Bis(pinacolato)diborane

Base Information

• Chemical Name: Bis(pinacolato)diborane
• CAS No.: 73183-34-3
• Molecular Formula: C12H24B2O4
• Molecular Weight: 253.942
• Hs Code.: 29349990
• European Community (EC) Number: 615-925-0
• UNII: I906W26P4U
• DSSTox Substance ID: DTXSID30369935
• Nikkaji Number: J698.829F
• Wikipedia: Bis(pinacolato)diboron
• Wikidata: Q4917161
• Mol file: 73183-34-3.mol

Synonyms:B(P)DB;bis(pinacolato)diboron

Chemical Property of Bis(pinacolato)diborane

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 0.15mmHg at 25°C
• Melting Point: 137-140 °C(lit.)
• Refractive Index: 1.432
• Boiling Point: 222.595 °C at 760 mmHg
• Flash Point: 88.423 °C
• PSA: 36.92000
• Density: 0.977 g/cm³
• LogP: 2.24920
• Storage Temp.: 0-6°C
• Sensitive.: moisture sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Soluble in tetrahydrofuran, dichloromethane, toluene, hexane and heptane. Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 254.1860696
• Heavy Atom Count: 18
• Complexity: 286

Purity/Quality:

99% ^*data from raw suppliers

Bis(pinacolato)diboron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-37/39-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)B2OC(C(O2)(C)C)(C)C
• Uses: It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, B2pin2 is not moisture-sensitive and can be handled in air. suzuki reaction Bis(pinacolato)diboron is used as a condensation agent in the preparation poly(arylene)s. Bis(pinacolato)diboron is an organoboranate with potential use as matrix metallo-proteinase (MMP-2) inhibitor. As a boron source in Pt-mediated diborations, coupling reactions; in Rh-or Ir-mediated borylations of alkanes and arenes, and in carbenoid chemistry.

Technology Process of Bis(pinacolato)diborane

There total 44 articles about Bis(pinacolato)diborane 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: 100.0%

2,3-dimethyl-2,3-butane diol (76-09-5) → bis(pinacol)diborane (73183-34-3)

Guidance literature:

With tetrakis(dimethylamido)diborane; In diethyl ether; at 20 ℃; for 18h; Conversion of starting material;

Reference yield: 79.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + tetrakis(dimethylamido)diborane (1630-79-1) → bis(pinacol)diborane (73183-34-3)

Guidance literature:

With hydrogenchloride; In diethyl ether; toluene; at 20 ℃; for 4h; Inert atmosphere; Cooling with ice;

DOI:10.15227/orgsyn.077.0176

Reference yield: 75.0%

cis-[Ir(4,4'-di-tert-butyl-2,2'-bipyridine)2(C8H12)(BO2C2(CH3)4)2][CF3SO3] → (C5H3N(C(CH3)3))2Ir(C8H12)(1+)*CF3SO3(1-)=[(C5H3N(C(CH3)3))2Ir(C8H12)][CF3SO3] (401797-12-4) + bis(pinacol)diborane (73183-34-3)

Guidance literature:

In benzene-d6; at 80°C;

DOI:10.1021/ja0173019

upstream raw materials:

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

1,2-B₂(NMe₂)2(catecholate)

4-tert-Butylcatechol

boron trichloride

Downstream raw materials:

1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Refernces

• 1、 Gong, Mingliang,Guo, Chenjun,Luo, Yunjie,Xie, Hongzhen,Zhang, Fangcao. "Hydroborative reduction of amides to amines mediated by La(CH2C6H4NMe2-: O)3". . p. 779 - 791. Retrieved 2022/01/22.
• 2、 Cruz, Tiago F. C.,Pereira, Laura C. J.,Waerenborgh, Jo?o C.,Veiros, Luís F.,Gomes, Pedro T.. "Hydroboration of terminal olefins with pinacolborane catalyzed by new 2-iminopyrrolyl iron(ii) complexes". . p. 3347 - 3360. Retrieved 2019/07/10.