2-bromo-5-nitrothiophene

• ChemBase ID: 74519
• Molecular Formular: C4H2BrNO2S
• Molecular Mass: 208.03318
• Monoisotopic Mass: 206.89896131
• SMILES: [N+](=O)(c1ccc(s1)Br)[O-]
• Canonical SMILES: [O-][N+](=O)c1ccc(s1)Br
• InChI: InChI=1S/C4H2BrNO2S/c5-3-1-2-4(9-3)6(7)8/h1-2H
• InChIKey: ZPNFMDYBAQDFDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromo-5-nitrothiophene
• IUPAC Traditional name: 2-bromo-5-nitrothiophene
• Synonyms: 2-Bromo-5-nitrothiophene; 2-Bromo-5-nitrothiophene; 2-溴-5-硝基噻吩

Database IDs

• CAS Number: 13195-50-1
• EC Number: 236-155-8
• MDL Number: MFCD00022493
• Beilstein Number: 120955
• PubChem SID: 162039438; 24878772
• PubChem CID: 83222

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.7944164
• LogD (pH = 7.4): 2.7944164
• Log P: 2.7944164
• Molar Refractivity: 35.4269 cm^3
• Polarizability: 14.1662655 Å^3
• Polar Surface Area: 43.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 42-46°C; 44-48 °C(lit.); 44-48°C
• Boiling Point: 235-237°C; 235-237°C
• Hydrophobicity(logP): 2.499

Safety Information

• Storage Warning: Irritant/Light Sensitive/Keep Cold
• 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: 95%; 97%
• Empirical Formula (Hill Notation): C4H2BrNO2S

DETAILS

Sigma Aldrich - 544531

Packaging
1, 5 g in glass bottle

REFERENCES

• Undergoes vicarious nucleophilic substitution of hydrogen at the 4-position; e.g., with chloromethyl phenyl sulfone and base, 2-bromo-5-nitro-4-(phenylsulfonylmethyl)thiophene is formed in 92% yield: Tetrahedron, 51, 8339 (1995). For an analogous example and reaction scheme, see 2-Nitrothiophene, A17464.
• For a review of vicarious nucleophilic substitution in heterocyclic compounds, see: Synthesis, 103 (1991).