5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

• ChemBase ID: 32917
• Molecular Formular: C10H15BN2O2
• Molecular Mass: 206.0493
• Monoisotopic Mass: 206.12265813
• SMILES: c1ncc(cn1)B1OC(C(O1)(C)C)(C)C
• Canonical SMILES: CC1(C)OB(OC1(C)C)c1cncnc1
• InChI: InChI=1S/C10H15BN2O2/c1-9(2)10(3,4)15-11(14-9)8-5-12-7-13-6-8/h5-7H,1-4H3
• InChIKey: WSRGGSAGSUEJKQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
• IUPAC Traditional name: 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
• Synonyms: 5-Pyrimidineboronic acid pinacol ester; Pyrimidyl-5-boronic acid pinacolate; 5-Pyrimidineboronic Acid Pinacol Ester; Pyrimidine-5-boronic acid pinacol ester; Pyrimidyl-5-boronic acid pinacol ester; 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; Pyrimidine-5-boronic acid, pinacol ester; Pyrimidine-5-boronic acid pinacol ester; 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine; 5-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)嘧啶; 嘧啶-5-硼酸频哪醇酯; 嘧啶-5-硼酸频哪酯

Database IDs

• CAS Number: 321724-19-0
• MDL Number: MFCD05155223
• PubChem SID: 160996224
• PubChem CID: 4192667

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.7671973
• LogD (pH = 7.4): 1.7672
• Log P: 1.7672
• Molar Refractivity: 52.3774 cm^3
• Polarizability: 22.215466 Å^3
• Polar Surface Area: 44.24 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 60-66°C; 60-66°C; 67-71 °C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• 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%; 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C10H15BN2O2

DETAILS

Sigma Aldrich - 704687

Packaging
250 mg in glass bottle

Toronto Research Chemicals - P997260

2-Methoxyphenylborornic Acid Pinacol Ester is used in the preparation of indole derivatives as selective inhibitors of all three members of the Pim kinase family. It is also used to prepare inhibitors of TGF-β1 and activin A signalling.

REFERENCES

• Nishiguchi, G.A. et al.: Bioorg. Med. Chem. Lett., 21, 6366 (2011)
• Ciayadi, R. et al.: Bioorg. Med. Chem. Lett., 21, 5642 (2011)