4410-99-5

Basic information

• Product Name: 2-Phenylethanethiol
• Synonyms: 2-Phenylethylthiol;PHENYLETHYL MERCAPTAN;PHENETHYL MERCAPTAN;2-PHENYLETHYL MERCAPTAN;2-PHENYLETHANETHIOL;BENZENEETHANETHIOL;BETA-PHENETHYL MERCAPTAN;BETA-PHENYLETHYL MERCAPTAN
• CAS NO: 4410-99-5
• Molecular Formula: C₈H₁₀S
• Molecular Weight: 138.23
• EINECS: 224-563-9
• Product Categories: thiol Flavor
• Mol File: 4410-99-5.mol
• Article Data: 20

Chemical Properties

• Melting Point: -30°C (estimate)
• Boiling Point: 97 °C
• Flash Point: 195 °F
• Appearance: Clear colorless/Liquid
• Density: 1.032 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.238mmHg at 25°C
• Refractive Index: n20/D 1.560(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.40±0.10(Predicted)
• Stability: Stable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1446618
• CAS DataBase Reference: 2-Phenylethanethiol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenylethanethiol(4410-99-5)
• EPA Substance Registry System: 2-Phenylethanethiol(4410-99-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 23-24/25-36/37
• RIDADR: UN 3334
• WGK Germany: 3
• F: 13
• Hazardous Substances Data: 4410-99-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylethanethiol is used as a derivatization reagent for phosphorylated sequences of peptides, which enhances ionization efficiency in matrix-assisted laser desorption/ionization mass spectrometry. This application aids in the analysis and identification of phosphorylated peptides, which are crucial in understanding various biological processes and potential drug targets.
Used in Nanotechnology:
2-Phenylethanethiol is utilized in the preparation of biicosahedral Au(25) clusters protected with various types of thiol ligands. These clusters have potential applications in catalysis, sensing, and drug delivery due to their unique size, stability, and electronic properties.
Used in Chemical Synthesis:
As a versatile organic compound, 2-Phenylethanethiol can be employed as a building block or intermediate in the synthesis of various complex organic molecules, particularly those containing thiol or phenyl groups. This application is relevant across multiple industries, including pharmaceuticals, materials science, and specialty chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 25, p. 1993, 1960 DOI: 10.1021/jo01081a044

InChI:InChI=1/C8H10S/c9-7-6-8-4-2-1-3-5-8/h1-5,9H,6-7H2

Upstream product

• 100-42-5 styrene 
• 103-63-9 1-phenyl-2-bromoethane 
• 7719-09-7 thionyl chloride 
• 60-12-8 2-phenylethanol 
• 7664-93-9 sulfuric acid 
• 860540-31-4 (2-phenyl)ethylsulfinylacetic acid 
• 622-24-2 2-phenylethyl chloride 
• 5654-72-8 2-phenylethyl thiocyanate 
• 99987-36-7 dimethyl-dithiocarbamic acid phenethyl ester 
• 3278-36-2 dithiocarbonic acid O-ethyl ester-S-phenethyl ester 
• 25558-00-3 3-Propinyl-2'-phenylethylsulfid 
• 141561-41-3 <(SR)-2-Chloro-2-phenylethyl>-2,3:5,6-di-O-isopropyliden-β-D-mannofuran 
• 100-39-0 benzyl bromide 
• 34372-24-2 1-benzylthio-2-phenylethane 

Downstream Products

• 101431-38-3 1-phenyl-2-(2-phenyl-ethanesulfinyl)-ethanol 
• 102317-98-6 1-(2,6-dichloro-benzyl)-4-phenethylmercapto-1,4-dihydro-pyridine-3-carboxylic acid amide 
• 27846-22-6 diphenethyl disulfide 
• 34292-93-8 2-phenylethanesulfonic acid 
• 64768-46-3 S-phenethyl 2-phenylethane-1-sulfonothioate 
• 104216-75-3 2-phenethylmercapto-propionic acid 
• 103-81-1 Benzeneacetamide 
• 35065-97-5 S-2-phenylethyl thioacetate 
• 112070-69-6 phenethyl-(tetra-O-acetyl-1-thio-β-D-galactopyranoside) 
• 90416-55-0 chloromethyl 2-phenylethyl sulfide 
• 121041-57-4 6-(phenethylthio)pyridazin-3-amine 
• 53603-17-1 S-phenethyl 4-methylbenzenesulfonothioate 
• 90923-56-1 (2-phenylethylthio)acetonitrile 
• 4973-48-2 trans,cis-bis<β-styryl> sulfide 

Relevant articles and documents

The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group

The invention provides a method for selectively removing benzyl, allyl and propargyl protecting groups by visible light or near visible light, namely a substrate containing benzyl, allyl or propargyl protecting groups. The method has the advantages of simple operation, safe and clean visible light or near visible light as excitation conditions, cheap and easily available reagents, high reaction yield, high reaction chemistry and regional selectivity, and is suitable for selective removal of benzyl, allyl and propargyl protecting groups in various substrates.

Spontaneous substitution of azulene-derived benzylic alcohols by thiols and its application to labeling/protection of biothiols

By mixing guaiazulene-3-methanol derivatives and thiols at room temperature, benzylic substitution of the alcohol proceeded to yield the corresponding sulfide. Because of the blue color of the guaiazulene derivative, this spontaneous reaction was used for labeling of paper-immobilized biothiols. By treatment with tris(2-carboxyethyl)phosphine hydrochloride, the guaiazulene-3-ylmethyl part of the sulfide could be removed and the original thiol recovered. Based on these findings, a guaiazulene-3-methanol derivative was used as a protective group for the synthesis of cysteine derivatives.

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.

A method for preparing thiol compounds

The invention provides a preparation method of a thiol compound. According to the preparation method, gas-liquid reaction is carried out on sulfuretted hydrogen and an organic compound containing carbon-carbon double bonds in a solid base catalyst and a reaction solvent through Michael addition under the conditions that the temperature is 20-80 DEG C and the pressure is 0.10-0.12MPa, so as to prepare the thiol compound. The preparation method is mild in reaction condition; the adopted solid base catalyst is strong in alkalinity; the alkaline catalysis position has relatively strong steric hindrance, and the applicability is wide; the solid base catalyst is easy to filter and recover, and can be repeatedly used after being activated; the reaction conversion rate and the selectivity are high; the side reaction is reduced; and the atomic economic utilization rate of the reaction is high.

Two-step three-component process for one-pot synthesis of 8-alkylmercaptocaffeine derivatives

A highly efficient, odourless and two-step three-component process for one-pot synthesis of some 8-alkylmercaptocaffeine derivatives has been described. The catalyst-free three-component reaction of alkyl bromides, thiourea, and 8-bromocaffeine gave 8-alkylmercaptocaffeine products in excellent to quantitative yields. In addition, the impact of parameters on sample reaction is discussed.

Inhibition of monoamine oxidase by 8-[(phenylethyl)sulfanyl]caffeine analogues

In a previous study we have investigated the monoamine oxidase (MAO) inhibitory properties of a series of 8-sulfanylcaffeine analogues. Among the compounds studied, 8-[(phenylethyl)sulfanyl]caffeine (IC50 = 0.223 μM) was found to be a particularly potent inhibitor of the type B MAO isoform. In an attempt to discover potent MAO inhibitors and to further examine the structure-activity relationships (SAR) of MAO inhibition by 8-sulfanylcaffeine analogues, in the present study a series of 8-[(phenylethyl)sulfanyl]caffeine analogues were synthesized and evaluated as inhibitors of human MAO-A and -B. The results document that substitution on C3 and C4 of the phenyl ring with alkyl groups and halogens yields 8-[(phenylethyl)sulfanyl]caffeine analogues which are potent and selective MAO-B inhibitors with IC50 values ranging from 0.017 to 0.125 μM. The MAO inhibitory properties of a series of 8-sulfinylcaffeine analogues were also examined. The results show that, compared to the corresponding 8-sulfanylcaffeine analogues, the 8-sulfinylcaffeins are weaker MAO-B inhibitors. Both the 8-sulfanylcaffeine and 8-sulfinylcaffeine analogues were found to be weak MAO-A inhibitors. This study also reports the MAO inhibition properties of selected 8-[(phenylpropyl)sulfanyl]caffeine analogues.

Thioacetate deprotection

A method of thioacetate deprotection by providing a compound of the formula R1—S—CO—R2, and reacting the compound with a quaternary ammonium cyanide salt in the presence of a protic solvent in an inert atmosphere to convert the compound to a product of the formula R1—SH. R1 is an organic group in which the bonding to sulfur is through a saturated carbon, and R2 is an aliphatic group.

A mild and practical deprotection method for benzyl thioethers

A highly effective and mild deprotection method was developed for benzyl thioethers using dibutylmagnesium in the presence of a catalytic amount of titanocene dichloride. This methodology is applicable to both aromatic and aliphatic benzyl thioethers.

Aliphatic thioacetate deprotection using catalytic tetrabutylammonium cyanide

A series of thiol-functionalized organic compounds were selected to analyze the scope and efficiency of a new thioacetate deprotection method using catalytic tetrabutylammonium cyanide (TBACN) to effect the transformation of a thioacetate group to a free thiol in the presence of a protic solvent. Particularly attractive are the mild reaction and workup conditions, reduced byproduct formation typically seen using literature methods and yields of greater than 80% for the free aliphatic thiols. This method is effective on aliphatic thiols with trityl, benzyl, p-halo-benzyl, phenethyl, phenoxyethyl, and cyclohexylethyl structural moieties, but it is not effective with thiophenols.

Synthesis of N-glyoxyl prolyl and pipecolyl amides and thioesters and evaluation of their in vitro and in vivo nerve regenerative effects

The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.