62260-99-5

Usage

Uses

Used in Organic Synthesis:
DICHLOROMETHYLDIISOPROPOXYBORANE is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds. Its unique properties allow for the efficient synthesis of complex organic molecules, making it a valuable asset in the field of organic chemistry.
Used in Medicinal Chemistry:
In the pharmaceutical industry, DICHLOROMETHYLDIISOPROPOXYBORANE is used as a key intermediate in the solid phase synthesis of aminoboronic acids. These aminoboronic acids have been identified as potent inhibitors of the hepatitis C virus NS3 proteinase, a crucial enzyme in the viral replication process. By targeting this enzyme, these inhibitors can help to combat the spread of the hepatitis C virus and potentially lead to the development of new antiviral therapies.
Overall, DICHLOROMETHYLDIISOPROPOXYBORANE is a versatile and valuable reagent in both organic synthesis and medicinal chemistry, with applications ranging from the formation of complex organic molecules to the development of novel antiviral agents.

InChI:InChI=1/C7H15BCl2O2/c1-5(2)11-8(7(9)10)12-6(3)4/h5-7H,1-4H3

Upstream product

• 5419-55-6 Triisopropyl borate 
• 2146-67-0 (dichloromethyl)lithium 
• 75-09-2 dichloromethane 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 105065-54-1 (4S,5S)-2-dichloromethyl-4,5-dicyclohexyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

Preparation of α,α-dihaloalkyl boronic esters

Esters of α,α-haloalkyl boronic acids are prepared by the addition of an alkali metal dialkylamide, or some other equivalent sterically hindered base to a mixture of a 1,1-dihaloalkane and a trialkyl borate in an organic solvent at a temperature between about -78° C. and +25° C. In one embodiment, diisopropyl (dichloromethyl)borate is formed by the addition of lithium diisopropylamide to a mixture of dichloromethane and triisopropyl borate in the presence of tetrahydrofuran as the solvent medium at a temperature between about -10° C. and +10° C.

A practical synthesis of (dichloromethyl)- and (1,1-dichloroethyl)boronic esters

Addition of lithium diisopropylamide or diethylamide to a mixture of triisopropyl borate and dichloromethane in THF at temperatures between -78 and 0°C leads to formation of (dichloromethyl)lithium and its capture by the borate ester. Anhydrous HCl converts the resulting borate salt to diisopropyl (dichloromethyl)boronate. Similarly, dimethyl (1,1-dichloroethyl)boronate is readily prepared from 1,1-dichloroethane and trimethyl borate. Sodium iodide converted butanediol (dichloromethyl)boronate to the (diiodomethyl)boronate.

Organoboranes. 31. A simple preparation of boronic esters from organolithium reagents and selected trialkoxyboranes

The reaction of methyllithium with trimethoxyborane at -78°C in ethyl ether yields a mixture of methylated boranes and their corresponding ate complexes. We have found that under the same conditions triisopropoxyborane reacts cleanly with methyllithium to form the lithium methyltriisopropoxyborate complex. Protonation of this complex with anhydrous hydrogen chloride quantitatively yields methyl diisopropoxyborane. This reaction of organolithium reagent with triisopropoxyborane appears to provide a general, valuable route to boronic esters. Other alkoxyboranes were examined for their selectivity for monomethylation by methyllithium. In addition to triisopropoxyborane, triisobutoxyborane and tri-sec-butoxyborane also give the methylboronic esters quantitatively. This development provides the first general preparation of boronic esters from organolithium reagents.