6454-02-0

Basic information

• Product Name: Methanone, benzo[b]thien-2-ylphenyl-
• CAS NO: 6454-02-0
• Molecular Formula: C15H10OS
• Molecular Weight: 238.31
• Mol File: 6454-02-0.mol

Chemical Properties

• CAS DataBase Reference: Methanone, benzo[b]thien-2-ylphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, benzo[b]thien-2-ylphenyl-(6454-02-0)
• EPA Substance Registry System: Methanone, benzo[b]thien-2-ylphenyl-(6454-02-0)

Safety Data

• Hazardous Substances Data: 6454-02-0(Hazardous Substances Data)

Upstream product

• 116496-01-6 benzo[b]thiophene-2-yl(phenyl)methanol 
• 55164-16-4 2,2'-dithiodibenzaldehyde 
• 4521-31-7 o-hydroxymethyl thiophenol 
• 29199-11-9 2-formylthiophenol 
• 5633-34-1 (benzoylmethylene)dimethylsulfurane 
• 22966-13-8 (2E)-3-(3-chlorophenyl)-1-phenylprop-2-en-1-one 
• 135364-97-5 tert-butyl benzoyl(tert-butoxycarbonyl)carbamate 
• 376584-76-8 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[b]thiophene 
• 201230-82-2 carbon monoxide 
• 95-15-8 Benzo[b]thiophene 
• 71-43-2 benzene 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 36967-85-8 benzoyl triflate 

Downstream Products

• 116496-01-6 benzo[b]thiophene-2-yl(phenyl)methanol 
• 129757-35-3 [5-Benzo[b]thiophen-2-yl-5-phenyl-thiazolidin-(2E)-ylidene]-cyano-acetic acid methyl ester 

Relevant articles and documents

Mechanochemical Solvent-Free Suzuki–Miyaura Cross-Coupling of Amides via Highly Chemoselective N?C Cleavage

Although cross-coupling reactions of amides by selective N?C cleavage are one of the most powerful and burgeoning areas in organic synthesis due to the ubiquity of amide bonds, the development of mechanochemical, solid-state methods remains a major challe

A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes

The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.

Copper-catalyzed double C-S bond formation for the synthesis of 2-acyldihydrobenzo[b]thiophenes and 2-acylbenzo[b]thiophenes

An efficient domino process is developed for the synthesis of diversely substituted 2,3-dihydrobenzo[b]thiophenes from 2-iodoketones using a Cu-catalyst and easily available xanthate as a sulfur surrogate in good yields. This domino method has been expanded for the synthesis of 2-acylbenzo[b]thiophenes usingin situgenerated iodine (I2) from by-product KI in high yields. Treatment of xanthate with the copper(ii)-catalyst reduced it to a Cu(i)-catalyst, which initiates the catalytic cycle. A possible mechanism has been proposed based on the results from XPS-analysis, an iodine color test and several other control experiments.

Trisulfur-Radical-Anion-Triggered C(sp2)-H Amination of Electron-Deficient Alkenes

A trisulfur-radical-anion (S3˙-)-triggered C(sp2)-H amination of α,β-unsaturated carbonyl derivatives with simple amines has been demonstrated. This protocol provides convenient access to a variety of synthetically valuable N-unprotected and secondary β-enaminones with absolute Z selectivity and tertiary β-enaminones with E selectivity. Mechanistic probe and electronic structure theory calculations suggest that S3˙- initiates the nucleophilic attacks via a thiirane intermediate.

Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation

Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C-H borylation/N-C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C-H borylation and divergent acyl and decarbonylative amide N-C(O) and C-C activation. The methodology diverts the traditional acylation and arylation regioselectivity, allowing us to directly utilize readily available arenes and amides to produce valuable ketone and biaryl motifs.

A palladium-catalyzed C-H functionalization route to ketones: Via the oxidative coupling of arenes with carbon monoxide

We describe the development of a new palladium-catalyzed method to generate ketones via the oxidative coupling of two arenes and CO. This transformation is catalyzed by simple palladium salts, and is postulated to proceed via the conversion of arenes into high energy aroyl triflate electrophiles. Exploiting the latter can also allow the synthesis of unsymmetrical ketones from two different arenes.

Cobalt-catalyzed acylation-reactions of (hetero)arylzinc pivalates with thiopyridyl ester derivatives

A cobalt-catalyzed acylation reaction of various primary, secondary and tertiary alkyl, benzyl and (hetero)aryl S-pyridyl thioesters with (hetero)arylzinc pivalates is reported. The thioesters were prepared directly from the corresponding carboxylic acids under mild conditions, thus tolerating sensitive functional groups. Acylations of α-chiral S-pyridyl esters proceeded with very high stereoretention leading to optically enriched α-chiral ketones.

Lithium-Free Synthesis of Sodium 2,2,6,6-Tetramethylpiperidide and Its Synthetic Applications

Lithium-free synthetic methods for sodium 2,2,6,6-tetramethylpiperide (NaTMP) have been developed using sodium dispersion as a sole sodium source. The prepared NaTMP was used as a Br?nsted base, that exhibited some differences in reactivities from LiTMP. (Figure presented.).

METHOD FOR SYNTHESIZING SODIUM 2,2,6,6-TETRAMETHYLPIPERIDIDES

There is a demand for the development of a technique according to which sodium 2,2,6,6-tetramethylpiperidides (Na-TMPs) can be economically and efficiently synthesized through simple operations including a small number of steps under mild conditions in a short period of time. Also, there is a demand for the development of a technique according to which high-quality Na-TMPs that do not contain lithium or lithium compounds such as Li-TMP can be synthesized. The method for synthesizing sodium 2,2,6,6-tetramethylpiperidides includes a step of obtaining sodium 2,2,6,6-tetramethylpiperidides by reacting, in a reaction solvent, 2,2,6,6-tetramethylpiperidines with a dispersion product obtained by dispersing sodium in a dispersion solvent or an organosodium compound having an aromatic ring obtained through a reaction with a dispersion product obtained by dispersing sodium in a dispersion solvent.

Decarboxylation with Carbon Monoxide: The Direct Conversion of Carboxylic Acids into Potent Acid Triflate Electrophiles

We report a new strategy for the conversion of carboxylic acids into potent acid triflate electrophiles. The reaction involves oxidative carbonylation of carboxylic acids with I2 in the presence of AgOTf, and is postulated to proceed via acyl hypoiodites that react with CO to form acid triflates. Coupling this chemistry with subsequent trapping with arenes offers a mild, room temperature approach to generate ketones directly from broadly available carboxylic acids without the use of corrosive and reactive Lewis or Bronsted acid additives, and instead from compounds that are readily available, stable, and functional group compatible.