2186-92-7

Basic information

• Product Name: P-ANISALDEHYDE DIMETHYL ACETAL
• Synonyms: 1-(dimethoxymethyl)-4-methoxy-benzen;1-(dimethoxymethyl)-4-methoxy-Benzene;Anisicaldehydedimethylacetal;P-ANISALDEHYDE DIMETHYL ACETAL;4-METHOXYBENZALDEHYDE DIMETHYL ACETAL;ANISALDEHYDE DIMETHYL ACETAL;ANISIC ALDEHYDE DMA;p-(dimethoxymethyl)anisole
• CAS NO: 2186-92-7
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.22
• EINECS: 218-577-4
• Product Categories: Biochemistry;Reagents for Oligosaccharide Synthesis
• Mol File: 2186-92-7.mol
• Article Data: 87

Chemical Properties

• Boiling Point: 85-87 °C0.1 mm Hg(lit.)
• Flash Point: 97°C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.07 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0171mmHg at 25°C
• Refractive Index: n20/D 1.505
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble
• Water Solubility: Miscible with alcohol and many organic solvents. Slightly miscible with water.
• BRN: 2048930
• CAS DataBase Reference: P-ANISALDEHYDE DIMETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: P-ANISALDEHYDE DIMETHYL ACETAL(2186-92-7)
• EPA Substance Registry System: P-ANISALDEHYDE DIMETHYL ACETAL(2186-92-7)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 2186-92-7(Hazardous Substances Data)

Usage

Description

P-ANISALDEHYDE DIMETHYL ACETAL, also known as 4-Methoxybenzaldehyde dimethyl acetal, is a clear colorless to light yellow liquid with a variety of applications across different industries. It is a versatile chemical compound that serves as a precursor, protecting group reagent, and flavor essence.

Uses

Used in Pharmaceutical Industry:
P-ANISALDEHYDE DIMETHYL ACETAL is used as a precursor for the synthesis of various pharmaceutical compounds, such as 1-methoxy-1-(4-methoxyphenyl)hept-2-yne, 2,5-dioxopyrrolidin-1-yl-3-((4R)-2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane-4-carboxamido)propanoate, and 1-(p-anisyl)-2-(2-methoxyethyl)-3-phenylindene. These compounds have potential applications in the development of new drugs and therapies.
Used in Chemical Synthesis:
P-ANISALDEHYDE DIMETHYL ACETAL is used as a protecting group reagent for diols, particularly in the synthesis of carbohydrates. This application is crucial in the development of complex organic molecules and the protection of functional groups during chemical reactions.
Used in Flavor and Fragrance Industry:
P-ANISALDEHYDE DIMETHYL ACETAL is used as a flavor essence in the production of sunflower, cyclamen, and jasmine fragrances. Its unique properties contribute to the creation of distinct and appealing scents in the perfume and aromatherapy industries.
Used in Chemical Reactions:
P-ANISALDEHYDE DIMETHYL ACETAL is involved in allylation reactions with allyltrimethylsilane, catalyzed by Iron(III) chloride. This reaction is essential in the synthesis of various organic compounds and contributes to the development of new materials and products in the chemical industry.

InChI:InChI=1/C12H18O3/c1-4-14-12(15-5-2)10-6-8-11(13-3)9-7-10/h6-9,12H,4-5H2,1-3H3

Upstream product

• 2299-73-2 N,N-bis(4-methoxybenzylidene)hydrazine 
• 67-56-1 methanol 
• 637-69-4 4-Methoxystyrene 
• 104-46-1 anethole 
• 104-93-8 p-methylanizole 
• 824-94-2 p-methoxybenzyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 124-41-4 sodium methylate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 
• 7647-01-0 hydrogenchloride 
• 119208-80-9 1,3,5-tris(4-methoxyphenyl)-2,4-diazapenta-1,4-diene 
• 616-42-2 dimethylsulfite 

Downstream Products

• 127877-16-1 2',4'-O-p-Methoxybenzylidene 5'-O-trityl-riboflavin 
• 120039-43-2 benzyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside 
• 132925-02-1 methyl 3-methoxy-3-(4-methoxyphenyl)-2,2-dimethylpropanoate 
• 117605-33-1 methyl 4,6-O-(4’-methoxybenzylidene)-α-D-glucopyranoside 
• 18929-63-0 methyl 4,6-O-para-methoxybenzylidene-α-D-glucopyranoside 
• 161443-22-7 methyl 4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 128271-00-1 (2R,3R,4S,5R,6S)-5-Benzyloxy-4,6-dimethoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-ol 
• 132488-48-3 methyl 2-acetamido-2-deoxy-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 141438-52-0 methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 141438-52-0 [(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester 
• 156928-37-9 methyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside 
• 37138-47-9 5-[Methoxy-(4-methoxy-phenyl)-methoxymethyl]-bicyclo[2.2.1]hept-2-ene 
• 162680-20-8 methyl 4,6-O-[(R)-(4-methoxyphenyl)methylene]-α-D-glucopyranoside 
• 169789-17-7 2-(trimethylsilyl)ethyl O-<2-azido-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranosyl>-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 

Relevant articles and documents

Microflow electroorganic synthesis without supporting electrolyte

Anodic methoxylation of several organic compounds has been successfully achieved in the absence of intentionally added supporting electrolyte using an electrochemical microflow system. The Royal Society of Chemistry 2005.

Electro-Oxidative Selective Esterification of Methylarenes and Benzaldehydes

A mild and green electro-oxidative protocol to construct aromatic esters from methylarenes and alcohols is herein reported. Importantly, the reaction is free of metals, chemical oxidants, bases, acids, and operates at room temperature. Moreover, the design of the electrolyte was found critical for the oxidation state and structure of the coupling products, a rarely documented effect. This electro-oxidative coupling process also displays exceptional tolerance of many fragile easily oxidized functional groups such as hydroxy, aldehyde, olefin, alkyne, as well as neighboring benzylic positions. The enantiomeric enrichment of some chiral alcohols is moreover preserved during this electro-oxidative coupling reaction, making it overall a promising synthetic tool.

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.

Chemoenzymatic Synthesis of 5-Hydroxymethylfurfural (HMF)-Derived Plasticizers by Coupling HMF Reduction with Enzymatic Esterification

Biobased plasticizers, as substitutes for phthalates, have been synthesized from 5-hydroxymethylfurfural (HMF) and carboxylic acids (or esters) through a chemoenzymatic cascade process that involves as its first step the reduction of 5-hydroxymethylfurfural into 2,5-bis(hydroxymethyl)furan (BHMF), followed by the esterification of BHMF with carboxylic acids (or esters) by using a supported lipase (Novozym 435). The reduction of HMF into BHMF is performed by using monodisperse metallic Co nanoparticles with a thin carbon shell (Co@C) with high activity and selectivity. After optimization of reaction conditions (temperature, hydrogen pressure, and solvent), it is possible to achieve 97 % conversion of HMF with 99 % selectivity to BHMF after 2 h reaction time. The reduction of HMF and esterification of BHMF using carboxylic acids or vinyl esters as acyl donors by lipase are optimized separately in batch and in fixed-bed continuous reactors. The coupling of two flow reactors (for reduction and subsequent esterification) working under optimized reaction conditions affords the diesters of BHMF in roughly 90 % yield with no loss of activity during 60 h of operation.