6-Bromo-1,8-naphthyridin-2-ol

Base Information

• Chemical Name: 6-Bromo-1,8-naphthyridin-2-ol
• CAS No.: 72754-05-3
• Molecular Formula: C₈H₅BrN₂O
• Molecular Weight: 225.044
• Hs Code.: 2933990090
• European Community (EC) Number: 676-940-6
• DSSTox Substance ID: DTXSID00501168
• Wikidata: Q72448387
• Mol file: 72754-05-3.mol

Synonyms:6-Bromo-1,8-naphthyridin-2-ol;72754-05-3;6-bromo-1,8-naphthyridin-2(1H)-one;6-bromo-1H-1,8-naphthyridin-2-one;6-Bromo-[1,8]naphthyridin-2(1H)-one;6-BROMO-[1,8]NAPHTHYRIDIN-2-OL;6-Bromo-2-hydroxy-1,8-naphthyridine;MFCD11226504;1,8-NAPHTHYRIDIN-2(1H)-ONE, 6-BROMO-;SCHEMBL1252408;SCHEMBL12687394;DTXSID00501168;BCEWGGGNOQNYKK-UHFFFAOYSA-N;MFCD07781151;AKOS005255296;AKOS015834766;AB64025;CS-W013051;1,8-Naphthyridin-2(1H)-one,6-bromo-;AC-25288;DS-12875;SY009001;6-Bromo-1,8-naphthyridin-2-ol, AldrichCPR;FT-0681283;6-Bromo-1,8-naphthyridin-2(1H)-one, 98%;EN300-366581;O11533;A837608;J-518281;Z1269131400

Chemical Property of 6-Bromo-1,8-naphthyridin-2-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >300℃
• Refractive Index: 1.639
• Boiling Point: 415.941 °C at 760 mmHg
• PKA: 9.93±0.20(Predicted)
• Flash Point: 205.354 °C
• PSA: 46.01000
• Density: 1.711 g/cm³
• LogP: 2.09790
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 223.95853
• Heavy Atom Count: 12
• Complexity: 229

Purity/Quality:

≥99% ^*data from raw suppliers

6-Bromo-1,8-naphthyridin-2-ol Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-22-41-37/38
• Safety Statements: 22-26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=O)NC2=NC=C(C=C21)Br
• Uses: 6-Bromo-1,8-naphthyridin-2(1H)-one is used as an organic chemical synthesis intermediate.

Technology Process of 6-Bromo-1,8-naphthyridin-2-ol

There total 3 articles about 6-Bromo-1,8-naphthyridin-2-ol 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: 93.0%

(E)-tert-butyl 3-(2-amino-5-bromopyridin-3-yl)acrylate (894853-42-0) → 6-bromo-1,8-naphthyridin-2(1H)-one (72754-05-3)

Guidance literature:

With sodium methylate; In methanol; for 2h; Heating / reflux;

Reference yield:

5-bromo-2-pyridylamine (1072-97-5) → 6-bromo-1,8-naphthyridin-2(1H)-one (72754-05-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-iodo-succinimide; trifluoroacetic acid / N,N-dimethyl-formamide / 19 h / 50 °C

2: palladium diacetate; tris-(o-tolyl)phosphine; ethyl nitrite; propiononitrile / N,N-dimethyl-formamide; isopropyl alcohol / 16 h / 90 °C / Inert atmosphere

3: sodium methylate / methanol / 3 h / Inert atmosphere; Reflux

With N-iodo-succinimide; ethyl nitrite; sodium methylate; palladium diacetate; tris-(o-tolyl)phosphine; trifluoroacetic acid; propiononitrile; In methanol; N,N-dimethyl-formamide; isopropyl alcohol;

Reference yield:

2-amino-3-iodo-5-bromopyridine (381233-96-1) → 6-bromo-1,8-naphthyridin-2(1H)-one (72754-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; tris-(o-tolyl)phosphine; ethyl nitrite; propiononitrile / N,N-dimethyl-formamide; isopropyl alcohol / 16 h / 90 °C / Inert atmosphere

2: sodium methylate / methanol / 3 h / Inert atmosphere; Reflux

With ethyl nitrite; sodium methylate; palladium diacetate; tris-(o-tolyl)phosphine; propiononitrile; In methanol; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

(E)-tert-butyl 3-(2-amino-5-bromopyridin-3-yl)acrylate

5-bromo-2-pyridylamine

2-amino-3-iodo-5-bromopyridine

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