2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

• ChemBase ID: 10020
• Molecular Formular: C10H20B2O4
• Molecular Mass: 225.8854
• Monoisotopic Mass: 226.15476992
• SMILES: B1(B2OCC(CO2)(C)C)OCC(CO1)(C)C
• Canonical SMILES: CC1(C)COB(OC1)B1OCC(CO1)(C)C
• InChI: InChI=1S/C10H20B2O4/c1-9(2)5-13-11(14-6-9)12-15-7-10(3,4)8-16-12/h5-8H2,1-4H3
• InChIKey: MDNDJMCSXOXBFZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane
• IUPAC Traditional name: 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane
• Synonyms: Bis(neopentanediolato)diboron; 5,5,5′,5′-Tetramethyl-2,2′-bi-1,3,2-dioxaborinane; Bis(neopentyl glycolato)diboron; 5,5,5',5'-Tetramethyl-2,2'-bi-1,3,2-dioxaborinane; Bis(neopentylglycolato)diboron; Bis(neopentyl glycolato)diboron; 5,5,5',5'-Tetramethyl-2,2'-bi(1,3,2-dioxaborinane); 双(新戊基 乙二醇)二硼; 5,5,5′,5′-四甲基-2,2′-二-1,3,2-二氧杂硼烷; 双(新戊基乙二醇)二硼

Database IDs

• CAS Number: 201733-56-4
• MDL Number: MFCD02093062
• Beilstein Number: 8839038
• PubChem SID: 24874048; 160973327
• PubChem CID: 2734316

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.9312
• LogD (pH = 7.4): 4.9312
• Log P: 4.9312
• Molar Refractivity: 51.499 cm^3
• Polarizability: 24.433949 Å^3
• Polar Surface Area: 36.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 170-178°C; 175-185°C; 180.5-184.5 °C(lit.)

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT; Irritant/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• 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: 96%; 97%
• Empirical Formula (Hill Notation): C10H20B2O4

DETAILS

Sigma Aldrich - 518808

Application
Reagent to prepare boronic acid esters.1
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - B504800

Makes borate adducts used for Suzuki coupling.

REFERENCES

• Wilson, K., et al.: Bioorg. Med. Chem. Lett., 20, 3925 (2010)
• Boronation reagent, cf Bis(pinacolato)diboron, L16088, which undergoes Pd-catalyzed coupling with aryl halides to give neopentylato boronic esters, more readily hydrolyzed to boronic acids than the corresponding pinacolato esters: Chem. Abs., 129, 290220 (1998). Found to be much more efficient than bis(pinacolato)diboron for the synthesis of hindered ortho-substituted arylboronic acids: Tetrahedron Lett., 46, 1671 (2005).