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

• ChemBase ID: 53289
• Molecular Formular: C9H17BO2
• Molecular Mass: 168.04108
• Monoisotopic Mass: 168.13216018
• SMILES: O1B(OC(C1(C)C)(C)C)C(=C)C
• Canonical SMILES: CC(=C)B1OC(C(O1)(C)C)(C)C
• InChI: InChI=1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3
• InChIKey: SVSUYEJKNSMKKW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane
• IUPAC Traditional name: 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane
• Synonyms: 4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane; 4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane; Isopropenylboronic acid pinacol ester; 2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Isopropenylboronic acid, pinacol ester; 2-异丙烯基-4,4,5,5-四甲基-1,3,2-二氧杂硼烷; 异丙烯基硼酸频哪醇酯

Database IDs

• CAS Number: 126726-62-3
• MDL Number: MFCD08276843
• PubChem SID: 24884621; 162058052
• PubChem CID: 10997426

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.581
• LogD (pH = 7.4): 2.581
• Log P: 2.581
• Molar Refractivity: 45.2158 cm^3
• Polarizability: 19.709911 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 47-49 °C/9 mbar; 47-49°C/6.75mm
• Flash Point: 107.6 °F; 42 °C; 42°C
• Density: 0.894; 0.894 g/mL at 25 °C
• Refractive Index: 1.4320; n20/D 1.4320

Safety Information

• Storage Warning: Flammable/Moisture Sensitive/Keep Cold/Store under Argon; MOISTURE SENSITIVE, KEEP COLD, FLAMMABLE
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-36/37/38-43
• Safety Statements: 26-36/37
• TSCA Listed: false
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 95+%
• Contains: phenothiazine as stabilizer
• Empirical Formula (Hill Notation): C9H17BO2

DETAILS

Sigma Aldrich - 663212

Packaging
5, 25 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura cross-coupling processes1
• Inverse-electron-demand Diels-Alder reaction2
• Simmons-Smith Cyclopropanation Reaction3
• Polyene cyclization4
• Stereoselective aldol reactions5
• Grubbs cross-metathesis reaction5
• Intramolecular Suzuki-Miyaura reaction5
• Stereoselective cross-metathesis6
• Dipolar cycloaddition7
• Iodosulfonylation8
• Asymmetric conjugate addition and intramolecular hydroacylation9 Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors10 9
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions
• Inverse-electron-demand Diels-Alder reaction2
• Simmons-Smith Cyclopropanation Reaction3
• Polyene cyclization4
• Stereoselective aldol reactions5
• Grubbs cross-metathesis reaction5
• Intramolecular Suzuki-Miyaura reaction5
• Stereoselective cross-metathesis6
• Dipolar cycloaddition
• Iodosulfonylation8
• Asymmetric conjugate addition and intramolecular hydroacylation9 Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors