729-81-7

Basic information

• Product Name: 1,3,5-Tris(trifluoromethyl)benzene
• Synonyms: 1,3,5-TRIS(TRIFLUOROMETHYL)BENZENE;1,3,5-TRIS(TRIFLUOROMETHYL)BENZENE 97%;1,3,5-Tris(trifluoromethyl)benzene97%;1,3,5-Tri(trifluoromethyl)benzene;1,3,5-Tris(trifluoromethyl)benzene, 97.5%
• CAS NO: 729-81-7
• Molecular Formula: C₉H₃F₉
• Molecular Weight: 282.11
• Product Categories: Benzene series;C9 to C12;Aryl;Halogenated Hydrocarbons
• Mol File: 729-81-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 9.0 °C
• Boiling Point: 120 °C750 mm Hg(lit.)
• Flash Point: 110 °F
• Appearance: /
• Density: 1.514 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.03E-05mmHg at 25°C
• Refractive Index: n20/D 1.359(lit.)
• CAS DataBase Reference: 1,3,5-Tris(trifluoromethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tris(trifluoromethyl)benzene(729-81-7)
• EPA Substance Registry System: 1,3,5-Tris(trifluoromethyl)benzene(729-81-7)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 729-81-7(Hazardous Substances Data)

Usage

Uses

1,3,5-tris(trifluoromethyl)benzene was used as a starting material in the synthesis of bis(2,4,6-tris(trifluoromethyl)phenyl)chloropnictines.It may be used as a starting material in the synthesis of 2,4,6-tris(trifluoromethyl)benzoic acid by reacting with n-butyllithium and carbon dioxide and in the synthesis of lithio derivative, via direct metalation with n-butyllithium.

General Description

1,3,5-tris(trifluoromethyl)benzene is a tri-substituted benzene. It has been synthesized by reacting benzene-1,3,5-tricarboxylic acid with SF4. Reports suggest that 1,3,5-tris(trifluoromethyl)benzene is a nonanesthetics and shows convulsant properties. Its vapor absorption spectra and corresponding solution spectra has been investigated. Its reaction with methyl lithium has been analyzed using semiempirical reaction modelling.

InChI:InChI=1/C7H4FNO4/c8-6-2-1-4(9(12)13)3-5(6)7(10)11/h1-3H,(H,10,11)

Upstream product

• 729-80-6 1,3,5-tris(trichloromethyl)benzene 
• 661-54-1 3,3,3-trifluoroprop-1-yne 
• 626-39-1 1,3,5-trisbromobenzene 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 554-95-0 benzene-1,3,5-tricarboxylic acid 
• 328-70-1 3,6-bis(trifluoromethyl)bromobenzene 
• 98-08-8 α,α,α-trifluorotoluene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 455-13-0 4-Iodobenzotrifluoride 
• 159566-31-1 C₂₁H₂₉F₉Sn 
• 73852-19-4 3,5-bis-trifluromethylphenylboronic acid 
• 69807-91-6 2-(3,5-bis-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane 

Downstream Products

• 114071-23-7 methyl 2,4,6-tris(trifluoromethyl)benzoate 
• 169304-46-5 bis<2,4,6-tris(trifluoromethy)lphenyl>fluorosilane 
• 681812-02-2 bis-(2,4,6-tris-trifluoromethyl-phenyl) fluoroborane 
• 182628-67-7 (η(5)-C5H4SiMe3)2Ti(C*C-SiMe3)2Au(C6H2(CF3)3-2,4,6) 
• 182628-64-4 (dimethylsulfane)Au(C₆H₂(CF₃)3-2,4,6) 
• 135103-74-1 <2,4,6-Tris(trifluoromethyl)phenyl>vinyl ketone 
• 135103-73-0 2,4,6-Tris(trifluoromethyl)acetophenone 
• 204193-60-2 1,1,1,3,3,3-Hexamethyl-2-(2,4,6-tris-trifluoromethyl-phenyl)-disilazane 
• 204193-59-9 Trimethylsilanyl-(2,4,6-tris-trifluoromethyl-phenyl)-amine 
• 135130-97-1 2,4,6-tris(trifluoromethyl)benzoyl chloride 
• 25753-22-4 2,4,6-tris(trifluoromethyl)aniline 
• 25753-21-3 2,4,6-Tris-(trifluormethyl)-benzamid 
• 179923-31-0 2,4,6-(F₃C)3C₆H₂B(OH)2 
• 681812-01-1 2,4,6-(CF₃)3C₆H₂BCl₂ 

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.

1-bromo-3,5-bis(trifhioromethyl)benzene: A versatile starting material for organometallic synthesis

1-Bromo-3,5-bis(trifluoromethyl)benzene (1) can be selectively prepared by treatment of 1,3-bis(fluorornethyl)benzene with N,N′-dibromo-5,5-dimethylhydantoin in strongly acidic media. A number of synthetically useful reactions via 3,5bis{trifluoromethyl)phenylmagnesium, -lithium, and -copper intermediates were accomplished. VCH Verlagsgesellschaft mbH, , 1996.

TRIFLUORMETHYLIERUNGSREAKTIONEN VON Te(CF3)2 MIT HALOGENBENZOLEN UND METHYLBENZOLEN

Substituent effects on yields and regioselectivity of photochemical and thermal trifluoromethylation reactions of Te(CF3)2 with halogen benzenes and methyl benzenes are investigated under comparable conditions.All reactions lead to trifluoromethylated products.The yields of the thermal are always higher than those of the corresponding photochemical reactions.The reactivity of the halobenzenes increases in the series C6H5-F a sidereaction, but H-substitution is the primary reaction pathway.During the reactions with iodobenzene tellurium containing compounds are also formed.The reactions with methyl benzenes show an increase in reactivity in the series hexamethylbenzene mesitylene toluene p-xylene.In all cases only ring substituted products are detected.Reactions with toluene and p-xylene yield tellurium containing compounds as well as addition products.The 19F-n.m.r spectra of the products are given.