2-Iodo-6-nitro-4-(trifluoromethyl)aniline

Base Information

• Chemical Name: 2-Iodo-6-nitro-4-(trifluoromethyl)aniline
• CAS No.: 543740-74-5
• Molecular Formula: C7H4F3IN2O2
• Molecular Weight: 332.021
• Hs Code.: 2927000090
• DSSTox Substance ID: DTXSID50478492
• Wikidata: Q82311911
• Mol file: 543740-74-5.mol

Synonyms:2-Iodo-6-nitro-4-(trifluoromethyl)aniline;543740-74-5;4-Amino-3-iodo-5-nitrobenzotrifluoride 95+%;Benzenamine, 2-iodo-6-nitro-4-(trifluoromethyl)-;SCHEMBL18825074;DTXSID50478492;XVVSZOLVVQYKIK-UHFFFAOYSA-N;MFCD14560546;AKOS005073456;MD-0030;CS-0207979;FT-0681700;G11668;A870475

Chemical Property of 2-Iodo-6-nitro-4-(trifluoromethyl)aniline

Chemical Property:

• PSA: 71.84000
• LogP: 3.90480
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 331.92696
• Heavy Atom Count: 15
• Complexity: 256

Purity/Quality:

98%min ^*data from raw suppliers

2-Iodo-6-nitro-4-(trifluoromethyl)aniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1[N+](=O)[O-])N)I)C(F)(F)F
• Uses: 2-Iodo-6-nitro-4-(trifluoromethyl)aniline is used for preparation of indoles and related heterocycles by base0catalyzed cyclization.

Technology Process of 2-Iodo-6-nitro-4-(trifluoromethyl)aniline

There total 4 articles about 2-Iodo-6-nitro-4-(trifluoromethyl)aniline 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: 80.0%

4-trifluoromethyl-2-nitroaniline (400-98-6) → 2-iodo-6-nitro-4-(trifluoromethyl)aniline (543740-74-5)

Guidance literature:

With iodine; silver sulfate; In ethanol; at 20 ℃; for 36h;

DOI:10.1016/S0040-4020(03)00073-5 DOI:10.1002/chem.200305090

Reference yield:

4-(trifluromethyl)acetanilide (349-97-3) → 2-iodo-6-nitro-4-(trifluoromethyl)aniline (543740-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; nitric acid / 3 h / -10 - 20 °C

2: potassium hydroxide / ethanol; water / 1 h / Reflux

3: silver(II) sulfate; iodine / ethanol / 36 h / 20 °C / Darkness

With silver(II) sulfate; iodine; nitric acid; acetic acid; potassium hydroxide; In ethanol; water;

DOI:10.1039/c6ob00002a

Reference yield:

N-[2-nitro-4-(trifluoromethyl)phenyl]acetamide (396-12-3) → 2-iodo-6-nitro-4-(trifluoromethyl)aniline (543740-74-5)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium hydroxide / ethanol; water / 1 h / Reflux

2: silver(II) sulfate; iodine / ethanol / 36 h / 20 °C / Darkness

With silver(II) sulfate; iodine; potassium hydroxide; In ethanol; water;

DOI:10.1039/c6ob00002a

upstream raw materials:

4-trifluoromethyl-2-nitroaniline

4-(trifluromethyl)acetanilide

N-[2-nitro-4-(trifluoromethyl)phenyl]acetamide

4-trifluoromethylphenylamine

Refernces

• 1、 Koradin, Christopher,Dohle, Wolfgang,Rodriguez, Alain L.,Schmid, Bertram,Knochel, Paul. "Synthesis of polyfunctional indoles and related heterocycles mediated by cesium and potassium bases". . p. 1571 - 1587. Retrieved 2007/10/03.