1-(benzenesulfonyl)-1H-pyrrole

• ChemBase ID: 79058
• Molecular Formular: C10H9NO2S
• Molecular Mass: 207.24896
• Monoisotopic Mass: 207.03539953
• SMILES: S(=O)(=O)(n1cccc1)c1ccccc1
• Canonical SMILES: O=S(=O)(n1cccc1)c1ccccc1
• InChI: InChI=1S/C10H9NO2S/c12-14(13,11-8-4-5-9-11)10-6-2-1-3-7-10/h1-9H
• InChIKey: PPPXRIUHKCOOMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(benzenesulfonyl)-1H-pyrrole
• IUPAC Traditional name: 1-(benzenesulfonyl)pyrrole
• Synonyms: 1-(phenylsulphonyl)-1H-pyrrole; 1-(phenylsulfonyl)-1H-pyrrole; 1-(Benzenesulfonyl)pyrrole; 1-(Phenylsulfonyl)pyrrole; 1-(Phenylsulfonyl)pyrrole; 1-(苯基磺酰基)吡咯

Database IDs

• CAS Number: 16851-82-4
• MDL Number: MFCD00067739
• Beilstein Number: 1619427
• PubChem SID: 162043821; 24867474
• PubChem CID: 140146

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.982504
• LogD (pH = 7.4): 1.982504
• Log P: 1.982504
• Molar Refractivity: 53.8371 cm^3
• Polarizability: 21.751894 Å^3
• Polar Surface Area: 39.07 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 87-90°C; 88-91 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C10H9NO2S

DETAILS

Sigma Aldrich - 438839

Packaging
1, 5 g in glass bottle

REFERENCES

• Useful protected pyrrole derivative which undergoes regioselective electrophilic substitution, e.g. Friedel-Crafts acylation, at the 3-position: Tetrahedron Lett., 22, 4899, 4901 (1981); Synthesis, 353 (1985) (review); J. Org. Chem., 48, 3214 (1983). The phenylsulfonyl group is readily cleaved by alkaline hydrolysis. For acylation followed by reduction as a route to 3-alkylpyrroles, see: J. Org. Chem., 64, 3379 (1999). See also 1-(Triisopropylsilyl)pyrrole, L13152.
• With a Grignard reagent, e.g. i-PrMgCl, transmetallation occurs at the 2-position, allowing access to 2-substituted derivatives by reaction with electrophiles: Org. Lett., 6, 293 (2004).