4250-49-1

Usage

Uses

Used in Organic Synthesis:
(4-bromophenyl)(dichloro)borane is used as a catalyst for various organic synthesis reactions, including cross-coupling and other transition metal-catalyzed reactions. Its application is crucial in the formation of complex organic molecules due to its ability to facilitate carbon-carbon and carbon-heteroatom bond formations.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4-bromophenyl)(dichloro)borane is used as a synthetic intermediate for the development of new drugs. Its role in creating complex molecular structures makes it a valuable tool in the synthesis of novel pharmaceutical compounds.
Used in Chemical Research:
(4-bromophenyl)(dichloro)borane is also utilized in chemical research as a reagent to study the properties and reactions of boron-based organometallic compounds. This helps in understanding the underlying mechanisms and potential applications of such compounds in various fields.

Upstream product

• 10026-13-8 phosphorus pentachloride 
• 855242-28-3 (i-C₄H₉O)2B(C₆H₄-4-Br) 
• 7726-95-6 bromine 
• 107134-72-5 [4-(dichloroboryl)phenyl]trimethylsilane 
• 108-86-1 bromobenzene 
• 1359224-18-2 Me₂NTol*BCl₃ 
• 10294-34-5 boron trichloride 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 28969-28-0 4-Bromphenylquecksilberchlorid 
• 13183-70-5 1,4-bis-(trimethylsilyl)benzene 

Downstream Products

• 10342-83-3 4'-Bromopropiophenone 
• 77509-48-9 2-(4-bromophenyl)-1,3,2-benzodioxaborole 
• 68716-49-4 p-bromophenylboronic acid pinacol ester 
• 97440-43-2 2-(4-bromo-phenyl)-naphtho[2,3-d][1,3,2]dioxaborole 
• 17806-48-3 3-(C₆H₄-4-Br)-1.2-C₂B₁₀H₁₁ 
• 207286-80-4 ethyl 4-bromo-α-methylenebenzenepropanoate 
• 101737-30-8 {-B(C₆H₄-4-Cl)-NH-}3 

Relevant academic research and scientific papers

Regio- and Stereoselective 1,2-Carboboration of Ynamides with Aryldichloroboranes

Catalyst-free 1,2-carboboration of ynamides is presented. Readily available aryldichloroboranes react with alkyl- or aryl-substituted ynamides in high yields with complete regio- and stereoselectivity to valuable β-boryl-β-alkyl/aryl α-aryl substituted enamides which belong to the class of trisubstituted alkenylboronates. The 1,2-carboboration reaction is experimentally easy to conduct, shows high functional group tolerance and broad substrate scope. Gram-scale reactions and diverse synthetic transformations convincingly demonstrate the synthetic potential of this method. The reaction can also be used to access 1-boraphenalenes, a class of boron-doped polycyclic aromatic hydrocarbons.

Regioselective electrophilic borylation of haloarenes

Haloarenes undergo direct borylation using amine:BCl3:AlCl3 in the ratio of 1:1:2. After esterification the pinacol boronate esters are isolated in good yield with regioselectivity controlled by steric and electronic effects.

One-pot chemoselective functionalization of arylsilanes via cascade metal-metal exchange reactions

A cascade-transmetallation sequence allows a one-pot conversion of arylsilanes into functionalized arylcoppers; they react with various types of electrophiles (allylic halides, acid chlorides, bromoalkynes); bimetallic zinc-copper-reagents can be prepared by this method either directly or in a sequential fashion.

Borylation of Arylsilanes, II. - Synthesis and Reactions of Silylated Dihalogenphenylboranes

Upon treatment with trihaloboranes 4a and 4b the bissilylated benzenes 1, 2, and 3 yield the silylated dihalogenphenylboranes 5a-7b under substitution of one silyl group only.The corresponding difluoroboranes 5c-7c are easily accessible by a new fluorination method under mild reaction conditions by treating the dichloroboranes with lithium fluoride in ether.Upon heating with excess 4 the exchange of the second silyl group occurs, too, yielding the position-isomeric diborylbenzenes 9, 10, and 11.The bromination of the silylated dichlorophenylboranes 5a-7a proceeds with high regioselectivity under desilylation yielding 12, 13, and 14.The dimethoxyboranes 15, 16, and 17, synthesized by methanolysis of the corresponding dichloroboranes, can be coupled with bromobenzene under palladium(0) catalysis to yield the position-isomeric silylated biphenyls 18, 19, and 20.