Cyclopenta[b]pyridine

Base Information

• Chemical Name: Cyclopenta[b]pyridine
• CAS No.: 533-37-9
• Molecular Formula: C8H9N
• Molecular Weight: 119.166
• Hs Code.: 29333990
• European Community (EC) Number: 208-564-1
• UNII: 18Z19A103W
• DSSTox Substance ID: DTXSID70201446
• Nikkaji Number: J147.225I
• Wikidata: Q27252043
• Mol file: 533-37-9.mol

Synonyms:6,7-Dihydro-5H-cyclopenta(b)pyridine;CPP;5H-Cyclopenta[b]pyridine,6,7-dihydro-;

Chemical Property of Cyclopenta[b]pyridine

Chemical Property:

• Appearance/Colour: clear colorless to brownish liquid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 117 °C
• Refractive Index: n20/D 1.544(lit.)
• Boiling Point: 212.2 °C at 760 mmHg
• PKA: 6.19±0.20(Predicted)
• Flash Point: 67.2 °C
• PSA: 12.89000
• Density: 1.066 g/cm³
• LogP: 1.57030
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 119.073499291
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

2,?3-?Cyclopentenopyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1CC2=C(C1)N=CC=C2
• Uses: 2,?3-?Cyclopentenopyridine is used as reactant/reagent for ruthenium-mediated dual catalytic reactions of isoquinoline via C-H activation and dearomatization for isoquinolone.

Technology Process of Cyclopenta[b]pyridine

There total 29 articles about Cyclopenta[b]pyridine 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: 99.0%

1H-cyclopenta[b]pyridine (270-88-2) → 2,3-cyclopentenopyridine (533-37-9)

Guidance literature:

With formic acid; C₂₉H₃₂ClIrNO; sodium formate; In water; for 16h; pH=4.5;

DOI:10.1002/chem.201500016

Reference yield: 77.0%

cyclopentanone (120-92-3) + Propargylamine (2450-71-7) → 2,3-cyclopentenopyridine (533-37-9)

Guidance literature:

sodium tetrachloroaurate dihydrate; In ethanol; at 78 ℃; for 7h;

DOI:10.1021/jo0347260

Reference yield: 74.0%

propynylamine + cyclopentanone (120-92-3) → 2,3-cyclopentenopyridine (533-37-9)

Guidance literature:

at 70 ℃; for 5h; Reagent/catalyst; Temperature; Autoclave; Ionic liquid; Microwave irradiation;

upstream raw materials:

2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine

3-(2-oxocyclopentyl)propanal

allyl alcohol

cyclopentanone

Downstream raw materials:

6,7-dihydro-5H-cyclopenta[b]pyridine 1-oxide

(+/-)-trans-octahydro[1]pyrindine

C₂₅H₂₉ClN₄O₃

(1aS,6aR) 2,6b-dihydro-1aH-oxireno[3,4]cyclopenta[1,2-b]pyridine

Refernces

• 1、 Sotnik, Svitlana O.,Subota, Andrii I.,Kliuchynskyi, Anton Y.,Yehorov, Dmytro V.,Lytvynenko, Anton S.,Rozhenko, Alexander B.,Kolotilov, Sergey V.,Ryabukhin, Sergey V.,Volochnyuk, Dmitriy M.. "Cu-Catalyzed Pyridine Synthesis via Oxidative Annulation of Cyclic Ketones with Propargylamine". . p. 7315 - 7325. Retrieved 2021/05/29.
• 2、 Han, Mingyang,Lin, Qing,Liu, Qingbin,Liu, Song,Ma, Ning,Solan, Gregory A.,Sun, Wen-Hua,Wang, Zheng,Yan, Xiuli. "Direct synthesis of ring-fused quinolines and pyridines catalyzed byNNHY-ligated manganese complexes (Y = NR2or SR)". . p. 8026 - 8036. Retrieved 2021/12/27.