5-Thien-2-yl-2-furaldehyde

Base Information

• Chemical Name: 5-Thien-2-yl-2-furaldehyde
• CAS No.: 32364-30-0
• Molecular Formula: C9H6 O2 S
• Molecular Weight: 178.20774
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60408285
• Nikkaji Number: J1.617.586B
• Wikidata: Q82213709
• Mol file: 32364-30-0.mol

Synonyms:32364-30-0;5-thien-2-yl-2-furaldehyde;5-(thiophen-2-yl)furan-2-carbaldehyde;5-thiophen-2-ylfuran-2-carbaldehyde;MFCD06740283;5-(2-thienyl)furan-2-carbaldehyde;2-Furancarboxaldehyde, 5-(2-thienyl)-;5-(2-thienyl)-2-furaldehyde;SCHEMBL9048215;DTXSID60408285;5-Thiophen-2-yl-furan-2-carbaldehyde;AKOS004117536;5-thien-2-yl-2-furaldehyde, AldrichCPR;MS-22460;SY326909;CS-0271015;FT-0645254;EN300-745524;F2167-0880

Chemical Property of 5-Thien-2-yl-2-furaldehyde

Chemical Property:

• Vapor Pressure: 0.000273mmHg at 25°C
• Melting Point: 36 °C
• Refractive Index: 1.613
• Boiling Point: 322.8°C at 760 mmHg
• Flash Point: 149°C
• PSA: 58.45000
• Density: 1.285g/cm³
• LogP: 2.82060
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 178.00885060
• Heavy Atom Count: 12
• Complexity: 172

Purity/Quality:

98% ^*data from raw suppliers

5-thien-2-yl-2-furaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=CC=C(O2)C=O

Technology Process of 5-Thien-2-yl-2-furaldehyde

There total 9 articles about 5-Thien-2-yl-2-furaldehyde 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: 95.0%

5-bromo-2-furancarboxaldehyde (1899-24-7) + thiophene boronic acid (6165-68-0) → 5-(thiophen-2-yl)furan-2-carboxaldehyde (32364-30-0)

Guidance literature:

With tetrabutylammomium bromide; palladium diacetate; potassium carbonate; In water; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.1c00746

Reference yield: 94.0%

2-thienyl chloride (96-43-5) + 5-formylfurane-2-boronic acid (27329-70-0) → 5-(thiophen-2-yl)furan-2-carboxaldehyde (32364-30-0)

Guidance literature:

2-thienyl chloride; 5-formylfurane-2-boronic acid; With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl; In dodecane; butan-1-ol; at 25 ℃; for 1h; Glovebox; Inert atmosphere;

With cesiumhydroxide monohydrate; In dodecane; water; butan-1-ol; at 80 ℃; for 4h; Glovebox; Inert atmosphere;

DOI:10.1002/ejoc.201200918

Reference yield: 79.0%

2-Iodothiophene (3437-95-4,149762-92-5) + (5-(diethoxymethyl)furan-2-yl)boronic acid (378185-02-5) → 5-(thiophen-2-yl)furan-2-carboxaldehyde (32364-30-0)

Guidance literature:

With triethylamine; palladium on activated charcoal; In ethanol; at 60 ℃; for 36h;

DOI:10.1055/s-2001-16759

upstream raw materials:

2-Iodothiophene

(5-(diethoxymethyl)furan-2-yl)boronic acid

2-bromothiophene

5-formylfurane-2-boronic acid

Refernces

• 1、 Kalo?lu, Murat,?ahan, Mehmet Hanifi,Dü?ünceli, Serpil Demir,?zdemir, ?smail. "Synthesis of Quinoxaline-Linked Bis(Benzimidazolium) Salts and Their Catalytic Application in Palladium-Catalyzed Direct Arylation of Heteroarenes". . . Retrieved 2021/09/13.
• 2、 Kieffer, Charline,Babin, Victor,Jouanne, Marie,Slimani, Ikram,Berhault, Yohann,Legay, Rémi,Sopková-de Oliveira Santos, Jana,Rault, Sylvain,Voisin-Chiret, Anne Sophie. "Sequential one pot double C[sbnd]H heteroarylation of thiophene using bromopyridines to synthesize unsymmetrical 2,5-bipyridylthiophenes". . p. 5509 - 5516. Retrieved 2017/08/22.