4856-95-5

Usage

Uses

Used in Chemical Synthesis:
Morpholineborane is used as a reducing agent for the synthesis of various compounds, including aldehydes and ketones. It is particularly effective in acid media where other reducing agents fail to perform due to their instability.
Used in Fossil Fuel and Steam Systems:
In the energy industry, Morpholineborane is used as a pH adjustment additive, functioning as a corrosion inhibitor in fossil fuel and steam systems. This application helps to protect equipment and infrastructure from the damaging effects of corrosion, thereby extending their lifespan and ensuring efficient operation.
Used in Ethanolysis:
Morpholineborane is involved in the ethanolysis process, where it produces a reducing system. This process is crucial for the synthesis of various chemicals and materials.
Used in the Synthesis of Rh Nanoparticle/Carbon Nanotube Catalysts:
Morpholineborane serves as a reducing agent in the synthesis of Rh nanoparticle and carbon nanotube catalysts. These catalysts are essential in various chemical reactions and industrial processes, contributing to the production of a wide range of products.
Used in the Reduction of Steroidal Ketones:
In the pharmaceutical industry, Morpholineborane is utilized for the stereoselective and regioselective reduction of steroidal ketones. This selective reduction is vital for the synthesis of specific steroidal compounds with desired properties and applications.
Used in Methanolic Cleavage:
Morpholineborane is also employed in the methanolic cleavage process, where it aids in the breaking down of certain chemical bonds. This application is significant in the synthesis of various organic compounds and materials.

InChI:InChI=1/C4H9NO.B.3H/c1-3-6-4-2-5-1;;;;/h5H,1-4H2;;;;/q;+3;3*-1

Upstream product

• 110-91-8 morpholine 
• 19287-45-7 diborane 
• 16940-66-2 sodium tetrahydroborate 
• 109-63-7 trifluoroborane diethyl ether 
• 10024-89-2 morpholin hydrochloride 
• 14905-85-2 morpholino carbamate 
• 10043-11-5 borane-ammonia complex 

Downstream Products

• 23328-69-0 4-chloromorpholine 
• 16887-00-6 chloride 
• 45422-42-2 morpholinium 
• 1333-74-0 hydrogen 
• 11113-50-1 boric acid 
• 110-91-8 morpholine 
• 150-46-9 triethyl borate 
• 63833-44-3 morpholino(p-tolyl)methanone 
• 1468-28-6 4-benzoylmorpholine 

Relevant academic research and scientific papers

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

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.

Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids

Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.

Amine-boranes bearing borane-incompatible functionalities: Application to selective amine protection and surface functionalization

The first general open-flask synthesis of amine-boranes with inexpensive and readily available reagents, such as sodium borohydride, sodium bicarbonate, water, and the desired amines is described. Even amines bearing borane-reactive functionalities, such as alkene, alkyne, hydroxyl, thiol, ester, amide, nitrile, and nitro are well tolerated. Some of these novel amine-boranes represent stable molecules containing potentially incompatible electrophilic and nucleophilic centers in proximity. This convenient scalable synthesis provides a novel class of organic ligands for surface functionalization, as demonstrated by the formation of self-assembled layers of thiol- and alkoxysilane-bearing amine-boranes on gold and silica surfaces, respectively.

PREPARATION OF AMINE-BORANES, INCLUDING AMMONIA BORANE

Disclosed herein is a method for preparing amine-boranes.

Open-Flask Synthesis of Amine-Boranes via Tandem Amine-Ammonium Salt Equilibration-Metathesis

An amine-ammonium salt equilibration-metathesis sequence provides high-purity amine-boranes in excellent yields from sodium borohydride in refluxing reagent-grade tetrahydrofuran in an open flask.

Nucleophilic displacement of ammonia from ammonia borane for the preparation of alkylamine-, pyridine- and phosphine-boranes

A near quantitative and safe preparation of a series of aliphatic amine- and phosphine-boranes from ammonia borane (AB) in refluxing THF has been achieved by exploiting the volatility of ammonia. A one-pot preparation of lithium aminoborohydrides from AB has also been described.

Amine-Boranes: Green hypergolic fuels with consistently low ignition delays

Complexation of amines with borane converts them to hypergols or decreases their ignition delays (IDs) multifold (with white fuming nitric acid as the oxidant). With consistently low IDs, amine-boranes represent a class of compounds that can be promising alternatives to toxic hydrazine and its derivatives as propellants. A structure-hypergolicity relationship study reveals the necessary features for the low ID.

Crown-ether-catalysed synthesis of amine borane and amine trideuterioborane adducts from NaBH4-NaBD4 in ether

Amine borane and amine trideuterioborane adducts have been obtained in good yield by the crown-ether-catalysed reaction of R3N*HCl with NaBH4 and NaBD4 in ether.The absence of isotopic exchange in the reaction with NaBD4 is demonstrated by IR and 11B and

Molecular addition compounds. 9. Effect of structure on the reactivities of representative borane-amine complexes in typical reactions such as hydrolysis, hydroboration, and reduction

A number of borane-amine complexes with widely different structural features in the amine portion was prepared and their reactivities toward typical B-H reactions, such as hydrolysis, hydroboration of 1-octene, and reduction of cyclohexanone, were studied. BH3-amine complexes containing an N-phenyl group are hydrolyzed by neutral hydroxylic solvents, while others require a strong acid medium for the hydrolysis. In hydroboration, BH3-N-phenylamine complexes react rapidly with 1-octene in THF at 25°C, while all other types require refluxing THF or toluene for reaction. Again, BH3-N-phenylamine complexes reduce cyclohexanone in THF at 25°C at reasonable rates, while others require acetic acid solvent or mineral or Lewis acids to achieve the desired reduction. Thus, among such borane-amine addition compounds, the BH3-N-phenylamines emerge as unique hydroborating and reducing agents. The results of the present study provide insights into the mechanisms of the hydroboration and reduction reactions. The rates of hydroboration of alkenes with BH3-amine complexes are inversely related to the stability of the adduct, arguing for a prior dissociation of the adduct, followed by the reaction of BH3 with the alkene. The reduction of cyclohexanone with BH3-amine complex in THF proceeds by an analogous dissociation mechanism. In acetic acid or in the presence of mineral or Lewis acids, a bimolecular attack of the BH3-amine complex on the protonated carbonyl group has been considered to be the most viable mechanistic pathway. However, this does not account for the effect of acids on hydrolytic behavior. Consequently, caution is urged in considering possible interpretation of the acid-enhanced reactions of amine-boranes.