4498-99-1

Basic information

• Product Name: 4-METHYLBENZYL MERCAPTAN
• Synonyms: (4-Methylphenyl)methanethiol, tech;4-Methylbenzyl mercaptan, 4-(Sulphanylmethyl)toluene, (4-Methylphenyl)methanethiol;p-Toluenemethanethiol;p-Tolylmethyl mercaptan;Benzenemethanethiol, 4-methyl-;P-TOLYLMETHANETHIOL;P-XYLYL MERCAPTAN;(P-METHYLPHENYL)METHANETHIOL
• CAS NO: 4498-99-1
• Molecular Formula: C₈H₁₀S
• Molecular Weight: 138.23
• EINECS: 224-796-6
• Product Categories: Sulphur Derivatives
• Mol File: 4498-99-1.mol

Chemical Properties

• Melting Point: 76℃
• Boiling Point: 116-118°C 35mm
• Flash Point: 116-118°C/35mm
• Appearance: /
• Density: 1,023 g/cm3
• Vapor Pressure: 0.192mmHg at 25°C
• Refractive Index: 1.5630
• Solubility: Sparingly Soluble.
• Sensitive: Air Sensitive
• BRN: 2411317
• CAS DataBase Reference: 4-METHYLBENZYL MERCAPTAN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLBENZYL MERCAPTAN(4498-99-1)
• EPA Substance Registry System: 4-METHYLBENZYL MERCAPTAN(4498-99-1)

Safety Data

• Hazard Codes: Xi
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
• Safety Statements: 23-24/25
• RIDADR: UN2810
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 4498-99-1(Hazardous Substances Data)

Usage

Uses

Used in Natural Gas Industry:
4-Methylbenzyl mercaptan is used as a scent additive for natural gas to provide it with a distinctive odor, enhancing safety by making gas leaks easily detectable.
Used in Food Industry:
In the food industry, 4-methylbenzyl mercaptan is utilized as a flavoring agent, contributing to the taste and aroma of various food products.
Used in Perfumery:
4-Methylbenzyl mercaptan is employed as a fragrance component in perfumes, adding depth and complexity to the scents.
Used in Pharmaceutical Synthesis:
This chemical compound is used in the synthesis of pharmaceuticals, playing a crucial role in the development of new medications.
Used as an Intermediate in Organic Compound Production:
4-Methylbenzyl mercaptan serves as an intermediate in the production of other organic compounds, facilitating the creation of a range of chemical products.
It is essential to handle 4-methylbenzyl mercaptan with care due to its potential to cause irritation to the skin, eyes, and respiratory system. Proper storage and use in well-ventilated areas are recommended to ensure safety.

InChI:InChI=1/C8H10S/c1-7-2-4-8(6-9)5-3-7/h2-5,9H,6H2,1H3

Upstream product

• 104-81-4 4-Methylbenzyl bromide 
• 96185-26-1 1-(2-hydroxyethyl)-4,6-diphenylpyridin-2-thione 
• 224043-70-3 O-propyl 4-methylbenzenecarbothioate 
• 72209-88-2 S-(4-methylbenzyl)isothiouronium bromide 
• 65094-22-6 diethyl (bromodifluoromethyl)phosphonate 
• 30085-48-4 S-(4-methylbenzyl) N,N-dimethylthiocarbamate 
• 104-87-0 4-methyl-benzaldehyde 
• 54850-42-9 carbamic acid-(4-methyl-benzyl ester) 
• 115412-23-2 p-methylbenzyl octyl sulfide 
• 17356-08-0 thiourea 
• 76950-78-2 1-(4-Methyl-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 
• 60410-77-7 bis(4-methylbenzenethiocarbonyl) sulphide 
• 589-18-4 4-Methylbenzyl alcohol 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 20193-94-6 bis-(4-methyl-benzyl)-disulfide 
• 78981-22-3 3-<(4-methylbenzyl)thio>propionic acid 
• 109212-79-5 3-Ethyl-3-(4-methyl-benzylsulfanyl)-pentanoic acid ethyl ester 
• 117487-64-6 3-Ethyl-2-formylamino-3-(4-methyl-benzylsulfanyl)-pentanoic acid ethyl ester 
• 33155-60-1 t-butyl p-tolylacetate 
• 403739-54-8 1-(4-methoxyphenyl)-2-(4-methylbenzylsulfanyl)ethanone 
• 18869-29-9 (E)-4,4'-dimethylstilbene 
• 5936-94-7 methyl p-methylbenzyl sulfone 
• 1039752-99-2 4-[(4-methylbenzyl)thio]-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 

Relevant articles and documents

Boc-S-methylbenzyl-(S)-2-amino-6-mercaptohexanoic acid: Preparation and application to the synthesis of a large cyclic disulfide peptide

A derivative of 2-amino-6-mercaptohexanoic acid (Amh) suitable for Boc solid phase synthesis has been prepared by conversion of the ε-NH2 group of lysine into a 4-methylbenzyl thioether. The derivative has been used in the synthesis of a 22-residue peptide with a 62-atom cyclic disulfide. Amh(Meb) is stable to acidolysis but can be conveniently deprotected, with simultaneous disulfide formation, by treatment with diphenyl sulfoxide and trichloromethylsilane.

Synthesis of difluoromethyl and deuterium-labeled difluoromethyl thioethers from aliphatic electrophiles

A one-pot difluoromethylthiolation of alkyl electrophiles with thiourea and diethyl bromodifluoromethylphosphonate is described. The transition-metal-free approach, readily available reagents, and mild conditions provide a practical way for the synthesis of difluoromethyl thioethers. By changing the "H" source to the most commonly used "D" sources CD3OD and D2O, this strategy enables efficient synthesis of SCF2D-substituted molecules in good yields with high levels of D incorporation.

Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans

The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).

Benzylic Thio and Seleno Newman-Kwart Rearrangements

The thermally induced OBn → SBn and OBn → SeBn migration reactions facilitate the rearrangement of O-benzyl thio- and selenocarbamates [BnOC(=X)NMe2] (X = S or Se) into their corresponding S-benzyl thio- and Se-benzyl selenocarbamates [BnXC(=O)NMe2] (X = S or Se). A series of substituted O-benzyl thio- and selenocarbamates were synthesized and rearranged in good yields of 33-88%. The reaction rates are higher for substrates with electron-donating groups in the 2 or 4 position of the aromatic ring, but the rearrangement also proceeds with electron-withdrawing substituents. The rearrangement follows first-order reaction kinetics and proceeds via a tight ion pair intermediate consisting of the benzylic carbocation and the thio- or selenocarbamate moiety. Computational studies support these findings.

Phosphorus Pentasulfide Mediated Conversion of Primary Carbamates into Thiols

In this paper, we report a method for the conversion of primary carbamates into thiols in the presence of phosphorus pentasulfide (P 2 S 5) in refluxing toluene. Presently, no method exists in the literature for conversion of carbamates into thiols and, to the best of our knowledge, it is the first report for this type of conversion. This method presents an indirect route for the conversion of alcohols into thiols via their carbamate derivatives that may be useful in the total synthesis of compounds containing a thiol functionality.

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.

Sulfur-and n-acyl carbonyl oxygen-assisted heterolysis of the C(=O)-S bond in excited-state (Z)-nacyl-α-dehydro(1-naphthyl)alanine thioesters

Irradiation of the title thioesters (Z)-1 in nitrogen-saturated 1,2- dichloroethane at wavelengths greater than 280 nm was found to afford (Z)-4-(1- naphthylmethylene)-5(4H)-oxazolone derivatives (Z)-2, (E)-2, alkyl-substituted thiols 3, and (E)-1 without

Preparation and in-vitro evaluation of 4-benzylsulfanylpyridine-2- carbohydrazides as potential antituberculosis agents

A set of 4-benzylsulfanylpyridine-2-carbohydrazides was synthesized and evaluated for in vitro antimycobacterial activity against Mycobacterium tuberculosis, non-tuberculous mycobacteria, and multidrug-resistant M. tuberculosis. The activities expressed as the minimum inhibitory concentration (MIC) fall into a range of 2 to 125 μmol/L, most often 4 to 32 μmol/L. The results revealed that the substituents on the benzyl moiety do not influence the antimycobacterial efficacy. The substances exhibited similar activities against sensitive and resistant strains of M. tuberculosis. Furthermore, compounds show low antiproliferative effect and cytotoxicity.

Mercaptomethylation of aromatics

Mercaptomethylarenes 2a - f were prepared in moderate yields by facile mercaptomethylation consisting of the metalation of the corresponding aromatics 1a - f with magnesium or butyllithium / magnesium bromide diethyl etherate, followed by the addition of O-propyl chlorothioformate, and the reduction with lithium aluminum hydride or sodium borohydride.

Mechanism of the Solution-Phase Reaction of Alkyl Sulfides Atomic Hydrogen. Reduction via a 9-S-3 Radical Intermediate

The low selectivity of benzyl alkyl sulfide fragmentation subsequent to its reaction with atomic hydrogen is indicative of a reaction that proceeds via an early transition state. The competitive reduction of a series of substituted-benzyl alkyl sulfides was insensitive to the substituent on the aromatic ring (ρ = -0.13, r = 0.99). The relative rates of fragmentation of a series of the substituted-benzyl alkyl sulfides gave a V-shaped Hammett plot. Both electron-donating and electron-withdrawing groups destabilized the transition state (ρ = +0.99, r = 0.999; ρ = -0.82, r = 0.992). Since the relative rates of disappearance of the alkyl benzyl sulfides are not substituent dependent, but the relative rates of fragmentation are, a 9-S-3 intermediate is preferred as the structure leading to products.