5-Bromo-3-cyanoindole

Base Information

• Chemical Name: 5-Bromo-3-cyanoindole
• CAS No.: 90271-86-6
• Molecular Formula: C9H5BrN2
• Molecular Weight: 221.056
• Hs Code.: 2933990090
• European Community (EC) Number: 877-129-1
• DSSTox Substance ID: DTXSID60394396
• Wikidata: Q72453837
• Mol file: 90271-86-6.mol

Synonyms:5-Bromo-3-cyanoindole;90271-86-6;5-bromo-1H-indole-3-carbonitrile;5-bromoindole-3-carbonitrile;1H-Indole-3-carbonitrile, 5-bromo-;MFCD04127133;5-Bromo-3-cyano-1H-indole;SCHEMBL186728;DTXSID60394396;ZPUQCVKBNRGSAP-UHFFFAOYSA-N;AMY13361;STK114336;AKOS000450265;CS-W022319;FS-2949;AC-24843;SY057627;FT-0646691;A852305;J-517018;5-Bromoindole-3-carbonitrile

Chemical Property of 5-Bromo-3-cyanoindole

Chemical Property:

• Vapor Pressure: 8.44E-07mmHg at 25°C
• Refractive Index: 1.726
• Boiling Point: 405.9 °C at 760 mmHg
• PKA: 13?+-.0.30(Predicted)
• Flash Point: 199.3 °C
• PSA: 39.58000
• Density: 1.74 g/cm³
• LogP: 2.80208
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 219.96361
• Heavy Atom Count: 12
• Complexity: 220

Purity/Quality:

99.0%, High purity. ^*data from raw suppliers

5-Bromo-3-cyanoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=CN2)C#N

Technology Process of 5-Bromo-3-cyanoindole

There total 15 articles about 5-Bromo-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: 97.0%

5-bromo-1H-indole (10075-50-0) + chlorosulfonamide isocyanate → 5-bromo-1H-indole-3-carbonitrile (90271-86-6)

Guidance literature:

In N,N-dimethyl-formamide; at -50 - 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/acs.jafc.9b04093

Reference yield: 91.0%

5-bromo-1H-indole (10075-50-0) + isocyanate de chlorosulfonyle (1189-71-5) → 5-bromo-1H-indole-3-carbonitrile (90271-86-6)

Guidance literature:

5-bromo-1H-indole; isocyanate de chlorosulfonyle; In acetonitrile; at 0 ℃; for 2h;

With N,N-dimethyl-formamide; In acetonitrile; at 0 ℃; for 2h;

DOI:10.3390/md16080274

Reference yield: 82.0%

4-isoxazoleboronic acid pinacol ester (928664-98-6) → 5-bromo-1H-indole-3-carbonitrile (90271-86-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; In water; dimethyl sulfoxide; at 130 ℃; for 16h; Inert atmosphere; Sealed tube;

DOI:10.1039/d0cc05439a

upstream raw materials:

5-bromo-1H-indole-3-carboxaldehyde

3-cyano-1H-indole

5-bromo-1H-indole

N,N,N,N,-tetramethylethylenediamine

Downstream raw materials:

4-(5-bromo-3-cyanoindol-1yl)benzoic acid ethyl ester

5-bromo-1-methyl-1H-indole-3-carbonitrile

5-chloro-1H-indole-3-carbonitrile

Refernces

• 1、 Liao, Ancai,Li, Lin,Wang, Tienan,Lu, Aidang,Wang, Ziwen,Wang, Qingmin. "Discovery of Phytoalexin Camalexin and Its Derivatives as Novel Antiviral and Antiphytopathogenic-Fungus Agents". . p. 2554 - 2563. Retrieved 2022/03/02.
• 2、 Carbone, Daniela,Parrino, Barbara,Cascioferro, Stella,Pecoraro, Camilla,Giovannetti, Elisa,Di Sarno, Veronica,Musella, Simona,Auriemma, Giulia,Cirrincione, Girolamo,Diana, Patrizia. "1,2,4-Oxadiazole Topsentin Analogs with Antiproliferative Activity against Pancreatic Cancer Cells, Targeting GSK3β Kinase". . p. 537 - 554. Retrieved 2020/12/01.