433-95-4

Basic information

• Product Name: 1,2-Bis(trifluoromethyl)benzene
• Synonyms: o-Bis(trifluoromethyl)benzene;o-Xylene, alpha,alpha,alpha,alpha',alpha',alpha'-hexafluoro-;1,2-BIS(TRIFLUOROMETHYL)BENZENE;1,2-BIS(TRIFLUROMETHYL)BENZENE;alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-o-xylene;α,α,α,α',α',α'-Hexafluoro-o-xylene
• CAS NO: 433-95-4
• Molecular Formula: C₈H₄F₆
• Molecular Weight: 214.11
• EINECS: 207-092-3
• Mol File: 433-95-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 142 °C
• Flash Point: 29.9 °C
• Appearance: /
• Density: 1.44
• Vapor Pressure: 13.7mmHg at 25°C
• Refractive Index: 1.3920-1.3960
• CAS DataBase Reference: 1,2-Bis(trifluoromethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(trifluoromethyl)benzene(433-95-4)
• EPA Substance Registry System: 1,2-Bis(trifluoromethyl)benzene(433-95-4)

Safety Data

• Hazard Codes: F
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 433-95-4(Hazardous Substances Data)

Usage

Description

1,2-Bis(trifluoromethyl)benzene is an organic compound characterized by its benzene ring with two trifluoromethyl groups attached to the first and second carbon atoms. This molecule is known for its unique properties, such as enhanced stability and reactivity due to the presence of the trifluoromethyl groups, making it a versatile compound in various chemical reactions and applications.

Uses

1. Used in Chemical Synthesis:
1,2-Bis(trifluoromethyl)benzene is used as a reagent for the preparation of biphenyls through the arylation of electron-deficient arenes with aryl halides. Its trifluoromethyl groups contribute to the stability and reactivity of the molecule, making it a valuable component in the synthesis of various organic compounds.
2. Used in Investigating Molecular Interactions:
1,2-Bis(trifluoromethyl)benzene is employed in research to study the effects of aromatic trifluoromethylation, fluorination, and methylation on intermolecular non-covalent interactions. The findings from these studies can provide valuable insights into the interactions between drug molecules and protein receptors, which is crucial for the development of new drugs and understanding their mechanisms of action.

InChI:InChI=1/C8H4F6/c9-7(10,11)5-3-1-2-4-6(5)8(12,13)14/h1-4H

Upstream product

• 651-91-2 2,3-bis(trifluoromethyl)-7-oxabicyclo<2,2,1>hepta-2,5-diene 
• 78167-41-6 (1S,4R)-5,6-Bis-trifluoromethyl-2-sila-bicyclo[2.2.2]octa-5,7-diene 
• 78-39-7 Triethyl orthoacetate 
• 78818-99-2 (1R,4S)-2,2-Dichloro-5,6-bis-trifluoromethyl-2-sila-bicyclo[2.2.2]octa-5,7-diene 
• 67078-75-5 2,2-dimethyl-1-oxa-2-silacyclohexa-3,5-diene 
• 692-50-2 hexafluoro-2-butyne 
• 84521-24-4 1-methyl-1-(trimethylsilyl)sila-α-pyran 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 71-43-2 benzene 
• 629-20-9 1,3,5,7-cyclooctatetraene 
• 2741-57-3 o-dichloromethyltrichloromethylbenzene 
• 1423-27-4 2-(trifluoromethyl)phenylboronic acid 
• 77152-08-0 trifluoromethylcopper(I) 
• 1073339-21-5 4,4,5,5-tetramethyl-2-(2-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 

Downstream Products

• 95-47-6 o-xylene 
• 312-95-8 1-difluoromethyl-2-trifluoromethyl-benzene 
• 1417658-13-9 5-chloro-N-(3-(trifluoromethyl)-2-trifluoromethylphenyl)-2-hydroxybenzamide 
• 727-99-1 2-trifluoromethylbenzophenone 
• 3822-20-6 2,3-ditrifluoromethylaniline 
• 603-11-2 3-nitrophthalic acid 
• 610-27-5 4-nitrophthalic acid 
• 42175-49-5 1,2,3,4-Tetrakis-(trifluormethyl)-benzol 
• 42175-56-4 2,3,4-Tris-(trifluormethyl)benzoesaeure 
• 42175-48-4 1,2,3-Tris-(trifluormethyl)-benzol 
• 42175-53-1 2,3-Bis-(trifluormethyl)benzamid 
• 42175-47-3 2,3-Bis-(trifluormethyl)benzoylfluorid 
• 42175-54-2 2,3-bis(trifluoromethyl)benzonitrile 
• 42175-55-3 2,3-Bis-(trifluormethyl)benzoesaeure 

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.

The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes

The first nucleophilic perfluoroalkylation of arenes is based on the arene π-system activation via (η6-arene)tricarbonylchromium complexes. Perfluoroalkyl anions generated from Me3SiRF and a fluoride ion source [Me4N]F exclusively attack the arene ligand under mild conditions. The formed negatively charged analogs of Meisenheimer adducts readily undergo a one-pot oxidation to perfluoroalkyl arenes.

Cooperative effect of silver in copper-catalyzed trifluoromethylation of aryl iodides using Me3SiCF3

An effective model of cooperative effect of silver for the coppercatalyzed trifluoromethylation of activated and unactivated aryl iodides to trifluoromethylated arenes using Me3SiCF3 was achieved with a broad substrate scope.