5-Nitrothiophene-2-Carboxaldehyde

Base Information

• Chemical Name: 5-Nitrothiophene-2-Carboxaldehyde
• CAS No.: 4521-33-9
• Molecular Formula: C5H3NO3S
• Molecular Weight: 157.15
• Hs Code.: 29349990
• European Community (EC) Number: 224-850-9
• NSC Number: 168226
• UNII: NB6CXG7SPH
• DSSTox Substance ID: DTXSID00196437
• Nikkaji Number: J203H
• Wikidata: Q72496332
• ChEMBL ID: CHEMBL4870182
• Mol file: 4521-33-9.mol

Synonyms:5-nitrothiophene-2-carboxaldehyde;NT-CA cpd

Chemical Property of 5-Nitrothiophene-2-Carboxaldehyde

Chemical Property:

• Appearance/Colour: yellow solid
• Vapor Pressure: 0.00137mmHg at 25°C
• Melting Point: 75-77 °C
• Refractive Index: 1.662
• Boiling Point: 297.2 °C at 760 mmHg
• Flash Point: 133.5 °C
• PSA: 91.13000
• Density: 1.534 g/cm³
• LogP: 1.99200
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: acetone: soluble1%, clear, yellow
• Water Solubility.: Insoluble in water.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 156.98336413
• Heavy Atom Count: 10
• Complexity: 156

Purity/Quality:

98% ^*data from raw suppliers

5-Nitrothiophene-2-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)[N+](=O)[O-])C=O
• General Description: 5-Nitrothiophene-2-carboxaldehyde is a key intermediate in the synthesis of 1-[(5-nitrothenylidene)amino]azoles, which were investigated for their potential as antichagasic agents. These derivatives exhibited in vitro trypanocidal activity comparable to Nifurtimox against *Trypanosoma cruzi*, the causative agent of Chagas disease, though they failed to fully eradicate the infection in vivo or prevent parasite survival in stored blood. 5-NITROTHIOPHENE-2-CARBOXALDEHYDE's role in forming these derivatives highlights its utility in medicinal chemistry for developing antiprotozoal agents, despite the limitations observed in biological efficacy.

Technology Process of 5-Nitrothiophene-2-Carboxaldehyde

There total 17 articles about 5-Nitrothiophene-2-Carboxaldehyde 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: 99.8%

(5-nitrothiophen-2-yl)methanol (20898-85-5) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Guidance literature:

With silica-supported Jones reagent; In dichloromethane; for 0.00269444h;

DOI:10.1016/j.tetlet.2006.05.157

Reference yield: 80.0%

5-nitrothiophene-2-carboxaldehyde diacetate (14289-24-8) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 65 ℃; for 8h;

Reference yield: 61.0%

2-(chloromethyl)-5-nitrothiophene (20898-86-6) → 5-nitro-2-thiophenecarboxaldehyde (4521-33-9) + 2-isopropylidenemethyl-5-nitrothiophene (74786-70-2) + 2-(2-methyl-2-nitropropyl)-5-nitrothiophene + 1,2-bis-(5-nitro-2-thienyl)ethylene

Guidance literature:

With lithium 2-nitropropane; In methanol; for 0.25h; Ambient temperature; Irradiation;

DOI:10.1016/0223-5234(94)90124-4

upstream raw materials:

thiophene-2-carbaldehyde

5-nitrothiophene-2-carboxaldehyde diacetate

(5'-nitro-2'-thienyl)methyl acetate

2-(chloromethyl)-5-nitrothiophene

Downstream raw materials:

(E)-3-(2-nitrothiophen-5-yl)propenoic acid

1-(5-nitro-[2]thienylmethylenamino)-piperidine

5-nitro-2-thiophene semicarbazone

2-((5-nitrothiophen-2-yl)methylene)hydrazinecarbothioamide

Refernces

Research for new antichagasic drugs

10.1248/cpb.39.1990

The research aimed to develop new antichagasic drugs to treat Chagas disease, a condition for which existing treatments have limitations due to mutagenicity, side effects, and non-curative action. The study synthesized a series of ten 1-[(5-nitrothenylidene)amino]azoles by reacting 5-nitrothiophene-2-carbaldehyde with various aminoazoles, including 1-aminopyrazole, 1-aminoimidazole, 1-amino-1,2,4-triazole, and others. The physical, spectroscopic, and biological properties of these derivatives were examined, with a focus on their antiprotozoal activity against Trypanosoma cruzi, the parasite causing Chagas disease, in comparison to the standard drug Nifurtimox. The conclusion was that while all synthesized compounds showed in vitro trypanocidal activity similar to Nifurtimox, they were not able to completely eradicate the infection in in vivo assays or prevent the survival of trypanosomes in stored blood. The chemicals used in the process included 5-nitrothiophene-2-carbaldehyde, various N-aminoazoles, p-toluene sulfonic acid as a catalyst, and solvents such as toluene, chloroform, ethanol, and ethyl acetate for the synthesis and purification steps.