5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde

Base Information

• Chemical Name: 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde
• CAS No.: 99698-10-9
• Molecular Formula: C₁₃H₁₀OS
• Molecular Weight: 214.288
• Mol file: 99698-10-9.mol

Synonyms:5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde

Chemical Property of 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde

There total 18 articles about 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde 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: 82.0%

5-bromo-2-thiophencarboxaldehyde (4701-17-1) + potassium (E)-trifluoro(styryl)borate (201852-49-5) → 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde (99698-10-9)

Guidance literature:

With 2C₈H₈NO₂^(1-)*2Cl^(1-)*2Pd⁽²⁺⁾; tetrabutylammomium bromide; potassium carbonate; In water; at 100 ℃; for 0.333333h; under 750.075 - 2250.23 Torr; stereoselective reaction; Sealed vessel; Microwave irradiation;

DOI:10.1021/jo802356n

Reference yield: 77.0%

5-Chloro-2-thiophenecarboxaldehyde (7283-96-7) + potassium (E)-trifluoro(styryl)borate (201852-49-5) → 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde (99698-10-9)

Guidance literature:

With C₁₈H₁₆Cl₂O₄Pd₂; caesium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); In N,N-dimethyl-formamide; at 120 ℃; for 34h; Inert atmosphere;

DOI:10.1021/jo901681s

Reference yield: 72.0%

(E)-2-(2-phenylethenyl)thiophene (3783-65-1,23516-73-6,26708-50-9,35568-97-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 5-[(E)-2-phenylethenyl]thiophene-2-carbaldehyde (99698-10-9)

Guidance literature:

With trichlorophosphate; 1.) RT, 1 h, 2.) 70 deg C, 3 h;

upstream raw materials:

(E)-2-(2-phenylethenyl)thiophene

N,N-dimethyl-formamide

styrene

5-bromo-2-thiophencarboxaldehyde

Downstream raw materials:

(E)-1-(5-methylthien-2-yl)-2-phenylethene

4,4,5,5-tetramethyl-2-{5-[2-(5-styryl-thiophen-2-yl)-vinyl]-thiophen-2-yl}[1,3]dioxolane

Refernces

• 1、 Nagaki, Aiichiro,Tsuchihashi, Yuta,Haraki, Suguru,Yoshida, Jun-ichi. "Benzyllithiums bearing aldehyde carbonyl groups. A flash chemistry approach". . p. 7140 - 7145. Retrieved 2015/07/01.
• 2、 Alacid, Emilio,Najera, Carmen. "Palladium-catalyzed cross-coupling reactions of potassium alkenyltrifluoroborates with organic halides in aqueous media". supporting information; experimental part. p. 2321 - 2327. Retrieved 2009/07/18.