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Borane-N,N-diethylaniline is widely utilized in organic synthesis as a reducing agent and catalyst.
Borane-N,N-diethylaniline is used in hydroboration reactions.
Borane-N,N-diethylaniline is effectively reduces carboxylic acids to corresponding alcohols.
CAS Number: 13289‑97‑9
EC (EINECS) Number: 236‑305‑2
PubChem Substance ID: 24850794
Molecular Formula: C₁₀H₁₅B N (C₆H₅N(C₂H₅)₂·BH₃)
Molecular Weight: ~163.07 g/mol
SYNONYMS:
Borane‑N,N‑diethylaniline complex, N,N‑Diethylaniline borane, N,N‑Diethylanilineborane, Diethylphenylamine‑borane, N,N‑diethylaniline)trihydroboron, Boron N,N‑diethylaniline, ANIL, DEANB, (N,N-Diethylaniline)trihydroboron, Diethylphenylamine-borane, NSC 239123, N,N-Diethylanilineborane, (N,N-diethylaniline)(trihydrido)boron, boron,N,N-diethylaniline, N,N-diethylanilinium, Borane N,N-Diethylaniline complex, Borane N,N-Diethylaniline, (N,N-diethylaniline)trihydroboron, Diethylphenylamine-borane, aniL, N,N-DIETHYLANILINE BORANE, ine compL, Borane-N,N-diethyL, boron,N,N-diethylaniline, BORANE-N,N-DIETHYLANILINE, Diethylphenylamine-borane, N,N-DiethylanilineBorane>n,n-diethylanilineborane,deanb, Borane-N,N-diisopropylethylmine, n,n-diethylaniline borane, borane-n,n-diethylaniline complex, borane-n,n-diethylaniline, n,n-diethylanilineborane, diethylaniline borane, n,n-diethylaniline trihydroboron, n.n diethylanilineborane, boron, n,n-diethylaniline, boron, n,n-diethylbenzenamine trihydro-, t-4, borane n,n-diethylaniline complex, 12084-74-1, 13289-97-9, 179043_ALDRICH, 188582-63-0, 84145-49-3, Borane N,N-diethylaniline complex, Borane, N,N-diethylaniline complex, boron, diethyl(phenyl)amine, boron, N,N-diethylaniline, Boron, (N,N-diethylbenzenamine)trihydro-, (T-4)-, C10H15BN, EINECS 236-305-2, (N,N-Diethylaniline)trihydroboron, NSC 239123, N,N-Diethylaniline - borane (1:1), EINECS 236-305-2, Borane, N,N-diethylaniline complex, (N,N-Diethylaniline)trihydroboron, Diethylphenylamine-borane, Benzenamine, N,N-diethyl-, compd. with borane (1:1), Borane-N,N-diethylaniline complex, AcroSeal, Borane-N,N-diethylaniline complex, N,N-Diethylaniline borane, boron, N,N-diethylaniline, MFCD00013187, (N,N-DIETHYLANILINE)TRIHYDROBORON, (T-4)-(N,N-DIETHYLBENZENAMINE)TRIHYDROBORON, BORON, (N,N-DIETHYLBENZENAMINE)TRIHYDRO-, (T-4)-, BORANE, COMPD. WITH N,N-DIETHYLANILINE (1:1), BORANE-N,N-DIETHYLANILINE, DIETHYLPHENYLAMINE-BORANE, N,N-DIETHYLANILINE BORANE COMPLEX, NSC-239123, N,N-diethylanilinium, N,N-Diethylanilineborane, boron, N,N-diethylaniline, BORANE-N,N-DIETHYLANILINE, N,N-DIETHYLANILINE BORANE, n,n-diethylanilineborane, deanb, BORANE-N,N-DIETHYLANILINE COMPLEX, (N,N-diethylaniline)trihydroboron, Borane-N,N-diethylaniline complex, N, N diethylaniline borane complex, (N,N-diethylaniline)(trihydrido)boron, n-diethylbenzenamine)trihydro-((beta-4)-boro
Borane-N,N-diethylaniline is a liquid borane complex (mp ~–30 °C), used as a selective, stable reducing agent in organic chemistry.
Borane-N,N-diethylaniline is a clear colorless to amber liquid.
Borane-N,N-diethylaniline, also known as N-Phenyldiethylamine, is used as an intermediate in the manufacture of pharmaceuticals, dyes, and other chemicals.
Borane-N,N-diethylaniline is an organoboron compound with the molecular formula C₁₀H₁₈BN and a molecular weight of 160.04–163.07 g/mol.
Borane-N,N-diethylaniline exists as a moisture-sensitive, colorless to pale yellow liquid at room temperature, with a boiling point of 213.5°C and a melting point range of -30 to -27°C.
Borane-N,N-diethylaniline is soluble in aprotic solvents such as tetrahydrofuran (THF) and methyl tert-butyl ether (MTBE) but decomposes in protic solvents like water.
USES and APPLICATIONS of BORANE-N,N-DIETHYLANILINE:
Borane-N,N-diethylaniline is employed for diastereoselective reductions of prochiral enones and ketones.
Borane-N,N-diethylaniline is used in borylation of aryl halides.
Borane-N,N-diethylaniline commonly reduces ketones, carboxylic acids, esters, amides, nitriles to alcohols or amines.
Borane-N,N-diethylaniline is applied in enantioselective reductions (e.g., CBS reductions) as a borane source.
Borane-N,N-diethylaniline serves as a research-use reagent for borane-mediated synthetic transformations.
Borane-N,N-diethylaniline is widely utilized in organic synthesis as a reducing agent and catalyst.
Borane-N,N-diethylaniline is used in hydroboration reactions.
Enantioselective reduction of ketones in presence of oxazaborolidine catalyst.
Borane-N,N-diethylaniline is effectively reduces carboxylic acids to corresponding alcohols.
Borane-N,N-diethylaniline is intended solely for professional manufacturing, laboratories, industrial/commercial applications, and educational institutions.
Borane-N,N-diethylaniline is not for medical or personal use.
-Uses of Borane-N,N-diethylaniline:
***Reactant for:
*Diastereoselective reduction of prochiral enone intermediates.
*Borylation of aryl halides.
*Reductions of ketones, acids, esters, amides, and nitriles.
*Investigations of borane source on enantioselectivity in enantiopure oxazaborolidine-catalyzed asymmetric borane reduction of ketones.
***Reactant for synthesis of:
*Chromanol derivatives as CETP inhibitors for the treatment of cardiovascular disease.
*Allylic alcohols via enantioselective reductions.
*Pinacolboranes for one-pot synthesis of unsymmetrical biaryls.
SCIENTIFIC RESEARCH APPLICATIONS of BORANE-N,N-DIETHYLANILINE:
Key Applications
*Hydroboration Reactions
Borane-N,N-diethylaniline is widely used in hydroboration reactions, where it adds across double or triple bonds to form organoboranes.
This reaction is essential for the synthesis of alcohols and other functional groups from alkenes and alkynes under mild conditions.
*Reduction Reactions
Borane-N,N-diethylaniline serves as a reducing agent for various functional groups:
*Ketones and Aldehydes:
Effective in the reduction of prochiral enone intermediates and other carbonyl compounds.
*Carboxylic Acids and Esters:
Borane-N,N-diethylaniline reduces carboxylic acids to alcohols efficiently.
*Amides and Nitriles:
Capable of reducing these compounds to their respective amines.
*Borylation of Aryl Halides
Borane-N,N-diethylaniline is utilized in the borylation of aryl halides, facilitating the formation of aryl-boron compounds that are pivotal in cross-coupling reactions such as Suzuki reactions.
*Synthesis of Chromanol Derivatives
Borane-N,N-diethylaniline is involved in the synthesis of chromanol derivatives which act as CETP inhibitors, relevant for cardiovascular disease treatment.
*Enantioselective Reductions
Borane-N,N-diethylaniline has been employed in enantioselective reductions using oxazaborolidine catalysts, achieving high enantiomeric excess in various substrates.
CHEMICAL CHARACTERISTICS of BORANE-N,N-DIETHYLANILINE:
Borane-N,N-diethylaniline is a Lewis acid–base adduct: borane coordinated to N,N‑diethylaniline via nitrogen-lone pair.
Borane-N,N-diethylaniline functions as a reducing agent in organic synthesis, offering a stable and less volatile alternative to BH₃·THF or BH₃·DMS.
CHEMICAL REACTIONS ANALYSIS of BORANE-N,N-DIETHYLANILINE:
TYPES OF REACTIONS
Borane-N,N-diethylaniline undergoes various types of chemical reactions, including:
*Reduction Reactions:
Borane-N,N-diethylaniline can act as a reducing agent in the reduction of ketones, acids, esters, amides, and nitriles.
*Borylation Reactions:
Borane-N,N-diethylaniline is used in the borylation of aryl halides.
*Substitution Reactions:
Borane-N,N-diethylaniline can participate in substitution reactions with various reagents.
COMMON REAGENTS AND CONDITIONS of BORANE-N,N-DIETHYLANILINE:
*Reduction Reactions:
Common reagents include and .
*Borylation Reactions:
Reagents such as are used.
*Substitution Reactions:
Various nucleophiles and electrophiles can be employed.
*Major Products
The major products formed from these reactions depend on the specific reagents and conditions used.
For example, reduction reactions typically yield the corresponding alcohols, while borylation reactions produce borylated aromatic compounds.
REACTION MECHANISM of BORANE-N,N-DIETHYLANILINE:
The synthesis proceeds via a two-step mechanism:
Coordination: Borane’s empty p-orbital accepts the amine’s lone pair, forming a Lewis adduct.
Ligand displacement: The stronger base (diethylaniline) replaces THF or SMe₂, driven by the stability of the resulting adduct.
MECHANISM OF ACTION of BORANE-N,N-DIETHYLANILINE:
The mechanism by which Borane-N,N-diethylaniline exerts its effects involves its ability to donate hydride ions (H-) in reduction reactions.
The boron atom in Borane-N,N-diethylaniline acts as a Lewis acid, facilitating the transfer of hydride ions to the substrate.
This mechanism is crucial in Borane-N,N-diethylaniline's role as a reducing agent in organic synthesis.
BIOLOGICAL ACTIVITY of BORANE-N,N-DIETHYLANILINE:
Borane-N,N-diethylaniline, also known as N,N-Diethylaniline borane (DEANB), is a versatile reagent in organic synthesis, particularly noted for its reducing properties.
Borane-N,N-diethylaniline's biological activity has garnered attention in various fields, including medicinal chemistry and materials science.
Borane-N,N-diethylaniline acts primarily as a reducing agent.
Borane-N,N-diethylaniline donates boron-hydrogen (B-H) bonds to target molecules, facilitating various biochemical reactions.
The specific pathways influenced by Borane-N,N-diethylaniline depend on the substrate involved but generally include:
*Diastereoselective Reduction :
Effective in reducing prochiral enone intermediates.
*Borylation Reactions :
Utilized in the borylation of aryl halides and other substrates.
*Enantioselective Reductions :
Capable of producing optically active compounds with high enantiomeric excess (ee).
MEDICINAL CHEMISTRY of BORANE-N,N-DIETHYLANILINE:
Borane-N,N-diethylaniline has potential applications in drug development, particularly in the synthesis of bioactive molecules.
Borane-N,N-diethylaniline has been investigated for use in:
*Boron Neutron Capture Therapy (BNCT) :
A cancer treatment approach where boron-containing compounds selectively accumulate in tumor cells and are activated by neutron irradiation, leading to cell death.
*Synthesis of CETP Inhibitors :
Borane-N,N-diethylaniline is used to synthesize chromanol derivatives that inhibit cholesteryl ester transfer protein (CETP), which is significant for cardiovascular disease treatment.
*Organic Synthesis
DEANB is employed extensively in synthetic organic chemistry due to its efficiency in hydroboration reactions:
*Hydroboration of Alkenes and Alkynes :
Borane-N,N-diethylaniline demonstrates excellent regioselectivity and chemo-selectivity, yielding high purity products under mild conditions.
KEY OBSERVATIONS of BORANE-N,N-DIETHYLANILINE:
*Physical State:
Unlike solid 9-BBN or solution-based borane-THF, Borane-N,N-diethylaniline is a neat liquid, simplifying handling and enabling higher reaction concentrations.
*Thermal Stability:
Borane-N,N-diethylaniline'high boiling point (213.5°C) allows its use as a solvent in high-temperature reactions, such as Claisen rearrangements, where other amine boranes (e.g., borane-dimethyl sulfide, bp 70–72°C) would evaporate.
*Enantioselectivity:
When combined with CBS catalysts, Borane-N,N-diethylaniline outperforms borane-THF in enantioselective ketone reductions, achieving >90% yield and high enantiomeric excess (e.g., 90% ee in formoterol intermediate synthesis).
*Catalytic Efficiency:
In hydroboration reactions, 10 mol% of Borane-N,N-diethylaniline catalyzes alkenyl catecholborane formation at 25°C, a milder condition compared to traditional methods requiring elevated temperatures or stronger Lewis acids.
PREPARATION METHODS of BORANE-N,N-DIETHYLANILINE:
*Reaction Overview
The most widely documented method involves the direct reaction of N,N-diethylaniline with borane-tetrahydrofuran (BH₃·THF).
This exothermic process proceeds via Lewis acid-base adduct formation, where the amine displaces THF from the borane complex.
*Experimental Protocol
Reagents:
Borane-THF complex (1.0 M in THF)
N,N-diethylaniline (neat)
*Conditions:
Temperature: 0–25°C under nitrogen atmosphere
Solvent: Tetrahydrofuran (THF)
Stoichiometry: 1:1 molar ratio
*Procedure:
N,N-Diethylaniline is added dropwise to stirred borane-THF at 0°C.
The mixture warms to room temperature, and the reaction completes within 1–2 hours.
THF is removed under reduced pressure, yielding the complex as a clear, colorless to amber liquid.
*Methodology
An alternative route employs borane-dimethyl sulfide (BH₃·SMe₂) as the boron source.
This method, demonstrated for Borane-N,N-diethylaniline in patent literature, is extrapolated here for diethylaniline due to analogous reactivity.
*Stepwise Process
Reagents:
Borane-dimethyl sulfide (1.0 M in SMe₂)
N,N-diethylaniline (neat)
*Conditions:
Temperature: 25°C → 40°C (to evaporate SMe₂)
Solvent: Toluene or heptane (1:1 v/v with reagent)
*Procedure:
N,N-Diethylaniline is added to BH₃·SMe₂ at room temperature.
The solution is heated to 40°C under nitrogen to distill off dimethyl sulfide (b.p. 38°C), leaving the borane complex in toluene.
*Advantages Over THF-Based Synthesis
Easier ligand removal: SMe₂’s low boiling point simplifies purification.
Scalability: Toluene’s high boiling point (110°C) facilitates large-scale reactions.
*Industrial Production Strategies
Continuous Flow Synthesis
Industrial plants optimize the BH₃·THF method using continuous flow reactors to:
Enhance heat dissipation (critical for exothermic reactions)
Minimize byproduct formation (e.g., oligomeric boranes)
Achieve throughputs exceeding 100 kg/day.
KEY OBSERVATIONS of BORANE-N,N-DIETHYLANILINE:
Borane-N,N-diethylaniline requires stringent moisture-free conditions and refrigeration due to its decomposition in protic environments.
Borane-N,N-diethylaniline's low flash point (21°C) necessitates careful handling to avoid ignition, similar to borane-THF and borane-dimethyl sulfide.
PHYSICAL and CHEMICAL PROPERTIES of BORANE-N,N-DIETHYLANILINE:
CAS Number: 13289‑97‑9
EC (EINECS) Number: 236‑305‑2
PubChem Substance ID: 24850794
Molecular Formula: C₁₀H₁₅B N (C₆H₅N(C₂H₅)₂·BH₃)
Molecular Weight: ~163.07 g/mol
Physical State: Clear - colorless to light yellow liquid
Appearance: Liquid; may vary from colorless to amber
Melting Point: –30 to –27 °C
Boiling Point: ~213.5 °C at 760 mmHg
Density: ~0.917 g/mL (25 °C)
Flash Point: ~21 °C (70 °F)
Refractive Index: 1.5245–1.5265 @20 °C (589 nm)
Vapor Pressure: ~0.163 mmHg @25 °C
Water Solubility: May decompose in water
CAS: 13289-97-9, 91-66-7
Color: Colorless to Amber
Flash Point: 63 °C
Assay Percent Range: 97%
Molecular Formula: C10H15BN
Linear Formula: C6H5N(C2H5)2·BH3
InChI Key: KHYAFFAGZNCWPT-UHFFFAOYSA-N
IUPAC Name: boron; N,N-diethylaniline
PubChem CID: 6335292
Percent Purity: 97%
Chemical Name or Material: Borane-N,N-diethylaniline complex
Melting Point: -30 °C to 27 °C
Density: 0.9200 g/mL
Infrared Spectrum: Authentic
Packaging: AcroSeal™ Glass bottle
Refractive Index: 1.5245 to 1.5265
MDL Number: MFCD00013187
Specific Gravity: 0.92
Solubility Information: Solubility in water: may decompose
SMILES: [B].CCN(CC)C1=CC=CC=C1
Molecular Weight (g/mol): 160.05
Formula Weight: 163.07
Physical Form: Liquid
IUPAC: BORANE-N,N-DIETHYLANILINE COMPLEX
CAS Number: 13289-97-9
Molecular Weight: 163.07
Formula: C10H18BN
SMILES: B.CCN(CC)C1=CC=CC=C1
Preferred IUPAC Name: N,N-DIETHYLANILINE BORANE
InChIKey: InChIKey=YPWBYWNNJVSNPQ-UHFFFAOYSA-N
Density: 0.917 g/mL at 25 °C (lit.)
Melting Point: −30 to −27 °C (lit.)
Molecular Formula: C10H18BN
Molecular Weight: 163.068
Flash Point: 70 °F
Exact Mass: 163.153229
PSA: 3.24000
LogP: 1.34890
Vapour Pressure: 0.163 mmHg at 25 °C
Index of Refraction: 1.5245–1.5265
Storage condition: Refrigerator
Water Solubility: MAY DECOMPOSE
Melting point: -30 to -27 °C
Boiling point: 213.5 °C at 760 mmHg
Flash point: 97.8 °C
Water solubility: MAY DECOMPOSE
Vapour Pressure: 0.163 mmHg at 25 °C
Molecular Formula: C10H16N
Molecular Weight: 150.2402
InChI: InChI=1/C10H15N/c1-3-11(4-2)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3/p+1
EINECS: 236-305-2
CAS Number: 13289-97-9
EC Number: 236-305-2
MDL Number: MFCD00013187
UNSPSC Code: 12352116
PubChem Substance ID: 24850794
NACRES: NA.22
Chemical Name: N,N-Diethylaniline boron
Synonym: Diethylaniline boron
Molecular Formula: C10H18BN
Molecular Weight: 163.07 g/mol
SMILES: B.CCN(CC)c1ccccc1
InChI: InChI=1S/C10H18BN/c1-3-12(11,4-2)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2,11H3
InChI Key: YPWBYWNNJVSNPQ-UHFFFAOYSA-N
Physical State: Liquid
Color: Clear, colorless to amber/yellow
Odor: No data available
Melting Point: −30 to −27 °C (lit.)
Boiling Point: No data available
Density: 0.917 g/mL at 25 °C (lit.)
Refractive Index: 1.5220 to 1.5265 (20 °C, 589 nm)
Flash Point: 21 °C (closed cup) / 70 °F
Water Solubility: May decompose
Partition Coefficient (Log P): No data available
Viscosity: No data available
Vapor Pressure: No data available
pH: No data available
Purity: ≥ 96.0 % (active hydrogen by titration)
Storage: Refrigerator recommended
FIRST AID MEASURES of BORANE-N,N-DIETHYLANILINE:
-Description of first-aid measures
*General advice:
Show this material safety data sheet to the doctor in attendance.
*If inhaled:
After inhalation:
Fresh air.
*In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with
water/ shower.
*In case of eye contact:
After eye contact:
Rinse out with plenty of water.
Call in ophthalmologist.
Remove contact lenses.
*If swallowed:
After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.
-Indication of any immediate medical attention and special treatment needed.
No data available
ACCIDENTAL RELEASE MEASURES of BORANE-N,N-DIETHYLANILINE:
-Environmental precautions:
Do not let product enter drains.
-Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.
Observe possible material restrictions.
Take up dry.
Dispose of properly.
Clean up affected area.
FIRE FIGHTING MEASURES of BORANE-N,N-DIETHYLANILINE:
-Extinguishing media:
*Suitable extinguishing media:
Carbon dioxide (CO2)
Foam
Dry powder
*Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.
-Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.
EXPOSURE CONTROLS/PERSONAL PROTECTION of BORANE-N,N-DIETHYLANILINE:
-Control parameters:
--Ingredients with workplace control parameters:
-Exposure controls:
--Personal protective equipment:
*Eye/face protection:
Use equipment for eye protection.
Safety glasses
*Body Protection:
protective clothing
*Respiratory protection:
Recommended Filter type: Filter A
-Control of environmental exposure:
Do not let product enter drains.
HANDLING and STORAGE of BORANE-N,N-DIETHYLANILINE:
-Conditions for safe storage, including any incompatibilities:
*Storage conditions:
Tightly closed.
Dry.
STABILITY and REACTIVITY of BORANE-N,N-DIETHYLANILINE:
-Chemical stability:
The product is chemically stable under standard ambient conditions (room temperature).
-Possibility of hazardous reactions:
No data available
