40133-23-1

Basic information

• Product Name: 2-(4-CHLORO-PHENYL)-THIOPHENE
• Synonyms: 2-(4-CHLORO-PHENYL)-THIOPHENE;AKOS BAR-1347;2-(p-Chlorophenyl)thiophene
• CAS NO: 40133-23-1
• Molecular Formula: C₁₀H₇ClS
• Molecular Weight: 194.68
• Mol File: 40133-23-1.mol
• Article Data: 46

Chemical Properties

• Melting Point: 83-84℃
• Boiling Point: 286℃
• Flash Point: 167℃
• Appearance: /
• Density: 1.246
• Vapor Pressure: 0.005mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-CHLORO-PHENYL)-THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLORO-PHENYL)-THIOPHENE(40133-23-1)
• EPA Substance Registry System: 2-(4-CHLORO-PHENYL)-THIOPHENE(40133-23-1)

Safety Data

• Hazardous Substances Data: 40133-23-1(Hazardous Substances Data)

Usage

General Description

2-(4-chloro-phenyl)-thiophene is a chemical compound with the molecular formula C10H7ClS. It is a member of the thiophene family, which are aromatic heterocyclic compounds containing a five-membered sulfur-containing ring. This particular compound features a chloro-substituted phenyl group attached to one of the carbon atoms in the thiophene ring. Thiophenes are widely used in organic synthesis and pharmaceuticals, and their derivatives have diverse applications in fields such as agrochemicals, materials science, and pharmaceuticals. The presence of the chloro group in 2-(4-chloro-phenyl)-thiophene can influence its reactivity and properties, making it valuable as a building block for the synthesis of more complex compounds with specific properties.

InChI:InChI=1/C10H7ClS/c11-9-5-3-8(4-6-9)10-2-1-7-12-10/h1-7H

Upstream product

• 188290-36-0 thiophene 
• 106-47-8 4-chloro-aniline 
• 673-41-6 p-chlorobenzenediazonium tetrafluoroborate 
• 3437-95-4 2-Iodothiophene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 649569-53-9 thioacetic acid S-[4-(4-chloro-phenyl)-4-oxo-butyl] ester 
• 106-39-8 bromochlorobenzene 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 108-90-7 chlorobenzene 
• 1003-09-4 2-bromothiophene 
• 81745-84-8 2-thienylzinc chloride 
• 1075-77-0 (E)-4-chlorocinnamic aldehyde 
• 1620635-60-0 (E)-1-chloro-4-(4,4-dibromobuta-1,3-dienyl)benzene 
• 136881-87-3 1-(p-chlorophenyl)-5-methyl-1,3-hexadiyn-5-ol 

Downstream Products

• 58386-03-1 [5-(p-Chlorophenyl)-2-thienylthio]-acetic Acid 
• 70466-82-9 5-(4-Chlorophenyl)thien-2-ylglyoxylic Acid (potassium Salt) 
• 480390-66-7 ethyl 4-[5-(4-chlorophenyl)-2-thienyl]benzoate 
• 1426057-53-5 10-(5-(4-chlorophenyl)thiophen-2-yl)benzo[h]quinoline 
• 84863-77-4 [5-(4-Chloro-phenyl)-thiophen-2-yl]-acetic acid methyl ester 
• 40133-14-0 5-(4-chlorophenyl)thiophene-2-carboxylic acid 
• 24680-29-3 [5-(4-chloro-phenyl)-thiophen-2-yl]-methanol 
• 24680-42-0 2-(5-(4-chlorophenyl)thiophen-2-yl)acetic acid 
• 24680-30-6 2-Chloromethyl-5-(4-chloro-phenyl)-thiophene 
• 38401-71-7 5-(4-chlorophenyl)thiophene-2-carboxaldehyde 
• 649569-56-2 methyl 5-(4-chlorophenyl)thiophene-2-carboxylate 
• 1401352-27-9 2-butyl-5-(5-(4-chlorophenyl)thiophen-2-yl)furan 

Relevant articles and documents

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex

The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight

Naturally occurring perylenequinonoid pigments (PQPs) have attracted considerable attention owing to their excellent properties of photosensitization. They have been widely investigated as an aspect of photophysics and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C-H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions of substrates was achieved even by a cercosporin-containing supernatant without organic solvent extraction and purification after liquid fermentation. Thus we set up a bridge between microbial fermentation and organic photocatalysis for chemical reactions in a sustainable, environmentally friendly manner.