38401-68-2

Basic information

• Product Name: 5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE
• Synonyms: AKOS BAR-0531;5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE;5-(4-METHYLPHENYL)THIOPHENE-2-CARBALDEHYDE;5-(4-METHYLPHENYL)-2-THIOPHENECARBALDEHYDE;RARECHEM AK MA K015
• CAS NO: 38401-68-2
• Molecular Formula: C₁₂H₁₀OS
• Molecular Weight: 202.27
• Mol File: 38401-68-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE(38401-68-2)
• EPA Substance Registry System: 5-P-TOLYL-THIOPHENE-2-CARBALDEHYDE(38401-68-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 38401-68-2(Hazardous Substances Data)

Usage

General Description

5-P-Tolyl-thiophene-2-carbaldehyde is a chemical compound that consists of a thiophene ring with a tolyl group attached at the 5-position and a carbaldehyde group attached at the 2-position. It is commonly used as a building block in the synthesis of various organic compounds. This chemical is known for its aromatic and aldehyde properties, making it a useful intermediate in the production of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and reactivity make it valuable in organic synthesis for creating complex molecules and functionalized materials. Additionally, 5-P-tolyl-thiophene-2-carbaldehyde has potential applications in the field of materials science and drug discovery due to its interesting properties.

Upstream product

• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 5720-05-8 4-methylphenylboronic acid 
• 16939-04-1 2-p-tolylthiophene 
• 68-12-2 N,N-dimethyl-formamide 
• 108-88-3 toluene 
• 38425-26-2 4-chloro-1-(4-methylphenyl)butan-1-one 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 98-03-3 thiophene-2-carbaldehyde 
• 106-38-7 para-bromotoluene 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 108967-85-7 5-Phenyl-2-{4-[(E)-2-(5-p-tolyl-thiophen-2-yl)-vinyl]-phenyl}-oxazole 
• 135491-49-5 2-[(E)-2-(5-p-Tolyl-thiophen-2-yl)-vinyl]-1H-benzoimidazole 
• 40808-21-7 5-(4-methylphenyl)thiophene-2-carboxylic acid 
• 61100-11-6 ethyl 5-(p-tolyl) thiophene-2-carboxylate 
• 1026010-24-1 3-(5-p-tolyl-thiophen-2-yl)-acryloyl chloride 
• 1374645-05-2 (E)-8-(2-(5-(4-methylphenyl)-2-thienyl)vinyl)-10,10-dimethyl-10H-pyrido[1,2-a]indolium perchlorate 

Relevant articles and documents

Synthesis of meso-tetraarylthienylporphyrins by Suzuki-Miyaura cross-coupling reaction and studying their UV-Vis absorption spectra

meso-Tetra(5-arylthien-2-yl)porphyrins and their copper complexes were synthesized by two different approaches using Suzuki-Miyaura cross-coupling reactions. The first, involving the formation of 5-arylthien-2-yl carbaldehydes, followed by condensation with pyrrole. The second is a direct process that involves the coupling of meso-tetra (5-bromothien-2-yl) porphyrins with the arylboronic acids. The yield of the second approach (40-50 %) was higher than the first approach (28-35 %). The UV-Vis absorption spectra of the synthesized porphyrins revealed bathochromic shifts when compared with the parent porphyrin. Additionally, the products showed no aggregation behaviour in solution (DCM), giving a linear correlation between absorption intensity and the concentration.

Stannylation of Aryl Halides, Stille Cross-Coupling, and One-Pot, Two-Step Stannylation/Stille Cross-Coupling Reactions under Solvent-Free Conditions

Solvent-free protocols for palladium-catalyzed stannylation of aryl halides, Stille cross-coupling, and one-pot, two-step stannylation/Stille cross-coupling (SSC) are reported for the first time. (Het)aryl halides bearing acceptor, donor, as well as sterically demanding substituents are stannylated and/or coupled in high yields. The reactions are catalyzed by conventional palladium(II) acetate/PCy3 [Pd(OAc)2/PCy3] under air, using available base CsF, and without the use of high purity reagents. The developed synthetic procedures are versatile, robust, and easily scalable. The absence of solvent, and the elimination of isolation procedures of aryl stannanes makes the SSC protocol simple, step economical, and highly efficient for the synthesis of biaryls in a one-pot two-step procedure.

Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes

In the present work, a series of α-hydroxyimine palladium complexes with bulky substituents (i.e., {[Ar-N=C(R)-C(R)2-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.