5-Chloro-1,6-naphthyridine

Base Information

• Chemical Name: 5-Chloro-1,6-naphthyridine
• CAS No.: 23616-32-2
• Molecular Formula: C8H5ClN2
• Molecular Weight: 164.594
• Hs Code.: 2933990090
• European Community (EC) Number: 672-893-0
• DSSTox Substance ID: DTXSID70480355
• Wikidata: Q82315067
• Mol file: 23616-32-2.mol

Synonyms:5-Chloro-1,6-naphthyridine;23616-32-2;5-Chloro[1,6]naphthyridine;5-chloro-[1,6]naphthyridine;1,6-Naphthyridine, 5-chloro-;MFCD01646205;SCHEMBL523735;DTXSID70480355;WXAOVVFKLPOPAM-UHFFFAOYSA-N;BCP08210;YAA61632;AKOS006276186;PB32262;DS-11174;SY017340;AM20050980;CS-0012633;FT-0645426;EN300-295335;A816805;J-517230;5-chloro-1,6-naphthyridine

Chemical Property of 5-Chloro-1,6-naphthyridine

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 106-107℃
• Refractive Index: 1.663
• Boiling Point: 307.889 °C at 760 mmHg
• PKA: 2.04±0.30(Predicted)
• Flash Point: 168.825 °C
• PSA: 25.78000
• Density: 1.35 g/cm³
• LogP: 2.28320
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 164.0141259
• Heavy Atom Count: 11
• Complexity: 140

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-chloro-1,6-naphthyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN=C2Cl)N=C1

Technology Process of 5-Chloro-1,6-naphthyridine

There total 8 articles about 5-Chloro-1,6-naphthyridine 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: 95.0%

1,6-naphthyridine-5(6H)-one (23616-31-1) → 5-chloro-[1,6]naphthyridine (23616-32-2)

Guidance literature:

1,6-naphthyridine-5(6H)-one; With trichlorophosphate; at 100 ℃; for 14h;

With sodium carbonate; In dichloromethane; water; at 0 ℃; pH=6 - 7; Product distribution / selectivity;

Reference yield:

2-trimethylsilylethynyl-3-pyridinecarbonitrile (97308-49-1) → 5-chloro-[1,6]naphthyridine (23616-32-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 14 h / 80 °C / Inert atmosphere

2.1: sodium carbonate; dihydrogen peroxide / water; acetone / 14 h / 20 °C

3.1: toluene-4-sulfonic acid / toluene / 14 h / Reflux

4.1: trichlorophosphate / 14 h / 100 °C

4.2: 0 °C / pH 6 - 7

With dihydrogen peroxide; sodium carbonate; trichlorophosphate; toluene-4-sulfonic acid; In water; acetone; toluene;

Reference yield:

2-(β,β-dimethoxyethyl)-3-pyridinecarbonitrile (97308-52-6) → 5-chloro-[1,6]naphthyridine (23616-32-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium carbonate; dihydrogen peroxide / water; acetone / 14 h / 20 °C

2.1: toluene-4-sulfonic acid / toluene / 14 h / Reflux

3.1: trichlorophosphate / 14 h / 100 °C

3.2: 0 °C / pH 6 - 7

With dihydrogen peroxide; sodium carbonate; trichlorophosphate; toluene-4-sulfonic acid; In water; acetone; toluene;

upstream raw materials:

1,6-naphthyridine-5(6H)-one

2-(2-hydroxy-ethyl)-nicotinic acid amide

7,8-dihydro-5H-pyrano[4,3-b]pyridin-5-one

2-trimethylsilylethynyl-3-pyridinecarbonitrile

Downstream raw materials:

trans-2-(2-(5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyrazin-2-yl)cyclopropyl)-3-methylimidazo[2,1-f][1,6]naphthyridine

3-methyl-2-((1S,2S)-2-(quinolin-2-yl)cyclopropyl)-3H-imidazo[4,5-f]quinoline

C₂₁H₁₉N₇

2,5-dichloro-1,6-naphthyridine

Refernces

• 1、 -. "INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS". Page/Page column 40; 42. . Retrieved 2022/02/05.
• 2、 -. "Octahydropyrrolo[3,4-c]pyrrole derivative and application method and application thereof". Paragraph 0171-0174. . Retrieved 2018/03/24.