5-nitrothiophene-2-carbonitrile

• ChemBase ID: 68610
• Molecular Formular: C5H2N2O2S
• Molecular Mass: 154.14658
• Monoisotopic Mass: 153.98369831
• SMILES: c1(ccc(s1)[N+](=O)[O-])C#N
• Canonical SMILES: N#Cc1ccc(s1)[N+](=O)[O-]
• InChI: InChI=1S/C5H2N2O2S/c6-3-4-1-2-5(10-4)7(8)9/h1-2H
• InChIKey: FLYONFCGDKAMIH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-nitrothiophene-2-carbonitrile
• IUPAC Traditional name: 5-nitrothiophene-2-carbonitrile
• Synonyms: 5-Nitrothiophene-2-carbonitrile; 5-Nitrothiophene-2-carbonitrile; 5-nitro-2-thiophenecarbonitrile; 2-Cyano-5-nitrothiophene; 5-Nitro-2-thiophenecarbonitrile; 2-氰基-5-硝基噻吩; 5-硝基噻酚-2-甲腈

Database IDs

• CAS Number: 16689-02-4
• EC Number: 000-000-0
• MDL Number: MFCD00052401
• Beilstein Number: 123934
• PubChem SID: 162034340; 24846074
• PubChem CID: 519294

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.8482035
• LogD (pH = 7.4): 1.8482035
• Log P: 1.8482035
• Molar Refractivity: 34.1499 cm^3
• Polarizability: 12.896552 Å^3
• Polar Surface Area: 66.93 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 42-46 °C; 43-45°C
• Hydrophobicity(logP): 1.07

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 3439; UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 20/21/22-36/37/38; 22-37/38-41
• Safety Statements: 26-36/37/39; 9-26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H318-H335; H331-H302-H312-H315-H319-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3439 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC); 95%; 95+%; 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C5H2N2O2S

REFERENCES

• For a review of vicarious nucleophilic substitution in heterocyclic compounds, see: Synthesis, 103 (1991).
• Undergoes vicarious nucleophilic substitution at the 4-position; e.g. with chloromethyl phenyl sulfone and base, 5-nitro-4-(phenylsulfonylmethyl)thiophene-2-carbonitrile is formed in 91% yield: Tetrahedron, 51, 8339 (1995). For analogous example and reaction scheme, see 2-Nitrothiophene, A17464.