2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• ChemBase ID: 139800
• Molecular Formular: C8H15BO2
• Molecular Mass: 154.0145
• Monoisotopic Mass: 154.11651012
• SMILES: B1(OC(C(O1)(C)C)(C)C)C=C
• Canonical SMILES: C=CB1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3
• InChIKey: DPGSPRJLAZGUBQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• IUPAC Traditional name: 2-ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane; 4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane; Vinylboronic acid pinacol ester; VINYLBORONIC ACID PINACOL ESTER; 2-乙烯基-4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷; 乙烯基硼酸频哪醇酯

Database IDs

• CAS Number: 75927-49-0
• MDL Number: MFCD00192492
• PubChem SID: 162234048; 24882546
• PubChem CID: 5233012

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.8193
• LogD (pH = 7.4): 2.8193
• Log P: 2.8193
• Molar Refractivity: 39.7211 cm^3
• Polarizability: 17.865597 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 34 °C; 93.2 °F
• Density: 0.908 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4300(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• UN Number: 3272
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-43
• Safety Statements: 36/37
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H317
• GHS Precautionary statements: P280
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3272 3/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: 95%; 98%
• Contains: phenothiazine as stabilizer
• Empirical Formula (Hill Notation): C8H15BO2

DETAILS

Sigma Aldrich - 633348

Packaging
1, 10 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura coupling reactions1
• Mizoroki-Heck reactions (cascade reaction)1
• Intramolecular Nozaki-Hiyama-Kishi reactions2
• Stereoselective Cu-catalyzed γ-selective and stereospecific coupling3
• Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes4
• Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions5
• Asymmetric Birch reductive alkylation6Reagent used in Preparation of
• Molecular tubes for lipid sensing7
• Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)8,9,10,2