4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane

• ChemBase ID: 10042
• Molecular Formular: C9H19BO3
• Molecular Mass: 186.05636
• Monoisotopic Mass: 186.14272487
• SMILES: O(B1OC(C(O1)(C)C)(C)C)C(C)C
• Canonical SMILES: CC(OB1OC(C(O1)(C)C)(C)C)C
• InChI: InChI=1S/C9H19BO3/c1-7(2)11-10-12-8(3,4)9(5,6)13-10/h7H,1-6H3
• InChIKey: MRWWWZLJWNIEEJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane
• IUPAC Traditional name: 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxa-borolane; [(Prop-2-yl)oxy]boronic acid, pinacol ester; 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Isopropoxyboronic acid, pinacol ester; 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Isopropyl pinacolyl borate; 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; 4,4,5,5-tetramethyl-2-(propan-2-yloxy)-1,3,2-dioxaborolane; 2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼烷; 2-异丙氧基-4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷

Database IDs

• CAS Number: 61676-62-8
• MDL Number: MFCD00192241
• Beilstein Number: 1906370
• PubChem SID: 24866125; 160973349
• PubChem CID: 5017741

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.2355
• LogD (pH = 7.4): 3.2355
• Log P: 3.2355
• Molar Refractivity: 46.4531 cm^3
• Polarizability: 20.639704 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 73 °C/15 mmHg(lit.); 73°C; 73°C/15mm; 73°C/15mm
• Flash Point: 109.4 °F; 42°C(107°F); 43 °C; 43°C
• Density: 0.912; 0.912 g/mL at 25 °C(lit.)
• Refractive Index: 1.409; 1.4090; n20/D 1.409(lit.)
• Hydrophobicity(logP): 2.609

Safety Information

• Storage Warning: Flammable/Irritant/Moisture Sensitive/Store under Argon; IRRITANT, MOISTURE SENSITIVE, FLAMMABLE; Moisture Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38
• Safety Statements: 16-26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-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

Product Information

• Purity: 95%; 97%; 98%
• Empirical Formula (Hill Notation): C9H19BO3

DETAILS

Sigma Aldrich - 417149

Application
Reagent for fluorenylborolane preparation.1
Reagent used to borylate arenes.
Packaging
5, 25, 100, 500 mL in glass bottle

REFERENCES

• Selective reagent for preparation of pinacol boronic esters, e.g. for preparation of allenyl or vinyl pinacol boronates from the Grignard or lithium reagents: Liebigs Ann. Chem., 881 (1987); Chem. Ber., 122, 1777 (1989); Tetrahedron Lett., 33, 6941 (1992).