[4-(methylsulfanyl)phenyl]boronic acid

• ChemBase ID: 9739
• Molecular Formular: C7H9BO2S
• Molecular Mass: 168.02116
• Monoisotopic Mass: 168.04163093
• SMILES: c1c(ccc(c1)SC)B(O)O
• Canonical SMILES: CSc1ccc(cc1)B(O)O
• InChI: InChI=1S/C7H9BO2S/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3
• InChIKey: IVUHTLFKBDDICS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(methylsulfanyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(methylsulfanyl)phenylboronic acid
• Synonyms: 4-Thioanisoleboronic acid; 4-(methylsulfanyl)phenylboronic acid; 4-(Methylthio)phenylboronic acid; 4-Thioanisoleboronic acid; 4-(Methylthio)benzeneboronic acid; 4-(Methylthio)phenylboronic acid; 4-(Methylsulfanyl)benzeneboronic acid; 4-(Methylsulfanyl)phenylboronic acid; 4-(Methylthio)benzeneboronic acid; 4-(Methylthio)phenylboronic acid; [4-(methylthio)phenyl]boronic acid; Thioanisole-4-boronic acid; 4-(Methylthio)benzeneboronic acid; 4-(甲基硫代)苯硼酸; 4-(甲基硫代)苯硼酸; 4-甲硫基苯硼酸

Database IDs

• CAS Number: 98546-51-1
• MDL Number: MFCD00093410
• Beilstein Number: 3247219
• PubChem SID: 24869239; 160973046
• PubChem CID: 2733959

CALCULATED PROPERTIES

• Acid pKa: 8.762232
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.294864
• LogD (pH = 7.4): 2.2767363
• Log P: 2.2951
• Molar Refractivity: 43.3624 cm^3
• Polarizability: 18.417099 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 210-212°C; 210-214 °C(lit.); 210-214°C; ca 208-212°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 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: 95%; 97%; 98%
• Impurities: <15% anhydride
• Linear Formula: CH3SC6H4B(OH)2

DETAILS

Sigma Aldrich - 456802

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5, 25 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura cross coupling reactions1 with 2-aryl-1-bromo-1-nitroethenes2 or alkynyl bromides3
• Addition reactions with naphthyridine N-oxides4
• Oxyarylation of Heck reaction intermediates for synthesis of THF derivatives5
• Sulfoxidation reactions6
• Copper-catalyzed halogenation7