328-70-1

Basic information

• Product Name: 3,5-Bis(trifluoromethyl)bromobenzene
• Synonyms: MBT-BR;5-BROMO-1,3-BIS(TRIFLUOROMETHYL)BENZENE;3,5-BIS(TRIFLUOROMETHYL)BROMINE BENZENE;3,5-BIS(TRIFLUOROMETHYL)BROMOBENZENE;3,5-BIS(TRIFLUOROMETHYL)-1-BROMOBENZENE;3,5-DI(TRIFLUOROMETHYL)BROMOBENZENE;1,3-BIS(TRIFLUOROMETHYL)-5-BROMOBENZENE;1-BROMO-3,5-BIS(TRIFLUOROMETHYL)BENZENE
• CAS NO: 328-70-1
• Molecular Formula: C₈H₃BrF₆
• Molecular Weight: 293
• EINECS: 206-334-5
• Product Categories: Fluorides;Trifluoromethylbenzene serise;Fluorobenzene;PHARMACEUTICAL INTERMEDIATES;Aromatic Hydrocarbons (substituted) & Derivatives;API intermediates;Miscellaneous;alkyl bromide;Morpholines/Thiomorpholines ,Isoxazoles
• Mol File: 328-70-1.mol
• Article Data: 13

Chemical Properties

• Melting Point: −16 °C(lit.)
• Boiling Point: 154 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.699 g/mL at 25 °C(lit.)
• Vapor Pressure: 15mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• Water Solubility: Immiscible with water.
• BRN: 2123669
• CAS DataBase Reference: 3,5-Bis(trifluoromethyl)bromobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Bis(trifluoromethyl)bromobenzene(328-70-1)
• EPA Substance Registry System: 3,5-Bis(trifluoromethyl)bromobenzene(328-70-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 328-70-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to slightly yellow liquid

Uses

1,3-Bis(trifluoromethyl)-5-bromobenzene is used to prepare the tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ion, which acts as a stabilizing counterion for electrophilic organic and organometallic cations.

Synthesis Reference(s)

The Journal of Organic Chemistry, 68, p. 3695, 2003 DOI: 10.1021/jo026903n

InChI:InChI=1/C8H3ClF6/c9-6-2-4(7(10,11)12)1-5(3-6)8(13,14)15/h1-3H

Upstream product

• 121-91-5 isophthalic acid 
• 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 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 109-65-9 1-bromo-butane 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 479411-92-2 2-(3-bromo-5-(trifluoromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 141889-58-9 ethyl 2-(N-acetyl)-5-<3,5-bis(trifluoromethyl)phenyl>pent-4-ynoate 
• 97878-08-5 tetrabutylammonium bis<α,α-bis(trifluoromethyl)benzenemethanolato(2-)-C²,O><3,5-bis(trifluoromethyl)phenyl>silicate (1-) 
• 119558-46-2 (3R,4S)-4-(3,5-Bis-trifluoromethyl-phenyl)-3-dimethylaminomethyl-tetrahydro-thiopyran-4-ol 
• 119558-46-2 (3S,4S)-4-(3,5-Bis-trifluoromethyl-phenyl)-3-dimethylaminomethyl-tetrahydro-thiopyran-4-ol 
• 175136-62-6 tris<3,5-bis(trifluoromethyl)phenyl>phosphane 
• 401-95-6 3,5-Bis(trifluoromethyl)benzaldehyde 
• 179117-29-4 chloro-N,N-diethylamino-(3,5-bis(trifluoromethyl)-phenyl)-phosphine 
• 349-59-7 3,5-bis(trifluoromethyl)styrene 
• 81613-61-8 3-(3,5-bis-trifluoromethyl-phenyl)-2-propyn-1-ol 
• 556-96-7 5-bromo-1,3-xylene 
• 35564-19-3 1-fluoro-3,5-bis-(trifluoromethyl)benzene 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 872210-38-3 {dimethyl[3,5-bis(trifluoromethyl)phenyl]silyl}methyl chloride 

Relevant articles and documents

Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Reactivity of a frustrated Lewis pair and small-molecule activation by an isolable arduengo carbene-B{3,5-(CF3)2C6H 3}3 complex

Tris[3,5-bis(trifluoromethyl)phenyl]borane reacts with the sterically demanding Arduengo carbenes 1,3-di-tert-butylimidazolin-2-ylidene and 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene to form isolable normal adducts. In the case of 1,3-di-tert-butylimidazolin-2-ylidene, the adduct exhibits dynamic behaviour in solution and frustrated-Lewis-pair (FLP) reactivity. Fast cleavage of dihydrogen and THF, the C-H activation of phenylacetylene, and carbon dioxide fixation were achieved by using solutions of this adduct in benzene. This adduct is stable at room temperature in the absence of suitable substrates; however, thermal rearrangement into an abnormal carbene-borane adduct can be observed. In contrast, the 1,3-bis(2,6- diisopropylphenyl)imidazolin-2-ylidene adduct exhibits no evidence of FLP reactivity or of dissociation in solution. DFT calculations confirmed the experimental behaviour and stability of these carbene-borane adducts. Frustrated but not frustrating: Arduengo carbene 1,3-di-tert-butylimidazolin-2-ylidene and tris[3,5-bis(trifluoromethyl)phenyl]borane form an isolable adduct (see scheme) that shows frustrated-Lewis-pair (FLP) reactivity towards H2, CO2, and other small molecules. Copyright

1,3-Bis(trifluoromethyl)benzene derivatives

A method of manufacture of 3,5-bis(trifluoromethyl)bromobenzene, comprising the addition of a brominating reagent to a mixture of 3,5-bis(trifluoromethyl)benzene together with at least one of sulphuric acid or oleum in the absence of acetic acid. A method of production of 3,5-bis(trifluoromethyl)acetophenone comprising the reaction of 3,5-bis(trifluoromethyl)phenyl magnesium bromide with acetyl chloride in the presence of cuprous chloride. A method of production of 3,5-bis(trifluoromethyl)acetophenone comprising the steps of reacting 3,5-bis(trifluoromethyl)phenyl magnesium bromide with acetic anhydride, adding water, and recovering the product by azeotropic distillation. A method of removal of impurities including 3,5-bis(trifluoromethyl)acetate, 4-bromobutyl acetate and 4-chlorobutyl acetate from a preparation of 3,5-bis(trifluoromethyl)acetophenone, the method comprising heating the 3,5-bis(trifluoromethyl)acetophenone with a dilute solution of alkali. A method of production of 3,5-bis(trifluoromethyl)phenyl magnesium bromide comprising the reaction of 3,5-bis(trifluoromethyl)bromobenzene with magnesium in a solvent whilst maintaining the temperature of the reactants above 20° C. and below the reflux temperature of the solvent.