21757-86-8

Usage

Uses

Used in Pharmaceutical Industry:
BenzeneMethanol, 4-broMo-.alpha.-(trichloroMethyl)is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical industry, BenzeneMethanol, 4-broMo-.alpha.-(trichloroMethyl)serves as a precursor in the production of agrochemicals, such as pesticides and herbicides, due to its reactivity and ability to form stable derivatives.
Used in Organic Chemistry Research:
BenzeneMethanol, 4-broMo-.alpha.-(trichloroMethyl)is utilized in organic chemistry research for studying its reactivity and exploring its potential applications in the synthesis of various organic compounds.
Used in Drug Discovery:
Due to its unique structure, BenzeneMethanol, 4-broMo-.alpha.-(trichloroMethyl)is employed in drug discovery processes to identify new drug candidates with potential therapeutic effects.
However, it is important to note that BenzeneMethanol, 4-broMo-.alpha.-(trichloroMethyl)is considered toxic and harmful if ingested or inhaled. Therefore, proper handling and safety measures should be taken during its use in various applications.

InChI:InChI=1/C8H6BrCl3O/c9-6-3-1-5(2-4-6)7(13)8(10,11)12/h1-4,7,13H

Upstream product

• 108-86-1 bromobenzene 
• 75-87-6 chloral 
• 18620-02-5 (4-bromophenyl)magnesium bromide 
• 106-37-6 1.4-dibromobenzene 
• 67-66-3 chloroform 
• 1122-91-4 4-bromo-benzaldehyde 
• 302-17-0 chloral hydrate 
• 7519-94-0 2,4,6-tris(4-bromophenyl)boroxin 
• 650-51-1 sodium trichloroacetate 

Downstream Products

• 6940-50-7 4-bromo-DL-mandelic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 126833-44-1 3-(4-Bromo-phenyl)-2,5-bis-ethoxycarbonyl-4-oxo-hexanedioic acid diethyl ester 
• 61693-77-4 1-(p-bromophenyl)-2,2-dichloroethanol 
• 4714-31-2 1-Brom-4-<1,2,2,2-tetrachlor-ethyl>-benzol 
• 38304-81-3 2-(4-bromo-phenyl)-1,1,1-trichloro-2-(4-chloro-phenyl)-ethane 
• 59424-80-5 C₁₅H₁₂BrCl₃O 
• 96264-88-9 1-(p-Bromphenyl)-1-<(p-(4-brombenzyl)phenyl)-2,2,2-trichloraethan 
• 5216-53-5 1,1-dichloro-2,2-bis(p-bromophenyl)ethane 
• 71570-70-2 C₁₆H₈Br₂Cl₆ 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 1620143-49-8 ethyl 1-(4-bromophenyl)-2,2,2-trichloroethyl carbonate 
• 881650-48-2 (Z)-1,4-bis(4-bromophenyl)-2,3-dichlorobut-2-ene-1,4-dione 
• 41262-33-3 1-(4-bromophenyl)-2,2,2-trichloroethan-1-one 

Relevant academic research and scientific papers

Pd-catalyzed synthesis of 1-(hetero)aryl-2,2,2-trichloroethanols using chloral hydrate and (hetero)arylboroxines

1-(Hetero)aryl-2,2,2-trichloroethanols are useful key intermediates for the synthesis of various bioactive compounds. Herein, we describe N-heterocyclic carbene (NHC)-coordinated cyclometallated palladium complex (CYP)-catalyzed (hetero)aryl addition of chloral hydrate using (hetero)arylboroxines, providing a new approach to 1-(hetero)aryl-2,2,2-trichloroethanols. Notably, PhS-IPent-CYP which coordinated the bulky yet flexible 2,6-di(pentan-3-yl)aniline (IPent)-based NHC showed good catalytic activities and promoted the transformation in 24-97% yields.

A novel β-(oxy)alkyl radical during copper(I)-mediated stereoselective synthesis of (Z)-ene-1,4-diones in a reaction of 2,2,2-trichloro-1-phenylethanone

A novel β-(oxy)alkyl radical derived from trichloro methyl compound containing neither a suitably located C-C multiple bond nor a leaving group or a H-atom at the β-position of the radical in a reaction of 2,2,2-trichloro-1-phenyl-ethanone with 2 mol equiv each of CuCl and bpy in refluxing DCE under a N2 atm underwent intramolecular heterolysis (just like formation of intact radical cation-anion pair) during stereoselective radical dimerization to Z-ene-1,4-dione along with small amount of reductive dechlorination product. The stereochemistry was established by X-ray diffraction spectroscopy of various solid crystalline products.

Decarboxylative trichloromethylation of aromatic aldehydes and its applications in continuous flow

Two new protocols for the efficient synthesis of 2,2,2- trichloromethylcarbinols, starting from aromatic aldehydes, have been developed. A combination of sodium trichloroacetate in the presence of malonic acid proved efficient for the transformation of el

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

Copper(I)-promoted synthesis of chloromethyl ketones from trichloromethyl carbinols

(Chemical Equation Presented) Reaction of several trichloromethyl carbinols with 2 equiv of CuCl/bpy in refluxing DCE for 3 h afforded chloromethyl ketones in excellent yield by 1,2-H shift in the copper-chlorocarbenoid intermediate.

CARBOXYLATION OF ARENES

A two-step procedure for the carboxylation of aromatic rings is described, involving the intermediate preparation of 1-aryl-2,2,2-trichloroethanols (1), which form the corresponding benzoic acids by treatment with NaOH/H2O2.

Studies on the rearrangement of (trichloromethyl)carbinols to α-chloroacetic acids

Phenyl(trichloromethyl)carbinol undergoes an unimolecular, predominantly intramolecular conversion into potassium α-chlorophenylacetate on stirring with 10percent aqueous potassium hydroxide at 0 deg C for several days.Besides providing an interesting example of a 1-2 chlorine shift, the reaction is of potential importance for the synthesis of α-chloro acids.The study of a variety of (trichloromethyl)carbinols shows the reaction is general for secondary (trichloromethyl)carbinols as well as trichloroethanol.The mechanism of the reaction involves the preliminary formation of an epoxide.Several mechanisms are considered for the conversion of the epoxide to the α-chloroacetate anion, but none accounts for all of the experimental facts.Tertiary carbinols break down at the epoxide stage into a ketone and carbon monoxide.