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
• Article Data: 40

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

Description

4-Iodobenzotrifluoride, also known as α,α,α-trifluoro-4-iodotoluene, is an organic compound characterized by its electron-deficient aromatic ring and a trifluoromethyl group. It is a clear red to pink liquid with the odor of halogenated benzene and is insoluble in water but miscible with various organic solvents such as benzene, toluene, ethanol, ether, and halogenated hydrocarbons. 4-Iodobenzotrifluoride is known for its special activity due to the presence of a fluorine atom in its molecular structure.

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 
• 591-50-4 iodobenzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 2314-97-8 iodotrifluoromethane 
• 5122-99-6 4-iodophenylboronic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 53451-91-5 1-[(4-methoxyphenyl)thio]-4-(trifluoromethyl)benzene 
• 73852-88-7 2-(4-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Downstream Products

• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 603-34-9 N,N-diphenylaminobenzene 
• 632-52-0 tetraphenylhydrazine 
• 36809-32-2 N-(4-trifluoromethylphenyl)-N-methylaniline 
• 101466-85-7 ethyl (E)-4-trifluoromethylcinnamate 
• 74670-68-1 1-(2,2-difluorovinyl)-4-(trifluoromethyl)benzene 
• 173546-21-9 3-(4-trifluoromethylphenyl)prop-2-yn-1-ol 
• 200358-06-1 5-[4-(trifluoromethyl)phenyl]thiophene-2-carbonitrile 
• 197231-98-4 3-(4-α,α,α-trifluoromethylphenyl)-N-methylpropiolamide 
• 402-50-6 1-trifluoromethyl-4-vinyl-benzene 
• 1813-97-4 1-allyl-4-(trifluoromethyl)benzene 
• 90035-34-0 4-(4-trifluoromethylphenyl)benzaldehyde 

Relevant articles and documents

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.

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.

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.