[3-(methoxycarbonyl)phenyl]boronic acid

• ChemBase ID: 10581
• Molecular Formular: C8H9BO4
• Molecular Mass: 179.96566
• Monoisotopic Mass: 180.05938917
• SMILES: c1(cccc(c1)B(O)O)C(=O)OC
• Canonical SMILES: COC(=O)c1cccc(c1)B(O)O
• InChI: InChI=1S/C8H9BO4/c1-13-8(10)6-3-2-4-7(5-6)9(11)12/h2-5,11-12H,1H3
• InChIKey: ALTLCJHSJMGSLT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [3-(methoxycarbonyl)phenyl]boronic acid
• IUPAC Traditional name: 3-(methoxycarbonyl)phenylboronic acid
• Synonyms: Methyl 3-boronobenzoate; 3-(Methoxycarbonyl)benzeneboronic acid; 3-Methoxycarbonylphenylboronic acid; 3-Methoxycarbonylphenylboronic acid; 3-Boronobenzoic Acid 1-Methyl Ester; m-Boronobenzoic Acid Methyl Ester; 3-(Carbomethoxy)phenylboronic Acid; 3-Methoxycarbonylbenzeneboronic Acid; m-(Methoxycarbonyl)boronic Acid; 3-(Methoxycarbonyl)phenylboronic Acid; 3-甲酸甲酯苯硼酸; 3-甲氧羰基苯硼酸

Database IDs

• CAS Number: 99769-19-4
• MDL Number: MFCD02093046
• PubChem SID: 160973888; 24881314
• PubChem CID: 2734714

CALCULATED PROPERTIES

• Acid pKa: 8.573759
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7870357
• LogD (pH = 7.4): 1.7593735
• Log P: 1.7874
• Molar Refractivity: 42.6288 cm^3
• Polarizability: 17.977407 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 205-207°C; 205-208 °C(lit.)

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: 97%; 98%
• Linear Formula: CH3O2CC6H4B(OH)2

DETAILS

Sigma Aldrich - 591130

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Suzuki-Miyaura cross-coupling1
• Iterative cross-coupling of boronate building blocks2
• Cross-coupling with aryl / alkenyl sulfonates3
• Synthesis of symmetrical biaryls via CuCl catalyzed homocoupling4
• Trifluoromethylation5
• Cyanation6

Toronto Research Chemicals - M261635

Used in the preparation of substituted pyrazolylpyrimidinamine derivative for use as protein kinase inhibitors.

REFERENCES

• Hara, K., et al.: New J. Chem., 27, 783 (2003)
• Winters, M., et al.: Chem. Eur. J., 13, 7385 (2003)
• James, D., et al.: Bioorg. Med. Chem. Lett., 18, 1784 (2003)