Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate

Base Information

• Chemical Name: Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate
• CAS No.: 89380-77-8
• Molecular Formula: C6H5NO5S
• Molecular Weight: 203.175
• Hs Code.: 2934999090
• Mol file: 89380-77-8.mol

Synonyms:Methyl3-hydroxy-5-nitro-2-thiophenecarboxylate;

Chemical Property of Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.623
• Boiling Point: 329.379 °C at 760 mmHg
• Flash Point: 153.003 °C
• PSA: 120.59000
• Density: 1.599 g/cm³
• LogP: 1.67170
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

methyl3-hydroxy-5-nitrothiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate

There total 1 articles about Methyl 3-hydroxy-5-nitro-2-thiophenecarboxylate 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: 29.0%

methyl 3-hydroxy-2-thiophenecarboxylate (5118-06-9) → methyl 3-hydroxy-4-nitrothiothiophene-2-carboxylate (89380-76-7) + methyl 3-hydroxy-5-nitrothiothiophene-2-carboxylate (89380-77-8)

Guidance literature:

With sulfuric acid; nitric acid; at -10 - 0 ℃;

Reference yield: 98.0%

(S)-1-(2-trifluoromethylphenyl)ethanol (79756-81-3,127733-44-2,127852-29-3,127852-27-1) + methyl 3-hydroxy-5-nitrothiothiophene-2-carboxylate (89380-77-8) → methyl 5-nitro-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate (929039-94-1)

Guidance literature:

(S)-1-(2-trifluoromethylphenyl)ethanol; methyl 3-hydroxy-5-nitrothiothiophene-2-carboxylate; With polymer supported triphenylphosphine; diethylazodicarboxylate; In dichloromethane; at 0 - 20 ℃; for 21.25h;

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 3h;

Reference yield: 98.0%

(S)-1-(2-(trifluoromethyl)phenyl)ethanol (79756-81-3,127733-44-2,127852-27-1,127852-29-3) + methyl 3-hydroxy-5-nitrothiothiophene-2-carboxylate (89380-77-8) → methyl 5-nitro-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate (929039-94-1)

Guidance literature:

(S)-1-(2-(trifluoromethyl)phenyl)ethanol; methyl 3-hydroxy-5-nitrothiothiophene-2-carboxylate; With PS-triphenylphosphine; di-tert-butyl-diazodicarboxylate; In dichloromethane; at 20 ℃; for 21.25h;

With hydrogenchloride; In 1,4-dioxane; water; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2008.08.077

upstream raw materials:

methyl 3-hydroxy-2-thiophenecarboxylate

Downstream raw materials:

methyl 5-amino-3-methoxythiophene-2-carboxylate

methyl 5-nitro-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate

methyl 3-{[(1R)-1-(2-chlorophenyl)ethyl]oxy}-5-nitro-2-thiophenecarboxylate

methyl (+/-)-5-nitro-3-(1-(2-(trifluoromethyl)phenyl)ethoxy)thiophene-2-carboxylate

Refernces

• 1、 Chao, Jianhua,Taveras, Arthur G.,Aki, Cynthia J.. "Synthesis of functionalized hydroxy-thiophene motifs as amido- and sulfonamido-phenol bioisosteres". scheme or table. p. 5005 - 5008. Retrieved 2009/12/01.