444-29-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Iodobenzotrifluoride is used as a reagent for the preparation of various pharmaceutical compounds. It plays a crucial role in the synthesis of cyclooxygenase-1 (COX-1) inhibitors, which are essential in the development of anti-inflammatory and pain-relieving medications.
Used in Chemical Research:
In the field of chemical research, 2-Iodobenzotrifluoride is utilized for the preparation and structure-activity relationship (SAR) studies of tricyclic 4,4-dimethyl-3,4-dihydrochromeno[3,4-d]imidazole derivatives. These derivatives are known as microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitors, which are significant in the development of anti-inflammatory drugs.
Used in Docking Studies:
2-Iodobenzotrifluoride is also employed in docking studies, which are essential for understanding the interaction between the compound and its target protein. This information is vital for the design and optimization of new drugs with improved efficacy and selectivity.

InChI:InChI=1/C7H4F3I/c8-7(9,10)5-3-1-2-4-6(5)11/h1-4H

Upstream product

• 88-17-5 2-(trifluoromethyl)benzenamine 
• 591-50-4 iodobenzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 98-08-8 α,α,α-trifluorotoluene 
• 384-22-5 2-nitrobenzotrifluoride 
• 351-36-0 N-acetyl-3-trifluoromethylbenzenamine 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2314-97-8 iodotrifluoromethane 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 462-80-6 benzyne 
• 76-05-1 trifluoroacetic acid 
• 811-68-7 silver(I) trifluoromethanethiolate 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 392-83-6 o-trifluoromethylphenyl bromide 
• 21235-67-6 1-<2-(trifluoromethyl)phenyl>-2-propanone 
• 104483-69-4 1-(3-methyl-1H-benzopyran-1-ylidene)propan-2-one 
• 105417-07-0 1-Trifluoromethyl-2-trifluorovinyl-benzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 157518-53-1 methyl (E)-3-<2-(trifluoromethyl)phenyl>propenoate 
• 174356-08-2 2-<2'-(trifluoromethyl)phenyl>imidazole 
• 147344-86-3 1-(phenylethynyl)-2-(trifluoromethyl)benzene 
• 200358-08-3 5-(2-trifluoromethylphenyl)thiophene-2-carbonitrile 
• 567-15-7 2,2′-bis(trifluoromethyl)-1,1′-biphenyl 
• 626-62-0 Cyclohexyl iodide 
• 336182-27-5 1-piperidinecarboxylic acid, 4-(2-trifluoromethylphenylmethyl),-1,1-dimethylethyl ester 

Relevant academic research and scientific papers

METHOD OF MANUFACTURING BIS(TRIFLUOROMEHTYL)BIPHENYL COMPOUND

A process for preparing a bis biphenyl compound according to example embodiments of the present invention is reacting a triflouromethylaniline compound with an alkali metal halide to form a halotrifluoride methylbenzene compound. The halotriflouromethylbenzene compound is subjected to coupling reaction under copper catalyst conditions. The productivity of bis biphenyl compounds can be improved.

Lipshutz-type bis(amido)argentates for directed: Ortho argentation

Bis(amido)argentate (TMP)2Ag(CN)Li2 (3, TMP-Ag-ate; TMP = 2,2,6,6-tetramethylpiperidido) was designed as a tool for chemoselective aromatic functionalization via unprecedented directed ortho argentation (DoAg). X-Ray crystallographic analysis showed that 3 takes a structure analogous to that of the corresponding Lipshutz cuprate. DoAg with this TMP-Ag-ate afforded multifunctional aromatics in high yields in processes that exhibited high chemoselectivity and compatibility with a wide range of functional groups. These included organometallics- A nd transition metal-susceptible substituents such as methyl ester, aldehyde, vinyl, iodo, (trifluoromethanesulfonyl)oxy and nitro groups. The arylargentates displayed good reactivity with various electrophiles. Chalcogen (S, Se, and Te) installation and azo coupling reactions also proceeded efficiently.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

The ortho-Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect

Presented herein is an intriguing effect of fluorine, and it allows difluoroenol silyl ethers to couple with aryliodanes in a redox-neutral manner to afford ortho-iodo difluoroalkylated arenes. The remaining iodide group provides a versatile platform for converting the products into various valuable difluoroalkylated arenes. The reaction shows excellent functional-group compatibility and broad substrate scope. A DFT mechanistic study suggests that the fluorine effect facilitates a subtle nucleophilic attack of the oxygen atom of enol silyl ethers onto aryliodanes, therefore leading to a rearrangement.

Aryl iodine compound containing carboxydifluoromethylene at ortho-position and preparation method thereof

The invention discloses a preparation method of an aryl iodine compound containing carboxydifluoromethylene at ortho-position. The preparation method is characterized by including: at the presence oftrimethylsilyl trifluoromethanesulfonate, allowing aryl iodine diacetate shown as a structural formula (I) and pentafluoroacetone enol silicon ether shown as a structural formula (II) to be in rearrangement reaction, and hydrolyzing under strong base to obtain the aryl iodine compound containing methylene difluoroacetate and shown as a structural formula (III), wherein R1 is selected from hydrogen, halogen, alkyl, alkoxy, carbalkoxy, halogenated alkyl, halogenated alkoxy, carbalkoxy substituted alkyl, amino substituted alkyl, carbalkoxy and amino substituted alkyl, cyano or nitro, and Ar is selected from benzene ring, naphthalene ring and thiophene ring. The preparation method has the advantages of being mild in reaction condition, high in selectivity and yield, easy-to-separate in productand simple in operation.

Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process

The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow diazotization/iododediazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross-coupled products.

Silver-Mediated Trifluoromethylthiolation-Iodination of Arynes

(Chemical Equation Presented). A one-pot trifluoromethylthiolation-iodination of arynes with trifluoromethylthiosilver (AgSCF3) and 1-iodophenylacetylene is described. This protocol allows rapid construction of o-trifluoromethylthiolated arene building blocks in moderate yields. These products were found to be excellent precursors for Yagupolskii-Umemoto-type electrophilic trifluoromethylation reagents.

Study on the degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3)

Degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3), which can only be generated in situ with mixing PhI(OAc)2 and TMSCF3 in the presence of CsF, was studied by ESI-MS and GC-MS combined with 19F-NMR. The important transient intermediate PhICF3+ was determined by ESI-MS, and the major volatile products containing CF3 were identified with the authentic compounds by using GC-MS, such as trifluoromethylbenzene, 2-iodobenzotrifluoride, 3-iodobenzotrifluoride, 4-iodobenzotrifluoride. Meanwhile, more evidences obtained with 19F-NMR were given for such degradation reaction. A possible rapid CF3 radical transfer reaction pathway was proposed to clarify such degradation progress based on the experimental results. Therefore, this study may be helpful in elucidating the intrinsic reactivity of PhI(OAc)(CF3) and the possible competing side reactions caused by such self-degradation pathway. Degradation of the highly reactive hypervalent trifluoromethylation iodine reagent PhI(OAc)(CF3), which can only be generated in situ with mixing PhI(OAc)2 and TMSCF3 in the presence of CsF, was studied by ESI-MS and GC-MS combined with 19F-NMR. The important transient intermediate PhICF3+ was determined by ESI-MS, and the major volatile products containing CF3 were identified with the authentic compounds by using GC-MS, such as trifluoromethylbenzene, 2-iodobenzotrifluoride, 3-iodobenzotrifluoride, 4-iodobenzotrifluoride. Meanwhile, more evidences obtained with 19F-NMR were given for such degradation reaction. A possible rapid CF3 radical transfer reaction pathway was proposed to clarify such degradation progress based on the experimental results. Therefore, this study may be helpful in elucidating the intrinsic reactivity of PhI(OAc)(CF3) and the possible competing side reactions caused by such self-degradation pathway.

Silver-Catalyzed C-H Trifluoromethylation of Arenes Using Trifluoroacetic Acid as the Trifluoromethylating Reagent

Direct trifluoromethylation of arenes using TFA as the trifluoromethylating reagent was achieved with Ag as the catalyst. This reaction not only provides a new protocol for aryl C-H trifluoromethylation, but the generation of CF3· from TFA may prove useful in other contexts and could potentially be extended to other trifluoromethylation reactions. (Chemical Equation Presented).

Silver-catalyzed formal insertion of arynes into Rf-I bonds

An unprecedented silver-catalyzed formal insertion of arynes into R f-I (Rf=CF3, C2F5) bonds has been developed. This protocol provides easy access to various ortho-perfluoroalkyl iodoarenes under mild conditions. In this insertion reaction, an ionic atom-transfer reaction of RfI occurs, and a silver-mediated metathesis process is involved in the efficient transfer of the electropositive iodine atom.