2,5-Thiophenedicarboxaldehyde
- Product Name
- 2,5-Thiophenedicarboxaldehyde
- CAS No.
- 932-95-6
- Chemical Name
- 2,5-Thiophenedicarboxaldehyde
- Synonyms
- THIOPHENE-2,5-DICARBALDEHYDE;S0509;2,5-Thiophenedial;TIMTEC-BB SBB000080;2,5-Diformylthiophene;Thiophene-2,5-dialdehyde;2,5-THIOPHENEDICARBOXALDEHYDE;THIOPHENE-2,5-DICARBOXALDEHYDE;2,Chemicalbook5-Diformylthiophene;2,5-Thiophenedicarboxaldehyde 99%
- CBNumber
- CB7192564
- Molecular Formula
- C6H4O2S
- Formula Weight
- 140.16
- MOL File
- 932-95-6.mol
2,5-Thiophenedicarboxaldehyde Property
- Melting point:
- 115-117 °C (lit.)
- Boiling point:
- 226.66°C (rough estimate)
- Density
- 1.327 (estimate)
- refractive index
- 1.5300 (estimate)
- storage temp.
- under inert gas (nitrogen or Argon) at 2–8 °C
- form
- solid
- Appearance
- 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 Chemistry Reference
- 2,5-Thiophenedicarboxaldehyde(932-95-6)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 429880
- Product name
- 2,5-Thiophenedicarboxaldehyde
- Purity
- 99%
- Packaging
- 1g
- Price
- $143
- Updated
- 2025/07/31
- Product number
- 429880
- Product name
- 2,5-Thiophenedicarboxaldehyde
- Purity
- 99%
- Packaging
- 5g
- Price
- $203.3
- Updated
- 2025/07/31
- Product number
- T368095
- Product name
- 2,5-Thiophenedicarboxaldehyde
- Packaging
- 2.5g
- Price
- $305
- Updated
- 2021/12/16
- Product number
- 081656
- Product name
- Thiophene-2,5-dicarbaldehyde
- Purity
- 97%
- Packaging
- 1g
- Price
- $177
- Updated
- 2021/12/16
- Product number
- 6H18-1-X1
- Product name
- Thiophene-2,5-dicarboxaldehyde
- Packaging
- 1g
- Price
- $192
- Updated
- 2021/12/16
2,5-Thiophenedicarboxaldehyde Chemical Properties,Usage,Production
Chemical Properties
PALE BROWN-ORANGE TO PALE BROWN POWDER
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.
Uses
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.
Synthesis Reference(s)
Synthesis, p. 316, 1988 DOI: 10.1055/s-1988-27553
General Description
2,5-Thiophenedicarboxaldehyde can be prepared from 2,5-bis(chloromethyl)thiophene by the application of Kr?hnke′s method.
Synthesis
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.
References
[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
2,5-Thiophenedicarboxaldehyde Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2,5-Thiophenedicarboxaldehyde manufacturers
- Product
- 2,5-Thiophenedicarboxaldehyde 932-95-6
- Price
- US $49.00-195.00/g
- Min. Order
- 5g
- Purity
- 0.98
- Supply Ability
- 10kg
- Release date
- 2024-10-25
- Product
- Thiophene-2,5-dicarboxaldehyde 932-95-6
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20T
- Release date
- 2020-01-02
- Product
- 2,5-Thiophenedicarboxaldehyde 932-95-6
- Price
- US $0.01/KG
- Min. Order
- 1KG
- Purity
- 98%;99%
- Supply Ability
- 500g; 1kg; 10kg; 25kg
- Release date
- 2020-01-08