6263-65-6

Usage

Uses

Used in Organic Synthesis:
(R)-1-Phenylethanethiol is used as a source of the thiol functional group in organic synthesis. It plays a crucial role in the formation of alkyl benzylthioethers through S-alkylation, which is an essential process in the synthesis of various organic compounds.
Used in Flavor and Fragrance Industry:
Due to its meat-like, pungent odor, (R)-1-Phenylethanethiol is utilized in the flavor and fragrance industry to create or enhance the aroma of certain products. Its characteristic smell can be used to mimic the scent of cooked meat, making it a valuable component in the development of artificial flavors and fragrances.
Used in the Food Industry:
(R)-1-Phenylethanethiol, or its isomer 2-phenylethanethiole, is reportedly present in mushroom and fermented shrimp and fish paste (trassi). This suggests that it may have applications in the food industry, particularly in enhancing the flavor of these types of products or contributing to the development of new flavor profiles.

Synthesis

No information was found on the synthesis of 1-phenylethylmercaptan, but its isomer, 2-phenylethanethiol, was prepared from (2-bromoethyl)benzene.

InChI:InChI=1/C8H10S/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3

Upstream product

• 52053-61-9 di(α-methylbenzyl)disulfide 
• 585-71-7 (1-bromoethyl)benzne 
• 98-86-2 acetophenone 
• 98-85-1 1-Phenylethanol 
• 64-04-0 phenethylamine 
• 54810-89-8 α-Isopropylamino-α-phenylpropionitril 
• 67385-07-3 S-(1-phenylethyl) ethanethioate 
• 64-19-7 acetic acid 
• 100-42-5 styrene 
• 137-07-5 2-amino-benzenethiol 
• 124908-16-3 1-phenylethyl thiocyanate 
• 141561-41-3 <(SR)-2-Chloro-2-phenylethyl>-2,3:5,6-di-O-isopropyliden-β-D-mannofuran 
• 29850-82-6 (+/-)-(S)-(1-phenyl-ethyl)-isothiourea; hydrobromide 
• 33877-15-5 (R)-(+)-styrene sulfide 

Downstream Products

• 13125-70-7 (+-)-methyl-(1-phenyl-ethyl)-sulfide 
• 50999-18-3 racem.-bis-(1-phenyl-ethyl)-disulfide 
• 103-81-1 Benzeneacetamide 
• 67385-07-3 S-(1-phenylethyl) ethanethioate 
• 345927-66-4 (2,4-dinitro-phenyl)-(1-phenyl-ethyl)-sulfide 
• 20803-99-0 racemic 2-((1-phenylethyl)thio)acetic acid 
• 91970-39-7 2,4-Dimethyl-4-phenyl-3-thia-buttersaeure 
• 69543-90-4 α-Phenaethyl-thionitrit 
• 96418-50-7 S-<α-Methyl-benzylmercapto>-thioglykolsaeure-methylester 
• 69652-49-9 1-Phenaethyl-allylsulfid 
• 42383-85-7 C₉H₁₂N₂S₂ 
• 33691-99-5 1-(1-Phenyl-ethylsulfanyl)-propan-2-one 
• 113472-37-0 Methyl-phosphonodithioic acid S,S-bis-(1-phenyl-ethyl) ester 
• 113034-06-3 Phenyl-phosphonodithioic acid S,S-bis-(1-phenyl-ethyl) ester 

Relevant academic research and scientific papers

Accelerated reduction and solubilization of elemental sulfur by 1,2-aminothiols

Nucleophilic 1,2-aminothiol compounds readily reduce typically-insoluble elemental sulfur to polysulfides in both water and nonpolar organic solvents. The resulting anionic polysulfide species are stabilized through hydrogen-bonding interactions with the proximal amine moieties. These interactions can facilitate sulfur transfer to alkenes.

1-aryl ethanesulfonic acid and preparation method of its derivative

The invention provides 1-aryl ethanesulfonic acid and a preparation method of its derivative. The preparation method comprises the following steps that (a) 1-aryl halogensated ethane represented in aformula (I) and sodium hydrosulfide react to generate 1-

Phosphorus pentasulfide mediated conversion of organic thiocyanates to thiols

In this paper we report an efficient and mild procedure for the conversion of organic thiocyanates to thiols in the presence of phosphorus pentasulfide (P2S5) in refluxing toluene. The method avoids the use of expensive and hazardous transition metals and harsh reducing agents, as required by reported methods, and provides an attractive alternative to the existing methods for the conversion of organic thiocyanates to thiols.

Ligand dependence of the synthetic approach and chiroptical properties of a magic cluster protected with a bicyclic chiral thiolate

Chiral gold clusters stabilised by enantiopure thiolates were prepared, size-selected and characterised by circular dichroism and mass spectrometry. The product distribution is found to be ligand dependent. Au25 clusters protected with camphorthiol show clear resemblance of their chiroptical properties with their glutathionate analogue. The Royal Society of Chemistry 2012.

Dutch Resolution: Separation of enantiomers with families of resolving agents. A status report

Dutch Resolution is the term given to the use of mixtures (families) of resolving agents in classical resolutions. In this status report an overview is given of the latest results and new (possible) families of resolving agents are introduced. The concept of families is discussed as well as the factors that come into play on use of families. Practical aspects of Dutch Resolution in particular and resolutions in general are discussed.

Flavour and fragrance compositions

Flavour and fragrance compositions comprising 1-mercapto-1-arylalkanes or derivatives thereof.

A general and mild synthesis of thioesters and thiols from halides

The conversion of a wide variety of halides to thioesters by reaction with potassium thiocetate under mild conditions is described, and the generality of the method is demonstrated.

Direct Conversion of Alcohols into Thiols

A simple one-pot reaction between alcohols and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawesson's reagent, LR) affords the corresponding thiols, accompanied by dehydration products, alkenes.Treatment of acyclic 1,4-diols with LR gives the 1,3-dienes. o-(Dihydroxymethyl)benzene derivatives yield the 1,3-dihydrobenzothiophenes when treated with LR.

Glycosylsulfenyl and (Glycosylthio)sulfenyl Halides (Halogeno and Halogenothio 1-Thioglycosides, Resp.): Preparation and Reaction with Alkenes

The disulfides 11-17 and 20 were prepared from 7, 9, and 18 via the dithiocarbonates 8, 10, and 19, respectively (Scheme 2).The structure of 11 and of 13 was established by X-ray analysis.Chlorolysis (SO2Cl2) of 11 gave mostly the sulfenyl chloride 24, characterized as the sulfenamide 26, a small amount of 21, characterized as the (glycosylthio)sulfenamide 23, and the glycosyl chloride 27 (Scheme 3).Bromolysis of 11 followed by treatment of the crude with PhNH2 yielded only 28.Chlorolysis of the diglycosyl disulfide 13, however, gave mostly the (glycosylthio)sulfenyl chloride 21 and 27, besides 24.Bromolysis of 13 (-> 22 and traces of 25) followed by treatment with PhNH2 gave an even higher proportion of 23.Similarly, 20 led to 29 and hence to 30.In solution (CH2Cl2) the sulfenyl chloride 24 decomposes faster than the (thio)sulfenyl chloride 21, and both interconvert.Addition of crude 24 to styrene (-78 deg C) yielded the chloro-sulfide 31 and some 37, both in low yields.The product of the addition of 24 to 1-methylcyclohexene was transformed into the triol 32.Silyl ethers of allylic alcohols reacted with 24 only at room temperature, yielding, after desilylation, isomer mixtures 33 and 34, and pure 35.Much higher yields were achieved for the addition of (thio)sulfenyl halides yielding halogeno-disulfides.Good diastereoselectivities were only obtained with 21, its cyclohexylidene-protected analogue, and 22, and this only in the addition to styrene (-> 36, 37, 38), to (E)-disubstituted alkenes (-> 46, 48, 49a,b, 50a,b, 53), and to trisubstituted alkenes (-> 47, 51, 52, 54, 55).Other monosubstituted alkenes (-> 41-45) and (Z)-hex-2-ene (-> 49c,d, 50c,d) reacted with low diastereoselectivities.Where structurally possible, a stereospecific trans-addition was observed: regioselectivity was observed in the addition to mono- and trisubstituted alkenes and to derivatives of allyl alcohols.The absolute configuration of the 2-chloro-disulfides was either established by X-ray analysis (47a) or determined by transforming (LiAlH4) the chloro-disulfides into known thiiranes (Scheme 5).Thus, 37, 48, and the mixtures of 49a/b and 50a/b gave the thiiranes 56, 61, and 64, respectively, in good-to-acceptable yields (Scheme 5).Harsher conditions transformed 56 into the thiols 57 and 58.Similarly, 61 gave 62.The enantiomeric excesses of these thiols were determined by GC analysis of their esters obtained with (-)-camphanoyl chloride.Addition of 21 to trimethylsilane, followed by LiAlH4 reduction and desilylation, gave the known 66 (63percent, e.e. 74percent).The diastereoselectivity of the addition of 21 to trans-disubstituted and trisubstituted alkenes is rationalized by assuming a preferred conformation of the (thio)sulfenyl chloride and destabilizing steric interactions with one of the alkene substituents, . . .

A Novel Transformation of Alcohols to Thiols

Treatment of alcohols with 2,4-bis(p-methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulphide (Lawesson reagent) gave the corresponding thiols.