1722-26-5

Basic information

• Product Name: Borane-triethylamine complex
• Synonyms: (C2H5)3NBH3;Borane, complex with triethylamine(1:1);Boron, (N,N-diethylethanamine)trihydro-, (T-4)-;n-diethylethanamine)trihydro-((beta-4)-boro;N-Triethyl borazane;Triethylamine base borane adduct;Triethylamine compound with borane (1:1);Triethylamine, compd. with borane (1:1)
• CAS NO: 1722-26-5
• Molecular Formula: C6H18BN
• Molecular Weight: 115.02
• EINECS: 217-022-3
• Product Categories: B (Classes of Boron Compounds);Boranes;Reduction;Synthetic Organic Chemistry
• Mol File: 1722-26-5.mol

Chemical Properties

• Melting Point: −4-−2 °C
• Boiling Point: 97 °C12 mm Hg(lit.)
• Flash Point: 20 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 0.783 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.444
• Storage Temp.: Refrigerator
• Water Solubility: MAY DECOMPOSE
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: Borane-triethylamine complex(CAS DataBase Reference)
• NIST Chemistry Reference: Borane-triethylamine complex(1722-26-5)
• EPA Substance Registry System: Borane-triethylamine complex(1722-26-5)

Safety Data

• Hazard Codes: F,C
• Statements: 11-20/21/22-34
• Safety Statements: 26-36/37/39-45-33-16
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 10-21
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 1722-26-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Borane-triethylamine complex is used as a reducing agent for hydroboration reactions, which are essential in the synthesis of various organic compounds. It is particularly useful in the formation of complex organic molecules due to its ability to selectively reduce specific functional groups.
Used in Ethanolysis:
In the ethanolysis of amine-borane adducts, Borane-triethylamine complex is used as a reactant, facilitating the conversion of amine-borane adducts into more stable and useful compounds.
Used in Photochemical Hydroboration:
Borane-triethylamine complex is employed in photochemical hydroboration, a process that involves the addition of borane to alkenes using light as a catalyst. This reaction is crucial in the synthesis of various organic molecules and materials.
Used in Oxidation of Carbon Nanotubes:
The complex is used as a reactant in the oxidation of single-walled carbon nanotubes, a process that can improve the solubility and processability of these materials for various applications, such as in electronics and composite materials.
Used in Synthesis of Silylboranate and N-Heterocyclic Carbene Borane Complexes:
Borane-triethylamine complex is used as a reactant in the synthesis of silylboranate and N-heterocyclic carbene borane complexes through Lewis base exchange with amine-boranes. These complexes have potential applications in catalysis and materials science.
Used in Boron Carbide Nitride Film Generation:
The complex plays an important role in the generation of boron carbide nitride films through low-pressure chemical vapor deposition. These films have potential applications in protective coatings, electronics, and other high-tech industries due to their unique properties, such as high hardness and thermal stability.

Purification Methods

Distil it in a vacuum using a 60cm glass helices-packed column. [Brown et al. J Am Chem Soc 64 325 1942, Ashby & Foster J Am Chem Soc 84 3407 1962, Matsuura & Tolcura Tetrahedron Lett 4703 1968, Beilstein 4 IV 329.]

InChI:InChI=1/C6H18BN/c1-4-8(7,5-2)6-3/h4-6H2,1-3,7H3

Upstream product

• 554-68-7 triethylamine hydrochloride 
• 16940-66-2 sodium tetrahydroborate 
• 121-44-8 triethylamine 
• 21841-57-6 aziridine borane 
• 16853-85-3 lithium aluminium tetrahydride 
• 1095-03-0 triphenylborane 
• 1333-74-0 hydrogen 
• 19287-45-7 diborane 
• 10294-34-5 boron trichloride 
• 7646-69-7 sodium hydride 
• 2890-88-2 (C₂H₅)3N*BCl₃ 
• 7637-07-2 boron trifluoride 
• 1116-39-8 triisobutylborane 
• 617-86-7 triethylsilane 

Downstream Products

• 30312-50-6 1-benzyl-2-iso-butyl-1.2-azaborolane 
• 19287-45-7 diborane 
• 51006-67-8 Et₃NBHCl₂ 
• 34989-11-2 (2,6-Cl₂-C₆H₃NH-BH)2NC₆H₃-2,6-Cl₂ 
• 34989-12-3 {BHNC₆H₃-2,6-Cl₂}3 
• 1188-92-7 Trihexylboran; Tri-n-hexylbor 
• 121-44-8 triethylamine 
• 22093-02-3 HB{N(CH₃)(CH₂CH₂C₆H₅)}2 
• 21777-52-6 {methyl(2-phenyl-ethyl)amino}borane 
• 1333-74-0 hydrogen 
• 21777-38-8 (methyl-benzylamino)borane 
• 21777-39-9 Bis--boran 
• 21777-37-7 2-methyl-2,3-dihydro-1H-2,1-benzazaborole 
• 2890-88-2 (C₂H₅)3N*BCl₃ 

Relevant articles and documents

Hydrodechlorination of Et3NBCl3 catalyzed by amorphous nickel boride - A mechanistic approach

The catalytic hydrodechlorination of BCl3 with molecular hydrogen in the presence of tertiary amines is a viable strategy for the energy-efficient generation of valuable B-H bonds. A mechanistic study based on experiments with isolated intermediates and deuterium labeling experiments is presented. The occurrence of the rate-limiting reverse reaction from the insoluble Et3NHCl adduct was identified as a major cause of low Et3NBH3 yields. In addition, amines with NCH2 units, which also serve in the corresponding cases as solvents, have a strong influence on the reaction kinetics; they are directly involved in the hydrogen transfer at elevated temperatures and assume the role of a cocatalyst. A catalytic cycle for the reaction on a nickel boride catalyst is proposed. Copyright

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.

The quest for silylhydroboranes: (Me3Si)3SiBH 2

Reaction of BH3.NEt3 with tris(trimethylsilyl) silylpotassium yielded the respective silylboranate. Abstraction of a hydride with B(C6F5)3 led to the neutral silylborane, which could be derivatised as an Et3N adduct. Treatment of the boranate with Cp2Ti(btmsa) resulted in exchange of THF coordinating to potassium by Cp2Ti(btmsa). The Royal Society of Chemistry.

Lanthanide(lll) and actinide(lll) complexes [M(BH4) 2(THF)5][BPh4] and [M(BH4) 2(18-crown-6)][BPh4] (M = Nd, Ce, U): synthesis, crystal structure, and density functional theory i

Treatment of [M(BH4)3(THF)3] with NEt 3HBPh3 in THF afforded the cationic complexes [M(BH 4)2(THF)5][BPh4] [M = U (1), Nd (2), Ce (3)] which were transforme

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.

Photoinduced Single-Electron Transfer as an Enabling Principle in the Radical Borylation of Alkenes with NHC–Borane

A photoinduced SET process enables the direct B?H bond activation of NHC–boranes. In contrast to common hydrogen atom transfer (HAT) strategies, this photoinduced reaction simply takes advantage of the beneficial redox potentials of NHC–boranes, thus obviating the need for extra radical initiators. The resulting NHC–boryl radical was used for the borylation of a wide range of α-trifluoromethylalkenes and alkenes with diverse electronic and structural features, providing facile access to highly functionalized borylated molecules. Labeling and photoquenching experiments provide insight into the mechanism of this photoinduced SET pathway.

Photocatalytic C-F Bond Borylation of Polyfluoroarenes with NHC-boranes

The first photoredox-catalyzed defluoroborylation of polyfluoroarenes with NHC-BH3 has been facilely achieved at room temperature via a single-electron-transfer (SET)/radical addition pathway. This new strategy makes full use of the advantage of photoredox catalysis to generate the key boryl radical via direct activation of a B-H bond. Good functional group tolerance and high regioselectivity offer this protocol incomparable advantages in preparing a wide array of valuable polyfluoroarylboron compounds. Moreover, both computational and experimental studies were performed to illustrate the reaction mechanism.

AMINE-BORANES BEARING BORANE-INTOLERANT FUNCTIONALITIES

Disclosed herein is the preparation of functional group containing amine-boranes from the corresponding amines. The mild reaction conditions allow for the direct preparation of several hitherto inaccessible amine-boranes containing a functional moiety, such as but not limited to, alkene, alkyne, hydroxyl, thiol, acetal, ester, amide, nitrile, nitro, and alkoxysilane.

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.

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.