5-Formyl-2-thiophenecarboxylic Acid

Base Information

• Chemical Name: 5-Formyl-2-thiophenecarboxylic Acid
• CAS No.: 4565-31-5
• Molecular Formula: C6H4O3S
• Molecular Weight: 156.162
• Hs Code.: 29349990
• European Community (EC) Number: 671-160-2
• DSSTox Substance ID: DTXSID90355995
• Nikkaji Number: J150.331F
• Wikidata: Q72479498
• ChEMBL ID: CHEMBL4280023
• Mol file: 4565-31-5.mol

Synonyms:4565-31-5;5-formylthiophene-2-carboxylic acid;5-Formyl-2-thiophenecarboxylic Acid;5-formyl-thiophene-2-carboxylic acid;2-Thiophenecarboxylic acid, 5-formyl-;5-Formylthenoic Acid;5-formyl-2-thiophene carboxylic acid;MFCD00191437;CHEMBL4280023;AI-942/25034147;SCHEMBL209887;5-formylthiophencarboxylic acid;5-formylthiophenecarboxylic acid;AMY3041;DTXSID90355995;5-formylthiophene-2-carboxylicacid;5-formyl-2-thiophencarboxylic acid;5-carboxy-2-thiophenecarboxaldehyde;2-formyl thiophen-5-carboxylic acid;5-formyl-thiophen-2-carboxylic acid;BDBM50467734;2-formyl-5-thiophene carboxylic acid;5-formyl-2-thiophene-carboxylic acid;AKOS000320197;PS-5881;Thiophene-2-carboxylic acid, 5-formyl-;5-FORMYL-2-THIOPHENECARBOXYLICACID;AC-23025;SY022710;BB 0259740;CS-0017900;F0336;FT-0620436;EN300-150101;5-Formyl-2-thiophenecarboxylic acid, AldrichCPR;A826868;Z1201619678;5-formylthiophene-2-carboxylate;5-Formylthiophene-2-carboxylic acid

Chemical Property of 5-Formyl-2-thiophenecarboxylic Acid

Chemical Property:

• Vapor Pressure: 3.58E-06mmHg at 25°C
• Melting Point: 169 °C
• Boiling Point: 371.378 °C at 760 mmHg
• PKA: 3.05±0.10(Predicted)
• Flash Point: 178.403 °C
• PSA: 82.61000
• Density: 1.515 g/cm³
• LogP: 1.25880
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 155.98811516
• Heavy Atom Count: 10
• Complexity: 157

Purity/Quality:

98% ^*data from raw suppliers

5-FormylthenoicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)C(=O)O)C=O
• Uses: 5-Formyl-2-thiophenecarboxylic acid is a thiophene derivative as immunomodulating agents useful in the treatment of autoimmune diseases.

Technology Process of 5-Formyl-2-thiophenecarboxylic Acid

There total 7 articles about 5-Formyl-2-thiophenecarboxylic 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: 93.0%

2,5-thiophenedicarboxaldehyde (932-95-6) → 5-formyl-2-thiophencarboxylic acid (4565-31-5)

Guidance literature:

With C₂₀H₂₅N₂⁽¹⁺⁾*Cl^(1-); water; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 4h; Schlenk technique;

DOI:10.3762/bjoc.9.65

Reference yield: 88.0%

2-(2-thienyl)-1,3-dioxolane (58268-08-9) + carbon dioxide (124-38-9,18923-20-1) → 5-formyl-2-thiophencarboxylic acid (4565-31-5)

Guidance literature:

2-(2-thienyl)-1,3-dioxolane; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

carbon dioxide; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1002/anie.201803369

Reference yield: 59.0%

5-formyl-thiophene-2-carboxylic acid methyl ester (67808-64-4) → 5-formyl-2-thiophencarboxylic acid (4565-31-5)

Guidance literature:

With potassium hydroxide; water; In tetrahydrofuran;

upstream raw materials:

carbon dioxide

1,3-dimethyl-2-(thiophen-2-yl)imidazolidine

thiophene-2-carbaldehyde

5-formyl-thiophene-2-carboxylic acid methyl ester

Downstream raw materials:

5-formyl-thiophene-2-carboxylic acid methyl ester

2-ethoxycarbonyl-thiophene-5-carboxaldehyde

5-(3-oxo-3H-isobenzofuran-1-ylidenemethyl)-thiophene-2-carboxylic acid

3-(3-thiophene)carboxyl-1-(2,5-dimethoxyphenyl)prop-2-en-1-one

Refernces

• 1、 Steib, Philip,Breit, Bernhard. "Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides". . p. 6572 - 6576. Retrieved 2018/05/08.
• 2、 Mahboobi, Siavosh,Dove, Stefan,Sellmer, Andreas,Winkler, Matthias,Eichhorn, Emerich,Pongratz, Herwig,Ciossek, Thomas,Baer, Thomas,Maier, Thomas,Beckers, Thomas. "Design of chimeric histone deacetylase- and tyrosine kinase-inhibitors: A series of Imatinib hybrides as potent Inhibitors of wild-type and mutant BCR-ABL, PDGF-Rβ, and histone deacetylases". scheme or table. p. 2265 - 2279. Retrieved 2009/12/31.