455-13-0

Basic information

• Product Name: 4-Iodobenzotrifluoride
• Synonyms: P-IODO TRIFLUORO TOLUENE;P-IODOBENZOTRIFLUORIDE;1-iodo-4-(trifluoromethyl)-benzen;BUTTPARK 45\01-80;4-IODO-1-TRIFLUOROMETHYLBENZENE;4-IODO-ALPHA,ALPHA,ALPHA-TRIFLUOROTOLUENE;4-IODOBENZOTRIFLUORIDE;4-(TRIFLUOROMETHYL)IODOBENZENE
• CAS NO: 455-13-0
• Molecular Formula: C₇H₄F₃I
• Molecular Weight: 272.01
• EINECS: 207-234-4
• Product Categories: Fluoro-contained Iodo series;Fluorine Compounds;Iodine Compounds
• Mol File: 455-13-0.mol

Chemical Properties

• Melting Point: −8.33 °C(lit.)
• Boiling Point: 185-186 °C745 mm Hg(lit.)
• Flash Point: 156 °F
• Appearance: Clear pale yellow to yellow or red/Liquid
• Density: 1.851 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.917mmHg at 25°C
• Refractive Index: n20/D 1.516(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 1944013
• CAS DataBase Reference: 4-Iodobenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodobenzotrifluoride(455-13-0)
• EPA Substance Registry System: 4-Iodobenzotrifluoride(455-13-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: 1760
• WGK Germany: 3
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 455-13-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4-Iodobenzotrifluoride is used as a substrate with an electron-deficient aromatic ring for the Mizoroki-Heck reaction with acrylic acid, resulting in the formation of 4-trifluoromethylcinnamic acid. This application takes advantage of the compound's reactivity in cross-coupling reactions, which are widely used in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Iodobenzotrifluoride is utilized as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the development of new drugs.
Used in Pesticide Industry:
4-Iodobenzotrifluoride is an important intermediate in the production of pesticides, particularly the insecticide fipronil. 4-Iodobenzotrifluoride's special activity, attributed to the fluorine atom in its molecular structure, makes it a key component in the synthesis of this widely used insect control agent.
Used in Herbicide Synthesis:
4-Iodobenzotrifluoride is also used in the synthesis of diphenyl ethers containing fluorine, which are herbicides. The presence of the fluorine atom in 4-Iodobenzotrifluoride contributes to the herbicidal properties of the final product, making it an essential intermediate in this application.

Preparation

Synthesis of 4-Iodotrifluorotoluene: Prepared by diazotization and iodination of 4-aminobenzotrifluoride or 4-Iodobenzotrifluoride is prepared by direct iodination with trifluorotoluene as raw material.

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

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 624-38-4 para-diiodobenzene 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 98-08-8 α,α,α-trifluorotoluene 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 378-77-8 sodium pentafluoropropionate 
• 591-50-4 iodobenzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 98-56-6 4-chlorobenzotrifluoride 
• 402-54-0 p-nitrobenzotrifluoride 
• 14505-17-0 p-nitrobenzylidyne tribromide 
• 619-75-0 1-dibromomethyl-4-nitro-benzene 
• 635702-14-6 palladium(II)I(C₆H₄CF₃-4)[(2-(PPh₂)C₆H₄-1-CH=NC₆H₄OMe] 

Downstream Products

• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 370-99-0 4-trifluoromethyldiphenylethyne 
• 104483-73-0 3,3-dimethyl-1-(p-ethynylphenyl)butan-2-one 
• 104483-72-9 3,3-dimethyl-1-(p-trifluoromethylphenyl)butan-2-one 
• 104483-71-8 4,4-dimethyl-1-(p-pyvaloylmethylphenyl)pent-1-yn-3-one 
• 92566-18-2 trans-p-trifluoromethyl-α,α'-difluorostilbene 
• 36809-32-2 N-(4-trifluoromethylphenyl)-N-methylaniline 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 98-08-8 α,α,α-trifluorotoluene 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 
• 115665-78-6 trans-1-(2-bromovinyl)-4-(trifluoromethyl)benzene 
• 1149-56-0 (E)-4-trifluoromethylstilbene 
• 345-88-0 1-phenyl-1-(4-trifluoromethylphenyl)ethylene 
• 150895-39-9 (1R,2R)-3-Iodo-6-trifluoromethyl-cyclohexa-3,5-diene-1,2-diol 

Relevant articles and documents

A convenient synthetic approach to a novel class of aryldifluoromethyl pyrimidine derivatives containing strobilurin motif as insecticidal agents

A series of aryldifluoromethyl pyrimidine compounds containing strobilurin were synthesized through bioelectronic isometric design with azoxystrobin as the lead compound and a convenient approach to aryldifluoromethylpyrimidine intermediates was developed, which features mild reaction conditions and simple operation. The title compounds and aryldifluoromethylpyrimidine intermediates were characterized by NMR and HRMS. Both 7c and 7l of the preliminary screening tests showed 100% inhibition against Mythimna separata at 100 mg/L. At 20 mg/L, the lethal rate of 7l against Mythimna separata can be up to 80%.

Palladium-Catalyzed Decarbonylative Iodination of Aryl Carboxylic Acids Enabled by Ligand-Assisted Halide Exchange

We report an efficient and broadly applicable palladium-catalyzed iodination of inexpensive and abundant aryl and vinyl carboxylic acids via in situ activation to the acid chloride and formation of a phosphonium salt. The use of 1-iodobutane as iodide source in combination with a base and a deoxychlorinating reagent gives access to a wide range of aryl and vinyl iodides under Pd/Xantphos catalysis, including complex drug-like scaffolds. Stoichiometric experiments and kinetic analysis suggest a unique mechanism involving C?P reductive elimination to form the Xantphos phosphonium chloride, which subsequently initiates an unusual halogen exchange by outer sphere nucleophilic substitution.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

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.

Generation of Organozinc Reagents from Arylsulfonium Salts Using a Nickel Catalyst and Zinc Dust

Readily available aryldimethylsulfonium triflates react with zinc powder under nickel catalysis via the selective cleavage of the sp2-hybridized carbon-sulfur bond to produce salt-free arylzinc triflates under mild conditions. This zincation displays superb chemoselectivity and thus represents a protocol that is complementary or orthogonal to existing methods. The generated arylzinc reagents show both high reactivity and chemoselectivity in palladium-catalyzed and copper-mediated cross-coupling reactions.

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.

Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides

A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.

A general electrochemical strategy for the Sandmeyer reaction

Herein we report a general electrochemical strategy for the Sandmeyer reaction. Using electricity as the driving force, this protocol employs a simple and inexpensive halogen source, such as NBS, CBrCl3, CH2I2, CCl4, LiCl and NaBr for the halogenation of aryl diazonium salts. In addition, we found that these electrochemical reactions could be performed using anilines as the starting material in a one-pot fashion. Furthermore, the practicality of this process was demonstrated in the multigram scale synthesis of aryl halides using highly inexpensive graphite as the electrode. A series of detailed mechanism studies have been performed, including radical clock and radical scavenger study, cyclic voltammetry analysis and in situ electron paramagnetic resonance (EPR) analysis.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.