Bis(catecholato)diboron

Base Information

• Chemical Name: Bis(catecholato)diboron
• CAS No.: 13826-27-2
• Molecular Formula: C12H8B2O4
• Molecular Weight: 237.815
• Hs Code.: 29349990
• European Community (EC) Number: 691-473-8
• DSSTox Substance ID: DTXSID40392951
• Nikkaji Number: J673.280A
• Wikidata: Q72444597
• Mol file: 13826-27-2.mol

Synonyms:13826-27-2;Bis(catecholato)diboron;2,2'-Bibenzo[d][1,3,2]dioxaborole;BIS(CATECHOLATO)DIBORANE;2,2'-Bi-1,3,2-benzodioxaborole;2-(1,3,2-benzodioxaborol-2-yl)-1,3,2-benzodioxaborole;MFCD09842343;2,2/'-Bis-1,3,2-benzodioxaborole;Bis(catecholato)diboron, 97%;AMY979;SCHEMBL3889220;C12H8B2O4;DTXSID40392951;AKOS015968999;AC-4650;CS-W019123;AS-15219;SY029763;B3757;FT-0636966;EN300-7368574;A807363;J-400816;2,2 inverted exclamation mark -Bi-1,3,2-benzodioxaborole;2-(2H-1,3,2-benzodioxaborol-2-yl)-2H-1,3,2-benzodioxaborole;2-(6,7-dihydro-1,3,2-benzodioxaborol-2-yl)-1,3,2-benzodioxaborole;Bis(catecholato)diborane

Chemical Property of Bis(catecholato)diboron

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Melting Point: 189-196 °C(lit.)
• Refractive Index: 1.593
• Boiling Point: 314.988 °C at 760 mmHg
• Flash Point: 144.3 °C
• PSA: 36.92000
• Density: 1.314 g/cm³
• LogP: 2.12100
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 238.0608691
• Heavy Atom Count: 18
• Complexity: 259

Purity/Quality:

99% ^*data from raw suppliers

Bis(catecholato)diborane ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: B1(OC2=CC=CC=C2O1)B3OC4=CC=CC=C4O3

Technology Process of Bis(catecholato)diboron

There total 15 articles about Bis(catecholato)diboron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

tetrakis(dimethylamido)diborane (1630-79-1) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2)

Guidance literature:

With HCl; In diethyl ether; byproducts: (Me2NH2)Cl; N2-atmosphere; addn. of slight excess catechol to B-compd., stirring at room temp. for several h; cooling in ice/water, dropwise addn. of excess 1 M HCl in Et2O, stirringat room temp. for 10 h, solvent removal (vac.), extn. into PhMe, filtra tion (Celite), solvent removal (vac.), washing (MeCN); further crop fromwashings; elem. anal.;

DOI:10.1021/ic980425a

Reference yield: 42.0%

2-chloro-1,3,2-benzodioxaborole (55718-76-8) → 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2)

Guidance literature:

With sodium amalgam; In toluene; under inert atm. chlorocatecholborane was dissolved in toluene, Na/Hg amalgam was added and heated at 90°C under N2 for 3 h; soln. was filtered and concd., pentane was added;

DOI:10.1021/om0208016

Reference yield: 38.0%

boron tribromide (10294-33-4) + benzene-1,2-diol (120-80-9,19481-10-8,37349-32-9) → 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2)

Guidance literature:

With sodium amalgam; In toluene; under inert atm. at 0°C to suspn. catechol in toluene BBr3 was added dropwise, react. mixt. was allowed to warm to room temp., solvent was removed, residue was dissolved in toluene, Na/Hg amalgam was added, heated at 90°C under N2 for 3 h; soln. was filtered and concd., pentane was added;

DOI:10.1021/om0208016

upstream raw materials:

1,2-B₂(NMe₂)2(catecholate)

2,3-dimethyl-2,3-butane diol

tetrakis(dimethylamido)diborane

B-(isothiocyanato)catecholborane

Downstream raw materials:

4-MeOC₆H₄CH(Bcat)CH₂(Bcat)

2-(2-phenylethyl)benzo-1,3,2-dioxaborole

2-((S)-1-Phenyl-ethyl)-benzo[1,3,2]dioxaborole

Refernces

Water as a Hydride Source in Palladium-Catalyzed Enantioselective Reductive Heck Reactions

10.1002/anie.201700195

The study reports a Pd-catalyzed asymmetric reductive Heck reaction using diboron–water as a hydride source. The researchers used N-aryl acrylamides as substrates and Pd(OAc)2 as the catalyst, along with tBuPhOX as the ligand and tetrahydroxydiboron as the diboron reagent. The reaction proceeds via intramolecular asymmetric carbopalladation of the substrates, followed by reduction of the C(sp3)-Pd intermediate using water as the hydride source, yielding enantioenriched 3,3-disubstituted oxindoles with high yields and enantioselectivities. The ligand plays a crucial role in determining both the enantioselectivity and the reaction pathways, allowing for either hydroarylation (reductive Heck) or carboborylation products. The study also demonstrates the synthesis of deuterated compounds by using heavy water (D2O) as a deuterium donor in combination with bis(catecholato)diboron.

A convenient and clean synthetic method for borasiloxanes by Pd-catalysed reaction of silanols with diborons

10.1039/c7cc02420g

The research focuses on the development of a convenient and clean synthetic method for borasiloxanes, which are valuable chemicals in materials chemistry due to their excellent heat resistance and unique properties applicable to various fields such as chemical sensors, electrolyte additives, and ceramic precursors. The study introduces a Pd-catalyzed selective Si-O-B bond-forming reaction through dehydrogenative O-borylation of a variety of silanols with easily available diborons, such as bis(pinacolato)diboron (B2pin2), bis(neopentyl glycolato)diboron (B2neop2), bis(hexylene glycolato)diboron (B2hexyl2), and bis(catecholato)diboron (B2cat2). The process is efficient, takes place under mild conditions, and generates only hydrogen gas as a byproduct, making it environmentally friendly. The successful use of diborons with Pd catalysts for borasiloxane synthesis is a unique point compared to previously reported methods, and the high activity of the commonly-used air-stable Pd acetate catalyst makes this method potentially applicable for modifying silanol group-containing materials like silicone polymers to improve their physical properties or add new chemical properties based on boron moieties. The study concludes that this new simple method for the preparation of Si-O-B compounds using readily available silanols and diboron reagents could have significant practical applications.