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

• ChemBase ID: 8893
• Molecular Formular: C12H24B2O4
• Molecular Mass: 253.93856
• Monoisotopic Mass: 254.18607005
• SMILES: B1(B2OC(C(O2)(C)C)(C)C)OC(C(O1)(C)C)(C)C
• Canonical SMILES: CC1(C)OB(OC1(C)C)B1OC(C(O1)(C)C)(C)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane
• 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)diboron; 4,4,4′,4′,5,5,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane; Bis(pinacolato)diboron; 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bis(1,3,2-dioxaborolane); 4,4',5,5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; B2Pin2; Bis(pinacolate)diboron; Bis(pinacolato) diborate; Bis(pinacolato)diborane; Diboron Pinacol Ester; Dipinacoldiboron; Pinacol Diborane; 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane; Bis(pinacolato)diboron 99%; 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane; Bis(Pinacolato)diborane; 双戊酰二硼; 双联频哪醇硼酸酯; 双戊酰二硼

Database IDs

• CAS Number: 73183-34-3
• MDL Number: MFCD00799570
• Beilstein Number: 7703552
• PubChem SID: 160972200; 24870893
• PubChem CID: 2733548
• Chemspider ID: 2015334
• Wikipedia Title: Bis(pinacolato)diboron

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.5764
• LogD (pH = 7.4): 4.5764
• Log P: 4.5764
• Molar Refractivity: 60.4776 cm^3
• Polarizability: 28.11265 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 133-139°C; 137 - 140°C; 137-140 °C; 137-140 °C(lit.); 137-140°C; 139-141°C; ca 135°C
• Hydrophobicity(logP): 3.106

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere
• Storage Warning: Irritant; IRRITANT, IRRITANT-HARMFUL, KEEP COLD
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39-60
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 96%; 98+%; 99%
• Empirical Formula (Hill Notation): C12H24B2O4

DETAILS

Apollo Scientific Ltd - OR5456

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

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

Toronto Research Chemicals - 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.

REFERENCES

• Ali, H.A. et al.: Arch. Pharm., 337, 183 (2004)
• Izumi, A. et al.: Chem. Lett., 7, 728 (2004)