CAS 73183-34-3|4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane|Bis(pinacolato)diboron|4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane|...

General Information

Structure

Molecular Formula

C₁₂H₂₄B₂O₄

Molecular Mass

253.93856

Exact Mass

254.18607005

Charge

InChI

InChI=1S/C12H24B2O4/c1-9(2)10(3,4)16-13(15-9)14-17-11(5,6)12(7,8)18-14/h1-8H3

InChIKey

IPWKHHSGDUIRAH-UHFFFAOYSA-N

Canonic Smiles

CC1(C)OB(OC1(C)C)B1OC(C(O1)(C)C)(C)C

Isomeric Smiles

B1(B2OC(C(O2)(C)C)(C)C)OC(C(O1)(C)C)(C)C

Calculated Properties

JChem

LogD (pH = 7.4)

4.58

LogD (pH = 5.5)

4.58

Log P

4.58

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-4.29

Polar Surface Area

36.92

Polarizability

30.46

Molar Refractivity

60.48

LOG S

-2.83

Data Source

Names and Identifiers

IUPAC Traditional name

4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane bis(pinacolato)diboron

Synonyms

Bis(pinacolato)diboronBis(pinacolato)diboron 99%Bis(pinacolato)diboron4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane双戊酰二硼双联频哪醇硼酸酯4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis(1,3,2-dioxaborolane)Bis(pinacolato) diboratePinacol DiboraneDiboron Pinacol EsterDipinacoldiboronBis(pinacolate)diboron4,4',5,5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolaneBis(pinacolato)diboraneB2Pin22-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane双戊酰二硼Bis(Pinacolato)diboraneB2pin2bis(pinacolato) diboratediboron pinacol esterpinacol diborane4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolan4,4',5,5'-octamethyl-2,2'-bi-1,3,2-dioxaborolaneoctamethyl-2,2'-bi(1,3,2-dioxaborolane)4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolanebis(pinacolato)diboranedipinacoldiboronbis(pinacolato)diboron4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1,3,2-dioxaborolan4,4,5,5,4',4',5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane)4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane)bis(pinacolate)diboron4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-1,3,2-dioxaborolane

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem SID

2487089316097220085382281

CAS Number

MDL Number

PubChem CID

Beilstein Number

Chemspider ID

Wikipedia Title

Bis(pinacolato)diboron

PubMed Citation Links

24553844238734071506507630318549269290213407046328847150286535393012391525089917258800221209534430034753331185853080207127377367301182372412369323495912265647843300080732365297

CHEBI ID

SureChEMBL Database

ACToR Database

CompTox Database

Reaxys Registry

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Apollo Scientific

OR5456

Versatile reagent for the preparation of boronic esters:J.Org.Chem.1995, 60,7508-7510.

Wikipedia

Bis(pinacolato)diboron

Sigma Aldrich

473294

Application
Reagent used for the cis-vicinal diborylation of acetylenes and olefins with Pt catalysis; borylation of aromatics by Pd catalysis.1
Substrate used in a new palladium-catalyzed cyclization of 1,6-enynes leading to homoallylic alkylboronates.
Used to construct a tetramethylpyrrolidine nitroxide scaffold for the synthesis of paramagnetic heterocycles by Suzuki coupling.
Packaging
1, 5, 25 g in glass bottle
100 g in poly bottle
500 g in glass bottle

TRC

B522770

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.

ChEBI

CHEBI:183312

A 1,3,2-dioxaborolane that is 4,4,5,5-tetramethyl-1,3,2-dioxaborolane in which the boron hydrogen at position 2 is replaced by a 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group. It is a reagent used in organic synthesis to synthesise pinacol boronic esters.

Molecule Details

References

PubChem Literature

From Data Sources

• Ali, H.A. et al.: Arch. Pharm., 337, 183 (2004)

• Izumi, A. et al.: Chem. Lett., 7, 728 (2004)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane bis(pinacolato)diboron

Synonyms

IUPAC name

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

Registration numbers

PubChem SID

2487089316097220085382281

CAS Number

MDL Number

PubChem CID

Beilstein Number

Chemspider ID