6-bromoquinoline-5-carbonitrile

Base Information

• Chemical Name: 6-bromoquinoline-5-carbonitrile
• CAS No.: 1188365-70-9
• Molecular Formula: C₁₀H₅BrN₂
• Molecular Weight: 233.067
• Mol file: 1188365-70-9.mol

Synonyms:

Chemical Property of 6-bromoquinoline-5-carbonitrile

Chemical Property:

• Boiling Point: 390.6±27.0 °C(Predicted)
• PKA: 2.35±0.15(Predicted)
• Density: 1.66±0.1 g/cm3(Predicted)

Purity/Quality:

98.5% ^*data from raw suppliers

6-BROMOQUINOLINE-5-CARBONITRILE 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-bromoquinoline-5-carbonitrile

There total 2 articles about 6-bromoquinoline-5-carbonitrile 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: 98.0%

6-Aminoquinoline-5-carbonitrile (54398-51-5) → 6-bromoquinoline-5-carbonitrile (1188365-70-9)

Guidance literature:

6-Aminoquinoline-5-carbonitrile; With copper(I) bromide; In acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

With tert.-butylnitrite; In acetonitrile; at 20 - 60 ℃; for 18h;

With hydrogenchloride; In water; acetonitrile; for 4h;

Reference yield:

6-nitroquinoline (613-50-3) → 6-bromoquinoline-5-carbonitrile (1188365-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide / N,N-dimethyl-formamide / 22 h / 20 °C

1.2: 3 h / Reflux

2.1: copper(I) bromide / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

2.2: 18 h / 20 - 60 °C

2.3: 4 h

With potassium hydroxide; copper(I) bromide; In N,N-dimethyl-formamide; acetonitrile;

Reference yield:

6-bromoquinoline-5-carbonitrile (1188365-70-9) → (R)-3-((5-fluoro-2-nitrophenyl)amino)-10-methyl-9,10,11,12-tetrahydro-8H-[1,4]diazepino[5',6':4,5]thieno[3,2-f]quinolin-8-one

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium methylate / methanol / 4 h / 90 °C

2.1: tert.-butylnitrite / acetonitrile / 1 h / 0 °C

2.2: 3 h / 0 - 20 °C

3.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 16 h / 110 °C

4.1: dichloromethane / 2 h / 0 - 25 °C

5.1: sodium methylate / methanol / 12 h / 90 °C

6.1: dmap; triethylamine / dichloromethane / 0.17 h / 20 °C

6.2: 4 h / 20 °C

7.1: m-chloroperoxybenzoic acid / dichloromethane / 3 h / 0 - 30 °C

8.1: oxalyl dichloride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

9.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

10.1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 1 h / 130 °C / Inert atmosphere; Microwave irradiation

With dmap; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tert.-butylnitrite; m-chloroperoxybenzoic acid; oxalyl dichloride; sodium methylate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

6-Aminoquinoline-5-carbonitrile

6-nitroquinoline

Refernces

• 1、 -. "MK2 INHIBITORS AND USES THEREOF". Paragraph 0229; 0231. . Retrieved 2016/04/09.
• 2、 -. "INHIBITORS OF VIRAL REPLICATION, THEIR PROCESS OF PREPARATION AND THEIR THERAPEUTICAL USES". Page/Page column 114-115. . Retrieved 2012/11/06.