2-Azabicyclo[2.2.2]octane

Base Information

• Chemical Name: 2-Azabicyclo[2.2.2]octane
• CAS No.: 280-38-6
• Molecular Formula: C7H13 N
• Molecular Weight: 111.1848
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID00182279
• Nikkaji Number: J11.396D
• Wikidata: Q83052933
• ChEMBL ID: CHEMBL1214433
• Mol file: 280-38-6.mol

Synonyms:2-Azabicyclo[2.2.2]octane;280-38-6;Isoquinuclidine;2-AZABICYCLO(2.2.2)OCTANE;3-azabicyclo[2.2.2]octane;BRN 0103113;2-aza-bicyclo[2.2.2]octane;MFCD01664956;5-20-04-00342 (Beilstein Handbook Reference);Isochinuclidin;acetic-phosphoricanhydride;SCHEMBL27542;CHEMBL1214433;SCHEMBL15192831;SCHEMBL20758936;SCHEMBL23982869;2-azabicyclo[2. 2. 2]octane;2-?Azabicyclo[2.2.2]?octane;DTXSID00182279;AKOS002678443;AKOS006350522;SB20155;AS-58429;LS-22483;CS-0054718;EN300-89472;P11101

Chemical Property of 2-Azabicyclo[2.2.2]octane

Chemical Property:

• Vapor Pressure: 1.58mmHg at 25°C
• Melting Point: 174 °C
• Boiling Point: 168.9°Cat760mmHg
• PKA: 11.62±0.20(Predicted)
• Flash Point: 47.5°C
• PSA: 12.03000
• Density: 0.934g/cm³
• LogP: 1.47720
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.104799419
• Heavy Atom Count: 8
• Complexity: 82.4

Purity/Quality:

98% ^*data from raw suppliers

2-Azabicyclo[2.2.2]octane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CCC1CN2

Technology Process of 2-Azabicyclo[2.2.2]octane

There total 8 articles about 2-Azabicyclo[2.2.2]octane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.6%

2-aza-bicyclo[2.2.2]octan-3-one (3306-69-2) → isoquinuclidine (280-38-6)

Guidance literature:

With hydrogen; sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 80 - 90 ℃; for 2h;

DOI:10.1081/SCC-120004848

Reference yield:

4-aminocyclohexanecarboxylic acid (1776-53-0) → isoquinuclidine (280-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Dowtherm(R) A / 250 °C

2: 96.6 percent / H₂ / Red-Al / toluene / 2 h / 80 - 90 °C

With diphenyl ether-biphenyl eutectic; hydrogen; sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene;

DOI:10.1081/SCC-120004848

Reference yield:

cis-4-aminocyclohexane-1-carboxylic acid (3685-23-2) → isoquinuclidine (280-38-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 245 - 290 °C / Bei schnellem Erhitzen

2: sodium amide; toluene

3: lithium alanate; diethyl ether

4: palladium/charcoal; ethanol / Hydrogenation

With palladium on activated charcoal; lithium aluminium tetrahydride; diethyl ether; ethanol; sodium amide; toluene;

DOI:10.1021/ja01544a038

upstream raw materials:

2-benzyl-2-aza-bicyclo[2.2.2]octane

2-aza-bicyclo[2.2.2]octan-3-one

4-aminocyclohexanecarboxylic acid

2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one

Downstream raw materials:

2-Nitrosoisoquinuclidine

2-aza-bicyclo[2.2.2]octane-2-carboxylic acid 4-[2-(5-methyl-isoxazole-3-carbonylamino)-ethyl]-benzenesulfonylamide

2-benzoyl-2-aza-bicyclo[2.2.2]octane

(2S)-2-[5-[2-(2-azabicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxoethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]-N-(2-pyridin-4-ylethyl)propan-1-amine

Refernces

• 1、 Chung, John Y. L.,Ho, Guo-Jie. "An improved preparation of 2-azabicyclo[2.2.2]octane". . p. 1985 - 1995. Retrieved 2007/10/03.
• 2、 -. "PEPTIDE COMPOUNDS DERIVED FROM BORONIC ACID". . . Retrieved 2008/06/13.