18739-99-6

Basic information

• Product Name: cinnamyl 4-tolyl thioether
• Synonyms: cinnamyl 4-tolyl thioether
• CAS NO: 18739-99-6
• Molecular Weight: 240.369
• Mol File: 18739-99-6.mol

Chemical Properties

• CAS DataBase Reference: cinnamyl 4-tolyl thioether(CAS DataBase Reference)
• NIST Chemistry Reference: cinnamyl 4-tolyl thioether(18739-99-6)
• EPA Substance Registry System: cinnamyl 4-tolyl thioether(18739-99-6)

Safety Data

• Hazardous Substances Data: 18739-99-6(Hazardous Substances Data)

Upstream product

• 2327-99-3 1-phenylpropadiene 
• 106-45-6 para-thiocresol 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 106-38-7 para-bromotoluene 
• 104-54-1 3-Phenylpropenol 
• 444575-79-5 carbonic acid 1,1-dimethylethyl 1-phenyl-2-propenyl ester 
• 103-19-5 di(p-tolyl) disulfide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4192-77-2 ethyl cinnamate 

Downstream Products

• 16215-11-5 trans-cinnamyl p-tolyl sulfone 
• 1421914-12-6 (E)-8-(4-phenylbuta-1,3-dien-1-ylidene)-1,4-dioxaspiro[4.5]decane 
• 20605-48-5 (E)-1-cinnamylsulfonyl-4-methylbenzene 
• 62158-92-3 (2,2,2-trifluoroethyl) (4-methylphenyl) sulfide 

Relevant articles and documents

Hemin Catalyzed Dealkylative Intercepted [2, 3]-Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2-Trifluorodiazoethane

A dealkylative intercepted [2, 3]-sigmatropic rearrangement reaction of allylic sulfides with 2, 2, 2-trifluorodiazoethane (CF3CHN2) is reported, the commercially available and biocompatible catalyst hemin was found to efficiently catalyze this transformation across a diverse set of allylic sulfides with in situ generated CF3CHN2, providing excellent yields (up to 99%) under mild condition without inert gas protection. In addition, CF3CHN2 exhibited unique reactivity toward this process compared with other frequently used diazo reagents. This work expands the range of carbene-mediated transformations catalyzed by hemin and introduces a concise and general strategy for exploiting new possibility of reactions concerning organosulfides. (Figure presented.).

E-Selective Hydrothiolation of Terminal Arylallenes with Arylthiols Catalyzed by Ni (PMe3)4

A catalytic system of regioselective synthesis of allyl sulfides via hydrothiolation of terminal arylallenes with arylthiols has been developed using nickel(0) complex Ni (PMe3)4 as a catalyst. In most cases the excellent to moderate

Ruthenium-catalyzed decarboxylative C-S cross-coupling of carbonothioate: synthesis of allyl(aryl)sulfide

A novel ruthenium-catalyzed decarboxylative cross-coupling of carbonothioate is disclosed. This method provides straightforward access to the corresponding allyl(aryl)sulfide derivatives in generally good to excellent yields under mild conditions and feat

Efficient dehydrative alkylation of thiols with alcohols catalyzed by alkyl halides

Alcohols can be efficiently converted into the useful thioethers by a transition metal- and base-free dehydrative S-alkylation reaction with thiols or disulfides by employing alkyl halides as the effective catalyst. This simple and efficient method is a green and practical way for the preparation of thioethers, as it tolerates a wide range of substrates such as aryl and alkyl thiols, as well as benzylic, allylic, secondary, tertiary, and even the less reactive aliphatic alcohols.

One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme

A new protocol for the thioetherification of structurally varied alcohols with aryl halides using Lawesson's reagent, catalysed by copper(I) iodide, and using diglyme as a safe solvent was developed. Using this method, the reactions of aryl halides proceeded efficiently, and the desired sulfides were obtained in high to excellent yields. The method uses alcohols as starting materials, which is a significant advantage over methods that start from thiols. Alcohols are widely commercially available in a much greater structural diversity than thiols, and they are also nontoxic and not foul-smelling. A reaction mechanism was proposed. A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.

Coupling reaction of magnesium alkylidene carbenoids with α-sulfonylallyllithiums: An efficient route to multi-substituted vinylallenes

A variety of vinylallenes were successfully synthesized from 1-chlorovinyl p-tolyl sulfoxides and allyl or vinyl sulfones. Allyl and vinyl sulfones served as α-sulfonylallyllithium sources were prepared from carbonyl compounds in three or four steps in good overall yields. The coupling reaction of α-sulfonylallyllithiums with magnesium alkylidene carbenoids, which were generated from 1-chlorovinyl p-tolyl sulfoxides and isopropylmagnesium chloride, afforded multi-substituted vinylallenes in up to 88% yield. Georg Thieme Verlag KG Stuttgart · New York.

Vanadium-catalyzed enantioselective oxidation of allyl sulfides

The enantioselective oxidation of allyl sulfides with a vanadyl complex of 3,5-diiodosalicylidene tert-leucinol as a catalyst and aqueous hydrogen peroxide as an oxidant afforded chiral allyl sulfoxides with high enantioselectivities of up to 97.3% ee and moderate yields.

Fast ruthenium-catalysed allylation of thiols by using allyl alcohols as substrates

The allylation of aromatic and aliphatic thiols, by using allyl alcohols as substrates, requires only minutes at ambient temperature with either a Ru Iv catalyst, [Ru(Cp*)(n3CH5)(CH 3CN)2](PF6)2 (2; Cp* = pentamethylcyclopentadienyl) or a combination of [Ru(Cp*)(CH 3CN)3](PF6) and camphor sulfonic acid. Quantitative conversion is normal and the catalyst possesses high functional-group tolerance. The use of [Ru(Cp*)(CH3CN) 3](PF6) alone affords poor results. A comparison is made to the results from catalytic runs based on the use of carbonates rather than alcohols, by using 2 as the catalyst, and it is shown that the products from the alcohols are formed faster, so there is no advantage in using a carbonate substrate. The observed branched-to-linear (b/1) ratios when using substituted alcohols decrease with time suggesting that the catalysts isomerise the products. A new methodology from which one can select the desired isomeric product is proposed. DFT calculations and NMR spectroscopic measurements, by using an arene sulfonic acid as co-catalyst, suggest that 6-complexes are not relevant for the catalytic system. Moreover, the DFT results indicate that l)any rf-complexes from the acids RC6H4SO 3H result from deprotonation of the acid, 2) complexation of the thiol, via the deprotonated sulfur atom, is preferred over complexation of the O atom of the sulfonate, RC6H4SO3and 3) a sulfonate O-atom complex will be difficult to detect.

ZrCl4 dispersed on dry silica gel provides a useful reagent for S-alkylation of thiols with alcohols under solvent-free conditions

ZrCl4 which is commercially available and not a costly compound, is a relatively safe chemical [LD50 [ZrCl4, oral rat] = 1688 mg Kg]. In this report we describe the use of ZrCl4 dispersed on dry silica gel as an efficient reagent for the efficient preparation of thioethers from thiols with alcohols under solvent-free conditions.