1-Iodoethynyl-2-nitrobenzene

Base Information

• Chemical Name: 1-Iodoethynyl-2-nitrobenzene
• CAS No.: 113783-27-0
• Molecular Formula: C8H4INO2
• Molecular Weight: 273.03
• Mol file: 113783-27-0.mol

Synonyms:1-Iodoethynyl-2-nitrobenzene

Chemical Property of 1-Iodoethynyl-2-nitrobenzene

Chemical Property:

• Melting Point: 68-70 °C
• Boiling Point: 328.7±34.0 °C(Predicted)
• PSA: 45.82000
• Density: 1.97±0.1 g/cm3(Predicted)
• LogP: 2.86200

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Iodoethynyl-2-nitrobenzene

There total 3 articles about 1-Iodoethynyl-2-nitrobenzene 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: 86.0%

trimethyl((2-nitrophenyl)ethynyl)silane (75867-47-9) → 1-(2-iodoethynyl)-2-nitrobenzene (113783-27-0)

Guidance literature:

With N-iodo-succinimide; silver nitrate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; Inert atmosphere; Darkness;

DOI:10.1016/j.tet.2009.06.098

Reference yield: 63.0%

2-ethynyl-1-nitrobenzene (16433-96-8) → 1-(2-iodoethynyl)-2-nitrobenzene (113783-27-0)

Guidance literature:

With tert.-butylhydroperoxide; potassium iodide; In methanol; water; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2010.02.074

Reference yield:

2-nitrophenyl bromide (577-19-5) → 1-(2-iodoethynyl)-2-nitrobenzene (113783-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine

2: silver nitrate; N-iodo-succinimide / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; copper(l) iodide; silver nitrate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1039/d0cc06418a

upstream raw materials:

trimethyl((2-nitrophenyl)ethynyl)silane

2-ethynyl-1-nitrobenzene

2-nitrophenyl bromide

Downstream raw materials:

indole-2,3-dione

Refernces

• 1、 Maduli, Elvis J. M.,Edeson, Steven J.,Swanson, Stephen,Procopiou, Panayiotis A.,Harrity, Joseph P. A.. "2-Iodoisatogens: Versatile intermediates for the synthesis of nitrogen heterocycles". supporting information. p. 390 - 392. Retrieved 2015/01/30.
• 2、 S?derberg, Bj?rn C.G.,Gorugantula, Sobha P.,Howerton, Chet R.,Petersen, Jeffrey L.,Dantale, Shubhada W.. "A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes". experimental part. p. 7357 - 7363. Retrieved 2009/12/04.