7145-99-5

Usage

Uses

Used in Chemical Synthesis:
5-METHYL-1,3-BENZODIOXOLE is used as a cation scavenger for the selective cleavage of 4-(3,4-dimethoxyphenyl)benzyl (DMPBn) ethers, yielding the corresponding deprotected products. This application takes advantage of its ability to react with cations in the presence of trifluoroacetic acid (TFA) in anhydrous CH2Cl2.
Used in Pharmaceutical Industry:
5-METHYL-1,3-BENZODIOXOLE serves as a starting material for the preparation of various pharmaceutical compounds. One such example is the synthesis of 1,3-Benzodioxole-5-carboxaldehyde through photooxidation using CBr4. 5-METHYL-1,3-BENZODIOXOLE can be further utilized in the development of drugs targeting specific biological pathways.
Used in Organic Synthesis:
In the field of organic synthesis, 5-METHYL-1,3-BENZODIOXOLE is used as a starting material to prepare other complex organic molecules. For instance, it can be treated with dichloromethylmethyl ether and TiCl4 to produce 6-Methyl-1,3-benzodioxole-5-carboxaldehyde, which can be further modified and used in the synthesis of various organic compounds.
Used in Flavor and Fragrance Industry:
Due to its unique chemical structure, 5-METHYL-1,3-BENZODIOXOLE can be used as a building block for the creation of novel fragrances and flavors. Its ability to form a variety of derivatives makes it a valuable component in the development of new scents and tastes for the consumer market.
Used in Material Science:
The unique properties of 5-METHYL-1,3-BENZODIOXOLE also make it a potential candidate for the development of new materials with specific characteristics. It can be used as a component in the synthesis of advanced polymers, coatings, and other materials with tailored properties for various applications, such as electronics, aerospace, and automotive industries.

InChI:InChI=1/C8H8O2/c1-6-2-3-7-8(4-6)10-5-9-7/h2-4H,5H2,1H3

Upstream product

• 120-57-0 piperonal 
• 495-76-1 piperonol 
• 141-52-6 sodium ethanolate 
• 16742-62-4 3,4-methylenedioxybenzaldehyde semicarbazone 
• 75-09-2 dichloromethane 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 40527-42-2 piperonal diethylacetal 
• 87306-69-2 2-[(Benzo[1,3]dioxol-5-ylmethyl)-amino]-2-methyl-propan-1-ol 
• 64-17-5 ethanol 
• 4439-02-5 3,4-methylenedioxyphenylacetonitrile 
• 3526-42-9 N-(benzo[d][1,3]dioxol-5-ylmethyl)benzenamine 
• 67-56-1 methanol 
• 7732-18-5 water 
• 65842-89-9 5-(6-bromo-benzo[1,3]dioxol-5-ylmethyl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 

Downstream Products

• 114824-91-8 3,4,5-trimethoxy-2'-methyl-4',5'-methylenedioxy-benzophenone 
• 5025-53-6 5-bromo-6-methylbenzo[d][1,3]dioxole 
• 2563-07-7 2-ethoxy-4-methylphenol 
• 117661-72-0 (3,4-methylenedioxy)-6-methylbenzyl chloride 
• 452-86-8 4-methyl-1,2-dihydroxybenzene 
• 106-44-5 p-cresol 
• 108-39-4 3-methyl-phenol 
• 109733-91-7 bis-(6-methyl-benzo[1,3]dioxol-5-yl)-methane 
• 52806-34-5 6-methylbenzo-1,3-dioxol-5-yl phenyl ketone 
• 295793-35-0 (6-methyl-1,3-benzodioxol-5-yl)-(4-nitrophenyl)-methanone 
• 58343-54-7 (6-methyl-1,3-benzodioxol-5-yl)carboxaldehyde 
• 891193-07-0 (E)-1-(2-methyl-4,5-methylenedioxyphenyl)-2-(2-hydroxyphenyl)ethene 
• 891193-10-5 1-(2-methyl-4,5-methylenedioxyphenyl)-2-(2,4-di-O-tert-butyldimethylsiloxyphenyl)ethene 
• 891193-12-7 1-(2-methyl-4,5-methylenedioxyphenyl)-2-(2,4-di-O-tert-butyldimethylsiloxyphenyl)ethene oxide 

Relevant academic research and scientific papers

Metal-Organic Framework-Confined Single-Site Base-Metal Catalyst for Chemoselective Hydrodeoxygenation of Carbonyls and Alcohols

Chemoselective deoxygenation of carbonyls and alcohols using hydrogen by heterogeneous base-metal catalysts is crucial for the sustainable production of fine chemicals and biofuels. We report an aluminum metal-organic framework (DUT-5) node support cobalt(II) hydride, which is a highly chemoselective and recyclable heterogeneous catalyst for deoxygenation of a range of aromatic and aliphatic ketones, aldehydes, and primary and secondary alcohols, including biomass-derived substrates under 1 bar H2. The single-site cobalt catalyst (DUT-5-CoH) was easily prepared by postsynthetic metalation of the secondary building units (SBUs) of DUT-5 with CoCl2 followed by the reaction of NaEt3BH. X-ray photoelectron spectroscopy and X-ray absorption near-edge spectroscopy (XANES) indicated the presence of CoII and AlIII centers in DUT-5-CoH and DUT-5-Co after catalysis. The coordination environment of the cobalt center of DUT-5-Co before and after catalysis was established by extended X-ray fine structure spectroscopy (EXAFS) and density functional theory. The kinetic and computational data suggest reversible carbonyl coordination to cobalt preceding the turnover-limiting step, which involves 1,2-insertion of the coordinated carbonyl into the cobalt-hydride bond. The unique coordination environment of the cobalt ion ligated by oxo-nodes within the porous framework and the rate independency on the pressure of H2 allow the deoxygenation reactions chemoselectively under ambient hydrogen pressure.

Photocatalytic carbanion generation-benzylation of aliphatic aldehydes to secondary alcohols

We present a redox-neutral method for the photocatalytic generation of carbanions. Benzylic carboxylates are photooxidized by single electron transfer; immediate CO2 extrusion and reduction of the in situ formed radical yields a carbanion capable of reacting with aliphatic aldehydes as electrophiles giving the Grignard analogous reaction product.

Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction

Ni(I)-mediated single-electron oxidative activation of alkyl halides has been extensively proposed as a key step in Ni-catalyzed cross-coupling reactions to generate radical intermediates. There are four mechanisms through which this step could take place: oxidative addition, outer-sphere electron transfer, inner-sphere electron transfer, and concerted halogen-atom abstraction. Despite considerable computational studies, there is no experimental study to evaluate all four pathways for Ni(I)-mediated alkyl radical formation. Herein, we report the isolation of a series of (Xantphos)Ni(I)-Ar complexes that selectively activate alkyl halides over aryl halides to eject radicals and form Ni(II) complexes. This observation allows the application of kinetic studies on the steric, electronic, and solvent effects, in combination with DFT calculations, to systematically assess the four possible pathways. Our data reveal that (Xantphos)Ni(I)-mediated alkyl halide activation proceeds via a concerted halogen-atom abstraction mechanism. This result corroborates previous DFT studies on (terpy)Ni(I)- and (py)Ni(I)-mediated alkyl radical formation, and contrasts with the outer-sphere electron transfer pathway observed for (PPh3)4Ni(0)-mediated aryl halide activation. This study of a model system provides insight into the overall mechanism of Ni-catalyzed cross-coupling reactions and offers a basis for differentiating electrophiles in cross-electrophile coupling reactions.

AN IMPROVED METHOD FOR THE PREPARATION OF ALKYLENEDIOXYBENZENE COMPOUNDS

This invention relates to an improved method for preparing alkylenedioxybenzene compounds of Formula I, from the corresponding ortho-dihydroxy aromatic compound of Formula II wherein n is 0, 1, 2 or 3; and R1 and R2 independently represent H, linear or branched C1 – C10 alkyl or alkenyl group, cycloalkyl group, halogen selected from C1, Br, I, nitro (-NO2), alkoxy (-OR) or SR thioether (-SR), wherein R is linear or branched alkyl group comprising C1-C6 carbon atoms.

En Route to a Practical Primary Alcohol Deoxygenation

A long-standing scientific challenge in the field of alcohol deoxygenation has been direct catalytic sp3 C-O defunctionalization with high selectivity and efficiency, in the presence of other functionalities, such as free hydroxyl groups and amines widely present in biological molecules. Previously, the selectivity issue had been only addressed by classic multistep deoxygenation strategies with stoichiometric reagents. Herein, we propose a catalytic late-transition-metal-catalyzed redox design, on the basis of dehydrogenation/Wolff-Kishner (WK) reduction, to simultaneously tackle the challenges regarding step economy and selectivity. The early development of our hypothesis focuses on an iridium-catalyzed process efficient mainly with activated alcohols, which dictates harsh reaction conditions and thus limits its synthetic utility. Later, a significant advancement has been made on aliphatic primary alcohol deoxygenation by employing a ruthenium complex, with good functional group tolerance and exclusive selectivity under practical reaction conditions. Its synthetic utility is further illustrated by excellent efficiency as well as complete chemo- and regio-selectivity in both simple and complex molecular settings. Mechanistic discussion is also included with experimental supports. Overall, our current method successfully addresses the aforementioned challenges in the pertinent field, providing a practical redox-based approach to the direct sp3 C-O defunctionalization of aliphatic primary alcohols.

Endothelin antagonists benzene oxygen benzene acetic acids and its preparation method and application

The invention provides a phenoxy phenylacetic acid endothelin antagonist shown in a formula (I) or a pharmaceutically acceptable salt thereof, and also provides a preparation method of the benzene oxygen phenylacetic acid endothelin antagonist or the pharmaceutically acceptable salt thereof, and an application thereof in preparation of a medicament for treating cardiovascular and cerebrovascular diseases, tumors, diabetes mellitus, nephrosis, asthma or hyperthyroidism.

The genetic incorporation of thirteen novel non-canonical amino acids

Thirteen novel non-canonical amino acids were synthesized and tested for suppression of an amber codon using a mutant pyrrolysyl-tRNA synthetase-tRNAPylCUA pair. Suppression was observed with varied efficiencies. One non-canonical amino acid in particular contains an azide that can be applied for site-selective protein labeling. The Royal Society of Chemistry 2014.

Iridium-catalyzed direct dehydroxylation of alcohols

Iridium-catalyzed direct dehydroxylation of alcohols with hydrazine was developed through a combination of the oxidation of alcohols and the Wolff-Kishner reduction. This protocol is simple to perform and highly efficient for a series of primary, benzylic and allylic alcohols. Iridium-catalyzed direct dehydroxylation of alcohols with hydrazine is developed through a combination of the oxidation of alcohols and Wolff-Kishner reduction. This protocol is simple to perform and highly efficient for a series of primary alcohols, especially benzylic and allylic ones. Copyright

Rhodium-catalyzed reductive decyanation of nitriles using hydrosilane as a reducing agent: Scope, mechanism and synthetic application

A rhodium-catalyzed reductive cleavage reaction of carbon-cyano bonds is developed using hydrosilane as a mild reducing agent. A wide range of nitriles, including aryl, benzyl, and p-hydrogen containing alkyl cyanides are applicable to this decyanation reaction. The method is also applicable to organic synthesis, in which benzyl cyanide is used as a benzyl anion equivalent and a cyano group functions as a removable ortho-directing group.

Nickel boride-mediated cleavage of 1,3-dithiolanes: A convenient approach to reductive desulfurization

1,3-Dithiolanes are rapidly cleaved by nickel boride, generating corresponding hydrocarbons in excellent yields. The hydrogenolysis is rapid at room temperature and does not require protection from the atmosphere. Mild reaction conditions, simple workup, and good yields of pure products are some of the major advantages of the procedure.