1459-48-9

Basic information

• Product Name: 4-(1-ADAMANTYL)ANILINE
• Synonyms: 4-(1-ADAMANTYL)ANILINE;1-(p-Aminophenyl)adamantane;4-(Adamantan-1-yl)phenylamine;Benzenamine,4-tricyclo[3.3.1.13,7]dec-1-yl-
• CAS NO: 1459-48-9
• Molecular Formula: C₁₆H₂₁N
• Molecular Weight: 227.34
• Product Categories: Adamantane derivatives
• Mol File: 1459-48-9.mol
• Article Data: 12

Chemical Properties

• Melting Point: 107-108℃
• Boiling Point: 367.4°C at 760 mmHg
• Flash Point: 154.1°C
• Appearance: /
• Density: 1.132±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.37E-05mmHg at 25°C
• Refractive Index: 1.623
• CAS DataBase Reference: 4-(1-ADAMANTYL)ANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(1-ADAMANTYL)ANILINE(1459-48-9)
• EPA Substance Registry System: 4-(1-ADAMANTYL)ANILINE(1459-48-9)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 1459-48-9(Hazardous Substances Data)

Usage

Description

4-(1-ADAMANTYL)ANILINE, also known as 4-(1-adamantyl)phenylamine, is an organic compound with the molecular formula C15H21N. It is characterized by its adamantyl group, which is a rigid and symmetrical carbon cage structure, attached to an aniline moiety. This unique structure endows 4-(1-ADAMANTYL)ANILINE with specific chemical and physical properties, making it a versatile compound for various applications.

Uses

Used in Pharmaceutical Industry:
4-(1-ADAMANTYL)ANILINE is used as a reactant in the preparation of pyrroledione derivatives, which are inhibitors of glycogen synthase kinase-3 (GSK-3). These inhibitors play a crucial role in the development of novel therapeutic agents for the treatment of various diseases, including neurodegenerative disorders, diabetes, and cancer. The adamantyl group in 4-(1-ADAMANTYL)ANILINE provides structural rigidity and enhances the binding affinity of the resulting pyrroledione derivatives to GSK-3, thereby improving their inhibitory potency.

InChI:InChI=1/C16H21N/c17-15-3-1-14(2-4-15)16-8-11-5-12(9-16)7-13(6-11)10-16/h1-4,11-13H,5-10,17H2

Upstream product

• 1459-49-0 1-(4-nitrophenyl)adamantane 
• 71-43-2 benzene 
• 768-95-6 1-adamanthanol 
• 103-84-4 Acetanilid 
• 108-88-3 toluene 
• 175881-22-8 4-(1-adamantyl)benzoic acid chloride 
• 7164-55-8 ethyl 4-(adamantan-1-yl)benzoate 
• 1459-55-8 4-(1-adamantyl)toluene 
• 768-90-1 1-Adamantyl bromide 
• 540-37-4 p-aminoiodobenzene 
• 1247829-32-8 tert-butyl [4-(adamantan-1-yl)phenyl]carbamate 
• 7123-78-6 4-(adamant-1-yl)benzoic acid 
• 780-68-7 1-phenyladamantane 
• 24569-89-9 1,3-dehydroadamantane 

Downstream Products

• 1247829-35-1 ethyl {[4-(adamantan-1-yl)phenyl]amino}oxoacetate 
• 2245-43-4 4-(1-Adamantyl)bromobenzene 

Relevant articles and documents

Modes of Micromolar Host-Guest Binding of β-Cyclodextrin Complexes Revealed by NMR Spectroscopy in Salt Water

Multitopic supramolecular guests with finely tuned affinities toward widely explored cucurbit[n]urils (CBs) and cyclodextrins (CDs) have been recently designed and tested as functional components of advanced supramolecular systems. We employed various spa

Adamantylation of N-aryl and N-arylalkyl acetamides in trifluoroacetic acid

Alkylation of N-aryl and N-arylalkyl acetamides with hydroxy adamantane derivatives in trifluoroacetic acid was studied. The differentiating effect of trifluoroacetic acid on the regio-selectivity of adamantylation of o-alkyl-substituted acetanilides was established, leading to energetically more stable products of para-substitution with respect to the alkyl group (the content of para-alkyl isomers is 93–94percent). This enabled the synthesis of adamantylaminoarenes in 83–99percent yields and with 95–99percent purity.

4-(1-Adamantyl)phenylalkylamines with potential antiproliferative activity

Background: In our previous publications we have described the synthesis of aminosubstituded diaryl adamantanes and their pharmacological evaluation in vitro and in vivo against many cancer cell lines. More recently, we have reported the synthesis of mono