2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride

Base Information

• Chemical Name: 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride
• CAS No.: 56239-25-9
• Molecular Formula: C6H9 N O . Cl H
• Molecular Weight: 147.605
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20505683
• NSC Number: 236633
• Mol file: 56239-25-9.mol

Synonyms:56239-25-9;2-OXA-3-AZABICYCLO[2.2.2]OCT-5-ENE HYDROCHLORIDE;2-Aza-3-oxa-bicyclo[2.2.2]oct-5-ene hydrochloride;2-oxa-3-azabicyclo[2.2.2]oct-5-ene;hydrochloride;2-oxa-3-aza-bicyclo[2.2.2]oct-5-ene hydrochloride;SCHEMBL2338352;DTXSID20505683;AIQPCXFIPDZVQJ-UHFFFAOYSA-N;MFCD17267844;NSC236633;AKOS015995879;NSC-236633;SY211449;CS-0246571;EN300-333252;2-Aza-3-oxa-bicyclo[2.2.2]oct-5-enehydrochloride;2-Oxa-3-azabicyclo[2.2.2]oct-5-ene, hydrochloride;Z1255502641;2-Oxa-3-azabicyclo[2.2.2]oct-5-ene--hydrogen chloride (1/1)

Chemical Property of 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride

Chemical Property:

• Vapor Pressure: 5.05mmHg at 25°C
• Melting Point: 164-168oC (DEC.)
• Boiling Point: 144.6°Cat760mmHg
• Flash Point: 44.3°C
• PSA: 21.26000
• Density: 1.075g/cm³
• LogP: 1.73920
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.0450916
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

2-Aza-3-oxa-bicyclo[2.2.2]oct-5-enehydrochloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C=CC1NO2.Cl

Technology Process of 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride

There total 3 articles about 2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride 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: 91.0%

1-chloro-1-nitrosocyclohexane (695-64-7) + cyclohexa-1,3-diene (1165952-91-9) → 1,1-diethoxycyclohexane (1670-47-9) + (+/-)-2-Oxa-3-azabicyclo[2.2.2]oct-5-ene hydrochloride (56239-25-9)

Guidance literature:

In tetrachloromethane; ethanol; at -20 ℃; for 480h;

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) + acetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester (740798-68-9) → 4-amino-cyclohex-2-enol; hydrochloride + 2-Oxa-3-azabicyclo<2.2.2>oct-5-ene hydrochloride (56239-25-9)

Guidance literature:

cyclohexa-1,3-diene; acetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester; With zinc trifluoromethanesulfonate; In toluene; for 4h;

With hydrogenchloride; at 20 ℃; for 0.75h; Title compound not separated from byproducts;

DOI:10.1039/b513397a

Reference yield:

cyclohexa-1,3-diene (1165952-91-9) → 4-amino-cyclohex-2-enol; hydrochloride + 2-Oxa-3-azabicyclo<2.2.2>oct-5-ene hydrochloride (56239-25-9)

Guidance literature:

cyclohexa-1,3-diene; With acetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester; In toluene; at 0 ℃; Molecular sieve; Inert atmosphere;

With hydrogenchloride; water; In toluene; Inert atmosphere;

DOI:10.1016/j.tet.2010.02.065

upstream raw materials:

1-chloro-1-nitrosocyclohexane

cyclohexa-1,3-diene

acetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester

Downstream raw materials:

N-acetyl-2-oxa-3-azabicyclo<2.2.2>oct-5-ene

(1S*,4R*)-4-aminocyclohex-2-enol

tert-butyl 2-oxa-3-azabicyclo[2.2.2]oct-5-ene-3-carboxylate

tert-butyl (+/-)-(1S,4R)-(4-hydroxycyclohex-2-enyl)carbamate

Refernces

• 1、 Calvet, Geraldine,Guillot, Regis,Blanchard, Nicolas,Kouklovsky, Cyrille. "Intermolecular nitroso Diels-Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium". . p. 4395 - 4401. Retrieved 2007/10/03.