1,2,3,6-Tetrahydropyridine

Base Information

• Chemical Name: 1,2,3,6-Tetrahydropyridine
• CAS No.: 694-05-3
• Molecular Formula: C5H9N
• Molecular Weight: 83.1332
• Hs Code.: 29333999
• European Community (EC) Number: 211-766-2
• NSC Number: 65443
• UN Number: 2410
• UNII: 26RLS9D255
• DSSTox Substance ID: DTXSID0075289
• Nikkaji Number: J66.610F
• Wikidata: Q27120829
• Metabolomics Workbench ID: 56817
• Mol file: 694-05-3.mol

Synonyms:1,2,3,6-Tetrahydropyridine;694-05-3;Pyridine, 1,2,3,6-tetrahydro-;3-piperideine;1,2,5,6-TETRAHYDROPYRIDINE;delta3-Piperidine;Delta(3)-piperideine;.DELTA.3-Piperidine;UNII-26RLS9D255;26RLS9D255;EINECS 211-766-2;NSC 65443;NSC-65443;UN2410;1,2,5,6-tetrahydro-;1,3,6-Tetrahydropyridine;1,5,6-Tetrahydropyridine;.delta.(sup 3)-Piperidine;1,2,5,6-tetrahyropyridine;1,2,3,6 tetrahydropyridine;1.2.3.6-Tetrahydropyridine;1,2,3,6-tetrahydro-pyridine;DTXSID0075289;CHEBI:47860;Tetrahydropyridine, 1,2,3,6-;AMY5955;1,2,3,6-Tetrahydropyridine [UN2410] [Flammable liquid];Pyridine, 1,2,5,6-tetrahydro-;BCP09736;NSC65443;AB7774;BBL104208;MFCD00005949;NA2410;STL558068;1,2,3,6-Tetrahydropyridine, 97%;AKOS005146194;UN 2410;A9177;FT-0659735;EN300-60665;J-670024;J-801023;Q-101878;Q27120829;F8889-0743

Chemical Property of 1,2,3,6-Tetrahydropyridine

Chemical Property:

• Appearance/Colour: Clear colorless to pale yellow liquid
• Vapor Pressure: 23.3mmHg at 25°C
• Melting Point: -48 °C(lit.)
• Refractive Index: n20/D 1.48(lit.)
• Boiling Point: 110.9 °C at 760 mmHg
• PKA: 10.22±0.10(Predicted)
• Flash Point: 16.1 °C
• PSA: 12.03000
• Density: 0.867 g/cm³
• LogP: 0.86470
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 83.073499291
• Heavy Atom Count: 6
• Complexity: 57
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.3% ^*data from raw suppliers

1,2,3,6-Tetrahydropyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1CNCC=C1
• Uses: Used to form ene-endo-spirocyclic ammonium ylids for [2,3]-sigmatropic rearrangement to pyrroloazepinones and oxazepinones.

Technology Process of 1,2,3,6-Tetrahydropyridine

There total 13 articles about 1,2,3,6-Tetrahydropyridine 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: 60.0%

N-benzylpyridinium bromide (2589-31-3) → 1,2,3,6-tetrahydropyridine (694-05-3) + N-Benzylpiperidine (2905-56-8)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; triethylammonium formate; potassium iodide; In dichloromethane; at 40 ℃; for 24h; Sealed tube;

DOI:10.1002/adsc.201201034

Reference yield: 30.0%

N-chloro-1,2,5,6-tetrahydropyridine (92885-06-8) → pyridine (110-86-1) + 1,2,3,6-tetrahydropyridine (694-05-3) + 2,3-dihydro<2,3-c>pyridine (67684-01-9)

Guidance literature:

With potassium tert-butylate; at 60 ℃; under 0.001 Torr; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(01)86146-9

Reference yield:

pyridine (110-86-1) + benzyl bromide (100-39-0) → 1,2,3,6-tetrahydropyridine (694-05-3) + N-Benzylpiperidine (2905-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 0.25 h / 85 °C / Reflux

2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium iodide; triethylammonium formate / dichloromethane / 24 h / 40 °C / Sealed tube

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; triethylammonium formate; potassium iodide; In dichloromethane; acetonitrile;

DOI:10.1002/adsc.201201034

upstream raw materials:

pyridine

1-cyano-1,2,3,6-tetrahydropyridine

pyridin-3-ylamine

N-chloro-1,2,5,6-tetrahydropyridine

Downstream raw materials:

1-benzoylpiperidine-cis-3,4-diol acetonide

1-benzoylpiperidine-trans-3,4-diol acetonide

ethyl 4-bromo-3-hydroxypiperidine-1-carboxylate

1-benzoylpiperidine-cis-3,4-diol

Refernces

• 1、 Wu, Jianjun,Tang, Weijun,Pettman, Alan,Xiao, Jianliang. "Efficient and chemoselective reduction of pyridines to tetrahydropyridines and piperidines via rhodium-catalyzed transfer hydrogenation". supporting information. p. 35 - 40. Retrieved 2013/03/13.
• 2、 Grishina,Borisenko,Nosan',Veselov,Ashkinadze,Karamov,Kornilaeva,Zefirov. "trans-Dihydroxypiperidines: Synthesis, Stereochemistry, and Anti-HIV Activity". . p. 195 - 199. Retrieved 2007/10/03.