86595-27-9

Basic information

• Product Name: DIISOPROPOXYMETHYLBORANE
• Synonyms: DIISOPROPOXYMETHYLBORANE;DIISOPROXYMETHYLBORANE
• CAS NO: 86595-27-9
• Molecular Formula: C₇H₁₇BO₂
• Molecular Weight: 144.02
• Product Categories: Boranes;Reduction;Synthetic Reagents
• Mol File: 86595-27-9.mol

Chemical Properties

• Boiling Point: 105-107 °C751 mm Hg(lit.)
• Flash Point: 45 °F
• Appearance: /
• Density: 0.781 g/mL at 25 °C(lit.)
• Vapor Pressure: 33mmHg at 25°C
• Refractive Index: n20/D 1.376(lit.)
• CAS DataBase Reference: DIISOPROPOXYMETHYLBORANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIISOPROPOXYMETHYLBORANE(86595-27-9)
• EPA Substance Registry System: DIISOPROPOXYMETHYLBORANE(86595-27-9)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39-36
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 86595-27-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DIISOPROPOXYMETHYLBORANE is used as a reducing agent for the selective reduction of carbonyl functional groups in organic molecules, which is crucial in the synthesis of various pharmaceutical compounds. Its ability to perform this reduction selectively contributes to the efficiency and specificity required in drug development processes.
Used in Chemical Industry:
In the chemical industry, DIISOPROPOXYMETHYLBORANE is employed as a reagent for the reduction of carbonyl groups in the synthesis of complex organic molecules. Its selective reduction capability is particularly valuable in creating specific chemical structures that are essential in the production of specialty chemicals and materials.
Used in Organic Synthesis:
DIISOPROPOXYMETHYLBORANE is used as a key reagent in organic synthesis for its selective reduction properties, facilitating the conversion of carbonyl groups to hydroxyl groups in a controlled manner. This selective reduction is vital for the synthesis of specific organic compounds that require precise structural modification.
Used in Research and Development:
In research and development settings, DIISOPROPOXYMETHYLBORANE is utilized as a tool for exploring new chemical reactions and pathways. Its unique reducing properties allow chemists to investigate the reactivity and behavior of various organic compounds, leading to advancements in synthetic methodologies and the discovery of new chemical entities.

InChI:InChI=1/C7H17BO2/c1-6(2)9-8(5)10-7(3)4/h6-7H,1-5H3

Upstream product

• 5419-55-6 Triisopropyl borate 
• 823-96-1 Trimethylboroxine 
• 917-54-4 methyllithium 
• 91083-27-1 (E)-1-hexenyldiisopropoxyborane 

Downstream Products

• 718642-13-8 (4-chlorophenyl)-methyl-borinic acid 
• 1240515-58-5 Li[MeB(5-Ms-pz)H₂] 
• 1240515-57-4 Li[MeB(3-Ms-pz)H₂] 
• 1240515-60-9 Li[MeB(3-mesityl-pz)(5-mesityl-pz)H] 
• 1240515-59-6 Li[MeB(3-mesityl-pz)2H] 
• 593-90-8 trimethylborane 
• 97782-77-9 (methyl)(phenyl)(isopropoxy)borane 
• 59073-99-3 methyldiphenylborane 
• 67-63-0 isopropyl alcohol 

Relevant articles and documents

PROCESS FOR SYNTHESIS OF DIALKOXYORGANOBORANES

The invention relates to a process for the synthesis of dialkoxyorganoboranes, in particular to a process for the synthesis of dialkoxyorganoboranes by an ester exchange reaction. Moreover, the invention relates to a process for the synthesis of organo-oxazaborolidine catalysts (organo-CBS) and of trialkylboroxins. Furthermore, the invention relates to methods of using dialkoxyorganoboranes for the preparation of organo-CBS catalysts and in Suzuki-type coupling reactions.

Organoboranes. 56. Systematic study of the reactions of 1-alkenylboronic esters with representative organolithium and grignard reagents to provide an efficient, selective synthesis of organyl-1-alkenylborinic esters

A selective reaction of the ate complexes formed with 1-alkenylboronic esters and organolithium or Grignard reagents, by treatment with either Br?nsted or Lewis acids at -78 °C to give the corresponding organylalkenylborinic esters, is explored in this study. This systematic, detailed study reveals that the nature of the alkoxy group on boron, the nature and the amount of the alkyllithium or Grignard reagent used, the solvent, the reaction temperature, and the nature and amount of the acid used all play significant roles in influencing both the yield and the selectivity achieved for the formation of the desired organylalkenylborinates. Optimized procedures for the syntheses of representative organylalkenylborinic esters in high yield are summarized.

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.