Quinuclidine

Base Information

• Chemical Name: Quinuclidine
• CAS No.: 100-76-5
• Molecular Formula: C7H13N
• Molecular Weight: 111.187
• European Community (EC) Number: 202-887-1
• UNII: XFX99FC5VI
• DSSTox Substance ID: DTXSID2057607
• Nikkaji Number: J108.948J
• Wikipedia: Quinuclidine
• Wikidata: Q1864086
• Metabolomics Workbench ID: 55856
• ChEMBL ID: CHEMBL1209648
• Mol file: 100-76-5.mol

Synonyms:Quinuclidine;Quinuclidines

Chemical Property of Quinuclidine

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Vapor Pressure: 1.5 mm Hg ( 20 °C)
• Melting Point: 157-160 °C(lit.)
• Refractive Index: 1.512
• Boiling Point: 149.5 °C at 760 mmHg
• PKA: 10.87±0.33(Predicted)
• Flash Point: 36.5 °C
• PSA: 3.24000
• Density: 0.97 g/cm³
• LogP: 1.04000
• Sensitive.: Air Sensitive
• Solubility.: H2O: very slightly soluble
• Water Solubility.: Soluble in alcohol, diethyl ether, water and organic solvents.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.104799419
• Heavy Atom Count: 8
• Complexity: 71.4

Purity/Quality:

99% ^*data from raw suppliers

Quinuclidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 24/25-38-41
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CN2CCC1CC2
• Uses: Quinuclidine acts as a catalyst, a chemical building block and is used in organic synthesis. It is employed to prepare quinine and alkaloids. It finds application as a ligand, which is useful in the studies of OsO4-catalyzed dihydroxylation of olefins. It plays an important role in the formation of onium salts used testing of PAC-antagonist activity.

Technology Process of Quinuclidine

There total 65 articles about Quinuclidine 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: 84.0%

3-quinuclidinone hydrochloride (1193-65-3) → Quinuclidine (100-76-5)

Guidance literature:

With potassium hydroxide; hydrazine; In diethylene glycol; at 160 ℃; for 3h;

DOI:10.1021/jacs.7b03539

Reference yield: 70.0%

4-(2-Hydroxyethyl)piperidine (622-26-4) → Quinuclidine (100-76-5)

Guidance literature:

With silica gel; In water; at 380 ℃; for 10h; Reagent/catalyst; Gas phase;

Reference yield: 65.0%

quinuclidine hydrochloride (39896-06-5) → Quinuclidine (100-76-5)

Guidance literature:

With water; sodium hydroxide;

DOI:10.1039/b917610a

upstream raw materials:

4-(2-Hydroxyethyl)piperidine

4-ethylpiperidine

tetrachloromethane

3-Quinuclidinone

Downstream raw materials:

4-Ethylpyridine

N-[2-(p-nitrophenyl)ethyl]quinuclidinium

N-methylquinuclidinium chloride

quinuclidinyl radical

Refernces

• 1、 Swain,Hershey. "-". . p. 1901. Retrieved 1972.
• 2、 Baidya, Mahiuddin,Kobayashi, Shinjiro,Brotzel, Frank,Schmidhammer, Uli,Riedle, Eberhard,Mayr, Herbert. "DABCO and DMAP - Why are they different in organocatalysis?". . p. 6176 - 6179. Retrieved 2007.
• 3、 Herrmann, Wolfgang A.,Kuchler Jose G.,Weichselbaumer, Georg,Herdtweck, Eberhardt,Kiprof, Paul. "Mehrfachbindungen zwischen Hauptgruppenelementen und Uebergangsmetallen LXIV. Methyl(trioxo)rhenium: Basenaddukte und Basenreaktionen. Kristallstruktur von -perrhenat". . p. 351 - 370. Retrieved 1989.
• 4、 Leonard,Elkin. "-". . p. 4635. Retrieved 1962.
• 5、 Weigel, William K.,Dang, Hoang T.,Yang, Hai-Bin,Martin, David B. C.. "Synthesis of amino-diamondoid pharmacophores: Via photocatalytic C-H aminoalkylation". supporting information. p. 9699 - 9702. Retrieved 2020/09/03.