[4-(methoxycarbonyl)phenyl]boronic acid

• ChemBase ID: 10043
• Molecular Formular: C8H9BO4
• Molecular Mass: 179.96566
• Monoisotopic Mass: 180.05938917
• SMILES: c1c(ccc(c1)B(O)O)C(=O)OC
• Canonical SMILES: COC(=O)c1ccc(cc1)B(O)O
• InChI: InChI=1S/C8H9BO4/c1-13-8(10)6-2-4-7(5-3-6)9(11)12/h2-5,11-12H,1H3
• InChIKey: PQCXFUXRTRESBD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(methoxycarbonyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(methoxycarbonyl)phenylboronic acid
• Synonyms: (4-(Methoxycarbonyl)phenyl)boronic acid; 4-Methoxycarbonylphenylboronic acid; Methyl 4-boronobenzoate; Methyl 4-boronobenzoate; 4-(Methoxycarbonyl)benzeneboronic acid; (4-Carbomethoxyphenyl)boronic acid; 4-Carbomethoxybenzeneboronic acid; 4-Methoxycarbonylbenzeneboronic acid; 4-borono-benzoic acid 1-methyl ester; p-(Methoxycarbonyl)boronic acid; p-(Methoxycarbonyl)phenylboronic acid; p-borono-benzoic acid methyl ester; Methyl p-boronobenzoate; 4-Methoxycarbonylphenylboronic acid; 4-甲酸甲酯苯硼酸; 4-甲氧羰基苯硼酸

Database IDs

• CAS Number: 99768-12-4
• MDL Number: MFCD01632203
• PubChem SID: 24881520; 160973350
• PubChem CID: 2734369

CALCULATED PROPERTIES

• Polarizability: 17.978323 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 8.510869
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.786979
• LogD (pH = 7.4): 1.7551634
• Log P: 1.7874
• Molar Refractivity: 42.6288 cm^3

PROPERTIES

Physical Property

• Melting Point: 197-200 °C(lit.); 197-200°C

Safety Information

• Storage Warning: IRRITANT; 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: 96%; 97%; 98%
• Empirical Formula (Hill Notation): C8H9BO4

DETAILS

Sigma Aldrich - 594539

Other Notes
Contains varying amount of anhydride
Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence1
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides2
• One-pot ipso-nitration of arylboronic acids3
• Copper-catalyzed nitration4
• Cyclocondensation followed by palladium-phosphine-catalyzed Suzuki-Miyaura coupling5
• Reagent used in Preparation of
• Biaryls via nickel-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl halides with arylboronic acid6†
• Chromenones and their bradykinin B1 antagonistic activit7†
• Pt nanoparticles@Photoactive metal-organic frameworks resulting in efficient hydrogen evolution via synergistic photoexcitation and electron injectio8†
• Salicylate-based thienylbenzoic acids as E. coli methionine aminopeptidase inhibitor9†