105202-02-6

Basic information

• Product Name: 3-Amino-4-iodobenzotrifluoride
• Synonyms: 3-AMINO-4-IODOBENZOTRIFLUORIDE;3-Amino-4-iodobenzotrifluoride 98%;3-Amino-4-iodobenzotrifluoride98%;2-Iodo-5-(trifluoromethyl)aniline, 6-Iodo-alpha,alpha,alpha-trifluoro-m-toluidine;3-AMino-4-iodobenzotrifluoride[2-Iodo-5-(trifluoroMethyl)aniline];2-Iodo-5-(trifluoromethyl)aniline【3-Amino-4-iodobenzotrifluoride】
• CAS NO: 105202-02-6
• Molecular Formula: C₇H₅F₃IN
• Molecular Weight: 287.02
• Product Categories: Fluorine series
• Mol File: 105202-02-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 102-114°C
• Flash Point: 104.098 °C
• Appearance: colorless to light yellow liquid
• Density: 1.949 g/cm³
• Vapor Pressure: 0.0226mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 3-Amino-4-iodobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-4-iodobenzotrifluoride(105202-02-6)
• EPA Substance Registry System: 3-Amino-4-iodobenzotrifluoride(105202-02-6)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 105202-02-6(Hazardous Substances Data)

Usage

Chemical Properties

colorless to light yellow liquid

Uses

3-Amino-4-iodobenzotrifluoride is a useful intermediate for the preparation of trifluoromethylindoles by coupling-annulation of alkynes with iodo(trifluoromethyl)anilines.

InChI:InChI=1/C9H5FO2/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-5H

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 400-98-6 4-trifluoromethyl-2-nitroaniline 
• 400-97-5 1-iodo-2-nitro-4-(trifluoromethyl)benzene 

Downstream Products

• 1333392-13-4 2-(hept-1-yn-1-yl)-5-(trifluoromethyl)aniline 
• 1333392-04-3 2-azido-1-(hept-1-yn-1-yl)-4-(trifluoromethyl)benzene 
• 199125-35-4 4-iodo-3-methylthiobenzotrifluoride 
• 105202-01-5 5-trifluoromethyl-N-phenylbenzo[d]thiazol-2-amine 
• 112146-11-9 2-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)acetonitrile 
• 684250-11-1 2-ethynyl-5-(trifluoromethyl)aniline 
• 92-30-8 2-(trifluoromethyl)-10H-phenothiazine 
• 914643-00-8 3-amino-2-chloro-4-ethylbenzotrifluoride 

Relevant articles and documents

Palladium-Catalyzed Incorporation of Two C1 Building Blocks: The Reaction of Atmospheric CO2 and Isocyanides with 2-Iodoanilines Leading to the Synthesis of Quinazoline-2,4(1H,3H)-diones

A Pd-catalyzed insertion and cycloaddition of CO2 and isocyanide into 2-iodoanilines under atmospheric pressure has been developed and affords quinazoline-2,4(1H,3H)-diones through the formation of new C-C, C-O, and C-N bonds under mild conditions. This reaction provides a new and practical method not only for the construction of quinazoline-2,4(1H,3H)-diones but also for the efficient utilization of carbon dioxide.

The Trifluoromethyl Group as a Bioisosteric Replacement of the Aliphatic Nitro Group in CB1 Receptor Positive Allosteric Modulators

The first generation of CB1 positive allosteric modulators (e.g., ZCZ011) featured a 3-nitroalkyl-2-phenyl-indole structure. Although a small number of drugs include the nitro group, it is generally not regarded as being "drug-like", and this is particularly true for aliphatic nitro groups. There are very few case studies where an appropriate bioisostere replaced a nitro group that had a direct role in binding. This may be indicative of the difficulty of replicating its binding interactions. Herein, we report the design and synthesis of ligands targeting the allosteric binding site on the CB1 cannabinoid receptor, in which a CF3 group successfully replaced the aliphatic NO2. In general, the CF3-bearing compounds were more potent than their NO2 equivalents and also showed improved in vitro metabolic stability. The CF3 analogue (1) with the best balance of properties was selected for further pharmacological evaluation. Pilot in vivo studies showed that (±)-1 has similar activity to (±)-ZCZ011, with both showing promising efficacy in a mouse model of neuropathic pain.

Gold-catalyzed transformation of 2-alkynyl arylazides: Efficient access to the valuable pseudoindoxyl and indolyl frameworks

An element of surprise: A series of functionalized 2-alkynyl arylazides has beed converted into 3-substituted indoles or 2,2-disubstituted indolin-3-ones in the presence of a gold(I) complex. Various oxygen or aryl nucleophiles can be used in this process to trap the intermediate α-imino gold carbene. The structural motifs of the products are found in a large variety of biologically active compounds and natural products. Copyright