(2-phenylethyl)boronic acid

• ChemBase ID: 1730
• Molecular Formular: C8H11BO2
• Molecular Mass: 149.98274
• Monoisotopic Mass: 150.08520999
• SMILES: OB(O)CCc1ccccc1
• Canonical SMILES: OB(CCc1ccccc1)O
• InChI: InChI=1S/C8H11BO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5,10-11H,6-7H2
• InChIKey: VPRUMANMDWQMNF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-phenylethyl)boronic acid
• IUPAC Traditional name: phenylethane boronic acid; PEBA
• Synonyms: Phenylethane Boronic Acid; 2-Phenylethylboronic acid; 2-Phenylethaneboronic acid; Phenethylboronic acid; Phenethylboronic acid; 2-Phenylethylboronic acid; PHENETHYLBORONIC ACID; 苯乙基硼酸; 2-苯基乙基硼酸

Database IDs

• CAS Number: 34420-17-2
• MDL Number: MFCD01631226
• PubChem SID: 160965186; 24881217; 46505107
• PubChem CID: 65389

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.841407
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.9916033
• LogD (pH = 7.4): 1.976446
• Log P: 1.9918
• Molar Refractivity: 40.2055 cm^3
• Polarizability: 17.161442 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.42
• LOG S: -1.92
• Solubility (Water): 1.82e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 76-81 °C(lit.); 82-84°C; 82-84°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37-60
• 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: 97%; 98%
• Linear Formula: C6H5CH2CH2B(OH)2

DETAILS

DrugBank - DB01963

Drug information: experimental

Sigma Aldrich - 588423

Other Notes
Contains varying amounts of anhydride
Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura cross-coupling reactions1
• Reactions with α-diazocarbonyl compounds2
• C-H functionalization of quinones3
• Cross-coupling with aromatic amines4
• Arylation and alkylation of diphenylisoxazole5Reactant used in studies of the stability of boronic esters to hydrolysis6