(2-ethoxyphenyl)boronic acid

• ChemBase ID: 32705
• Molecular Formular: C8H11BO3
• Molecular Mass: 165.98214
• Monoisotopic Mass: 166.08012461
• SMILES: c1(c(cccc1)OCC)B(O)O
• Canonical SMILES: CCOc1ccccc1B(O)O
• InChI: InChI=1S/C8H11BO3/c1-2-12-8-6-4-3-5-7(8)9(10)11/h3-6,10-11H,2H2,1H3
• InChIKey: DGFCTCGCMKEILT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-ethoxyphenyl)boronic acid
• IUPAC Traditional name: 2-ethoxyphenylboronic acid
• Synonyms: 2-Ethoxybenzeneboronic acid; 2-Ethoxyphenylboronic acid; 2-Ethoxyphenylboronic acid; 2-Ethoxybenzeneboronic acid; 2-(Ethoxy)benzeneboronic acid; 2-Ethoxyphenylboronic acid; 2-乙氧基苯硼酸; 邻乙氧基苯硼酸

Database IDs

• CAS Number: 213211-69-9
• MDL Number: MFCD00674027
• PubChem SID: 24869076; 160996012
• PubChem CID: 2734902

CALCULATED PROPERTIES

• Acid pKa: 8.420218
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7290813
• LogD (pH = 7.4): 1.6902095
• Log P: 1.7296
• Molar Refractivity: 41.8153 cm^3
• Polarizability: 17.892942 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 97-102 °C(lit.); 98-101°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: 98%
• Linear Formula: C2H5OC6H4B(OH)2

DETAILS

Sigma Aldrich - 455520

Other Notes
Contains varying amounts of anhydride.
Packaging
1, 10 g in glass bottle
Application
Reactant involved in Suzuki-Miyaura cross-coupling reactions for synthesis of pyridines and pyrimidines1, reactions of bromo-N-methylpyrrole2, or synthesis of diarylbenzophenones3Reactant involved in:
• Ipso-amidation with nitriles4
• Studies of the effect of biaryl phosphine ligand structure on C-N and C-C bond formation5
• Oxidative coupling via C-H arylation6