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Methallylphenyl sulfide, with the chemical formula C10H12S, is a colorless to pale yellow liquid that emits a garlic-like odor. It is a naturally occurring chemical compound found in garlic, onions, and other Allium species. METHALLYLPHENYL SULFIDE is recognized for its antioxidant and antimicrobial properties, which have garnered interest for its potential applications in food preservation and as a natural alternative to synthetic antioxidants and preservatives. Moreover, it has been studied for its potential health benefits, such as reducing the risk of cardiovascular diseases and cancer, making it a promising compound for both the food industry and health sciences.

702-00-1

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702-00-1 Usage

Uses

Used in the Food Industry:
Methallylphenyl sulfide is utilized as a flavoring agent due to its characteristic garlic-like aroma, enhancing the taste and aroma of various food products.
Used in Food Preservation:
Leveraging its antimicrobial properties, methallylphenyl sulfide is studied for its potential use in food preservation, helping to extend the shelf life of perishable items and maintaining food safety.
Used as a Natural Antioxidant:
Given its antioxidant characteristics, methallylphenyl sulfide is considered a natural alternative to synthetic antioxidants, which can be used to prevent the oxidation of fats and oils in food products, thereby preserving their quality and nutritional value.
Used in Health Sciences:
Methallylphenyl sulfide is being investigated for its potential health benefits, such as its role in reducing the risk of cardiovascular diseases and cancer, indicating its possible use in the development of health-promoting products or as a supplement.
Overall, methallylphenyl sulfide is a versatile compound with a range of applications in both the food industry and health sciences, offering benefits as a flavoring agent, preservative, antioxidant, and potential health promoter.

Check Digit Verification of cas no

The CAS Registry Mumber 702-00-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,0 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 702-00:
(5*7)+(4*0)+(3*2)+(2*0)+(1*0)=41
41 % 10 = 1
So 702-00-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H12S/c1-9(2)8-11-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3

702-00-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-methylprop-2-enylsulfanylbenzene

1.2 Other means of identification

Product number -
Other names methallyl phenyl thioether

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:702-00-1 SDS

702-00-1Relevant articles and documents

Yb(iii)-catalysedsyn-thioallylation of ynamides

Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen

supporting information, p. 7521 - 7524 (2021/08/05)

Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.

Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements

Xu, Xiaofei,Li, Chang,Tao, Zhihao,Pan, Yuanjiang

supporting information, p. 1245 - 1249 (2017/08/15)

A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.

Expanding the horizon of intermolecular trapping of in situ generated α-oxo gold carbenes: Efficient oxidative union of allylic sulfides and terminal alkynes via C-C bond formation

Li, Jiabin,Ji, Kegong,Zheng, Renhua,Nelson, Jonathan,Zhang, Liming

supporting information, p. 4130 - 4133 (2014/04/03)

With a new P,S-bidentate phosphine as the ligand to gold(i), the α-oxo gold carbenes generated in situ via gold-catalyzed intermolecular oxidation of terminal alkynes were effectively trapped by various allylic sulfides, resulting in the formation of α-aryl(alkyl)thio-γ,δ- unsaturated ketones upon facile [2,3]sigmatropic rearrangements. This journal is the Partner Organisations 2014.

Highly chemoselective synthesis of aryl allylic sulfoxides through calcium hypobromite oxidation of aryl allylic sulfides

Pace, Vittorio,Castoldi, Laura,Holzer, Wolfgang

supporting information; experimental part, p. 967 - 972 (2012/03/11)

A highly chemoselective oxidation of widely substituted aryl allylic sulfides, prepared by allylation of arylthioethers with KF-Celite, to the corresponding aryl allylic sulfoxide was achieved by employing calcium hypobromite. Neither over-oxidation to sulfones nor halogenation of the aromatic rings was observed. The protocol may be successfully applied for the oxidation of substituted allylic systems (i.e., 2-haloallyl) that per se could interact with the oxidizing agent.

Catalytic activation of diazo compounds using electron-rich, defined iron complexes for carbene-transfer reactions

Holzwarth, Michael S.,Alt, Isabel,Plietker, Bernd

supporting information; experimental part, p. 5351 - 5354 (2012/07/14)

Carbene transfer: The electron-rich iron complex Bu4N[Fe(CO) 3(NO)] efficiently catalyzes different carbene-transfer reactions. Various diazo compounds can be used. The high stability of the employed iron complexes is demonstrated by the generation of the diazo reagent in situ and a sequential iron-catalyzed allylic sulfenylation/Doyle-Kirmse reaction. Copyright

Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V.* Reactions of 2-(α-chloroalkyl)thiiranes with organolithium compounds

Tomashevskii,Sokolov,Potekhin

experimental part, p. 1822 - 1825 (2011/04/17)

2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro-and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)-and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2- dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed. Pleiades Publishing, Ltd., 2010.

On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides

Peppe, Clovis,Borges De Castro, Lierson

experimental part, p. 678 - 683 (2009/10/30)

The reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur, selenium) towards organyl halides (organyl = alkyl, allyl, benzyl, acyl) was examined. A practical one-pot method to prepare organyl phenyl chalcogenides indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better organyl halides capable to produce stable carbocations.

Synthesis of allylsilanes by reductive lithiation of thioethers

Streiff, Stephane,Ribeiro, Nigel,Desaubry, Laurent

, p. 7592 - 7598 (2007/10/03)

Although much work in reductive lithiation has been done, the utilization of allylthioethers bearing various substituents to prepare allylsilanes has not been explored. The main reason clearly stems from the anticipated lack of regioselectivity. We describe herein the first study on the regioselectivity of the reductive silylation involving dissymmetric allylthioethers. We surveyed a broad spectrum of parameters and showed that this process displays a great dependence of the reaction conditions. We also discovered that an electron transporter, DBB or naphthalene, can cleave THF at room temperature by sonication, to generate a strong base, 4-lithiobutoxide. This feature was successfully exploited to the straightforward synthesis of bis-silanes in one pot. Examples are provided for maximizing both the chemical yield and the regioselectivity of the reductive silylation through the tuning of the reaction conditions. By changing these conditions, several allylsilanes can be selectively synthesized from one thioether.

Aromatic Allylsulfenylation with in Situ Generated Allylic Thiols under the Heck Conditions

Harayama, Hiroto,Nagahama, Takayuki,Kozera, Toyohiro,Kimura, Masanari,Fugami, Keigo,Tanaka, Shuji,Tamaru, Yoshinao

, p. 445 - 456 (2007/10/03)

A wide structural variety of S-allylic thiocarbamates 2 can be prepared in good yields by the rearrangement of O-allylic thiocarbamates 1 under three different conditions: thermal activation (neat, 120-150°C), palladium(0) (25-65 °C), and palladium(II) catalysis (25-65°C). Of the two possible regioisomers of unsymmetrical S-allylic thiocarbamates 2, those of higher thermodynamic stability can be prepared in high purity under either thermal activation or palladium(0) catalysis. Although the thermodynamically less stable regioisomers of 2 are, in general, hard to be prepared in high purity, some of them (e.g., 2d and 2h′) can be obtained with an exclusive or high selectivity by the catalysis of palladium(II). The stereoisomeric pair of 2j and 2j′ can be prepared selectively by the palladium(0)-catalyzed rearrangement of 1j and 1k, respectively. These reactions proceed with retention of configuration at the allylic stereocenters, S-Allylic (2) and S-alkyl thiocarbamates (7) undergo fragmentation to generate thiolates in the presence of inorganic bases (e.g., K2CO3, K2CO3·-Et4N+I-) by heating in an aprotic solvent; the thus-formed thiolates react with aromatic iodides and vinyl bromides in the presence of palladium(0) complexes to furnish aryl and vinyl sulfides, respectively. A wide variety of aryl sulfides can be prepared in good yields irrespective of the kind of substituents and their substitution positions (o-, m-, p-) under conditions B [Pd(OAc)2, PPh3, K2CO3·Et4N+I-, dioxane, 100°C]. Under conditions E [Pd(OAc)2, PPh3, Cs2CO3, dioxane, 100°C], better yields result specifically for the sulfenylation of aromatic iodides bearing substituents having large Hammett σ constants.

Clocking Tertiary Cyclopropylcarbinyl Radical Rearrangements

Engel, Paul S.,He, Shu-Lin,Banks,Ingold,Lusztyk

, p. 1210 - 1214 (2007/10/03)

Three independent methods have been employed to estimate the rate constant, k1, for ring-opening of the 2-cyclopropyl-2-propyl radical, 1, at room temperature. These three estimates are based on chemical trapping of 1 and the ring-opened 4-methylpent-3-ene-1-yl radical by thiophenol (k1 = (1.65 ± 0.41) × 107 M-1 s-1), 9-azabicyclo[3.3.1]nonane-N-oxyl (k1 = (1.76 ± 0.34) × 107 M-1 s-1) and 2,2,6,6-tetramethylpiperidine-N-oxyl (k1 = (2.1 ± 0.4) × 107 M-1 s-1) and absolute rate constants for nonrearranging radicals structurally related to 1. The mean value for k1) ((1.84 ± 0.4) × 107 M-1 s-1) should be used when 1 is employed as a tertiary alkyl free radical clock at ambient temperatures.

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