34636-09-4

Usage

Uses

Used in Epoxy Resin Industry:
Benzyldiisopropylamine is used as a curing agent for epoxy resins, where it functions to harden the resin and enhance the mechanical and chemical properties of the final product. This application is crucial in the production of epoxy adhesives, coatings, and sealants, ensuring their durability and performance.
Used in Organic Synthesis:
In the realm of organic synthesis, Benzyldiisopropylamine serves as a stabilizer and inhibitor, contributing to the controlled progression of chemical reactions and the prevention of unwanted side reactions. This role is essential for maintaining the quality and yield of synthesized products.
Used as an Intermediate in Chemical Synthesis:
Benzyldiisopropylamine is utilized as an intermediate in the synthesis of a range of chemicals, including pharmaceuticals, agricultural chemicals, and other specialty chemicals. Its presence in these synthesis processes is vital for the creation of diverse and complex chemical compounds.
Safety Considerations:
It is important to handle Benzyldiisopropylamine with care due to its potential to cause irritation to the skin, eyes, and respiratory system. Proper safety measures should be implemented during its use to minimize health risks to individuals involved in its application.

InChI:InChI=1/C13H21N/c1-11(2)14(12(3)4)10-13-8-6-5-7-9-13/h5-9,11-12H,10H2,1-4H3

Upstream product

• 100-52-7 benzaldehyde 
• 108-18-9 diisopropylamine 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 67-64-1 acetone 
• 100-46-9 benzylamine 
• 4111-54-0 lithium diisopropyl amide 
• 100-44-7 benzyl chloride 
• 10342-97-9 N,N-diisopropylmethylamine 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 220928-32-5 4-benzyl-3H-bis[1,2]dithiolo[4,3-b:3',4'-d]pyrrole-3,5(4H)-dithione 
• 220928-28-9 4-Benzyl-3H,4H,5H-bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5-dione 
• 250379-51-2 N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)benzylamine 
• 220928-33-6 4-Benzyl-3H-bis[1,2]dithiolo[4,3-b:3,4-d]pyrrole-3,5(4H)-dione 
• 318295-43-1 4-Benzyl-3H,4H,5H-bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5-dithione 
• 54166-20-0 3,3-diphenylcyclobutanone 
• 871943-76-9 C₁₃H₂₀N⁽¹⁺⁾*I^(1-) 
• 73732-23-7 N,N-diisopropyl-4-methylbenzenesulfonamide 
• 102-97-6 Benzyl-isopropyl-amin 
• 1232167-50-8 1-methyl-3-phenethylindolin-2-one 

Relevant academic research and scientific papers

Preparation and reactivity of terminal gold(i) amides and phosphides

Nucleophilic terminal gold(i) amides have been prepared and their reactivity toward a variety of electrophiles has been explored. For the first time these frequently proposed intermediates were isolated and shown to be unreactive in the amination of π-bonds. The first crystallographically determined terminal group 11 metal phosphide was also synthesized. Preliminary DFT studies have been conducted to understand the structure and reactivity of these complexes.

BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant

A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.

Desymmetric enantioselective reduction of cyclic 1,3-diketones catalyzed by a recyclable p-chiral phosphinamide organocatalyst

The P-stereogenic phosphinamides are a structurally novel skeletal class which has not been investigated as chiral organocatalysts. However, chiral cyclic 3-hydroxy ketones are widely used as building blocks in the synthesis of natural products and bioactive compounds. However, general and practical methods for the synthesis of such chiral compounds remain underdeveloped. Herein, we demonstrate that the P-stereogenic phosphinamides are powerful organocatalysts for the desymmetric enantioselective reduction of cyclic 1,3-diketones, providing a useful method for the synthesis of chiral cyclic 3-hydroxy ketones. The protocol displays a broad substrate scope that is amenable to a series of cyclic 2,2-disubstituted five- and six-membered 1,3-diketones. The chiral cyclic 3-hydroxy ketone products bearing an all-carbon chiral quaternary center could be obtained with high enantioselectivities (up to 98% ee) and diastereoselectivities (up to 99:1 dr). Most importantly, the reactions could be practically performed on the gram scale and the catalysts could be reused without compromising the catalytic efficiency. Mechanistic studies revealed that an intermediate formed from P-stereogenic phosphinamide and catecholborane is the real catalytically active species. The results disclosed herein bode well for designing and developing other reactions using P-stereogenic phosphinamides as new organocatalysts.

Cine-Silylative Ring-Opening of α-Methyl Azacycles Enabled by the Silylium-Induced C-N Bond Cleavage

Described herein is the development of a borane-catalyzed cine-silylative ring-opening of α-methyl azacycles. This transformation involves four-step cascade processes: (i) exo-dehydrogenation of alicyclic amine, (ii) hydrosilylation of the resultant enamine, (iii) silylium-induced cis-β-amino elimination to open the ring skeleton, and (iv) hydrosilylation of the terminal olefin. The present borane catalysis also works efficiently for the C-N bond cleavage of acyclic tertiary amines. On the basis of experimental and computational studies, the silicon atom was elucidated to play a pivotal role in the β-amino elimination step.

Reduction of Amides to Amines under Mild Conditions via Catalytic Hydrogenation of Amide Acetals and Imidates

A simple and general protocol was developed for selective conversion of amides into amines. Amides were converted into amide acetals and imido esters by O-alkylation and then hydrogenated without isolation into amines under very mild reaction conditions over standard hydrogenation catalysts. Triethyloxonium tertafluoroborate, methyl trifluoromethanesulfonate, dimethyl sulfate and ethyl chloroformate were validated as alkylating agent. The synthetic utility of this approach was demonstrated by the selective carbonyl reduction of peptide groups. Carbonyl reduction of peptide group proceeds chemoselective without racemization of the neighboring chiral center. (Figure presented.).

Direct Reductive Amination of Carbonyl Compounds Catalyzed by a Moisture Tolerant Tin(IV) Lewis Acid

Despite the ever-broadening applications of main-group ‘frustrated Lewis pair’ (FLP) chemistry to both new and established reactions, their typical intolerance of water, especially at elevated temperatures (>100 °C), represents a key barrier to their mainstream adoption. Herein we report that FLPs based on the Lewis acid iPr3SnOTf are moisture tolerant in the presence of moderately strong nitrogenous bases, even under high temperature regimes, allowing them to operate as simple and effective catalysts for the reductive amination of organic carbonyls, including for challenging bulky amine and carbonyl substrate partners. (Figure presented.).

Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines

This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).

Expanding the Boundaries of Water-Tolerant Frustrated Lewis Pair Hydrogenation: Enhanced Back Strain in the Lewis Acid Enables the Reductive Amination of Carbonyls

The development of a boron/nitrogen-centered frustrated Lewis pair (FLP) with remarkably high water tolerance is presented. As systematic steric tuning of the boron-based Lewis acid (LA) component revealed, the enhanced back-strain makes water binding increasingly reversible in the presence of relatively strong base. This advance allows the limits of FLP's hydrogenation to be expanded, as demonstrated by the FLP reductive amination of carbonyls. This metal-free catalytic variant displays a notably broad chemoselectivity and generality.

REACTIONS OF STANNYL CATIONS

The present invention relates to a method of reducing, cleaving and/or coupling at least one C=O, C-O, C=C or C=N bond of a compound, using a reagent comprising a stannyl cation.

The synthesis of sterically hindered amines by a direct reductive amination of ketones

An atom-economical methodology for the synthesis of sterically hindered tertiary amines was developed, which is based on complementary Rh- and Ru-catalyzed direct reductive amination of ketones with primary and secondary amines using carbon monoxide as a deoxygenating agent.