3395-83-3

Basic information

• Product Name: p-(dimethoxymethyl)toluene
• Synonyms: p-(dimethoxymethyl)toluene;p-(Dimethoxymethyl)toluol;1-(Dimethoxymethyl)-4-methylbenzene;1-Dimethoxymethyl-4-methylbenzene;p-Methylbenzaldehyde dimethyl acetal;p-Tolualdehyde dimethyl acetal;Benzene, 1-(dimethoxymethyl)-4-methyl-;Einecs 222-244-9
• CAS NO: 3395-83-3
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.21696
• EINECS: 222-244-9
• Mol File: 3395-83-3.mol

Chemical Properties

• Boiling Point: 196.2°Cat760mmHg
• Flash Point: 58.4°C
• Appearance: /
• Density: 0.986g/cm³
• Vapor Pressure: 0.567mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: p-(dimethoxymethyl)toluene(CAS DataBase Reference)
• NIST Chemistry Reference: p-(dimethoxymethyl)toluene(3395-83-3)
• EPA Substance Registry System: p-(dimethoxymethyl)toluene(3395-83-3)

Safety Data

• Hazardous Substances Data: 3395-83-3(Hazardous Substances Data)

Usage

Uses

Used in Fragrance and Flavoring Industry:
p-(dimethoxymethyl)toluene is used as a key ingredient in the production of fragrances and flavorings due to its aromatic properties, enhancing the sensory experience of various consumer products.
Used in Solvent Applications:
p-(dimethoxymethyl)toluene serves as a solvent in various chemical processes, facilitating reactions and improving the efficiency of industrial operations.
Used as an Intermediate in Organic Synthesis:
p-(dimethoxymethyl)toluene is utilized as an intermediate in the synthesis of other organic compounds, contributing to the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
With its potential applications in the pharmaceutical sector, p-(dimethoxymethyl)toluene may be involved in the development of new drugs or medicinal compounds, benefiting healthcare and therapeutics.
Used in Cosmetic Industry:
p-(dimethoxymethyl)toluene also finds use in the cosmetic industry, where it may contribute to the formulation of skincare products, hair care products, or other cosmetic formulations, leveraging its aromatic and chemical properties.
However, it is crucial to handle p-(dimethoxymethyl)toluene with care due to its potential health and environmental hazards if not properly managed, ensuring safety and sustainability in its applications across industries.

InChI:InChI=1/C10H14O2/c1-8-4-6-9(7-5-8)10(11-2)12-3/h4-7,10H,1-3H3

Upstream product

• 616-42-2 dimethylsulfite 
• 104-87-0 4-methyl-benzaldehyde 
• 67-56-1 methanol 
• 106-42-3 para-xylene 
• 2698-14-8 1-methyl-4-(prop-1-enyl)benzene 
• 149-73-5 trimethyl orthoformate 
• 7450-04-6 1-((trimethylsilyl)methyl)-4-methylbenzene 
• 3395-81-1 4-chlorobenzaldehyde dimethyl acetal 
• 74-88-4 methyl iodide 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 124-41-4 sodium methylate 
• 35779-32-9 1,3,5-tris(4-methylphenyl)-2,4-diazapenta-1,4-diene 

Downstream Products

• 56377-70-9 (α-chloro-4-methyl-benzyl)-methyl ether 
• 63523-40-0 N-(methoxy-p-tolyl-methyl)-4-methyl-thiobenzamide 
• 22911-22-4 1-methyl-4-(trimethoxymethyl)benzene 
• 93943-06-7 4-(methoxymethyl)benzaldehyde 
• 623-27-8 terephthalaldehyde, 
• 1571-08-0 methyl 4-formylbenzoate 
• 124828-71-3 1-methoxy-1-(p-tolyl)hept-2-yne 
• 114533-85-6 1-Methyl-4-(1,3,3-trimethoxy-propyl)-benzene 
• 87505-91-7 2-<(4-methylphenyl)methoxymethyl>-2-(trimethylsiloxy)cyclobutanone 
• 106732-38-1 1-((R)-1-Methoxy-2-methyl-but-3-enyl)-4-methyl-benzene 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 104-87-0 4-methyl-benzaldehyde 
• 911798-06-6 meso-1,2-bis-(4-dimethylphenyl)-1,2-dimethoxyethane 
• 89986-85-6 1,2-dimethoxy-1,2-di(4-methylphenyl)ethane 

Relevant articles and documents

Enantioselective, Catalytic Multicomponent Synthesis of Homoallylic Amines Enabled by Hydrogen-Bonding and Dispersive Interactions

We report a one-step catalytic, enantioselective method for the preparation of homoallylic N-Boc amines directly from acetals. Reactive iminium ion intermediates are generated in situ through the combination of an acetal, a chiral thiourea catalyst, trialkylsilyl triflate, and N-Boc carbamate and are subsequently trapped by a variety of allylsilane nucleophiles. No homoallylic ether byproducts are detected, consistent with allylation of the iminium intermediate being highly favored over allylation of the intermediate oxocarbenium ion. Acetals derived from aromatic aldehydes possessing a variety of functional groups and substitution patterns yield homoallylic amines with excellent levels of enantiomeric enrichment. Experimental and computational data are consistent with an anchoring hydrogen-bond interaction between the protioiminium ion and the amide of the catalyst in the enantiodetermining transition state, and with stereodifferentiation achieved through specific noncovalent interactions (NCIs) with the catalyst pyrenyl moiety. Evidence is provided that the key NCI in the major pathway is a π-stacking interaction, contrasting with the cation-πinteractions invoked in previously studied reactions promoted by the same family of aryl-pyrrolidino-H-bond-donor catalysts.

MOF-808 as a recyclable catalyst for the photothermal acetalization of aromatic aldehydes

Metal-organic frameworks (MOFs) show promise for catalysis applications due to their porosity, high internal surface area, and structural adaptability. Typical acetylation reactions of aldehydes require elevated temperatures and excess alcohol to drive the reactions to completion. In this current work, MOF-808 is used as a heterogeneous catalyst for acetylation of aldehydes in methanol using a mild photothermal process. Optimized conditions gave 72% yield of 2-(dimethoxymethyl)naphthalene in the presence of 10 mol% MOF-808 at 45 °C using only a fluorescent lamp. MOF-808 can be recycled up to 5 times with no loss in catalytic activity. A proof-of-principle substrate scope demonstrates the potential utility for aromatic and aliphatic substrates.

Thiol-initiated photocatalytic oxidative cleavage of the C=C bond in olefins and its extension to direct production of acetals from olefins

The oxidative cleavage of olefins to produce aldehydes/ketones is an important reaction in organic syntheses. In this manuscript, a mild and operationally simple protocol for the aerobic oxidation of olefins to produce carbonyl compounds was realized over ZnIn2S4under visible light, using air as the oxidant and a thiol as the initiator. It was proposed that the photogenerated holes over ZnIn2S4attack the thiol to produce thiyl radicals, which initiate the oxidative cleavage of the C=C bond in olefins to produce aldehydes/ketones. By further coupling with the condensation between the as-obtained aldehydes/ketones and alcohols, this strategy can also be applied to the production of different acetals directly from the olefins. This study demonstrates a new pathway to realize the oxidative cleavage of olefins to produce aldehydes/ketones, and also provides a new protocol for the production of acetals directly from the olefins.

Practical acetalization and transacetalization of carbonyl compounds catalyzed by recyclable PVP-I

A novel PVP-I catalyzed acetalizations/transacetalizations of carbonyl compounds has been developed processing with a mild and easy handling fashion. Different types of Acyclic and cyclic acetals were prepared from carbonyl compounds or their acetals successfully. Further applications of newly developed catalytic combination were testified. This protocol featured with simplicity of operation, mild reaction condition, short reaction time, recyclable of catalyst and broad substrates scope with excellent yields.

Amino acid derivative, feed composition and application thereof

The invention provides an amino acid derivative, a feed composition and application thereof, and belongs to the technical field of animal feed additives. The amino acid derivative is a compound with astructure shown as a formula (I), and a stereoisomer, a tautomer, a solvate, a metabolite, a feed acceptable salt or a prodrug thereof. In formula (I) shown in the specification, Z is a C1-C3 alkylene group. X is an indole ring group with a structure shown as a formula (II). The formula (II) is shown in the specification, wherein Y is phenyl with the structure shown in the formula (III) shown inthe specification. The amino acid derivative is used as an animal feed additive, and can promote the growth of animals and improve the feed conversion.

Formation of Acetals and Ketals from Carbonyl Compounds: A New and Highly Efficient Method Inspired by Cationic Palladium

The development of a new, highly efficient, and simple method for masking carbonyl groups as acetals and ketals is described. This methodology relies on the nature of the palladium catalyst to direct the acetalization/ketalization reaction. This new protocol is mild and proceed with a very low catalyst loading at ambient temperatures. The method has been extended to a wide variety of different carbonyl compounds with various steric encumbrances to form the corresponding acetals and ketals in excellent yields.

Multicomponent Aromatic and Benzylic Mannich Reactions through C?H Bond Activation

Multicomponent Mannich reactions through C?H bond activation are described. These transformations allowed for the straightforward generation of densely substituted benzylic and homo-benzylic amines in good yields. The reaction involves a reaction between two transient species: an organometallic species, generated by transition-metal-catalyzed sp2 or sp3 C?H bond activation and an in situ generated imine. The use of an acetal as an aldehyde surrogate was found essential for the reaction to proceed. The process could be successfully applied to RhIII-catalyzed sp2 C?H bond functionalization and extended to CuII-catalyzed sp3 C?H bond functionalization.

Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction

A new enzymatic protocol based on lipase-catalyzed cascade toward (E)-α,β-unsaturated carboxylic esters is presented. The proposed methodology consists of elementary organic processes starting from acetals and cyanoacetic acid leading to the formation of desired products in a cascade sequence. The combination of enzyme promiscuous abilities gives a new opportunity to synthesize complex molecules in the one-pot procedure. Results of studies on the influence of an enzyme type, solvent, and temperature on the cascade reaction course are reported. The presented methodology provides meaningful qualities such as significantly simplified process, excellent E-selectivity of obtained products and recycling of a biocatalyst.

Unique chemoselective Mukaiyama aldol reaction of silyl enol diazoacetate with aldehydes and acetals catalyzed by MgI2 etherate

Functionalized diazo acetoacetates are prepared by an efficient Mukaiyama aldol reaction between 3-TBSO-2-diazo-3-butenoate with aldehydes and acetals under mild reaction conditions. A variety of substituted aldehydes and the corresponding acetals are both accessible in good to excellent yields through this methodology. MgI2 etherate (MgI2·(OEt2)n) is the preferred catalyst and, the addition proceeds without decomposition of the diazo moiety. In addition, this MgI2·(OEt2)n-catalyzed Mukaiyama aldol reaction shows unique chemoselectivity towards aldehydes and acetals.

Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions

A molecularly defined NiII-complex catalyzing the chemoselective acetalization of aldehydes with alcohols under neutral conditions is reported. The reaction is general, efficient and showed a wide substrate scope (including aliphatic aldehydes) as well as excellent functional group tolerance. Reusability of the present nickel catalyst is also demonstrated.