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)

Refernces

• 1、 Lawlor, Fiona J.,Norman, Nicholas C.,Pickett, Nigel L.,Robins, Edward G.,Nguyen, Paul,Lesley, Gerry,Marder, Todd B.,Ashmore, Jennifer A.,Green, Jennifer C.. "Bis-Catecholate, Bis-Dithiocatecholate, and Tetraalkoxy Diborane(4) Compounds: Aspects of Synthesis and Electronic Structure". . p. 5282 - 5288. Retrieved 1998.
• 2、 Welch,Shore. "Boron heterocycles. V. Preparation and characterization of selected heteronuclear diboron ring systems". . p. 225 - 230. Retrieved 1968.
• 3、 Leong, Bi-Xiang,Lee, Jiawen,Li, Yan,Yang, Ming-Chung,Siu, Chi-Kit,Su, Ming-Der,So, Cheuk-Wai. "A Versatile NHC-Parent Silyliumylidene Cation for Catalytic Chemo- And Regioselective Hydroboration". supporting information. p. 17629 - 17636. Retrieved 2019/11/11.
• 4、 Braunschweig, Holger,Claes, Christina,Guethlein, Frank. "Dehydrocoupling of catecholborane catalyzed by group 4 compounds". body text. p. 144 - 145. Retrieved 2012/06/29.