2-bromo-1H-indole

Base Information

• Chemical Name: 2-bromo-1H-indole
• CAS No.: 139409-34-0
• Molecular Formula: C8H6 Br N
• Molecular Weight: 196.046
• DSSTox Substance ID: DTXSID10473105
• Nikkaji Number: J464.644D
• Wikidata: Q72457318
• Mol file: 139409-34-0.mol

Synonyms:2-bromo-1H-indole;139409-34-0;2-BROMOINDOLE;bromoindole;1H-Indole, 2-bromo-;bromo-indole;2-brom-1H-indole;SCHEMBL261138;DTXSID10473105;ZPRQXVPYQGBZON-UHFFFAOYSA-N;AMY38317;MFCD08234621;AKOS006284012;AC-26875;CS-0437618;FT-0601806;F84126;A854312;J-508179

Chemical Property of 2-bromo-1H-indole

Chemical Property:

• Vapor Pressure: 0.000738mmHg at 25°C
• Boiling Point: 316.9°C at 760 mmHg
• PKA: 15.34±0.30(Predicted)
• Flash Point: 145.5°C
• PSA: 15.79000
• Density: 1.660
• LogP: 2.93040
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 194.96836
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

98%Min ^*data from raw suppliers

2-Bromoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(N2)Br

Technology Process of 2-bromo-1H-indole

There total 17 articles about 2-bromo-1H-indole 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: 99.0%

N-[2-(2,2-dibromoethenyl)phenyl]methanesulfonamide (1259577-20-2) → 2-bromo-1H-indole (139409-34-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 100 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1039/c4ra00603h

Reference yield: 98.0%

C9H8(2)HBr2NO2S (1401452-08-1) → 2-bromo-1H-indole (139409-34-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 100 ℃; for 0.0833333h; Microwave irradiation;

DOI:10.1039/c4ra00603h

Reference yield: 96.0%

indole (120-72-9) → 2-bromo-1H-indole (139409-34-0)

Guidance literature:

With brominating reagent;

DOI:10.1039/a905024h

upstream raw materials:

indole

2-oxoindole

2-iodo-1H-indole

ethyl bromoacetate

Downstream raw materials:

2-phenyl-indole

2,4-diphenyl-9H-pyrimido[4,5-b]indole

2-bromo-1-phenyl-1H-indole

2-[4-(trifluoromethyl)phenyl]-1H-indole

Refernces

• 1、 Dobbs, Adrian P.,Jones, Keith,Veal, Ken T.. "Heteroaryl radicals in synthesis: Radical cyclisation reactions of 2-bromoindoles". . p. 2149 - 2160. Retrieved 1998.
• 2、 Chen, Chen,Ding, Jie,Liu, Liying,Huang, Yujie,Zhu, Bolin. "Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics". supporting information. p. 200 - 205. Retrieved 2021/10/29.
• 3、 Zeidan, Nicolas,Bognar, Sabine,Lee, Sophia,Lautens, Mark. "Palladium-catalyzed synthesis of 2-cyanoindoles from 2-gem-dihalovinylanilines". supporting information. p. 5058 - 5061. Retrieved 2017/11/07.