5354-08-5

Usage

Structure

Contains a benzene ring fused with a dioxole ring and a methylthio group attached at the 5-position.

Classification

Organic compound

Applications

a. Building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds
b. Used as a fragrance ingredient in perfumes and personal care products

Properties

a. Aromatic and sweet odor
b. Reactivity due to its unique structure

Biological activities

a. Antioxidant properties
b. Anti-inflammatory properties

Notable uses

a. In the fragrance industry for its pleasant smell
b. As a starting material for the development of new pharmaceuticals and agrochemicals

Upstream product

• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 
• 624-92-0 Dimethyldisulphide 
• 5271-38-5 2-methylmercapto-ethanol 
• 5876-51-7 5-iodo-1,3-benzodioxole 
• 6698-13-1 4-bromo-benzo[1,3]dioxole 
• 67-68-5 dimethyl sulfoxide 
• 74-88-4 methyl iodide 
• 274-09-9 Methylenedioxybenzene 
• 86538-93-4 5-thiocyano-1,3-benzodioxole 

Downstream Products

• 68560-11-2 2-methylthio-4,5-methylenedioxynitrobenzene 
• 5279-41-4 5-bromo-6-(methylthio)-1,3-benzodioxole 
• 100-68-5 methyl-phenyl-thioether 
• 4421-09-4 piperonylonitrile 

Relevant academic research and scientific papers

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Palladium-catalyzed intermolecular transthioetherification of aryl halides with thioethers and thioesters

Functional group transfer reactions are an important synthetic tool in modern organic synthesis. Herein, we developed a new palladium-catalyzed intermolecular transthioetherification reaction of aryl halides with thioethers and thioesters. The synthetic utility and practicality of this catalytic protocol are demonstrated in a wide range of successful transformations (>70 examples). This catalytic protocol is applicable in carbonylative coupling processes as well, and the first example of carbonylative methylthioesterification of aryl halides has been achieved. Notably, this work also provides an approach to using natural products, such as methionine and selenomethionine, as the functional group sources.

Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.

Investigation of the scope and mechanism of copper catalyzed regioselective methylthiolation of aryl halides Dedicated to Professor Dr. Irina Beletskaya

Methylthiolation of structurally diverse aryl halides was accomplished under fluoride free conditions using catalytic amounts of CuI, and DMSO as the methylthiolation source. Optimization studies unveiled several varieties of promoters among which Zn(OAc)2 was found ideal. The analogous reaction with DMSO-d6 afforded corresponding deuterated aryl methyl thioether with 99% purity. Mechanistic studies revealed CuSMe as the active methylthiolation agent.

COMPOUNDS AS HSP90 INHIBITORS

The invention provides novel compounds of formula (I) wherein: one of the a, b, c or d members is a nitrogen atom and the remaining members are carbon atoms; and R3 is a radical selected from the group consisting of: —S—R14 and —CH2—R15. The compounds of formula (I) are useful for treating diseases mediated by a heat shock protein 90 (Hsp 90)

FUSED AMINO PYRIDINE AS HSP90 INHIBITORS

The present invention relates to HSP90 inhibitors containing fused amino pyridine core that are useful as inhibitors of HSP90 and their use in the treatment of HSP90 related diseases and disorders such as cancer, an autoimmune disease, or a neurodegenerative disease.

SAFROLE REPLACEMENTS

A compound or mixture of compounds of formula (I): wherein R = straight chain or branched C1-3 alkyl or alkenyl is provided. Methods for their preparation, their use as perfume materials for application to a variety of substrates and their use in flavouring and in articles of manufacture is also provided.

Synthesis of 6,7-Methylenedioxy-3,4-dihydro-1-methylbenzothienopyridine

Synthesis of the title compound, a potential inhibitor of mouse brain monoamine oxidase, is described.The preparation proceeds in eight steps from 1,3-benzodioxole in 1.9percent overall yield.The novel hydrogenolysis of an aryl thiocyanate to the aryl methyl sulfide is reported.