281-27-6

Basic information

• Product Name: 1-Azaadamantane
• Synonyms: 1-Azaadamantane;1-Azatricyclo[3.3.1.13,7]decane
• CAS NO: 281-27-6
• Molecular Formula: C₉H₁₅N
• Molecular Weight: 137.2221
• Mol File: 281-27-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 196.2°Cat760mmHg
• Flash Point: 64.9°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0.403mmHg at 25°C
• Refractive Index: 1.552
• CAS DataBase Reference: 1-Azaadamantane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azaadamantane(281-27-6)
• EPA Substance Registry System: 1-Azaadamantane(281-27-6)

Safety Data

• Hazardous Substances Data: 281-27-6(Hazardous Substances Data)

Usage

Also Known As

1-azatricyclo[3.3.1.1(3,7)]decane

Type of Compound

Bicyclic organic compound

Contains

Nitrogen atom within its molecular structure

Derived from

Adamantane (a hydrocarbon with a unique diamond-like shape)

Usage

Building block in organic synthesis

Application

Precursor in the production of pharmaceuticals and agrochemicals

Chemical and Physical Properties

Exhibits interesting properties due to its rigid and three-dimensional structure

Field of Relevance

Medicinal chemistry and material science

Potential Use

Chiral building block in asymmetric synthesis

Field of Interest

Organic chemistry

InChI:InChI=1/C9H15N/c1-7-2-9-3-8(1)5-10(4-7)6-9/h7-9H,1-6H2

Upstream product

• 31588-69-9 3,5,7-triamino-1-azaadamantane 
• 128315-94-6 3-methoxy-7α-iodomethyl-3-borabicyclo<3.3.1>nonane 
• 31588-65-5 3,5,7-trinitro-1-azaadamantane 
• 42949-24-6 1-azaadamantane-4-one 
• 117013-37-3 3,5,7-tribromo-1-azaadamantane 
• 128315-96-8 7α-hydroxymethyl-3-azabicyclo<3.3.1>nonane 

Downstream Products

• 67468-61-5 4-(1-methyl-1-phenylethyl)benzaldehyde 

Relevant articles and documents

HETEROADAMANTANES AND THEIR DERIVATIVES. 13. SYNTHESIS OF 1-AZAADAMANTANE AND SOME DERIVATIVES OF IT

3,5,7-Tribromo-1-azaadamantane is made by the action of sodium nitrite on 3,5,7-triamino-1-azaadamantane in concentrated hydrobromic acid.The reduction of this compound with hydrazine hydrate in the presence of a nickel catalyst gives azaadamantane.

ORGANOBORON COMPOUNDS. CDVI. CONVERSION OF 1-BORAADAMANTANE TO 1-AZAADAMANTANE

The reaction between 1-boraadamantane and ethyldichloramine results in the formation of 3-ethyl-3-azabicyclononane, which is converted to 1-ethyl-1-azoniumadamantane chloride by reaction with SOCl2.Hofmann degradation of the quaternary salt leads to 1-azaadamantane.

A novel method of synthesis of 1-azaadamantane from 1-boraadamantane

A novel and convenient method for the synthesis of 1-azaadamantane (I) from the 1-boraadamantane-tetrahydrofuran complex (XIII) is described.This is based on an intramolecular reaction of organic azides with organoboron compounds.Treatment of the boron cage compound XIII with iodine and an excess of sodium azide followed by oxidation (H2O2, OH-) affords 7α-hydroxymethyl-3-azabicyclononane (VII), cyclization of which leads to I in 40percent overall yield.Some new boron cage compounds were also isolated, diazidoborane (XIV) being of particular interest.