5-AMINO-3-CYANOINDOLE

Base Information

• Chemical Name: 5-AMINO-3-CYANOINDOLE
• CAS No.: 159768-57-7
• Molecular Formula: C₉H₇N₃
• Molecular Weight: 157.175
• Hs Code.: 2933990090
• Mol file: 159768-57-7.mol

Synonyms:5-Amino-1H-indole-3-carbonitrile;5-Amino-3-cyanoindole; 5-Aminoindole-3-carbonitrile

Chemical Property of 5-AMINO-3-CYANOINDOLE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.721
• Boiling Point: 447.5°Cat760mmHg
• PKA: 15.00±0.30(Predicted)
• Flash Point: 224.5°C
• PSA: 65.60000
• Density: 1.33g/cm³
• LogP: 2.20298
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature

Purity/Quality:

99% ^*data from raw suppliers

3-Cyano-5-nitroindole 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-AMINO-3-CYANOINDOLE

There total 3 articles about 5-AMINO-3-CYANOINDOLE 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: 91.4%

5-nitro-1H-indole-3-carbonitrile (7147-14-0) → 5-amino-1H-indole-3-carbonitrile (159768-57-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; at 25 ℃; for 4h; under 2068.65 Torr;

DOI:10.1016/j.bioorg.2021.105417

Reference yield:

5-nitro-1H-indole-3-carbaldehyde (6625-96-3) → 5-amino-1H-indole-3-carbonitrile (159768-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride; sodium formate / 2 h / 110 °C / Acidic conditions

2: hydrogen; 5%-palladium/activated carbon / ethanol / 4 h / 25 °C / 2068.65 Torr

With 5%-palladium/activated carbon; hydroxylamine hydrochloride; hydrogen; sodium formate; In ethanol;

DOI:10.1016/j.bioorg.2021.105181

Reference yield:

5-nitroindole (6146-52-7) → 5-amino-1H-indole-3-carbonitrile (159768-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trichlorophosphate / 0.5 h / 0 °C

1.2: 20 °C

2.1: hydroxylamine hydrochloride; sodium formate / 2 h / 110 °C / Acidic conditions

3.1: hydrogen; 5%-palladium/activated carbon / ethanol / 4 h / 25 °C / 2068.65 Torr

With 5%-palladium/activated carbon; hydroxylamine hydrochloride; hydrogen; sodium formate; trichlorophosphate; In ethanol; 1.1: |Vilsmeier-Haack Formylation / 1.2: |Vilsmeier-Haack Formylation;

DOI:10.1016/j.bioorg.2021.105181

upstream raw materials:

5-nitro-1H-indole-3-carbonitrile

5-nitro-1H-indole-3-carbaldehyde

5-nitroindole

Downstream raw materials:

5-nitro-1H-indole-3-carbonitrile

Refernces

• 1、 Zhang, Ting-jian,Tu, Shun,Zhang, Xu,Wang, Qiu-yin,Hu, Sen-sen,Zhang, Yi,Zhang, Zhen-hao,Wang, Zhao-ran,Meng, Fan-hao. "Amide-based xanthine oxidase inhibitors bearing an N-(1-alkyl-3-cyano-1H-indol-5-yl) moiety: Design, synthesis and structure-activity relationship investigation". supporting information. . Retrieved 2021/10/25.