22607-75-6

Basic information

• Product Name: 4-AZATRICYCLO[4.3.1.1(3,8)]UNDECAN-5-ONE
• Synonyms: AKOS BC-0498;4-AZATRICYCLO[4.3.1.1(3,8)]UNDECAN-5-ONE;4-AZAHOMOADAMANTAN-5-ONE;4-azatricyclo(4.3.1.1(sup3,8))undecan-5-one;5-Azatricyclo[4.3.1.13,8]undecane-4-one;NSC 145164
• CAS NO: 22607-75-6
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• Product Categories: Adamantane derivatives;Carbonyl Compounds;Lactams;Organic Building Blocks
• Mol File: 22607-75-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 316-318 °C(lit.)
• Boiling Point: 344 °C at 760 mmHg
• Flash Point: 201.3 °C
• Appearance: /
• Density: 1.103±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 6.78E-05mmHg at 25°C
• Refractive Index: 1.522
• Solubility: chloroform: soluble2.5%, clear, colorless
• PKA: 15.95±0.20(Predicted)
• CAS DataBase Reference: 4-AZATRICYCLO[4.3.1.1(3,8)]UNDECAN-5-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AZATRICYCLO[4.3.1.1(3,8)]UNDECAN-5-ONE(22607-75-6)
• EPA Substance Registry System: 4-AZATRICYCLO[4.3.1.1(3,8)]UNDECAN-5-ONE(22607-75-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: CM0732000
• HazardClass: IRRITANT
• Hazardous Substances Data: 22607-75-6(Hazardous Substances Data)

Usage

General Description

4-Azatricyclo[4.3.1.1]undecan-5-one is formed during the Beckman rearrangement of adamantanone oxime. Crystal structure of 4-azatricyclo[4.3.1.1]undecan-5-one (homoazaadamantanone) has been studied.

InChI:InChI=1/C10H15NO/c12-10-8-2-6-1-7(3-8)5-9(4-6)11-10/h6-9H,1-5H2,(H,11,12)

Upstream product

• 51157-95-0 adamantane-2-spiro-3'-oxaziridine 
• 700-58-3 2-Adamantanone 

Downstream Products

• 1215765-89-1 4-phenylsulfanyl-4-azatricyclo[4.3.1.1(3,8)]undecan-5-one 
• 50722-62-8 4-nitroso-4-azatricyclo[4.3.1.1(3,8)]undecan-5-one 
• 54530-10-8 5-methyl-5-azahomoadamantan-4-one 
• 1426047-32-6 N-(4-trifluoromethylbenzyl)-6,7,8,9,10,11-hexahydro-5H-5,9:7,11-dimethano[1,2,4]triazolo[4,3-a]azonin-3-one 
• 1426047-31-5 N-benzyl-6,7,8,9,10,11-hexahydro-5H-5,9:7,11-dimethano[1,2,4]triazolo[4,3-a]azonin-3-one 
• 1426047-28-0 3-(4-trifluoromethylphenyl)-6,7,8,9,10,11-hexahydro-5H-5,9:7,11-dimethano[1,2,4]triazolo[4,3-a]azonine 
• 1426047-27-9 3-(4-bromophenyl)-6,7,8,9,10,11-hexahydro-5H-5,9:7,11-dimethano[1,2,4]triazolo[4,3-a]azonine 
• 24280-74-8 4-azatricyclo[4.3.1.13.8 ] undecane hydrochloride 
• 22776-74-5 4-Azatricyclo[4.3.1.1(3,8)]undecane 
• 102197-24-0 4-(3'-phenylpropen-2'-yl)-4-azatricyclo<4.3.1.1^3,8>undecane hydrochloride 
• 102197-31-9 4-(p-nitrocinnamoyl)-4-azatricyclo<4.3.1.1^3,8>undecane 
• 102197-32-0 4-<(m-trifluoromethyl)cinnamoyl>-4-azatricyclo<4.3.1.1^3,8>undecane 
• 102197-22-8 4-(p-nitrobenzoyl)-4-azatricyclo<4.3.1.1^3,8>undecane 
• 102197-29-5 4-(m-nitrobenzoyl)-4-azatricyclo<4.3.1.1^3,8>undecane 

Relevant articles and documents

SYNTHESIS AND TRANSFORMATIONS OF OXAZIRIDINES. ADAMANTANE-2-SPIRO-3'-OXAZIRIDINE AND ITS N-ALKYL DERIVATIVES

Unsubstituted and N-substituted adamantane-2-spiro-3'-oxaziridine were synthesized by the oxidation of Schiff bases, obtained from adamantanone and alkyl(aryl)amines, with peroxyacetic acid.The thermal rearrangement of the N-substituted derivatives leads to N-substituted 5-azahomoadamantan-4-ones, while fragmentation under the influence of Fe(II) ions leads to derivatives of bicyclononane in the form of N-substituted amides.Adamantane-2-spiro-3'-oxaziridine gives different transformation products, i.e., adamantanone in the first case and 5-azahomoadamantan-4-one in the second.