[(1E)-3-phenylprop-1-en-1-yl]boronic acid

• ChemBase ID: 142144
• Molecular Formular: C9H11BO2
• Molecular Mass: 161.99344
• Monoisotopic Mass: 162.08520999
• SMILES: B(/C=C/Cc1ccccc1)(O)O
• Canonical SMILES: OB(/C=C/Cc1ccccc1)O
• InChI: InChI=1S/C9H11BO2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-6,8,11-12H,7H2/b8-4+
• InChIKey: GMGWFDHLFMBIDS-XBXARRHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1E)-3-phenylprop-1-en-1-yl]boronic acid
• IUPAC Traditional name: (1E)-3-phenylprop-1-en-1-ylboronic acid
• Synonyms: trans-3-phenylpropen-1-yl-boronic acid; trans-3-Phenyl-1-propen-1-ylboronic acid; 反式-3-苯基丙烯-1-基-硼酸; 反式-3-苯基-1-丙烯基-1-硼酸

Database IDs

• CAS Number: 129423-29-6
• MDL Number: MFCD06202527
• PubChem SID: 162236374; 24883207
• PubChem CID: 11041016

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.5234
• LogD (pH = 7.4): 2.5234
• Log P: 2.5234
• Molar Refractivity: 44.981 cm^3
• Polarizability: 18.846685 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C9H11BO2

DETAILS

Sigma Aldrich - 642606

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Carbonylative arylation of allenols1
• Oxidative cross-coupling with (trifluoromethyl)trimethylsilane2
• Suzuki-Miyaura coupling reactions3,4
• three-component reductive coupling with alkynes5
• Enantioselective conjugation to vinyl 2-pyridylsulfones6