5-Nitro-2-furoic acid

Base Information

• Chemical Name: 5-Nitro-2-furoic acid
• CAS No.: 645-12-5
• Molecular Formula: C5H3 N O5
• Molecular Weight: 157.083
• European Community (EC) Number: 211-432-6
• NSC Number: 6452
• UNII: UTY7TN9FTP
• DSSTox Substance ID: DTXSID00214746
• Wikidata: Q72494720
• ChEMBL ID: CHEMBL1186
• Mol file: 645-12-5.mol

Synonyms:5-nitro-2-furoic acid;NFCA;nitrofurate

Chemical Property of 5-Nitro-2-furoic acid

Chemical Property:

• Vapor Pressure: 5.83E-05mmHg at 25°C
• Melting Point: 185-189 ºC
• Refractive Index: 1.4798 (estimate)
• Boiling Point: 332.4°C at 760 mmHg
• PKA: 2.06±0.10(Predicted)
• Flash Point: 154.8°C
• Density: 1.8109 (rough estimate)
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 157.00112220
• Heavy Atom Count: 11
• Complexity: 186

Purity/Quality:

98%,99%, ^*data from raw suppliers

Nitrofurate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 68-36/37/38-40
• Safety Statements: 37/39-36/37-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(OC(=C1)[N+](=O)[O-])C(=O)O
• Uses: 5-Nitro-2-furoic acid is a representative of 2-substituted 5-nitrofurans. A number of nitrofurans have been used as antibacterial, antiprotozoal, and anthelmintic drugs in humans and animals. 2-Substituted 5-nitrofurans have been used worldwide as human and veterinary medicines, food preservatives, and feed additives, and they are utilized in human medicine as antibacterial agents. Therefore, the relationship between the antibacterial effect and the mutagenicity of these compounds and their oxidized metabolites is important. Comparison of the antibacterial effects and genotoxic potencies of nitrofuran drugs and their oxidative metabolites may provide a new direction for selecting nitrofuran drugs for human use. 5-Nitro-2-furoic acid was used in the preparation of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles. The FT-IR and FT-Raman spectra of 5-Nitro-2-furoic acid has also been studied. 5-Nitro-2-furoic acid was used in the preparation of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles.

Technology Process of 5-Nitro-2-furoic acid

There total 24 articles about 5-Nitro-2-furoic acid 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: 84.0%

5-nitrofurane-2-carboxaldehyde (698-63-5) → 5-nitro-2-furoic acid (645-12-5)

Guidance literature:

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In water; acetonitrile; at 10 ℃; for 1h;

DOI:10.1021/jo00354a037

Reference yield: 74.0%

5-nitro-2-furancarboxaldehyde dimethylhydrazone (69819-71-2) → 5-nitrofuran-2-carbonitrile (59-82-5) + 5-nitro-2-furoic acid (645-12-5)

Guidance literature:

With silica-supported selenamide; dihydrogen peroxide; In tert-butyl alcohol; at 55 ℃; for 20h;

Reference yield: 73.0%

methanol (67-56-1) + 5-nitrofuran-2-carboxaldehyde (555-15-7) → 5-nitro-2-furoic acid (645-12-5) + methyl 5-nitrofuran-2-carboxylate (1874-23-3)

Guidance literature:

With silica-supported selenamide; dihydrogen peroxide; at 55 ℃; for 140h;

upstream raw materials:

2-furanoic acid

5-nitrofurane-2-carboxaldehyde

5-nitrofuran-2-carbonitrile

furan-2,5-dicarboxylic acid

Downstream raw materials:

C₅₈H₆₆N₂O₁₈Si

succinic acid

ammonia

methylammonium carbonate

Refernces

• 1、 Choi, Hojune,Koh, Han Joong,Ali, Dildar,Yang, Kiyull,Koo, In Sun. "Rate-product correlations for the solvolysis of 5-nitro-2-furoyl chloride". . p. 3293 - 3297. Retrieved 2013/01/15.
• 2、 Chaubey, Girija S.,Kharsyntiew, Bansiewdor,Mahanti, Mahendra K.. "Oxidation of substituted 2-furaldehydes by quinolinium dichromate: A kinetic study". . p. 83 - 87. Retrieved 2007/10/03.