88996-23-0

Basic information

• Product Name: BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX
• Synonyms: BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX;N,N-Diisopropylethylamine borane;Borane-N,N-diisopropylethylamine;Diisopropylethylamine borane;Borane N,N-diisopropylethylamine complex
• CAS NO: 88996-23-0
• Molecular Formula: C₈H₂₂BN
• Molecular Weight: 143.08
• Product Categories: Industrial/Fine Chemicals;Boranes;Reduction;Synthetic Reagents
• Mol File: 88996-23-0.mol

Chemical Properties

• Melting Point: 15-17 °C(lit.)
• Flash Point: 40 °C
• Appearance: /
• Density: 0.822 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.46(lit.)
• CAS DataBase Reference: BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX(CAS DataBase Reference)
• NIST Chemistry Reference: BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX(88996-23-0)
• EPA Substance Registry System: BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX(88996-23-0)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: 1992
• WGK Germany: 3
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 88996-23-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX is used as a reactant for the preparation of modifiable bidentate systems via nitrogen-carbon rearrangement. This allows for the development of new compounds with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX is used as a reactant for the preparation of bioactive boranophosphonic acids. These acids have potential applications in the development of new drugs and therapeutic agents.
Used in Nucleic Acid Chemistry:
BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX is used as a reactant for the preparation of precursors for the synthesis of boronated oligonucleotide sequences. This is important in the development of new techniques for nucleic acid manipulation and analysis.
Used in Organic Chemistry:
In organic chemistry, BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX is used as a reactant for the synthesis of dithymidine boranophosphate via the oxathiaphospholane approach. This method allows for the creation of new organic compounds with potential applications in various fields.
Used in Biochemistry:
BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX is used as a reactant for the preparation of adenosine boranothiotriphosphate ribonucleoside and thymidine boranothiotriphosphate deoxyribonucleoside. These compounds have potential applications in the study of nucleic acid structure and function.
Used in Inorganic Chemistry:
In inorganic chemistry, BORANE-N,N-DIISOPROPYLETHYLAMINE COMPLEX is used as a reactant for the preparation of borane-amine complexes. These complexes have potential applications in various chemical reactions and processes, as well as in the development of new materials and catalysts.

Upstream product

• 16940-66-2 sodium tetrahydroborate 
• 7087-68-5 N-ethyl-N,N-diisopropylamine 
• 24270-55-1 ammonium sulfate 
• 7664-41-7 ammonia 
• 19287-45-7 diborane 
• 121-43-7 Trimethyl borate 

Relevant articles and documents

Activation of sodium borohydride via carbonyl reduction for the synthesis of amine- And phosphine-boranes

A highly versatile synthesis of amine-boranes via carbonyl reduction by sodium borohydride is described. Unlike the prior bicarbonate-mediated protocol, which proceeds via a salt metathesis reaction, the carbon dioxide-mediated synthesis proceeds via reduction to a monoformatoborohydride intermediate. This has been verified by spectroscopic analysis, and by using aldehydes and ketones as the carbonyl source for the activation of sodium borohydride. This process has been used to produce borane complexes with 1°-, 2°-, and 3°-amines, including those with borane reactive functionalities, heteroarylamines, and a series of phosphines.

The role of ammonia in promoting ammonia borane synthesis

Ammonia promotes the synthesis of pure ammonia borane (AB) in excellent yields from sodium borohydride and ammonium sulfate in tetrahydrofuran under ambient conditions. An examination of the influence of added ammonia reveals that it is incorporated into the product AB, contrary to its perceived function as a catalyst or a co-solvent. Mechanistic studies point to a nucleophilic attack by ammonia on ammonium borohydride with concurrent dehydrogenation to yield AB.

Electrophilic C-H borylation and related reactions of B-H boron cations

Catalytic procedures are described for the amine-directed borylation of aliphatic and aromatic tertiary amine-boranes. Sequential double borylation is observed in cases where two or more C-H bonds are available that allow 5-center or 6-center intramolecular borylation. The HNTf2-catalyzed borylation of benzylamine-boranes provides a practical means for the synthesis of ortho-substituted arylboronic acid derivatives, suitable for Suzuki-Miyaura cross-coupling applications.

One-pot synthesis of ammonia-borane and trialkylamine-boranes from trimethyl borate

A one-pot procedure for the preparation of ammonia borane from trimethyl borate in 90% yield and >99% purity has been reported. This methodology has been modified to prepare a series of trialkylamine-boranes in 70-82% yields from trimethyl borate and lithium hydride/aluminum chloride in the presence of the corresponding trialkylamine.