274-07-7

Basic information

• Product Name: CATECHOLBORANE
• Synonyms: Benzcatechinborane;Benzo[1,3,2]dioxaborole;C6H5BO2;Catecholatoborane;Pyrocatecholborane;RARECHEM AK VD 0002;CATECHOLBORANE;1,3,2-BENZODIOXABOROLE
• CAS NO: 274-07-7
• Molecular Formula: C₆H₅BO₂
• Molecular Weight: 119.91
• EINECS: 205-991-5
• Product Categories: BoranesOrganometallic Reagents;Boronic Acids and Derivatives;Borylation Reagents;Reduction;Synthetic Reagents;Boranes;Boronic Acids and Derivatives;Borylation Reagents;Chemical Synthesis;Organometallic Reagents;Synthetic Reagents
• Mol File: 274-07-7.mol

Chemical Properties

• Melting Point: 12 °C(lit.)
• Boiling Point: 50 °C50 mm Hg(lit.)
• Flash Point: 36 °F
• Appearance: /liquid
• Density: 1.125 g/mL at 25 °C(lit.)
• Vapor Pressure: 17.554mmHg at 25°C
• Refractive Index: n20/D 1.507(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with diethyl ether, tetrahydrofuran, dichloromethane, c
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 972072
• CAS DataBase Reference: CATECHOLBORANE(CAS DataBase Reference)
• NIST Chemistry Reference: CATECHOLBORANE(274-07-7)
• EPA Substance Registry System: CATECHOLBORANE(274-07-7)

Safety Data

• Hazard Codes: F,C
• Statements: 11-19-34-67-65-63-48/20-14-40-37
• Safety Statements: 26-36/37/39-45-62-16-43
• RIDADR: UN 2924 3/PG 2
• WGK Germany: 3
• F: 1-10
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 274-07-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Catecholborane is used as a reducing agent for the transition metal-catalyzed hydroboration of alkenes, which is a crucial step in the synthesis of various organic compounds. This application takes advantage of its ability to selectively reduce specific functional groups in a molecule, making it a valuable tool in organic chemistry.
Used in Pharmaceutical Industry:
Catecholborane is used to prepare B-alkylcatecholboranes, which are essential intermediates in the synthesis of amides and macrocyclic lactams from carboxylic acids. These compounds are often found in pharmaceuticals, making catecholborane an important reagent in the development of new drugs.
Used in Stereoselective Reduction:
Catecholborane is used as a stereoselective reducing agent to convert beta-hydroxy ketones to syn 1,3-diols. This selective reduction is crucial in the synthesis of complex organic molecules, particularly in the pharmaceutical and agrochemical industries.
Used in Suzuki Reaction:
Catecholborane reacts with alkyne through hydroboration to form trans vinyl borane, which is a precursor to the Suzuki reaction. The Suzuki reaction is a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biologically active compounds and advanced materials.

Purification Methods

It is a moisture-sensitive flammable liquid which is purified by distillation in a vacuum under a N2 atmosphere and stored under N2 at 0-4o. It liberates H2 when added to H2O or MeOH. A solution in THF, after 25hours at 25o, has residual hydride of 95% (under N2) and 80% (under air) [Brown & Gupta J Am Chem Soc 97 5249 1975].

InChI:InChI=1/C6H5BO2/c1-2-4-6-5(3-1)8-7-9-6/h1-4,7H

Upstream product

• 13292-87-0 dimethyl sulfide borane 
• 120-80-9 benzene-1,2-diol 
• 37737-62-5 tris(catecholato)diboron 
• 62486-16-2 catecholborane-d₁ 
• 14044-65-6 borane-THF 
• 13292-87-0 dimethylsulfide borane complex 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 121589-95-5 2-(2'-methylaminoethoxy)-o-phenylene-1,3,2-dioxaborolane 
• 51901-85-0 bromocatecholborane 
• 540-72-7 sodium thiocyanide 
• 201230-82-2 carbon monoxide 
• 172266-59-0 (CO)5Mn(BO₂C₆H₄) 
• 71-43-2 benzene 
• 172266-60-3 (CO)5Re(BO₂C₆H₄) 

Downstream Products

• 37490-23-6 (E)-1-vinyl-2-cyclohexyl-catecholborane 
• 5507-10-8 (2E,4Z)-5-(Benzo[1,3,2]dioxaborol-2-yloxy)-1,3,5-triphenyl-penta-2,4-dien-1-one 
• 536-75-4 4-Ethylpyridine 
• 136962-67-9 (R)-1-phenylethyl-1,3,2-benzodioxaborole 
• 196212-80-3 2-((S)-1-Phenyl-ethyl)-benzo[1,3,2]dioxaborole 
• 459-47-2 1-ethyl-4-fluorobenzene 
• 897049-54-6 2-(1-pentafluorophenyl-ethyl)-benzo[1,3,2]dioxaborole 
• 2251-81-2 ethylpentafluorobenzene 
• 3982-67-0 ethylmesitylene 

Relevant articles and documents

Boryl-dihydrideborate osmium complexes: Preparation, structure, and dynamic behavior in solution

The metal fragment Os(CO)(PiPr3)2 stabilizes boryl-dihydrideborate species, which can be viewed as snapshots of states of B-H oxidative addition of a R2BH molecule and frustrated B-H bond activation of a second one. Complex OsH2(η2-CH2=CHEt)(CO)(PiPr3)2 (2) shows a tendency to dissociate the olefin. The resulting dihydride OsH2(CO)(PiPr3)2 (3) rapidly coordinates catecholborane (HBcat) and pinacolborane (HBpin) to give the corresponding σ-borane derivatives OsH2(η2-HBR2)(CO)(PiPr3)2 (BR2 = Bcat (4), Bpin (5)). Complex 4 reacts with a second molecule of HBcat to release H2 and to afford the octahedral boryl dihydride borate derivative Os(Bcat)(κ2-H2Bcat)(CO)(PiPr3)2 (6), which undergoes a thermally activated Bcat site exchange process in solution. Borane displaces catecholborane from the dihydride-borate of 6 to generate the boryl-tetrahydrideborate Os(Bcat)(κ2-H2BH2)(CO)(PiPr3)2 (7). This compound and the Bpin counterpart Os(Bpin)(κ2-H2BH2)(CO)(PiPr3)2 (8) have also been prepared by reaction of the corresponding Os(BR2)Cl(CO)(PiPr3)2 with Na[BH4].

New economical, convenient procedures for the synthesis of catecholborane

Catecholborane was conveniently synthesized by the reaction of tri-O-phenylene bis-borate (2) with diborane in triglyme or tetraglyme at moderate temperatures (70-80 °C). The product, catecholborane, can be distilled out in 85% yield with >97% purity. The

Kinetics of the reduction of pinacolone by borane-dimethyl sulfide and catecholborane in THF

The kinetics of the reduction of the ketone, pinacolone by borane-dimethyl sulfide and catecholborane have been investigated in tetrahydrofuran. Both overall reactions are composed of several subsequent and in part competing reactions. The use of commerci

Synthesis of Unsymmetrical Diboron(5) Compounds and Their Conversion to Diboron(5) Cations

Reaction of the bis-catecholatodiboron-NHC adducts B2Cat2(NHC) (NHC = IMe (tetramethylimidazol-2-ylidene), IMes (1,3-dimesitylimidazol-2-ylidene), IDIPP (1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)) with BCl3 results in the replacement of the catecholato group bound to the four-coordinate boron atom with two chlorides to yield diboron(5) Lewis acid-base adducts of the formula CatBBCl2(NHC). These compounds are precursors to diboron(5) monocations, accessed by adding AlCl3 or K[B(C6F5)4] as halide abstraction agents in the presence of a Lewis base. The substitution of the chlorides of CatBBCl2(NHC) for hydrides was achieved using Bu3SnH and a halide abstracting agent to form 1,1-dihydrodiboron(5) compounds, CatBBH2(NHC). Attempts to generate diboron(4) monocations of formula [CatBB(Y)(NHC)]+ (Y = Cl, H) led to the rapid formation of CatBY.

Trans -2 - substituted cycloalkyl three fluoro potassium borate synthesis method (by machine translation)

The invention discloses trans - 2 - substituted cyclohexyl three fluoro potassium borate synthesis method, which belongs to the field of organic synthesis. From the cyclic ketone starting curing and reagent or lithium reagent addition subsequently dehydrated and gets substituted alkenes, subsequently with the catechol borane or after aminol borane addition reaction, fluorine hydride potassium direct quenching treatment to obtain trans - 2 - substituted cyclohexyl three fluoro potassium borate, the catechol borane to obtain the racemate product, [...] photoinitiators enantiomerically pure product. The method has low cost, convenient source of raw materials, the operation is simple, and has industrial amplifying of the prospect. (by machine translation)

Synthesis of catechol-, pinacol-, and neopentylglycolborane through the heterogeneous catalytic B-B hydrogenolysis of diboranes(4)

A new synthetic approach to hydroboranes catechol-, pinacol-, and neopentylglycolborane has been developed. Starting from diboranes(4) B 2cat2, B2pin2, or B 2neop2, the respective boranes were obtained by heterogeneously catalyzed cleavage of the B-B bond in the respective diboranes with hydrogen. Group10 metals were found to be effective catalysts for this reaction. Copyright

PYRIDO[4,3-B]INDOLE AND PYRIDO[3,4-B]INDOLE DERIVATIVES AND METHODS OF USE

This disclosure is directed to pyrido[4,3-b]indole and pyrido [3,4-b] indole derivatives. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

Spiroborate catalyzed reductions with N,N-diethylaniline borane

Reduction of esters, amides, and ketones by N,N-diethylaniline borane is accelerated by catalysts derived from spiroborate complexes. Esters are reduced at ambient temperature in less than 4 h with this amine borane and 5 mol % spiroborate 6. Functional group selectivity shows ketone and tertiary amide reduction is faster than ester or nitrile reduction.

BOOTSTRAP SYNTHESIS OF BORANES

Metal hydride materials react with BZ3 compounds in the presence of ligand to form BH3-L compounds. A compound of the formula HBZ2 is prepared from a compound of the formula BZ3 by reacting a first amount of a compound of the formula HBZ2 with a metal hydride material "MH" and a compound "L" to form a material of the formula BH3-L, and then reacting the BH3-L thus formed with a compound of the formula BZ3 to form HBZ2 in a second amount greater than the first amount of HBZ2. Z is selected from alkoxy, aryloxy, amido, arylamido, doubly substituted alkoxy, doubly substituted aryloxy, doubly substituted amido, doubly substituted arylamido, alkoxy-amido, and aryloxy-arylamido. When Z is bidentate, then HBZ2 has a ring structure. "L" is selected from ethers, aromatic ethers, amines, aromatic amines, heterocyclic nitrogen compounds, sulfides, aromatic sulfides, and heterocyclic sulfur compounds. "L" becomes a ligand in the BH3-L material.

Preparation of (E)-1-alkenylboronic acid pinacol esters via transfer of alkenyl group from boron to boron

Two synthetic routes to (E)-1-alkenylboronic acid pinacol esters 3 were investigated. Hydroboration of 1-alkynes 1 with 1,3,2-benzodioxaborole (catecholborane), in situ generated by the reaction of BH3 in THF with catechol, proceeded in the presence of a catalytic amount of dicyclohexylborane in THF at room temperature to give the corresponding (E)-1-alkenylboronic acid catechol esters 2. Treatment of the resultant esters 2 with 2,3-dimethyl-2,3-butanediol (pinacol) easily afforded the desired products 3, which are insensitive to air, moisture and chromatography, in good to high overall yields. The sequential reaction is a highly efficient route to 3 from BH3 in THF in a one-pot manner. Alternatively, hydroboration of 1 with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolborane) was achieved in the presence of a catalytic amount of dicyclohexylborane at room temperature under neat conditions to afford the corresponding products 3 directly in good to excellent yields. This route is extremely efficient and environmentally benign from the viewpoints of making good use of pinacolborane and of using no solvent, and is capable of using a variety of alkynes 1 including functionalized ones such as HCCCH2Cl and HCCCH2OTHP.