1-(benzenesulfonyl)-1H-indole

• ChemBase ID: 92566
• Molecular Formular: C14H11NO2S
• Molecular Mass: 257.30764
• Monoisotopic Mass: 257.0510496
• SMILES: n1(c2c(cccc2)cc1)S(=O)(=O)c1ccccc1
• Canonical SMILES: O=S(=O)(n1ccc2c1cccc2)c1ccccc1
• InChI: InChI=1S/C14H11NO2S/c16-18(17,13-7-2-1-3-8-13)15-11-10-12-6-4-5-9-14(12)15/h1-11H
• InChIKey: VDWLCYCWLIKWBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(benzenesulfonyl)-1H-indole
• IUPAC Traditional name: 1-(benzenesulfonyl)indole
• Synonyms: 1-(Benzenesulfonyl)indole; Benzenesulfonic acid indolide; NSC 237040; NSC 683530; 1-(Phenylsulfonyl)indole; 1-(Phenylsulphonyl)indole; 1-(PHENYLSULFONYL)INDOLE; 1-(苯基磺酰)吲哚; 1-(苯基磺酰基)吲哚

Database IDs

• CAS Number: 40899-71-6
• EC Number: 000-000-0
• MDL Number: MFCD00134318
• Beilstein Number: 1286712
• PubChem SID: 162079264; 24862680
• PubChem CID: 315017

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0013819
• LogD (pH = 7.4): 3.0013819
• Log P: 3.0013819
• Molar Refractivity: 70.1648 cm^3
• Polarizability: 29.266722 Å^3
• Polar Surface Area: 39.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 77-79°C; 78-80 °C(lit.); 78-80°C
• Boiling Point: 192°C/3mm

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C14H11NO2S

DETAILS

Sigma Aldrich - 366633

Packaging
5 g in glass bottle
Application
Reactant for preparation of:
• Antiplasmodial agents1
• Antifungal agents2
• Anti HIV-1 agents3
• Agonists of the histamine H4 receptor4
• Antibacterial agents5
• Camalexin analogs6
• CDK inhibitors and cytotoxic agents7
• Histone Deacetylase inhibitors8

REFERENCES

• Protected indole derivative which can be lithiated selectively at the 2-position. Reaction with electrophiles, followed by cleavage of the N-sulfonyl group with NaOH, leads to 2-substituted indoles: J. Org. Chem., 38, 3324; 43, 4684 (1978); 45, 3382 (1980). Dilithiation can also take place, with the second metallation occurring at the o-position of the sulfonyl benzene ring: J. Heterocycl. Chem., 18, 807 (1981).