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

Chemical Properties

4-Iodobenzotrifluoride is a clear red to pink liquid with has the odor of halogenated benzene, is insoluble in water, and is miscible with benzene, toluene, ethanol, ether, halogenated hydrocarbons, etc.

Uses

4-Iodobenzotrifluoride may be employed as substrate with electron-deficient aromatic ring, during Mizoroki-Heck reaction with acrylic acid, to afford 4-trifluoromethylcinnnamic acid. It undergoes aminocarbonylation in DMF using phosphoryl chloride to give N,N-dimethyl-(4-trifluoromethyl)benzamide.

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.

Application

The fluorine atom in the molecular structure of 4-iodotrifluorotoluene makes it have special activity. It is an important pesticide and pharmaceutical intermediate. It can be used as the intermediate of the insecticide fipronil and used for the synthesis of diphenyl ethers containing fluorine herbicide.

General Description

4-Iodobenzotrifluoride undergoes aminocarbonylation in DMF using phosphoryl chloride to give N,N-dimethyl-(4-trifluoromethyl)benzamide. Mechanism of the copper-free Sonogashira cross-coupling reaction of 4-iodobenzotrifluoride with differently para-substituted phenylacetylenes has been investigated.

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 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 378-77-8 sodium pentafluoropropionate 
• 591-50-4 iodobenzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 5122-99-6 4-iodophenylboronic acid 
• 2926-29-6 Langlois reagent 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 
• 540-37-4 p-aminoiodobenzene 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 619-75-0 1-dibromomethyl-4-nitro-benzene 

Downstream Products

• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 370-99-0 4-trifluoromethyldiphenylethyne 
• 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 
• 200358-06-1 5-[4-(trifluoromethyl)phenyl]thiophene-2-carbonitrile 
• 90035-34-0 4-(4-trifluoromethylphenyl)benzaldehyde 

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.

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.