1,6-Naphthyridine

Base Information

• Chemical Name: 1,6-Naphthyridine
• CAS No.: 253-72-5
• Molecular Formula: C8H6N2
• Molecular Weight: 130.15
• Hs Code.: 29339900
• European Community (EC) Number: 640-546-2
• UNII: S1T14P7OW7
• DSSTox Substance ID: DTXSID8059762
• Nikkaji Number: J100.390I
• Wikidata: Q27116907
• Metabolomics Workbench ID: 55441
• Mol file: 253-72-5.mol

Synonyms:1,6-Naphthyridine;253-72-5;[1,6]Naphthyridine;1,6-Diazanaphthalene;1,6-Pyridopyridine;Pyrido[4,3-b]pyridine;MFCD00059750;UNII-S1T14P7OW7;S1T14P7OW7;CHEBI:36627;1,6Naphthyridine;[1,6]-naphthyridine;SCHEMBL139749;DTXSID8059762;2,8-dihydro-1,6-naphthyridine;[1,6]Naphthyridine, AldrichCPR;1,6-naphthyridine, 2,8-dihydro-;BCP21492;SC3611;AKOS006229985;AB02371;AC-7911;CS-W011109;SY022984;TS-01705;A5122;AM20051000;BB 0261505;FT-0602655;N0462;EN300-104688;Q27116907;Z1201618481

Chemical Property of 1,6-Naphthyridine

Chemical Property:

• Vapor Pressure: 0.0136mmHg at 25°C
• Melting Point: 231-233°C
• Refractive Index: 1.653
• Boiling Point: 267.3 °C at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 118.3 °C
• PSA: 25.78000
• Density: 1.183 g/cm³
• LogP: 1.62980
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 130.053098200
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

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

1,6-Naphthyridine >97.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=CN=C2)N=C1

Technology Process of 1,6-Naphthyridine

There total 19 articles about 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: 71.0%

(E)-3-(dimethylamino)acrolein (927-63-9,692-32-0) + 4-N-pivaloylaminopyridine (70298-89-4) → 1,6-naphthyridine (253-72-5)

Guidance literature:

4-N-pivaloylaminopyridine; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 3h;

(E)-3-(dimethylamino)acrolein; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h;

With hydrogenchloride; for 3h; Heating;

DOI:10.1055/s-2006-926229

Reference yield: 71.0%

4-N-pivaloylaminopyridine (70298-89-4) + 3-dimethylaminoacrolein (927-63-9) → 1,6-naphthyridine (253-72-5)

Guidance literature:

4-N-pivaloylaminopyridine; With n-butyllithium; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h; Inert atmosphere;

3-dimethylaminoacrolein; In tetrahydrofuran; hexane; at -70 - 0 ℃; for 3h; Inert atmosphere;

DOI:10.1002/jhet.4111

Reference yield: 69.0%

4-aminopyridine (504-24-5) + glycerol (56-81-5,25618-55-7,64333-26-2,8013-25-0) → 1,6-naphthyridine (253-72-5)

Guidance literature:

With sulfuric acid; sodium 3-nitrobenzenesulfonate sulfuric acid; at 130 ℃;

upstream raw materials:

1,2,3,4-tetrahydro-1,6-naphthyridine

5-hydrazinyl-1,6-naphthyridine

6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl acetate

2-(trimethylsilylethynyl)pyridine-3-carboxaldehyde

Downstream raw materials:

5-benzyl-5H-[1,6]naphthyridine-6-carboxylic acid ethyl ester

5-(4-benzyloxy-benzyl)-5H-[1,6]naphthyridine-6-carboxylic acid ethyl ester

5,6,7,8-tetrahydro-6-cinnamyl-1,6-naphthyridine

5,6,7,8-tetrahydro-6-n-amyl-1,6-naphthyridine

Refernces

• 1、 Giam, C. S.,Ambrozich, Deborah. "A New Approach to the Preparation of 1,6- and 1,7-Naphthyridines". . p. 265 - 266. Retrieved 1984.
• 2、 Ucar, Sefa,Dastan, Arif. "One-pot homo- and cross-coupling of diazanaphthalenes via C-H substitution: Synthesis of Bis- and Tris-diazanaphthalenes". . p. 4013 - 4022. Retrieved 2020/09/21.
• 3、 Held, Ingmar,Xu, Shangjie,Zipse, Hendrik. "Modular design of pyridine-based acyl-transfer catalysts". . p. 1185 - 1196. Retrieved 2008/02/02.