[(E)-2-(4-chlorophenyl)ethenyl]boronic acid

• ChemBase ID: 64160
• Molecular Formular: C8H8BClO2
• Molecular Mass: 182.41192
• Monoisotopic Mass: 182.03058758
• SMILES: B(/C=C/c1ccc(Cl)cc1)(O)O
• Canonical SMILES: OB(/C=C/c1ccc(cc1)Cl)O
• InChI: InChI=1S/C8H8BClO2/c10-8-3-1-7(2-4-8)5-6-9(11)12/h1-6,11-12H/b6-5+
• InChIKey: HWSDRAPTZRYXHN-AATRIKPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(E)-2-(4-chlorophenyl)ethenyl]boronic acid
• IUPAC Traditional name: (E)-2-(4-chlorophenyl)ethenylboronic acid
• Synonyms: trans-2-(4-Chlorophenyl)vinylboronic acid; trans-2-(4-Chlorophenyl)ethenylboronic acid; trans-2-(4-Chlorophenyl)vinylboronic acid; 反式-2-(4-氯苯基)乙烯基硼酸

Database IDs

• CAS Number: 154230-29-2
• MDL Number: MFCD02093767
• PubChem SID: 162029899; 24874345
• PubChem CID: 642694

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.8931794
• LogD (pH = 7.4): 2.8915632
• Log P: 2.8932
• Molar Refractivity: 45.1848 cm^3
• Polarizability: 18.9263 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 9.820618

PROPERTIES

Physical Property

• Melting Point: 165 °C (dec.)(lit.)

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Linear Formula: ClC6H4CH=CHB(OH)2

DETAILS

Sigma Aldrich - 523569

Other Notes
Contains varying amounts of anhydride
Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• Synthesis of biarylketones and phthalides1
• Trifluoromethylation2
• Asymmetrical Michael addition for preparation of chromanes3
• Cobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds4
• 1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydes5
• Petasis reactions6