[(1E)-pent-1-en-1-yl]boronic acid

• ChemBase ID: 74811
• Molecular Formular: C5H11BO2
• Molecular Mass: 113.95064
• Monoisotopic Mass: 114.08520999
• SMILES: B(/C=C/CCC)(O)O
• Canonical SMILES: CCC/C=C/B(O)O
• InChI: InChI=1S/C5H11BO2/c1-2-3-4-5-6(7)8/h4-5,7-8H,2-3H2,1H3
• InChIKey: SYKWJOZHNDPWIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1E)-pent-1-en-1-yl]boronic acid; (pent-1-en-1-yl)boronic acid
• IUPAC Traditional name: (1E)-pent-1-en-1-ylboronic acid; pent-1-en-1-ylboronic acid
• Synonyms: 1-Pentenylboronic acid; (1E)-(Pent-1-en-1-yl)boronic acid; 1-Pentenylboronic acid; 1-Penten-1-ylboronic acid; 1-PENTENYLBORONIC ACID; 1-戊烯基硼酸

Database IDs

• CAS Number: 59239-44-0; 104376-24-1
• EC Number: 000-000-0
• MDL Number: MFCD01074677
• Beilstein Number: 2038297
• PubChem SID: 24880927; 162039729
• PubChem CID: 5702651

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.7024819
• LogD (pH = 7.4): 1.7010614
• Log P: 1.7025
• Molar Refractivity: 29.487 cm^3
• Polarizability: 12.92032 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 9.876747

PROPERTIES

Physical Property

• Melting Point: 100-105 °C(lit.); 79-81°C

Safety Information

• Storage Warning: Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 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: 98%
• Empirical Formula (Hill Notation): C5H11BO2

DETAILS

Sigma Aldrich - 578452

Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Synthesis of 8-alkenylborondipyrromethene dyes via Liebeskind-Srogl cross-coupling starting from 8-thiomethyl-substituted BODIPY1
• Rhodium and palladium catalyzed substitution reactions with enyne acetates and carbonates2
• Halogenation and protodeauration reactions of organogold phosphine complexes3
• Lewis acid catalyzed Nazarov reaction4
• Palladium-catalyzed tandem intramolecular C-N and intermolecular Suzuki coupling process5,6