5-Chloro-4-nitrothiophene-2-carboxylic acid

Base Information

• Chemical Name: 5-Chloro-4-nitrothiophene-2-carboxylic acid
• CAS No.: 89166-85-8
• Molecular Formula: C₅H₂ClNO₄S
• Molecular Weight: 207.594
• Hs Code.: 29349990
• ChEMBL ID: CHEMBL4129718
• DSSTox Substance ID: DTXSID20527608
• Wikidata: Q82396826
• Mol file: 89166-85-8.mol

Synonyms:5-chloro-4-nitrothiophene-2-carboxylic acid;89166-85-8;MFCD00828481;C5H2ClNO4S;5-CHLORO-4-NITROTHIOPHENE-2-CARBOXYLICACID;SCHEMBL1456043;CHEMBL4129718;DTXSID20527608;FZKDYXWPDMALDM-UHFFFAOYSA-N;AKOS000281357;CS-W006570;DS-10309;4-nitro-5-chloro-2-thiophenecarboxylic acid;5-Chloro-4-nitro-thiophene-2-carboxylic acid;EN300-100256;A861296;J-517368

Chemical Property of 5-Chloro-4-nitrothiophene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.669
• Boiling Point: 390.406 °C at 760 mmHg
• Flash Point: 189.911 °C
• PSA: 111.36000
• Density: 1.801g/cm³
• LogP: 2.53110
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 206.9393064
• Heavy Atom Count: 12
• Complexity: 218

Purity/Quality:

97% ^*data from raw suppliers

5-Chloro-4-nitrothiophene-2-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Statements: 20/21/22
• Safety Statements: 7/47-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1[N+](=O)[O-])Cl)C(=O)O

Refernces

REDUCTIVE ACETYLATION OF NITROCARBOXYLIC ACIDS OF THE THIOPHENE AND FURAN SERIES OR THEIR ESTERS

10.1007/BF00842830

The research explores a method for producing acetylamino derivatives of thiophene and furan carboxylic acids or their esters through reductive acetylation using reduced iron in a mixture of acetic acid and acetic anhydride. The purpose is to develop an efficient method for synthesizing these compounds, which are valuable intermediates in drug synthesis. The study concludes that this method yields good results, particularly for 5-alkyl-4-nitro-2-thiophenecarboxylic acids and their esters, achieving higher yields compared to previous methods using skeletal nickel. For instance, a yield of about 80% was achieved for 4-acetylamino-2-thiophenecarboxylic acid from a mixture of nitroacids. The research also demonstrates the stability of certain functional groups under these conditions, such as the retention of chlorine in 4-nitro-5-chloro-2-thiophenecarboxylic acid and partial debromination in 4-nitro-5-bromo-2-thiophenecarboxylic acid. The study provides detailed experimental procedures and characterizes the synthesized compounds through yields, melting points, and elemental analysis.