2-Nitrofuran

Base Information

• Chemical Name: 2-Nitrofuran
• CAS No.: 609-39-2
• Molecular Formula: C4H3 N O3
• Molecular Weight: 113.073
• European Community (EC) Number: 625-946-7
• NSC Number: 59983
• UNII: 17EZI4D981
• DSSTox Substance ID: DTXSID80870682
• Nikkaji Number: J489H
• Wikidata: Q27116311
• Metabolomics Workbench ID: 55043
• Mol file: 609-39-2.mol

Synonyms:2-NITROFURAN;609-39-2;Nitrofuran;5-Nitrofuran;Furan, 2-nitro-;Furan, nitro-;Nitrofuran (VAN);AI3-23606;NSC 59983;BRN 0112523;UNII-17EZI4D981;27194-24-7;17EZI4D981;NSC-59983;5-17-01-00296 (Beilstein Handbook Reference);2-Nitrofurane;2-Nitrofuran, 97%;SCHEMBL30623;CHEBI:34890;DTXSID80870682;BCP23236;NSC59983;AKOS015900364;LS-70264;AM20100483;FT-0632538;EN300-139040;Q-103253;Q27116311;2-nitro-fura

Chemical Property of 2-Nitrofuran

Chemical Property:

• Appearance/Colour: solid
• Melting Point: 29-33 °C(lit.)
• Refractive Index: 1.4543 (estimate)
• Boiling Point: 84 °C13 mm Hg(lit.)
• Flash Point: 88 C (closed cup)
• PSA: 58.96000
• Density: 1.5808 (rough estimate)
• LogP: 1.71100
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Methanol
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 113.011292958
• Heavy Atom Count: 8
• Complexity: 97.9

Purity/Quality:

97%min ^*data from raw suppliers

2-Nitrofuran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 7-23-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=COC(=C1)[N+](=O)[O-]
• General Description: 2-Nitrofuran, also known as 5-nitrofuran, is a nitroheteroaryl compound that has demonstrated significant anti-leishmanial activity in vitro. Studies indicate that derivatives of 2-nitrofuran, particularly when incorporated into 1,3,4-thiadiazole-based structures, exhibit potent inhibitory effects against *Leishmania major* promastigotes and amastigotes at non-cytotoxic concentrations. Compared to nitrothiophene analogues, 2-nitrofuran derivatives generally show higher anti-parasitic efficacy, suggesting their potential as promising candidates for anti-leishmanial drug development.

Technology Process of 2-Nitrofuran

There total 6 articles about 2-Nitrofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 3.0%

2-furyltrimethylsilane (1578-33-2) → 2-nitrofuran (609-39-2) + trimethyl(5-nitro-2-furyl)silane (120823-76-9)

Guidance literature:

With nitronium tetrafluoborate; In acetonitrile; at -40 ℃; for 1h;

DOI:10.1016/0022-328X(88)80334-6

Reference yield:

2-furanoic acid (88-14-2) → 2-nitrofuran (609-39-2) + 5-nitro-2-furoic acid (645-12-5)

Guidance literature:

With nitric acid; acetic anhydride;

Reference yield:

2-furanoic acid (88-14-2) + nitric acid (7697-37-2,78989-43-2) + acetic anhydride (108-24-7) → 2-nitrofuran (609-39-2) + 5-nitro-2-furoic acid (645-12-5)

Guidance literature:

at -10 ℃;

upstream raw materials:

1-(2-furyl)-1-ethanone

acetic anhydride

2-furanoic acid

2-furyltrimethylsilane

Downstream raw materials:

methyl hydrogen fumarate

5-cyclohexyl-5-hydrofuran-2-one

3-cyclohexylfuran-2(5H)-one

5-octyl-5H-furan-2-one

Refernces

Synthesis and in vitro anti-leishmanial activity of 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]- and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines

10.1016/j.bmc.2008.02.052

The research focuses on the synthesis and in vitro anti-leishmanial activity of nitroheteroaryl-1,3,4-thiadiazole-based compounds, specifically 1-[5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines and 1-[5-(5-nitrothiophen-2-yl)-1,3,4-thiadiazol-2-yl]-4-aroylpiperazines. The study involves the synthesis of these compounds using reactants such as 5-nitro-2-arylidene diacetates, thiosemicarbazide, ammonium ferric sulfate, and various aroyl chlorides. The synthesized compounds were then tested for their anti-leishmanial activity against both promastigote and amastigote forms of Leishmania major. The experiments utilized MTT assay to determine the IC50 values, which indicate the potency of the compounds. The analysis included the calculation of the logarithm of the partition coefficient (LogP) to assess the lipophilicity of the compounds, which is an important factor in their biological activity. The results showed that most of the synthesized compounds exhibited potent anti-leishmanial activity at non-cytotoxic concentrations, with 5-nitrofuran derivatives generally being more active than the corresponding 5-nitrothiophene analogues.