33187-62-1

Basic information

• Product Name: N-(1-ADAMANTYL)ANILINE
• Synonyms: AKOS BC-0488;N-(1-ADAMANTYL)ANILINE;N-Phenyl-1-adamantanamine;NSC 194593;N-PhenyladaMantan-1-aMine
• CAS NO: 33187-62-1
• Molecular Formula: C₁₆H₂₁N
• Molecular Weight: 227.34
• Product Categories: Adamantane derivatives
• Mol File: 33187-62-1.mol
• Article Data: 20

Chemical Properties

• Melting Point: 75-82℃
• Boiling Point: 355.7 °C at 760 mmHg
• Flash Point: 177.4 °C
• Appearance: /
• Density: 1.141±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.08E-05mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: N-(1-ADAMANTYL)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-ADAMANTYL)ANILINE(33187-62-1)
• EPA Substance Registry System: N-(1-ADAMANTYL)ANILINE(33187-62-1)

Safety Data

• Hazardous Substances Data: 33187-62-1(Hazardous Substances Data)

Usage

General Description

N-(1-Adamantyl)aniline, also known as 1-Adamantylphenylamine, is a chemical compound that is commonly used as an intermediate in the synthesis of various organic compounds. It is a primary aromatic amine, consisting of an aniline group attached to the adamantane scaffold. N-(1-ADAMANTYL)ANILINE is known for its excellent thermal and chemical stability and is often used in the production of dyes, pharmaceuticals, and other organic chemicals. N-(1-Adamantyl)aniline is also used as a catalyst and as a building block for the synthesis of various functional materials. Additionally, it has been studied for its potential applications in organic electronics and optoelectronics due to its interesting electronic and optical properties.

InChI:InChI=1/C16H21N/c1-2-4-15(5-3-1)17-16-9-12-6-13(10-16)8-14(7-12)11-16/h1-5,12-14,17H,6-11H2

Upstream product

• 768-95-6 1-adamanthanol 
• 62-53-3 aniline 
• 24569-89-9 1,3-dehydroadamantane 
• 142-04-1 aniline hydrochloride 
• 100-61-8 N-methylaniline 
• 768-94-5 1-Adamantanamine 
• 98-80-6 phenylboronic acid 
• 768-90-1 1-Adamantyl bromide 
• 108-86-1 bromobenzene 
• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 1253603-87-0 N-(1-adamantyl)-N-(trimethylsilyl)benzenamine 
• 7575-82-8 1-nitroadamantane 
• 100-59-4 phenylmagnesium chloride 

Downstream Products

• 1253603-87-0 N-(1-adamantyl)-N-(trimethylsilyl)benzenamine 
• 1253603-83-6 N-(1-adamanthyl)-N-phenylmethaneamide 
• 126832-02-8 N-(1-adamantyl)-4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)aniline N-oxide 
• 126831-98-9 N-(1-adamantyl)-4-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)aniline 

Relevant articles and documents

Synthesis ofN-aryl amines enabled by photocatalytic dehydrogenation

Catalytic dehydrogenation (CD)viavisible-light photoredox catalysis provides an efficient route for the synthesis of aromatic compounds. However, access toN-aryl amines, which are widely utilized synthetic moieties,viavisible-light-induced CD remains a significant challenge, because of the difficulty in controlling the reactivity of amines under photocatalytic conditions. Here, the visible-light-induced photocatalytic synthesis ofN-aryl amines was achieved by the CD of allylic amines. The unusual strategy using C6F5I as an hydrogen-atom acceptor enables the mild and controlled CD of amines bearing various functional groups and activated C-H bonds, suppressing side-reaction of the reactiveN-aryl amine products. Thorough mechanistic studies suggest the involvement of single-electron and hydrogen-atom transfers in a well-defined order to provide a synergistic effect in the control of the reactivity. Notably, the back-electron transfer process prevents the desired product from further reacting under oxidative conditions.

Transition-Metal-Free N-Arylation of Amines by Triarylsulfonium Triflates

A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.

The invention relates to a N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method (by machine translation)

The invention discloses a to N, N - disubstituted hydrazide as ligand copper catalysis C - N coupling method, the method uses the aromatic halides with amine compound as a raw material, in order to alcohol compound as the solvent, in order to copper or copper compound as a catalyst, in order to as formula I or formula II as shown by a N, N - disubstituted hydrazide as a ligand, the presence of a base, in the 10 - 130 °C generating C - N coupled reaction for generating N - aryl compound: the invention mild reaction conditions, high chemical selectivity, substrate and wide range of application, simplicity of operation, product is simple and easy to separation and environmental protection, the obtained product yield is higher. Wherein R1, R2 is selected from methyl, phenyl, 4 - methoxyphenyl, 4 - nitro-phenyl, 2 - methylphenyl, 2 - isopropyl phenyl; R3 is hydrogen or methoxy. (by machine translation)