allyl)-phenyl-amine 
• 201654-28-6 2-Ethyl-2-methyl-1,2,3,4-tetrahydro-quinolin-7-ylamine 
• 104665-99-8 N-(1-ethyl-1-methyl-propyl)-aniline 

Relevant articles and documents

Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N -Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach

An efficient metal-free domino reaction leading to structural/electronically divergent 1,2-dihydropyridines from easily accessible propargyl vinyl anilines via N-phenyl 3-aza-Cope sigmatropic rearrangement is reported with good to excellent yields using 1,2-dichlorobenzene as solvent under thermal conditions. Spirocyclic substitution is also tolerated under the present optimized conditions.

A convenient method for the aromatic amino-claisen rearrangement of N-(1,1-disubstituted-allyl)anilines

N-(1,1-Disubstituted-allyl)anilines are rearranged cleanly and in high yield to 2-(3,3-disubstituted-allyl)anilines using a catalytic amount of p-toluenesulfonic acid in acetonitrile/water (10:1).

REACTIONS OF NITROGEN NUCLEOPHILES WITH 1-BROMOALLENES: REGIOSELECTIVE SYNTHESIS OF PROPARGYLAMINES

The results of a study on the reactivity of 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes 2 towards nitrogen nucleophiles, such as aqueous ammonia, lithium amide, aliphatic and aromatic amines allowed us to propose new methods for the synthesis of propargylamines, 1, with an available acetylenic hydrogen.The regio- and the stereoselectivity of these reactions are examined and possible mechanisms are discussed.