[1-(benzenesulfonyl)-1H-indol-2-yl]boronic acid

• ChemBase ID: 64790
• Molecular Formular: C14H12BNO4S
• Molecular Mass: 301.12538
• Monoisotopic Mass: 301.05800927
• SMILES: n1(c(cc2c1cccc2)B(O)O)S(=O)(=O)c1ccccc1
• Canonical SMILES: OB(c1cc2c(n1S(=O)(=O)c1ccccc1)cccc2)O
• InChI: InChI=1S/C14H12BNO4S/c17-15(18)14-10-11-6-4-5-9-13(11)16(14)21(19,20)12-7-2-1-3-8-12/h1-10,17-18H
• InChIKey: HXWLCYMHOULBJZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [1-(benzenesulfonyl)-1H-indol-2-yl]boronic acid
• IUPAC Traditional name: 1-(benzenesulfonyl)indol-2-ylboronic acid
• Synonyms: 1-(phenylsulfonyl)-1H-indol-2-ylboronic acid; 1-(Phenylsulphonyl)-1H-indole-2-boronic acid; 1-(Phenylsulfonyl)-2-indoleboronic acid; 1-(Phenylsulfonyl)-2-indoleboronic acid; 1-(Phenylsulfonyl)-2-indolylboronic acid; 1-(苯基磺酰)-1H-吲哚-2-基硼酸; 1-(苯基磺酰)-2-吲哚基硼酸

Database IDs

• CAS Number: 342404-46-0
• MDL Number: MFCD03086094
• PubChem SID: 24880137; 162030529
• PubChem CID: 2776228

CALCULATED PROPERTIES

• Acid pKa: 8.656789
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.9215991
• LogD (pH = 7.4): 2.8986237
• Log P: 2.9219
• Molar Refractivity: 73.9636 cm^3
• Polarizability: 32.461067 Å^3
• Polar Surface Area: 79.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 125-130 °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: C6H5SO2NC8H5B(OH)2

DETAILS

Sigma Aldrich - 563862

General description
Contains varying amounts of anhydride
Packaging
1 g in glass bottle
Application
Reactant for:
• Synthesis of bioactive indolo[3,2-j]phenanthridine alkaloid, calothrixin B, via an allene-mediated electrocyclic reaction1
• Preparation of arenes via palladium and tris(tert-butyl)phosphine-catalyzed Suzuki cross-coupling2
• Structure-guided development of TbcatB inhibitors as trypanocides3
• Chemoselective and stereoselective oxidative palladium/diamine-catalyzed cross-coupling reactions4
• Petasis boronic Mannich reactions under microwave conditions5