2-nitrobenzene-1-sulfonamide

• ChemBase ID: 92275
• Molecular Formular: C6H6N2O4S
• Molecular Mass: 202.18784
• Monoisotopic Mass: 202.00482768
• SMILES: S(=O)(=O)(c1c(cccc1)[N+](=O)[O-])N
• Canonical SMILES: [O-][N+](=O)c1ccccc1S(=O)(=O)N
• InChI: InChI=1S/C6H6N2O4S/c7-13(11,12)6-4-2-1-3-5(6)8(9)10/h1-4H,(H2,7,11,12)
• InChIKey: GNDKYAWHEKZHPJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-nitrobenzene-1-sulfonamide
• IUPAC Traditional name: 2-nitrobenzenesulfonamide
• Synonyms: NSC 23381; NSC 629275; 2-Nitrobenzenesulfonamide; 2-Sulphamoylnitrobenzene; 2-(Aminosulphonyl)nitrobenzene; 2-Nitrobenzenesulphonamide 98%; 2-Nitrobenzenesulfonamide; 2-硝基苯磺酰胺

Database IDs

• CAS Number: 5455-59-4
• EC Number: 000-000-0
• MDL Number: MFCD00009807
• Beilstein Number: 2214215
• PubChem SID: 24853717; 162078973
• PubChem CID: 138510

CALCULATED PROPERTIES

• Acid pKa: 8.597971
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.51895386
• LogD (pH = 7.4): 0.49569595
• Log P: 0.51926076
• Molar Refractivity: 44.5364 cm^3
• Polarizability: 17.645538 Å^3
• Polar Surface Area: 103.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 188-194°C; 190-192 °C(lit.); 190-192°C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37; 26-37/39
• 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: 98%; 98+%
• Linear Formula: O2NC6H4SO2NH2

DETAILS

Sigma Aldrich - 228907

Packaging
25 g in poly bottle
5 g in glass bottle
Application
Reactant involved in synthesis of:
• Cyclic nitrogen compounds via intramolecular hydroamination1
• Pentacyclic lycopodium alkaloid huperzine-Q2
• Pyrrolidines3
• Intermolecular C-H insertion reactions4,5Reactant involved in intermolecular amination of allyl alcohols6

REFERENCES

• Reagent for synthesis of medium-ring amines via N-alkylation, e.g. with ω-bromo alkanols under Mitsunobu conditions (DEAD/PPh₃), and cyclization of the resulting ω-bromo alkylsulfonamides (Cs₂CO₃/Bu₄NI): Synlett, 697 (2002) and references therein. See also 2-Nitrobenzenesulfonyl chloride, B21522.