645-54-5

Usage

Uses

Used in Organic Synthesis:
2-Phenylethanethioamide is used as a key intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its reactivity and functional groups allow for a wide range of chemical transformations, making it a valuable component in the development of new molecules with desired properties.
Used in Halogenation Reactions:
In the field of organic chemistry, 2-phenylethanethioamide can be used as a substrate for halogenation reactions, where it reacts with halogenating agents such as N-bromo and N-chloro succinimides. These reactions introduce halogen atoms (bromine or chlorine) into the molecule, which can be further utilized in subsequent synthetic steps or provide new functional groups for further reactions.
Used in the Synthesis of Primary Amines:
2-Phenylethanethioamide can also be used in the synthesis of primary amines through the reaction with phthalimides. This process involves the formation of an intermediate, which can be hydrolyzed to yield the desired primary amine. This method is particularly useful for the preparation of amines that are difficult to synthesize through other routes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 4742, 1993 DOI: 10.1021/jo00069a046Synthesis, p. 887, 1979 DOI: 10.1055/s-1979-28861

InChI:InChI=1/C8H9NS/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)

Upstream product

• 140-29-4 phenylacetonitrile 
• 103-81-1 Benzeneacetamide 
• 298-06-6 O,O-Diethyl hydrogen phosphorodithioate 
• 98-86-2 acetophenone 
• 60899-79-8 O,S-diethyl-dithiophosphoric acid 
• 74974-19-9 benzylmethyleneimine 
• 122-78-1 phenylacetaldehyde 
• 41904-21-6 1-methylsulphinyl-1-methylthio-2-phenylethylene 
• 103-80-0 phenylacetyl chloride 
• 64-17-5 ethanol 
• 6277-02-7 3-oxo-2-phenylpentanenitrile 
• 7783-06-4 hydrogen sulfide 
• 124-40-3 dimethyl amine 
• 7664-41-7 ammonia 

Downstream Products

• 15055-59-1 2-benzyl-4,5-dimethyl-thiazole 
• 7210-74-4 2-benzyl-4-methyl-thiazole 
• 90923-93-6 2-benzyl-thiazol-4-one 
• 29947-33-9 2-(2-benzyl-thiazol-4-yl)-benzothiazole 
• 97753-42-9 N-Thiophenacetyl-phenylacetamidin 
• 54614-87-8 N-hydroxymethyl-2-phenyl-thioacetamide 
• 29942-08-3 6-(2-benzyl-thiazol-4-yl)-benzothiazole 
• 55868-14-9 8-benzyl-acenaphtho[1,2-d]thiazole 
• 538-74-9 dibenzyl sulfide 
• 140-29-4 phenylacetonitrile 
• 89984-38-3 (E)-3-Morpholin-4-yl-N-[1-morpholin-4-yl-meth-(E)-ylidene]-2-phenyl-thioacrylamide 
• 101777-61-1 2-benzyl-1-(2-dimethylamino-ethyl)-4,5-dihydro-1H-imidazole 
• 64-04-0 phenethylamine 
• 103-81-1 Benzeneacetamide 

Relevant academic research and scientific papers

Structure-activity relationship study of thiazolyl-hydroxamate derivatives as selective histone deacetylase 6 inhibitors

Several human diseases are associated with aberrant epigenetic pathways mediated by histone deacetylases (HDACs), especially HDAC6, a class IIb HDACs, which has emerged as an attractive target for neurodegenerative and autoimmune disease therapeutics. In a previous study, we developed the novel HDAC6-selective inhibitor 9a ((E)-N-hydroxy-4-(2-styrylthiazol-4-yl)butanamide) and showed that it has anti-sepsis activity in vivo. In this study, we conducted structure-activity relationship (SAR) studies to optimize the activity and selectivity of HDAC6, synthesizing its derivatives with various aliphatic linker sizes and cap structures. We identified 6u ((E)-N-hydroxy-3-(2-(4-fluorostyryl)thiazol-4-yl)propanamide), which has nanomolar inhibition activity and a 126-fold selectivity for HDAC6 over HDAC1. Through the docking analyses of 6u against HDAC subtypes, we revealed the importance of the optimal aliphatic linker size, as well as the electronic substituent effect and rigidity of the aryl cap group. Thus, we suggest a new rationale for the design of HDAC6-selective inhibitors.

Domino aryne precursor: Efficient construction of 2,4-disubstituted benzothiazoles

An aryne precursor with a potential to perform domino aryne chemistry was proposed and synthesized. The reaction of this reagent with benzothioamide derivatives could afford 2,4-disubstituted benzothiazole with sequential incorporation of C-S, C-N, and C-C bonds on the consecutive three positions of the aryne precursor.

Metal-free, one-pot oxidative conversion of aldehydes to primary thioamides in aqueous media

One-pot tandem reactions of a variety of aldehydes with aqueous ammonia, molecular iodine, and O,O-diethyl dithiophosphoric acid readily afford the corresponding primary thioamides. This is an inexpensive, practical, and metal-free way of accessing various thioamides from aldehydes in aqueous media. The pure products are obtained simply by filtration followed by successive washing with aqueous sodium thiosulfate and water. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Microwave-assisted synthesis of potent PDE7 inhibitors containing a thienopyrimidin-4-amine scaffold

A series of novel thienopyrimidin-4-amines have been synthesized and evaluated as phosphodiesterase (PDE) inhibitors. A rationale for the observed selectivity against PDE7 has been obtained from molecular modelling studies on the most active compounds. This journal is the Partner Organisations 2014.

CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N,S- acetals: A new way to prepare disubstituted maleic anhydrides

The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N,X(X=O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N,O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N,NR-acetalspenta-atomic cyclic ketene-N,S-acetalshexa-atomic cyclic ketene-N,S-acetals. Invariably the catalytic cycle begins with the formation of a carbamoyl methyl radical. This leads to a cascade of reactions, including a radical polar crossover step, which ends with the formation of the maleimide nucleus, or precursors of this. Products from the RC of the hexa-atomic cyclic ketene-N,S-acetals, were efficiently transformed into disubstituted maleic anhydrides.

Novel selective thiazoleacetic acids as CRTH2 antagonists developed from in silico derived hits. Part 1

Structure-activity relationships of three related series of 4-phenylthiazol-5-ylacetic acids, derived from two hits emanating from a focused library obtained by in silico screening, have been explored as CRTH2 (chemoattractant receptor-homologous molecule expressed on Th2 cells) antagonists. Several compounds with double digit nanomolar binding affinity and full antagonistic efficacy for human CRTH2 receptor were obtained in all subclasses. The most potent compound was [2-(4-chloro-benzyl)-4-(4-phenoxy-phenyl)-thiazol-5-yl]acetic acid having an binding affinity of 3.7 nM and functional antagonistic effect of 66 nM in a BRET and 12 nM in a cAMP assay with no functional activity for the other PGD2 DP receptor (27 μM in cAMP).

The BF3·OEt2-assisted conversion of nitriles into thioamides with Lawesson's reagent

A method for the thiolysis of nitriles by applying Lawesson's reagent and facilitated by the addition of boron trifluoride-diethyl ether complex is reported. The method opens an easy access to primary thioamides. Aromatic, benzylic, and aliphatic nitriles were converted into the corresponding thioamides in high to quantitative yields (even in unfavorable cases, e.g., ortho-substitut-ed benzonitriles). The reaction was performed in 1,2-dimethoxyethane-tetrahydrofuran or toluene-diethyl ether solvent mixtures at 20-50°C, and exhibited considerable selectivity in the case of multifunctional nitrile substrates, such as cyanomethyl N-acetylphenylalaninate, benzoylacetonitrile, 4-cyanobenzamide, 4-acetylbenzonitrile, or pent-3-enenitrile. Georg Thieme Verlag Stuttgart.

Synthesis of (4R,5S)-melithiazols F and I

Palladium-catalyzed cyclization-methoxycarbonylation of (2R,3S)-3-methylpenta-4-yne-1,2-diol (8) derived from the (2R,3S)-epoxybutanoate 7 followed by methylation gave the tetrahydro-2-furylidene acetate (-)-9, which was converted into the left-half aldehyde (+)-4. A Wittig reaction between (+)-4 and the phosphoranylide derived from the bithiazole-type phosphonium iodide 5 using lithium bis(trimethylsilyl)-amide afforded (+)-(4R,5S)- melithiazol F (1), whose spectroscopic data were identical with those of the natural product 1. Moreover, the synthesis of (+)-(4R,5S)-melithiazol I (2), was achieved by the same synthetic strategy as that of (+)-(4R,5S)-melithiazol F (1). The antifungal activity of the synthetic melithiazols F (1) and I (2) against the phytopathogenic fungus, Phytophthora capsici, was evaluated by using a paper disc assay method. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Efficient lactam synthesis

Lactams, libraries of lactams, and an efficient method of synthesizing a lactam, including a γ-lactam, in which an α-diazoacetamide of the general structure (I) is reacted under conditions promoting intramolecular C—H insertion, for example in the presenc

Efficient lactam synthesis

Lactams, libraries of lactams, and an efficient method of synthesizing a lactam, including a γ-lactam, in which an α-diazoacetamide of the general structure (I) is reacted under conditions promoting intramolecular C—H insertion, for example in the presenc