1-Azabicyclo[2.2.2]octane-4-carbonitrile

Base Information

• Chemical Name: 1-Azabicyclo[2.2.2]octane-4-carbonitrile
• CAS No.: 26458-78-6
• Molecular Formula: C8H12N2
• Molecular Weight: 136.197
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70181052
• Nikkaji Number: J1.631.101D
• Wikidata: Q72459202
• Mol file: 26458-78-6.mol

Synonyms:quinuclidine-4-carbonitrile;26458-78-6;4-Cyanoquinuclidine;1-Azabicyclo[2.2.2]octane-4-carbonitrile;1-Azabicyclo(2.2.2)octane-4-carbonitrile;MFCD00276610;4-Cyanoquinuclidin;4- Cyanoquinuclidine;SCHEMBL351511;DTXSID70181052;CEMKLAOKVLRABO-UHFFFAOYSA-N;AMY37769;BCP04570;4-Cyano-1-azabicyclo[2.2.2]octane;AKOS006230597;AB93506;DS-18461;SY078718;CS-0044040;FT-0768361;F10816;A818456;4-Quinuclidinecarbonitrile;Quinuclidine-4-carbonitrile

Chemical Property of 1-Azabicyclo[2.2.2]octane-4-carbonitrile

Chemical Property:

• Vapor Pressure: 0.0417mmHg at 25°C
• Melting Point: 129-130 °C
• Refractive Index: 1.537
• Boiling Point: 238.7 °C at 760 mmHg
• PKA: 8.02±0.12(Predicted)
• Flash Point: 97.4 °C
• PSA: 27.03000
• Density: 1.09 g/cm³
• LogP: 0.93378
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 136.100048391
• Heavy Atom Count: 10
• Complexity: 167

Purity/Quality:

99%, ^*data from raw suppliers

4-Cyanoquinuclidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CCC1(CC2)C#N
• Uses: 4-Cyanoquinuclidine is an intermediate used to prepare pleuromutilin (P610500) derivatives as antimicrobials.

Technology Process of 1-Azabicyclo[2.2.2]octane-4-carbonitrile

There total 15 articles about 1-Azabicyclo[2.2.2]octane-4-carbonitrile 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: 76.0%

1-(2-chloroethyl)piperidine-4-carbonitrile hydrochloride (111041-03-3) → 4-cyanoquinuclidine (26458-78-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 - 0 ℃; other reagents: phenyl potassium, sodium hydride;

DOI:10.1135/cccc19951536

Reference yield: 66.3%

→ 4-cyanoquinuclidine (26458-78-6)

Guidance literature:

Reference yield: 65.3%

→ 4-cyanoquinuclidine (26458-78-6) + lithium diisopropyl amide (4111-54-0)

Guidance literature:

upstream raw materials:

4-cyano-1-methyl-quinuclidinium; chloride

1-(2-chloroethyl)piperidine-4-carbonitrile hydrochloride

tris-(2-chloro-ethyl)-amine

acetonitrile

Downstream raw materials:

4-hydroxymethylquinuclidine

(4-aminophenyl)(1-aza-bicyclo[2,2,2]oct-4-yl)-methanone

1-azabicyclo[2.2.2]octane-4-carboxylic acid hydrochloride

4-ethynylquinuclidine

Refernces

• 1、 -. "Anti-Hiv Quinuclidine Compounds". Page/Page column 2-3; 5. . Retrieved 2008/12/07.
• 2、 Kanai, Takeo,Nomoto, Seiichiro,Komatsu, Yuhki,Ogura,Katsuyuki. "NEW AND EFFICIENT SYNTHESES OF 4-CARBAMOYLQUINUCLIDINE". . p. 2137 - 2142. Retrieved 2007/10/02.