4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide

• ChemBase ID: 77979
• Molecular Formular: C12H18BNO4S
• Molecular Mass: 283.15162
• Monoisotopic Mass: 283.10495946
• SMILES: B1(c2ccc(cc2)S(=O)(=O)N)OC(C(O1)(C)C)(C)C
• Canonical SMILES: CC1(C)OB(OC1(C)C)c1ccc(cc1)S(=O)(=O)N
• InChI: InChI=1S/C12H18BNO4S/c1-11(2)12(3,4)18-13(17-11)9-5-7-10(8-6-9)19(14,15)16/h5-8H,1-4H3,(H2,14,15,16)
• InChIKey: XDDLLUBKOZYOMY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1-sulfonamide
• IUPAC Traditional name: 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide
• Synonyms: 4-Sulfamoylphenylboronic acid, pinacol ester; 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulphonamide; 4-Sulphamoylbenzeneboronic acid, pinacol ester; 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)benzenesulfonamide; 4-Sulfamoylphenylboronic Acid Pinacol Ester

Database IDs

• CAS Number: 214360-51-7
• MDL Number: MFCD06657806
• PubChem SID: 162042818
• PubChem CID: 16414190

CALCULATED PROPERTIES

• Acid pKa: 9.811126
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.5335803
• LogD (pH = 7.4): 2.5320394
• Log P: 2.5336
• Molar Refractivity: 67.871 cm^3
• Polarizability: 29.292324 Å^3
• Polar Surface Area: 78.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold

Product Information

• Purity: 97%; 98%

DETAILS

Toronto Research Chemicals - S699055

Used for preparation of Valdecoxib.

REFERENCES

• Daidone, G., et al.: Arch. Pharm. Pharm. Med. Chem., 332, 50 (1999)
• Frolund, B., et al.: J. Med. Chem., 45, 2454 (1999)
• Li, W., et al.: J. Med. Chem., 46, 1706 (1999)