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Borane-N,N-diethylaniline is typically referred to as a borane-amine complex, which belongs to a class of reagents that are widely used in organic synthesis, particularly in reduction reactions.
Borane-N,N-diethylaniline is a chemical complex formed by the combination of borane (BH₃), a reactive and electron-deficient compound, with N,N-diethylaniline, an organic amine that acts as a Lewis base due to the lone pair of electrons on its nitrogen atom.
Borane-N,N-diethylaniline is in the reduction of carbonyl-containing functional groups, such as aldehydes, ketones, esters, and carboxylic acids, converting them into alcohols.
CAS Number: 13289-97-9
Molecular Formula: C10H18BN
Molecular Weight: 163.07
EINECS Number: 236-305-2
Synonyms: Boron, (N,N-diethylbenzenamine)trihydro-, (T-4)-, (N,N-Diethylaniline)trihydroboron, NSC 239123, EINECS 236-305-2, DTXSID8065400, (T-4)-(N,N-Diethylbenzenamine)trihydroboron, DTXCID2034120, 236-305-2, 13289-97-9, N,N-Diethylaniline Borane, N,N-Diethylanilineborane, Borane-N,N-Diethylaniline, Diethylphenylamine-borane, (Diethyl(phenyl)ammonio)trihydroborate, 1104455-83-5, diethylaniline borane, boron, N,N-diethylaniline, MFCD00013187, borane diethylaniline, borane-N,N-diethyl aniline, SCHEMBL184484, 26K6GV6T5D, SCHEMBL5585967, KHYAFFAGZNCWPT-UHFFFAOYSA-N, N,N-Diethylaniline borane complex, YPWBYWNNJVSNPQ-UHFFFAOYSA-N, BCP13080, AKOS015833632, AS-55590, DB-042145, D2581, Borane, compd. with N,N-diethylaniline (1:1), D78343, F14239, BORANE-N,N-DIETHYLANILINE, BORANE-N,N-DIETHYLANILINE COMPLEX, N,N-DIETHYLANILINE BORANE, n,n-diethylanilineborane,deanb, n-diethylbenzenamine)trihydro-((beta-4)-boro, (N,N-diethylaniline)trihydroboron, Borane-N,N-diethylaniline complex,97%, N, N diethylaniline borane complex
Borane-N,N-diethylaniline, also known as N-Phenyldiethylamine, is used as an intermediate in the manufacture of pharmaceuticals, dyes, and other chemicals.
Ungraded products supplied by TCI America are generally suitable for common industrial uses or for research purposes but typically are not suitable for human consumption or therapeutic use.
In this complex, the nitrogen atom of the diethylaniline molecule donates a pair of electrons to the empty orbital of the boron atom, creating a dative covalent bond and stabilizing the otherwise highly reactive borane species.
Borane-N,N-diethylaniline is a coordination complex composed of borane (BH₃) and N,N-diethylaniline, an organic compound that features a benzene ring substituted with a nitrogen atom bonded to two ethyl groups.
In this complex, the nitrogen atom of N,N-diethylaniline donates a lone pair of electrons to the electron-deficient boron atom of borane, forming a Lewis acid–base adduct.
This interaction not only stabilizes the highly reactive borane molecule but also enhances its solubility and handling properties, making it a practical reagent for synthetic organic chemistry.
Borane itself is a highly reactive molecule that tends to form dimers (B₂H₆) or polymers when isolated, due to its electron deficiency and instability.
By forming a complex with a tertiary amine like Borane-N,N-diethylaniline, borane is effectively "tamed," allowing it to be used under more manageable laboratory conditions without the need for high-pressure containment or specialized storage.
The complex is typically a stable, air-sensitive compound, often stored as a solution in an anhydrous organic solvent such as tetrahydrofuran (THF) or dichloromethane, and must be protected from moisture and oxygen to prevent hydrolysis or oxidation.
The borane–N,N-diethylaniline complex serves as a milder and more easily handled alternative to gaseous borane, which is toxic, flammable, and difficult to store safely.
Because the amine stabilizes the borane, the complex is often easier to weigh, store, and dissolve in organic solvents, making it practical for laboratory and industrial use.
Borane-N,N-diethylaniline can also be used in the hydroboration of alkenes and alkynes, where the boron atom adds across a double or triple bond, leading to the formation of organoboranes, which are valuable intermediates in organic chemistry.
Borane-N,N-diethylaniline is usually a colorless to light yellow liquid or solid, depending on purity and temperature, and should be handled under inert atmosphere conditions (e.g., nitrogen or argon), as it can be sensitive to air and moisture, potentially leading to decomposition or unwanted side reactions.
Borane-N,N-diethylaniline is a well-defined chemical complex created by the coordination of borane (BH₃), a highly reactive and electron-deficient molecule, with N,N-diethylaniline, an aromatic tertiary amine in which the nitrogen atom is bonded to two ethyl groups and one phenyl ring.
The nitrogen atom of the N,N-diethylaniline molecule donates a lone electron pair to the empty p-orbital of the boron atom in borane, forming a stable dative covalent bond (also called a coordinate bond), which helps stabilize the otherwise volatile borane species.
This type of borane–amine complex plays a crucial role in organic chemistry because borane alone is a dangerous, unstable gas, and must be stabilized for safe use in the laboratory or industrial environments.
By forming a complex with amines like N,N-diethylaniline, borane becomes a bench-stable reagent, meaning it can be handled at room temperature in liquid or solid form under inert conditions, without the need for specialized gas-handling equipment.
This stabilization dramatically broadens its applicability and convenience in synthetic protocols.
Borane-N,N-diethylaniline is a versatile, efficient, and safer alternative to free borane, prized for its role in chemoselective reductions, hydroboration, and organoboron chemistry.
Its ability to combine high reactivity with manageable stability has made it a cornerstone reagent in advanced organic synthesis, contributing significantly to progress in pharmaceuticals, materials science, and fine chemical manufacturing.
Borane-N,N-diethylaniline is a stable borane–amine complex that allows chemists to harness the powerful reducing and synthetic capabilities of borane in a more controlled, safer, and user-friendly form, making it a valuable reagent in both academic research and industrial chemical processes.
Borane–N,N-diethylaniline retains the reactivity of borane, particularly its ability to function as a reducing agent and participate in hydroboration reactions.
This complex is widely used for the reduction of a wide variety of functional groups, including aldehydes, ketones, carboxylic acids, esters, amides, nitriles, and even epoxides, converting them to the corresponding alcohols or amines under relatively mild conditions.
The reagent is especially useful in chemoselective reductions, where specific functional groups can be targeted without affecting others in the same molecule.
Melting Point: −30 to −27 °C (lit.)
Density: 0.917 g/mL at 25 °C (lit.)
Refractive Index: 1.5245 – 1.5265
Flash Point: 70 °F
Storage Temperature: Refrigerator
Form: Liquid
Color: Clear colorless to yellow
Water Solubility: May decompose
Borane-N,N-diethylaniline must be handled with extreme caution.
Like all borane reagents, it is highly flammable, and its vapors may form explosive mixtures with air.
Borane-N,N-diethylaniline is also toxic if inhaled, ingested, or absorbed through the skin, and can cause serious burns and respiratory irritation.
Borane-N,N-diethylaniline should only be used in fume hoods with proper personal protective equipment (PPE), and any spills or exposure should be addressed immediately using appropriate safety protocols.
Borane-N,N-diethylanilines are also used in the synthesis of boron-containing polymers, doping agents for semiconductors, or as precursors to boron-containing catalysts, due to their ability to donate boron atoms in a controlled manner.
Another important use of this complex is in hydroboration, a reaction where boron adds across the carbon–carbon double or triple bonds in alkenes or alkynes, forming organoboranes that can later be oxidized or transformed into alcohols, halides, or other valuable intermediates.
The regioselectivity and stereoselectivity of hydroboration reactions can be fine-tuned by the choice of borane complex, making Borane–N,N-diethylaniline a valuable reagent in asymmetric synthesis, natural product synthesis, and medicinal chemistry.
Borane–N,N-diethylaniline is best known for its use as a powerful and selective reducing agent.
Borane-N,N-diethylaniline is commonly employed in the reduction of polar functional groups, particularly carbonyl-containing compounds such as aldehydes, ketones, carboxylic acids, and esters.
Under the right conditions, it can even reduce nitriles, amides, and oximes, giving access to a variety of alcohols and amines, depending on the substrate and reaction setup.
Unlike harsher reducing agents such as lithium aluminum hydride (LiAlH₄), which often require strong basic conditions and produce violent reactions with water, borane–amine complexes offer gentler, more controlled reductions and can be used in solvents like THF, diglyme, or dichloromethane.
Borane-N,N-diethylaniline is a powerful and versatile reagent in modern chemistry, enabling a wide range of reductions and synthetic transformations that would be difficult or hazardous with free borane alone.
Borane-N,N-diethylanilines formation as a complex with N,N-diethylaniline allows it to be stored, handled, and applied more safely and precisely, making it indispensable in both research laboratories and certain industrial chemical processes.
Another prominent application of this complex lies in hydroboration reactions, where the borane adds across the carbon–carbon multiple bonds of alkenes and alkynes, leading to the formation of organoborane intermediates.
These intermediates are highly useful and can be further transformed into alcohols, halides, amines, or other functional groups through oxidative or substitution reactions.
Hydroboration using Borane–N,N-diethylaniline is often highly regioselective and stereoselective, making it a valuable strategy in asymmetric synthesis, particularly for building chiral centers in complex organic molecules, including pharmaceuticals, agrochemicals, and natural products.
Beyond standard reduction and hydroboration chemistry, this borane complex is also useful in metal-catalyzed processes and has been explored in the synthesis of boron-containing polymers, flame retardants, and electronic materials.
Due to its ability to donate boron in a controlled manner, it may serve as a precursor to other boron-containing compounds used in catalysis or materials engineering.
Despite these advantages, the compound is not without hazards.
Borane-N,N-diethylaniline is highly flammable and reactive, especially with air and moisture, and may release hydrogen gas or undergo spontaneous ignition if handled improperly.
Borane-N,N-diethylaniline also poses significant health risks, as both borane and amines can be toxic or irritating to the skin, eyes, and respiratory system, especially in vapor form.
Borane-N,N-diethylaniline must always be handled with strict safety precautions, including the use of fume hoods, inert atmosphere (such as nitrogen or argon), protective gloves, and goggles, along with emergency protocols for spills and exposure.
Uses:
Borane–N,N-diethylaniline span across several important domains of chemistry, including selective reductions, hydroboration, reductive amination, asymmetric synthesis, and materials development, making it a highly versatile and valuable reagent in both research laboratories and industrial-scale chemical production.
Borane-N,N-diethylaniline is primarily used as a reagent in organic synthesis, where it plays a vital role in facilitating highly selective reduction reactions of various functional groups under mild and controlled conditions.
One of its most important applications is in the reduction of carbonyl-containing compounds—such as aldehydes, ketones, esters, carboxylic acids, and amides—to their corresponding alcohols or amines, which are key intermediates in the production of pharmaceuticals, agrochemicals, fine chemicals, and polymers.
Because this borane complex is a gentler alternative to more reactive reducing agents like lithium aluminum hydride (LiAlH₄), it is often preferred in synthetic processes that require functional group selectivity, where certain parts of a molecule must be transformed without disturbing others.
Borane-N,N-diethylaniline can reduce a carboxylic acid to an alcohol while leaving ketones or esters in the same molecule untouched, a capability that is crucial in multi-step organic synthesis where precision is essential.
Another major use of Borane-N,N-diethylaniline lies in hydroboration reactions, where it reacts with alkenes and alkynes by adding across their double or triple bonds to form organoborane intermediates.
These intermediates can then be converted into alcohols, alkyl halides, or amines, or be used in cross-coupling reactions to form new carbon–carbon bonds.
This makes the compound extremely valuable in the synthesis of chiral alcohols, complex natural products, and medicinal compounds, particularly when regioselectivity and stereochemistry are critical.
In asymmetric synthesis, Borane-N,N-diethylaniline has been used in combination with chiral auxiliaries or catalysts to introduce chirality into organic molecules, enabling the selective production of enantiomerically pure compounds, which are essential in the pharmaceutical industry where the biological activity of a drug often depends on its stereochemistry.
Beyond reductions and hydroboration, this complex is also employed in reductive amination reactions, where it facilitates the formation of amines from aldehydes or ketones in the presence of amines, offering a clean, efficient route to a wide variety of substituted amines.
This reaction is commonly used in the development of active pharmaceutical ingredients (APIs), dyes, and specialty chemicals.
In addition to its uses in synthetic organic chemistry, Borane–N,N-diethylaniline has been explored in materials science as a precursor to boron-containing polymers, boron-doped semiconductors, and flame-retardant materials, due to its ability to donate boron in a controlled fashion.
In such applications, it is often used in thin-film deposition, ceramic material synthesis, or polymer modification, where boron’s electronic and structural properties are desirable.
In academic and industrial laboratories, it is often chosen for its ease of handling compared to gaseous borane, its solubility in common organic solvents, and its ability to perform reactions under milder, less hazardous conditions, which improves safety, scalability, and environmental compatibility in chemical processes.
Borane–N,N-diethylaniline serves as a highly effective and versatile reagent in a broad spectrum of synthetic organic chemistry applications, where its unique ability to provide controlled and selective reduction is exploited to transform a wide variety of functional groups into more reactive or valuable derivatives.
Its use is particularly prevalent in the pharmaceutical industry, where it enables the selective reduction of sensitive compounds without causing unwanted side reactions or degradation of delicate molecular frameworks, thus facilitating the synthesis of complex drug molecules with high purity and yield.
One of the foremost applications of this complex is in the chemoselective reduction of carboxylic acids and their derivatives to alcohols, a transformation that often presents significant challenges with more aggressive reagents.
The gentle nature of Borane–N,N-diethylaniline allows it to achieve such conversions without affecting other reducible groups such as ketones or aldehydes within the same molecule, thereby streamlining synthetic routes and minimizing the need for protection and deprotection steps during multi-stage synthesis.
Additionally, this reagent excels in the hydroboration of alkenes and alkynes, where it facilitates the regio- and stereoselective addition of boron and hydrogen across carbon–carbon multiple bonds.
The resulting organoborane intermediates are versatile synthetic building blocks that can be further transformed into alcohols, halides, or cross-coupling partners, enabling the construction of complex carbon skeletons with precise control over the three-dimensional arrangement of atoms.
This is especially important in the preparation of chiral centers in natural products, agrochemicals, and pharmaceuticals, where the biological activity of the final compound depends heavily on its stereochemistry.
Borane–N,N-diethylaniline is also employed in reductive amination protocols, a powerful method for synthesizing substituted amines, which are ubiquitous in pharmaceuticals, dyes, and fine chemicals.
By reducing imines or iminium intermediates formed in situ from aldehydes or ketones and amines, this complex provides a clean and efficient route to diverse amine compounds under relatively mild conditions, often with excellent selectivity and minimal by-product formation.
In the realm of asymmetric synthesis, when combined with chiral ligands or auxiliaries, Borane–N,N-diethylaniline enables the synthesis of enantiomerically enriched molecules, a critical requirement for producing safer and more effective drugs.
This reagent's compatibility with various chiral catalysts makes it a cornerstone in methodologies aimed at constructing molecules with high stereochemical fidelity.
Beyond synthetic organic chemistry, the compound’s ability to donate boron atoms in a controlled manner renders it useful in materials chemistry and polymer science.
Borane-N,N-diethylaniline acts as a precursor in the synthesis of boron-containing polymers, flame retardants, and boron-doped semiconductor materials, where precise control over boron incorporation is necessary to tune the material properties such as conductivity, thermal stability, or chemical resistance.
In advanced material fabrication, Borane–N,N-diethylaniline can be used in processes like chemical vapor deposition (CVD) or thin-film preparation, where its volatility and reactivity are harnessed to create uniform coatings or layers with specific electronic or mechanical characteristics.
From a practical standpoint, this complex is favored in both laboratory and industrial settings because it is significantly easier and safer to handle than gaseous borane, which requires specialized equipment and conditions.
Its solubility in common organic solvents allows it to be readily incorporated into standard reaction protocols, improving reproducibility and scalability.
Additionally, its relatively mild reaction conditions translate to reduced energy consumption, fewer hazardous by-products, and increased operator safety, aligning with green chemistry principles.
Safety Profile:
Borane-N,N-diethylaniline presents several significant hazards due to its chemical nature as a borane–amine complex, which combines the reactive and potentially dangerous properties of both borane and organic amines.
One of the primary hazards associated with this compound is its high flammability and pyrophoricity, meaning that it can ignite spontaneously upon exposure to air or moisture.
This property requires that it be handled only under strict inert atmosphere conditions—such as in a glove box or under a nitrogen or argon blanket—to prevent accidental ignition or fire.
In addition to its flammability, Borane–N,N-diethylaniline is highly reactive with water and moisture, producing hydrogen gas upon contact, which not only increases the risk of fire and explosion but can also lead to pressure buildup in closed containers.
This reaction also results in the release of corrosive and potentially toxic by-products, making spills and accidental releases dangerous to both personnel and the environment.
Borane-N,N-diethylaniline is also considered toxic and harmful if inhaled, ingested, or absorbed through the skin. Exposure to its vapors or aerosols can cause severe respiratory irritation, coughing, difficulty breathing, and potential lung damage.
Direct skin contact may result in chemical burns, redness, and blistering, while eye exposure can cause severe irritation, pain, and possible long-term damage.
Because it contains an organic amine, there is also the possibility of sensitization or allergic reactions in susceptible individuals.
