5820-22-4

Usage

Uses

Used in Chemical Industry:
Methallyl phenyl ether is used as a specialty chemical intermediate for the production of various polymers, resins, and other organic compounds, contributing to the development of a wide range of chemical products.
Used as a Solvent:
In the chemical industry, Methallyl phenyl ether serves as a solvent for various applications, facilitating chemical reactions and processes that require a solvent medium.
Used in Epoxy Resins:
Methallyl phenyl ether has potential applications as a reactive diluent in epoxy resins, enhancing the properties of the resin and improving its performance in various applications.
Used in Adhesive Formulations:
It is also utilized as a component in adhesive formulations, where it contributes to the adhesive's bonding properties and overall performance.
Methallyl phenyl ether's applications reflect its importance in the chemical industry, where it plays a multifaceted role in the creation and enhancement of various products.

InChI:InChI=1/C10H12O/c1-9(2)8-11-10-6-4-3-5-7-10/h3-7H,1,8H2,2H3

Upstream product

• 563-47-3 3-Chloro-2-methylpropene 
• 108-95-2 phenol 
• 20443-63-4 3-benzenesulfonyloxy-2-methyl-propene 
• 100-67-4 potassium phenolate 
• 10178-53-7 1-bromo-2-((2-methylallyl)oxy)benzene 
• 138621-73-5 carbonic acid 2-methylallyl ester phenyl ester 
• 820-71-3 methallyl acetate 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 5820-20-2 ((2-methylprop-1-en-1-yl)oxy)benzene 
• 156642-47-6 1-iodo-2-((2-methylallyl)oxy)benzene 
• 591-50-4 iodobenzene 
• 1313761-30-6 (2-((2-methylallyl)oxy)phenyl)boronic acid 
• 1458-98-6 2-methyl-3-bromo-1-propene 

Downstream Products

• 20944-88-1 2-(methylallyl)phenol 
• 6337-33-3 2,2-dimethyl-2,3-dihydro-1-benzofuran 
• 6395-29-5 2-(2-methyl-1-propenyl)phenol 
• 15895-57-5 2,3-Epoxy-2-methyl-1-phenoxypropane 
• 5820-20-2 ((2-methylprop-1-en-1-yl)oxy)benzene 
• 15895-54-2 2-methyl-3-phenoxy-propane-1,2-diol 
• 75668-40-5 (3-Bromo-2-methoxy-2-methyl-propoxy)-benzene 
• 75329-10-1 (2,2-Dichloro-1-methyl-cyclopropylmethoxy)-benzene 
• 86497-73-6 2,5-Dimethyl-2,5-bis-phenoxymethyl-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester 
• 107970-09-2 (2,3-Dibromo-2-methyl-propoxy)-benzene 
• 92403-94-6 3-phenoxy-2-methyl-1-propanol 
• 108-95-2 phenol 
• 1575-67-3 2-(2-methyl-allyl)-malonic acid diethyl ester 

Relevant academic research and scientific papers

On the toxicity of phenols to fast growing cells. A QSAR model for a radical-based toxicity

The cytotoxicities of a series of simple phenols as well as estrogenic phenols such as octyl and nonyl phenols, Bisphenol A, diethylstilbestrol, estradiol, estriol, equilin and equilenin were studied in a fast growing murine leukemia cell line. The use of calculated homolytic bond dissociation energies (BDE) as the electronic parameter led to the development of a Quantitative Structure-Activity Relationship model with superior results; one which established the importance of relatively low BDE values in enhancing toxicity to rapidly multiplying cells. The correlation equation that emerged is as follows: log 1/C= -0.19BDE + 0.21 log P + 3.11. It suggests that toxicity is closely related to mostly homolytic cleavage of the phenolic O-H bond and overall hydrophobicity of the phenol.

Investigating the microwave-accelerated Claisen rearrangement of allyl aryl ethers: Scope of the catalysts, solvents, temperatures, and substrates

The microwave-accelerated Claisen rearrangement of allyl aryl ethers was investigated, in order to gain insight into the scope of the catalysts, solvents, temperatures, and substrates. Among the catalysts examined, phosphomolybdic acid (PMA) was found to greatly accelerate the reaction in NMP, at temperatures ranging from 220 to 300 °C. This method was found to be useful for preparing several intermediates previously reported in the literature using precious metal catalysts such as Au(I), Ag(I), and Pt(II). Additionally, substrates bearing bromo and nitro groups on the aryl portion required careful tailoring of the reaction conditions to avoid complex product profiles.

A Construction of α-Alkenyl Lactones via Reduction Radical Cascade Reaction of Allyl Alcohols and Acetylenic Acids

An iron-catalyzed cascade reaction of radical reduction of allyl alcohols and acetylenic acids to construct polysubstituted α-alkenyl lactones has been developed. In this paper, various allyl alcohols can form allyl ester intermediates and are further transformed into alkyl radicals, which form products through intramolecular reflex-Michael addition. In addition, this method can be used to prepare spirocycloalkenyl lactones. Interestingly, this protocol can be used to synthesize the skeleton structure of natural products. Moreover, the product can be further transformed into a β-methylene tetrahydrofuran and tetrahydrofuran diene.

Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones

A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).

Method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis

The invention provides a method for compounding benzofuran derivatives by adding C-O bonds into olefin molecules through non-metallic Lewis acid catalysis. The method includes step 1, subjecting raw materials, namely phenol derivatives, to three-step reactions to obtain olefin serving as a reaction substrate; step 2, adding non-metallic Lewis acid and methylbenzene into the reaction substrate obtained in the step 1, and obtaining the benzofuran derivatives after reaction. The method has the advantages that the non-metallic Lewis acid is taken as a catalyst during reaction, so that pollution ofresidual metal catalysts to products is avoided, and troubles in post-treatment are omitted.

Radical Hydrodehalogenation of Aryl Bromides and Chlorides with Sodium Hydride and 1,4-Dioxane

A practical method for radical chain reduction of various aryl bromides and chlorides is introduced. The thermal process uses NaH and 1,4-dioxane as reagents and 1,10-phenanthroline as an initiator. Hydrodehalogenation can be combined with typical cyclization reactions, proving the nature of the radical mechanism. These chain reactions proceed by electron catalysis. DFT calculations and mechanistic studies support the suggested mechanism.

Palladium-Catalyzed Tandem Oxidative Arylation/Olefination of Aromatic Tethered Alkenes/Alkynes

We describe herein a palladium-catalyzed tandem oxidative arylation/olefination reaction of aromatic tethered alkenes/alkynes for the synthesis of dihydrobenzofurans and 2 H-chromene derivatives. This reaction features a 1,2-difunctionalization of C?C π-bond with two C?H bonds using O2as terminal oxidant at room temperature. The products obtained are valuable synthons and important scaffolds in biological agents and natural products.

Development and Mechanistic Study of Quinoline-Directed Acyl C-O Bond Activation and Alkene Oxyacylation Reactions

The intramolecular addition of both an alkoxy and acyl substituent across an alkene, oxyacylation of alkenes, using rhodium catalyzed C-O bond activation of an 8-quinolinyl ester is described. Our unsuccessful attempts at intramolecular carboacylation of ketones via C-C bond activation ultimately informed our choice to pursue and develop the intramolecular oxyacylation of alkenes via quinoline-directed C-O bond activation. We provide a full account of our catalyst discovery, substrate scope, and mechanistic experiments for quinoline-directed alkene oxyacylation.

Diarylation of alkenes by a Cu-catalyzed migratory insertion/cross-coupling cascade

A strategy for the catalytic diarylation of alkenes is presented. The method involves the migratory insertion of alkenes into an Ar-Cu complex to generate a new C(sp3)-Cu complex, which subsequently undergoes reaction with an aryl iodide to constitute a vicinal diarylation of an alkene. The method provides access to benzofuran- and indoline-containing products. Furthermore, highly diastereoselective examples are presented, allowing access to complex, stereochemically rich structures from simple alkene starting materials.

Insertion of an Alkene into an ester: Intramolecular oxyacylation reaction of alkenes through acyl C-O bond activation

Atom economy and esters: compatible now! The first catalytic insertion of a C-C bond into an acyl C-O bond was achieved using rhodium catalysts (see scheme). The products are β-alkoxy ketones with a fully substituted carbon center. Quinoline chelating groups were employed to stabilize the Rh-alkoxide intermediate.