2,5-Thiophenedicarboxaldehyde

Base Information

• Chemical Name: 2,5-Thiophenedicarboxaldehyde
• CAS No.: 932-95-6
• Molecular Formula: C6H4O2S
• Molecular Weight: 140.163
• Hs Code.: 29349990
• European Community (EC) Number: 627-004-0
• DSSTox Substance ID: DTXSID50343151
• Nikkaji Number: J472.325B
• Wikidata: Q72508839
• Metabolomics Workbench ID: 127415
• ChEMBL ID: CHEMBL2229528
• Mol file: 932-95-6.mol

Synonyms:2,5-Thiophenedicarboxaldehyde;Thiophene-2,5-dicarbaldehyde;932-95-6;2,5-Thiophenedicarbaldehyde;Thiophene-2,5-dicarboxaldehyde;2,5-Diformylthiophene;2,5-Thiophenedial;2,5-Diformylthiophen;BIDD:GT0835;SCHEMBL178830;2,5-thiophene dicarboxaldehyde;CHEMBL2229528;DTXSID50343151;BCP27894;2,5-Thiophenedicarboxaldehyde, 99%;MFCD00216592;STL324623;AKOS015855708;2,5-THIOPHENENEDICARBOXALDEHYDE;AC-5193;CS-W016463;AS-38473;AM20080613;FT-0600251;EN300-624191;A844510

Chemical Property of 2,5-Thiophenedicarboxaldehyde

Chemical Property:

• Appearance/Colour: pale brown-orange to pale brown powder
• Vapor Pressure: 0.00102mmHg at 25°C
• Melting Point: 115-117 °C(lit.)
• Refractive Index: 1.668
• Boiling Point: 302 °C at 760 mmHg
• Flash Point: 136.5 °C
• PSA: 62.38000
• Density: 1.37 g/cm³
• LogP: 1.37310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 139.99320054
• Heavy Atom Count: 9
• Complexity: 110

Purity/Quality:

99% ^*data from raw suppliers

2,5-Thiophenedicarboxaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C(SC(=C1)C=O)C=O
• Uses: 2,5-Thiophenedicarboxaldehyde acts as a reagent in the synthesis of N,N''-bis-(mercaptophenylimine)thiophenedicarboxaldehyde Schiff base, and also functions as an intermediate in many organic synthesis. 2,5-Thiophenedicarboxaldehyde may be employed in the following studies:Asymmetric synthesis of bis-homoallylic alcohols.Synthesis of new symmetrical arylene bisimide derivatives. As dialdehyde monomer in the synthesis of silicon-containing poly(p-phenylenevinylene)-related copolymers having uniform p-conjugated segment regulated by organosilicon units.Synthesis of 2,5-bis[2-(5-N-isopropylamidino)benzimidazoyl]thiophene hydrochloride.

Technology Process of 2,5-Thiophenedicarboxaldehyde

There total 3 articles about 2,5-Thiophenedicarboxaldehyde 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: 73.0%

2,5-dibromothiophen (3141-27-3) + Trimethyl borate (121-43-7,63156-11-6) → thiophene (188290-36-0,8014-23-1,25233-34-5) + 2,5-thiophenedicarboxaldehyde (932-95-6) + thiophene-2,5-diboronic acid (26076-46-0)

Guidance literature:

With aluminium; In N,N-dimethyl-formamide; byproducts: Al(3+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;

DOI:10.1039/b200744b

Reference yield:

N-(1-deoxy-D-erythro-2-pentulos-1-yl)glycine → 1,3-thiazole (288-47-1) + furfural (98-01-1) + thiophene-2-carbaldehyde (98-03-3) + 4,5-Dihydro-2-methylthiophen-3-(2H)-on (74015-70-6,13679-85-1) + 5-Methylfurfural (620-02-0) + 5-methylthiophene-2-carboxaldehyde (13679-70-4) + 2-Acetylthiazole (24295-03-2,260998-74-1) + 2-butyrylthiophene (5333-83-5) + perillene (539-52-6) + benzofuran, 4,7-dimethyl- (28715-26-6) + 2,5-thiophenedicarboxaldehyde (932-95-6)

Guidance literature:

With L-Cysteine; at 100 ℃; for 2h;

DOI:10.1016/j.foodchem.2021.131137

Reference yield:

2,5-dimethylene-2,5-dihydrothiophene (66806-34-6) → 5-hydroxymethyltiophene-2-carbaldehyde (53821-57-1) + 2,5-thiophenedicarboxaldehyde (932-95-6)

Guidance literature:

In dichloromethane; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4039(00)73143-1

upstream raw materials:

2,5-dimethylene-2,5-dihydrothiophene

2,5-dibromothiophen

Trimethyl borate

Downstream raw materials:

3,3'-diphenyl-4H,4'H-4,4'-thiophene-2,5-diylbismethylene-bis-isoxazol-5-one

2,2'-(2,5-thiophenediyl)bis(4,5-diphenylimidazole)

di-(hydroxymethyl)-2,5 thiophene

2,5-bis<(benzylimino)methyl>thiophene

Refernces

• 1、 Laza, Carine,Dunach, Elisabet,Serein-Spirau, Francoise,Moreau, Joel J. E.,Vellutini, Luc. "Novel synthesis of arylboronic acids by electroreduction of aromatic halides in the presence of trialkyl borates". . p. 373 - 375. Retrieved 2007/10/03.