26458-74-2

Basic information

• Product Name: 1-azabicyclo[2.2.2]octan-4-ol
• Synonyms: 1-azabicyclo[2.2.2]octan-4-ol;Quinuclidin-4-ol
• CAS NO: 26458-74-2
• Molecular Formula: C₇H₁₃NO
• Molecular Weight: 127.1842
• Mol File: 26458-74-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 226.5 °C at 760 mmHg
• Flash Point: 115.5 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 0.0161mmHg at 25°C
• Refractive Index: 1.555
• PKA: 9.07±0.20(Predicted)
• CAS DataBase Reference: 1-azabicyclo[2.2.2]octan-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-azabicyclo[2.2.2]octan-4-ol(26458-74-2)
• EPA Substance Registry System: 1-azabicyclo[2.2.2]octan-4-ol(26458-74-2)

Safety Data

• Hazardous Substances Data: 26458-74-2(Hazardous Substances Data)

Usage

General Description

1-Azabicyclo[2.2.2]octan-4-ol is a chemical compound with the molecular formula C7H13NO. It is a bicyclic organic compound containing a seven-membered ring with a nitrogen atom and a hydroxyl group. 1-Azabicyclo[2.2.2]octan-4-ol is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. It is also used in the production of fine chemicals, as well as in laboratory research and industrial applications. 1-Azabicyclo[2.2.2]octan-4-ol is known for its potential as an intermediate in the synthesis of various bioactive compounds, making it an important compound for chemical and pharmaceutical industries.

InChI:InChI=1/C7H13NO/c9-7-1-4-8(5-2-7)6-3-7/h9H,1-6H2

Downstream Products

• 171723-79-8 quinuclidin-4-yl biphenyl-2-ylcarbamate 
• 440676-07-3 (2R)-2-cyclohexyl-2-hydroxy-2-phenylacetic acid 1-azabicyclo[2.2.2]oct 4-yl ester 
• 320348-14-9 oxothien-2-yl-acetic acid 1-azabicyclo[2.2.2]oct-4-yl ester 
• 1047672-37-6 1-azabicyclo[2.2.2]oct-4-yl (3-phenyl-2-thienyl)carbamate 
• 1047672-25-2 1-azabicyclo[2.2.2]oct-4-yl (5-phenyl-1,3-thiazol-4-yl)carbamate 
• 1047672-29-6 1-azabicyclo[2.2.2]oct-4-yl (4-phenyl-3-thienyl)carbamate hydrochloride 
• 1047672-65-0 1-azabicyclo[2.2.2]oct-4-yl (2-phenyl-3-thienyl)carbamate hydrochloride 
• 1047673-45-9 1-azabicyclo[2.2.2]oct-4-yl [5-(3-chlorophenyl)-1,3-thiazol-4-yl]carbamate hydrochloride 
• 1047673-22-2 1-azabicyclo[2.2.2]oct-4-yl [5-(4-fluorophenyl)-1,3-thiazol-4-yl]carbamate hydrochloride 
• 1047673-68-6 1-azabicyclo[2.2.2]oct-4-yl {5-[3-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl}carbamate hydrochloride 
• 869113-09-7 Umeclidinium bromide 
• 461648-39-5 α,α-diphenyl-1-azabicyclo[2.2.2]octane-4-methanol 
• 2181-19-3 4-bromo-quinuclidine 
• 320348-13-8 2-hydroxy-2,2-dithien-2-ylacetic acid 1-azabicyclo[2.2.2]oct-4-yl ester 

Relevant articles and documents

Regioselective oxyfunctionalization of unactivated tertiary and secondary C-H bonds of alkylamines by methyl(trifluoromethyl)dioxirane in acid medium

Tetrafluoroborate salts of primary, secondary, and tertiary alkylamines are resistant toward N oxidation by methyl(trifluoromethyl)dioxirane (1b), which allows the selective oxidation of aliphatic tertiary and secondary C-H bonds in the alkyl side chain. The oxidations are carried out at 0°C with a ketone-free solution of methyl(trifluoromethyl)-dioxirane (1b) in methylene chloride. By this procedure, within 3 h the tertiary C-H bonds of acyclic, cyclic, and polycyclic amines 2a-e are hydroxylated to give the corresponding amino alcohols 3a-e. In the case of the acyclic amines 2a,b longer reaction times were necessary, and in the strong acid medium the corresponding amino acetamides 4a,b were obtained through Ritter reaction with the solvent acetonitrile. The strong electron-withdrawing nature of the ammonium group deactivates the oxidation of even tertiary C-H bonds at the α and β positions. Secondary C-H bonds of the linear aliphatic primary amines 2f-h were oxidized exclusively at the ∈ position to give the 2,3,4,5-tetrahydro-6-alkylpyridines 6f-h after intramolecular condensation of the corresponding amino ketones 5f-h.