960-71-4

Basic information

• Product Name: TRIPHENYLBORANE
• Synonyms: BORON TRIPHENYL;TRIPHENYLBORANE;TRIPHENYLBORINE;TRIPHENYLBORON;borine,triphenyl;Triphenyboron;triphenyl-boran;TRIPHENYLBORON, POWDER, WATER
• CAS NO: 960-71-4
• Molecular Formula: C₁₈H₁₅B
• Molecular Weight: 242.12
• EINECS: 213-504-2
• Product Categories: Boron;Precursors by Metal;Vapor Deposition Precursors;BoronAlphabetic;Micro/Nanoelectronics;Solution Deposition Precursors;TP - TZ;organoboron and borato-metal complexes
• Mol File: 960-71-4.mol

Chemical Properties

• Melting Point: 145 °C(lit.)
• Boiling Point: 65-67 °C
• Flash Point: 1 °F
• Appearance: off-white/Powder
• Density: 0.898 g/mL at 25 °C
• Water Solubility: Soluble in aromatic solvents. Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 1961313
• CAS DataBase Reference: TRIPHENYLBORANE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIPHENYLBORANE(960-71-4)
• EPA Substance Registry System: TRIPHENYLBORANE(960-71-4)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-36/37/38-22-19-40-36/37
• Safety Statements: 16-26-33-36-24/25-22-36/37
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• RTECS: ED2367500
• F: 10-23
• TSCA: No
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 960-71-4(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Applications:
Triphenylborane is used as a catalyst in the polymerization of acrylic esters. It forms a complex with pyridine, known as pyridine-triphenylborane complex, which acts as a catalyst for this process. This catalyst is particularly useful for the production of polymers with controlled molecular weights and narrow molecular weight distributions.
Used in Chemical Synthesis:
Triphenylborane is used as an intermediate in the synthesis of various organic compounds. For example, it is involved in the hydrocyanation of butadiene to produce adiponitrile, an important industrial chemical used in the manufacture of nylon and other polymers. Additionally, triphenylborane is used in the synthesis of 3-phenyl-cyclohexene by reacting with acetic acid cyclohex-2-enyl ester in the presence of palladium bis(dibenzylideneacetone) and triphenylphosphine as a catalyst. This reaction is an example of the Heck reaction, a widely used method for forming carbon-carbon bonds in organic synthesis.
Used in the Production of Pyridine-Triphenylborane Complex:
Triphenylborane is used as a precursor in the production of the pyridine-triphenylborane complex. This complex is a valuable catalyst for various chemical reactions, including the polymerization of acrylic esters mentioned earlier. The formation of this complex highlights the versatility of triphenylborane as a starting material for the synthesis of other catalytically active species.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 5564, 1987 DOI: 10.1021/jo00234a011

Hazard

TRIPHENYLBORANE is a severe eye irritant.

Purification Methods

Recrystallise the borane three times from Et2O or *C6H6 under N2 and dry it at 130o. It can be distilled in a high vacuum at 300-350o and has been distilled (b 195-215o/~15mm) in vacuum using a bath temperature of 240-330o. N2 is introduced into the apparatus before dismantling. It forms complexes with amines. [Nielsen et al. Chem Ind (London) 1069 1957, Wittig et al. Justus Liebigs Ann Chem 563 110 1949, Bent & Dorfman J Am Chem Soc 57 1259 1935, Beilstein 16 IV 1623.]

InChI:InChI=1/C18H15B/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H

Upstream product

• 60-29-7 diethyl ether 
• 96080-52-3 dipropyl phenylboronate 
• 927-77-5 n-propylmagnesium bromide 
• 873-51-8 phenylborondichloride 
• 3029-30-9 naphthalene-1,4-dicarbonitrile 
• 98689-31-7 tetramethylammonium methyltriphenylborate 
• 143-66-8 sodium tetraphenyl borate 
• 123-91-1 1,4-dioxane 
• 19287-45-7 diborane 
• 71-43-2 benzene 
• 16853-85-3 lithium aluminium tetrahydride 
• 100-56-1 phenylmercury(II) chloride 
• 121-43-7 Trimethyl borate 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 2294-95-3 5,5,5-Triphenyl-1-pentanol 
• 65859-86-1 Triphenyl-n-butylborate lithium salt 
• 1450-63-1 1,1,4,4-tetraphenyl-1,3-butadiene 
• 93-98-1 N-phenyl benzoyl amide 
• 85483-55-2 triphenyl(N,N,N-trimethyl-p-phenylammonium)borate 
• 76100-62-4 4,4,4-triphenyl-butyronitrile 
• 60243-35-8 Diphenyl-(1-phenyl-2-methylallyloxy)-boran 
• 22639-07-2 diphenylborinic acid pyridoxyl ester 
• 3657-10-1 Cyclohexylisocyanid(N,B)triphenylboran 
• 56797-48-9 diethyl(phenyl)borane 
• 24697-43-6 diphenyl thiocyanborane 
• 20191-10-0 N,N''-Bis-diphenylboryl-N,N',N'',N'''-tetramethyl-oxamidin 
• 833-81-8 (E)-1,2-diphenylpropene 
• 779-51-1 cis-α-methylstilbene 

Relevant articles and documents

Sublimation study of triphenyl boron and the bond-dissociation enthalpy of B-C6H5

The sublimation pressures of triphenyl boron, B(C6H5)3, in the temperature range 340 to 380 K have been determined from simultaneous measurements of the rate of mass effusion and torsional recoil.The measured vapor pressures expressed by the equations: log10(pK/p0) = (9.52 +/- 0.07) - (5.326 +/- 0.026)*103(K/T), log10(pτ/p0) = (10.08 +/- 0.06) - (5.518 +/- 0.022)*103(K/T) where pK and pτ are the pressures measured by the Knudsen effusion and torsional recoil techniques, respectively, and p0 = 101.325 kPa, confirm that triphenyl boron is a monomer in the vapor phase in the temperature range of the measurements.The mean standard molar enthalpy and entropy of sublimation (p0 = 101.325 kPa) derived from these equations are: ΔsubH0m = (103.8 +/- 2.5) kJ*mol-1 and ΔsubS0m = (187.6 +/- 7.6) J*K-1*mol-1.The mean molar bond-dissociation enthalpy (B-C6H5) is calculated to be (459 +/- 11.6) kJ*mol-1.

[4-tBu-2,6-{P(O)(OiPr)2}2C6H 2SnL]+: An NHC-stabilized organotin(II) cation and related derivatives

The organotin(II) salts [4-tBu-2,6-{P(O)(OiPr)2} 2C6H2SnL]X (1: X=B[3,5-(CF3) 2C6H3)]4; 2: X=BPh4) and [4-tBu-2,6-{P(O)(OiPr)2}2

Stabilization and Transfer of the Transient [MesP4]- Butterfly Anion Using BPh3

The transient bicyclo[1.1.0]tetraphosphabutane anion, generated from white phosphorus (P4) and MesLi (Mes=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. This Lewis acid stabilized anion can be used as an [RP4]- transfer agent, reacting cleanly with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions, and with the trityl cation to form a neutral, nonsymmetrical, all-carbon-substituted P4derivative. This reaction path enables a simple, stepwise functionalization of white phosphorus. Trap and transfer: The bicyclo[1.1.0]tetraphosphabutane anion (see scheme, center), generated from P4 and MesLi (Mes=2,4,6-tBu3C6H2), can be trapped by BPh3 in THF. The anion can be used as an [RP4]- transfer agent, reacting with neutral Lewis acids (B(C6F5)3, BH3, and W(CO)5) to afford unique singly and doubly coordinated butterfly anions and with the trityl cation to form a neutral, nonsymmetrical P4 derivative.

Borane-protected cyanides as surrogates of h-bonded cyanides in [FeFe]-hydrogenase active site models

Triarylborane Lewis acids bind [Fe2(pdt)(CO)4(CN) 2]2- [1]2- (pdt2- = 1,3-propanedithiolate) and [Fe2(adt)(CO)4(CN) 2]2- [3]2- (adt2- = 1,3-azadithiolate, HN(CH2S-)2) to give the 2:1 adducts [Fe2(xdt)(CO)4(CNBAr3) 2]2-. Attempts to prepare the 1:1 adducts [1(BAr 3)]2- (Ar = Ph, C6F5) were unsuccessful, but related 1:1 adducts were obtained using the bulky borane B(C6F4-o-C6F5)3 (BAr F3). By virtue of the N-protection by the borane, salts of [Fe2(pdt)(CO)4(CNBAr3)2] 2- sustain protonation to give hydrides that are stable (in contrast to [H1]-). The hydrides [H1(BAr3)2]- are 2.5-5 pKa units more acidic than the parent [H1]-. The adducts [1(BAr3)2]2- oxidize quasi-reversibly around -0.3 V versus Fc0/+ in contrast to ca. -0.8 V observed for the [1]2-/- couple. A simplified synthesis of [1] 2-, [3]2-, and [Fe2(pdt)(CO) 5(CN)]- ([2]-) was developed, entailing reaction of the diiron hexacarbonyl complexes with KCN in MeCN.

METHOD FOR SYNTHESIZING ORGANIC MAGNESIUM COMPOUND, METHOD FOR SYNTHESIZING ORGANIC BORONIC ACID COMPOUND, AND COUPLING METHOD

An object is to establish a technology with which an organic magnesium compound can be easily and efficiently synthesized at a low cost with few steps that do not involve a complex chemical method. A method for synthesizing an organic magnesium compound includes, in a reaction solvent, reacting an organic halide represented by General Formula I (Ra—Xa) with a dispersion product obtained by dispersing sodium in a dispersion solvent to obtain an organic sodium compound represented by General Formula II (Ra—Na), and reacting the obtained organic sodium compound with a magnesium halide represented by General Formula III (Mg—(Xb)2) to obtain an organic magnesium compound represented by General Formula IV (Ra—Mg—Xb).

Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale

A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.

Controlling the Lewis Acidity and Polymerizing Effectively Prevent Frustrated Lewis Pairs from Deactivation in the Hydrogenation of Terminal Alkynes

Two strategies were reported to prevent the deactivation of Frustrated Lewis pairs (FLPs) in the hydrogenation of terminal alkynes: reducing the Lewis acidity and polymerizing the Lewis acid. A polymeric Lewis acid (P-BPh3) with high stability was designed and synthesized. Excellent conversion (up to 99%) and selectivity can be achieved in the hydrogenation of terminal alkynes catalyzed by P-BPh3. This catalytic system works quite well for different substrates. In addition, the P-BPh3 can be easily recycled.

Iodine-catalyzed synthesis of N,N'-chelate organoboron aminoquinolate

We disclose a novel method for the synthesis of fluorescent N,N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr4/ R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.

Examining the Effects of Monomer and Catalyst Structure on the Mechanism of Ruthenium-Catalyzed Ring-Opening Metathesis Polymerization

The mechanism of Ru-catalyzed ring-opening metathesis polymerization (ROMP) is studied in detail using a pair of third generation ruthenium catalysts with varying sterics of the N-heterocyclic carbene (NHC) ligand. Experimental evidence for polymer chelation to the Ru center is presented in support of a monomer-dependent mechanism for polymerization of norbornene monomers using these fast-initiating catalysts. A series of kinetic experiments, including rate measurements for ROMP, rate measurements for initiation, monomer-dependent kinetic isotope effects, and activation parameters were useful for distinguishing chelating and nonchelating monomers and determining the effect of chelation on the polymerization mechanism. The formation of a chelated metallacycle is enforced by both the steric bulk of the NHC and by the geometry of the monomer, leading to a ground-state stabilization that slows the rate of polymerization and also alters the reactivity of the propagating Ru center toward different monomers in copolymerizations. The results presented here add to the body of mechanistic work for olefin metathesis and may inform the continued design of catalysts for ROMP to access new polymer architectures and materials.

PHOTOBASE GENERATOR

There is provided a photobase generator and a photosensitive resin composition containing the photobase generator. The photobase generator includes an ammonium salt represented by general formula (1). In formula (1), R1 to R4 independently represent an alkyl group having 1 to 18 carbon atoms or Ar, wherein at least one of R1 to R4 represents Ar; Ar represents an aryl group having 6 to 14 carbon atoms (excluding carbon atoms contained in a substituent as mentioned below), wherein some of hydrogen atoms in the aryl group may be independently substituted by an alkyl group having 1 to 18 carbon atoms or the like; Y+ represents an ammonio group represented by general formula (2) or (3); and E represents a hydrogen atom or a group represented by general formula (5).