6-BROMO-5-NITRO-ISOQUINOLINE

Base Information

• Chemical Name: 6-BROMO-5-NITRO-ISOQUINOLINE
• CAS No.: 850197-72-7
• Molecular Formula: C₉H₅BrN₂O₂
• Molecular Weight: 253.055
• Hs Code.: 2933499090
• Mol file: 850197-72-7.mol

Synonyms:6-Bromo-5-nitroisoquinoline;

Chemical Property of 6-BROMO-5-NITRO-ISOQUINOLINE

Chemical Property:

• Vapor Pressure: 6.12E-05mmHg at 25°C
• Refractive Index: 1.707
• Boiling Point: 356.1 °C at 760 mmHg
• PKA: 2.99±0.21(Predicted)
• Flash Point: 169.2 °C
• PSA: 58.71000
• Density: 1.747 g/cm³
• LogP: 3.42870
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

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

6-Bromo-5-nitro-isoquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-BROMO-5-NITRO-ISOQUINOLINE

There total 1 articles about 6-BROMO-5-NITRO-ISOQUINOLINE 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%

6-bromo-isoquinoline (34784-05-9) → 5-nitro-6-bromoisoquinoline (850197-72-7)

Guidance literature:

6-bromo-isoquinoline; With sulfuric acid; Inert atmosphere;

With potassium nitrate; at 0 ℃; for 2h; Inert atmosphere;

With ammonium hydroxide; In water; pH=8 - 9; Cooling with ice; Inert atmosphere;

DOI:10.1016/j.tet.2009.09.110

Reference yield:

5-nitro-6-bromoisoquinoline (850197-72-7) → C34H24N2

Guidance literature:

Multi-step reaction with 3 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / water; tetrahydrofuran / 24 h / Reflux

2: triethyl phosphite / 1,2-dichloro-benzene / 24 h / 150 °C

3: sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine / toluene / 8 h / 80 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-tert-butyl phosphine; palladium diacetate; potassium carbonate; sodium t-butanolate; triethyl phosphite; In tetrahydrofuran; water; 1,2-dichloro-benzene; toluene; 1: |Suzuki Coupling;

Reference yield:

5-nitro-6-bromoisoquinoline (850197-72-7) + 2-pinacolboranyl-4,5-dimethoxybenzoic acid methyl ester (1201566-80-4) → 2-(5-nitroisoquinolin-6-yl)-4,5-dimethoxybenzoic acid methyl ester (1201566-89-3)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In acetonitrile; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.ejmech.2011.02.065

upstream raw materials:

6-bromo-isoquinoline

Downstream raw materials:

2-(5-nitroisoquinolin-6-yl)-4,5-dimethoxybenzoic acid methyl ester

Refernces

• 1、 Zhu, Gui-Dong,Gong, Jianchun,Claiborne, Akiyo,Woods, Keith W.,Gandhi, Viraj B.,Thomas, Sheela,Luo, Yan,Liu, Xuesong,Shi, Yan,Guan, Ran,Magnone, Shayna R.,Klinghofer, Vered,Johnson, Eric F.,Bouska, Jennifer,Shoemaker, Alexander,Oleksijew, Anatol,Stoll, Vincent S.,Jong, Ron De,Oltersdorf, Tilman,Li, Qun,Rosenberg, Saul H.,Giranda, Vincent L.. "Isoquinoline-pyridine-based protein kinase B/Akt antagonists: SAR and in vivo antitumor activity". . p. 3150 - 3155. Retrieved 2007/10/03.