5-Bromo-4-nitrothiophene-2-carboxylic acid

Base Information

• Chemical Name: 5-Bromo-4-nitrothiophene-2-carboxylic acid
• CAS No.: 89283-24-9
• Molecular Formula: C5H2BrNO4S
• Molecular Weight: 252.045
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80362411
• Wikidata: Q82145463
• Mol file: 89283-24-9.mol

Synonyms:5-bromo-4-nitrothiophene-2-carboxylic acid;89283-24-9;Cambridge id 5256123;SCHEMBL11458447;DTXSID80362411;AMY16194;CCG-2461;MFCD00582675;AKOS016001844;NCGC00240839-01;AS-65472;5-bromo-4-nitrothiophene-2-carboxylicacid;4-nitro-5-bromo-2-thiophenecarboxylic acid;CS-0044235;F14534;AB00076873-01;A861253;SR-01000201298;SR-01000201298-1;5-Bromo-4-nitrothiophene-2-carboxylic acid4-nitrothiophene-2-carboxylic acid

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

Chemical Property:

• PSA: 111.36000
• LogP: 2.64020
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 250.88879
• Heavy Atom Count: 12
• Complexity: 218

Purity/Quality:

97% ^*data from raw suppliers

5-Bromo-4-nitrothiophene-2-carboxylic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1[N+](=O)[O-])Br)C(=O)O
• General Description: 2-Thiophenecarboxylic acid, 5-bromo-4-nitro- is a nitro-substituted thiophene derivative that can undergo reductive acetylation to form acetylamino derivatives, though partial debromination may occur under these conditions. 2-Thiophenecarboxylic acid, 5-bromo-4-nitro- serves as a valuable intermediate in drug synthesis, particularly when modified through reactions such as reductive acetylation, which can yield high-purity products with retained or altered halogen substituents depending on the reaction conditions.

Technology Process of 5-Bromo-4-nitrothiophene-2-carboxylic acid

There total 4 articles about 5-Bromo-4-nitrothiophene-2-carboxylic 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:

5-bromothiophene-2-carboxylic acid (7311-63-9) + sulfuric acid (7664-93-9) + nitric acid (7697-37-2,78989-43-2) → 5-bromo-4-nitro-thiophene-2-carboxylic acid (89283-24-9) + 2-bromo-3,5-dinitro-thiophene (2160-38-5)

Guidance literature:

Reference yield:

methyl 5-bromo-4-nitrothiophene-2-carboxylate (38239-32-6) → 5-bromo-4-nitro-thiophene-2-carboxylic acid (89283-24-9)

Guidance literature:

With sulfuric acid;

Reference yield:

5-bromo-2-thiophenecarboxylic acid methyl ester (62224-19-5) → 5-bromo-4-nitro-thiophene-2-carboxylic acid (89283-24-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; nitric acid / -5 °C

2: aqueous sulfuric acid

With sulfuric acid; nitric acid;

upstream raw materials:

methyl 5-bromo-4-nitrothiophene-2-carboxylate

5-bromothiophene-2-carboxylic acid

sulfuric acid

nitric acid

Downstream raw materials:

3-nitrothiophene

2-bromo-3-nitrothiophene

4-Acetylamino-5-bromo-thiophene-2-carboxylic acid

4-Amino-5-bromo-thiophene-2-carboxylic acid; hydrobromide

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.

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