methyl 5-nitrofuran-2-carboxylate

• ChemBase ID: 85731
• Molecular Formular: C6H5NO5
• Molecular Mass: 171.1076
• Monoisotopic Mass: 171.01677227
• SMILES: [N+](=O)(c1ccc(o1)C(=O)OC)[O-]
• Canonical SMILES: [O-][N+](=O)c1ccc(o1)C(=O)OC
• InChI: InChI=1S/C6H5NO5/c1-11-6(8)4-2-3-5(12-4)7(9)10/h2-3H,1H3
• InChIKey: UTLKCGPAJUYGOM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 5-nitrofuran-2-carboxylate
• IUPAC Traditional name: methyl 5-nitrofuran-2-carboxylate
• Synonyms: Methyl 5-nitro-2-furoate; Methyl 5-nitro-2-furoate; Methyl 5-nitrofuran-2-carboxylate; 5-Nitrofuran-2-carboxylic acid methyl ester; methyl 5-nitrofuran-2-carboxylate; 5-硝基-2-糠酸甲酯; 5-甲基-2-糠酸甲酯

Database IDs

• CAS Number: 1874-23-3
• EC Number: 000-000-0
• MDL Number: MFCD00051956
• Beilstein Number: 165132
• PubChem SID: 24871689; 162072847
• PubChem CID: 94882

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.0662446
• LogD (pH = 7.4): 1.0662446
• Log P: 1.0662446
• Molar Refractivity: 36.048 cm^3
• Polarizability: 13.7913475 Å^3
• Polar Surface Area: 82.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 78-82 °C(lit.); 78-82°C; 79 - 81°C
• Hydrophobicity(logP): 1.03

Safety Information

• Storage Warning: Irritant
• RTECS: LV2013000
• German water hazard class: 3
• Risk Statements: 68
• Safety Statements: 36/37
• TSCA Listed: 否
• GHS Pictograms: GHS08
• GHS Hazard statements: H341
• GHS Precautionary statements: P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 97%; 98%
• Empirical Formula (Hill Notation): C6H5NO5

DETAILS

Sigma Aldrich - 480509

Packaging
1, 5 g in glass bottle

REFERENCES

• For a review of vicarious nucleophilic substitution in heterocyclic compounds, see: Synthesis, 103 (1991).
• The nitro-group is susceptible to nucleophilic displacement (compare 1,4-Dinitrobenzene, A10293): J. Heterocycl. Chem., 18, 1241 (1981). This has been used as the basis of a synthesis of diaryl ethers involving Diels-Alder addition and decarboxylative aromatization of the adduct: J. Chem. Soc., Perkin 1, 1231 (1990):
  
• Undergoes vicarious nucleophilic substitution of hydrogen at the 3-position. For example with chloromethyl phenyl sulfone and base, 2-nitro-3-(phenylsulfonylmethyl)furan is formed in 75% yield: Tetrahedron, 51, 8339 (1995). For analogous example and reaction scheme, see 2-Nitrothiophene, A17464.