2,5-Thiophenedicarboxaldehyde

Bezeichnung:2,5-Thiophenedicarboxaldehyde

CAS-Nr932-95-6

Englisch Name:2,5-Thiophenedicarboxaldehyde

CBNumberCB7192564

SummenformelC6H4O2S

Molgewicht140.16

MOL-Datei932-95-6.mol

2,5-Thiophenedicarboxaldehyde physikalisch-chemischer Eigenschaften

Schmelzpunkt	115-117 °C (lit.)
Siedepunkt	226.66°C (rough estimate)
Dichte	1.327 (estimate)
Brechungsindex	1.5300 (estimate)
storage temp.	under inert gas (nitrogen or Argon) at 2–8 °C
Aggregatzustand	solid
Aussehen	Yellow to brown Solid
InChI	InChI=1S/C6H4O2S/c7-3-5-1-2-6(4-8)9-5/h1-4H
InChIKey	OTMRXENQDSQACG-UHFFFAOYSA-N
SMILES	C1(C=O)SC(C=O)=CC=1
NIST chemische Informationen	2,5-Thiophenedicarboxaldehyde(932-95-6)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
HS Code	29349990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

2,5-Thiophenedicarboxaldehyde Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
PALE BROWN-ORANGE TO PALE BROWN POWDER
Verwenden
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.
Verwenden
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.
Synthesis Reference(s)
Synthesis, p. 316, 1988 DOI: 10.1055/s-1988-27553
Allgemeine Beschreibung
2,5-Thiophenedicarboxaldehyde can be prepared from 2,5-bis(chloromethyl)thiophene by the application of Krhnke′s method.
Synthese

3141-27-3

68-12-2

932-95-6

General method: n-Butyllithium solution (2.5 M hexane solution, 0.91 ml, 2.28 mmol, 1.1 eq.) was slowly added to a solution of 2,5-dibromothiophene (3a, 0.5 g, 2.07 mmol) in tetrahydrofuran (THF, 20 ml) under argon protection and at -78°C. The reaction mixture was slowly warmed to 0°C over 30 min. Subsequently, anhydrous N,N-dimethylformamide (DMF, 182 mg, 2.48 mmol, 1.2 eq.) was added and the reaction mixture was stirred at room temperature for 2 hours. Tert-butyl lithium solution (1.7 M pentane solution, 1.58 ml, 2.69 mmol, 1.3 eq.) was added again at -78 °C and the reaction mixture was stirred for 5 min. Next, an excess of anhydrous N,N-dimethylformamide (1 ml) was added and the reaction mixture was stirred overnight at room temperature. After completion of the reaction, the solution was poured into 1N hydrochloric acid (HCl, 10 ml) and stirred for 20 min. After neutralization with aqueous sodium bicarbonate (NaHCO3), the aqueous phase was extracted with dichloromethane (3 x 30 ml). The organic phases were combined, dried with anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate, 6:1) to afford 2,5-thiophenedicarboxaldehyde (8a, 123 mg, 42% yield) as a yellow amorphous solid.
Einzelnachweise
[1] Chemistry of Materials, 2014, vol. 26, # 24, p. 7229 - 7235
[2] Tetrahedron Letters, 2013, vol. 54, # 22, p. 2795 - 2798
[3] Organic Letters, 2012, vol. 14, # 1, p. 78 - 81
[4] Journal of the American Chemical Society, 1995, vol. 117, # 9, p. 2467 - 2478

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