4316-35-2

Usage

Uses

Used in Pharmaceutical Industry:
(1,1-Dimethoxyethyl)benzene is used as an intermediate in the synthesis of various pharmaceutical compounds. Its ability to participate in the bismuth triflate catalyzed deprotection of acetals makes it a valuable component in the development of new drugs and medications.
Used in Chemical Synthesis:
In the chemical industry, (1,1-Dimethoxyethyl)benzene is used as a building block for the synthesis of various organic compounds. Its unique structure allows it to be a versatile starting material for the creation of a wide range of products, including specialty chemicals, dyes, and additives.
Used in Research and Development:
Due to its involvement in the bismuth triflate catalyzed deprotection of acetals, (1,1-Dimethoxyethyl)benzene is also used in research and development laboratories. Scientists and researchers utilize (1,1-DIMETHOXYETHYL)BENZENE to study and understand the mechanisms of various chemical reactions, which can lead to the discovery of new synthetic pathways and the development of novel compounds with potential applications in various industries.

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

Upstream product

• 67-56-1 methanol 
• 15755-09-6 formimidomethylester hydrochloride 
• 98-86-2 acetophenone 
• 149-73-5 trimethyl orthoformate 
• 6230-62-2 (1-ethoxyvinyl)benzene 
• 22293-10-3 (1-diazoethyl)benzene 
• 4747-13-1 α-methoxystyrene 
• 92694-71-8 cyclohexylammonium α-phenylvinyl ethyl phosphate 
• 3674-77-9 2-methyl-2-phenyl-1,3-dioxolane 
• 629-05-0 n-octyne 
• 1600-27-7 mercury(II) diacetate 
• 118-75-2 chloranil 
• 536-74-3 phenylacetylene 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 4747-13-1 α-methoxystyrene 
• 67808-80-4 1-phenyl-1,1-bis(phenylseleno)ethane 
• 66270-89-1 [1-(vinyloxy)vinyl]benzene 
• 87986-30-9 3,3-Dimethoxy-2-phenyl-butyric acid ethyl ester 
• 87986-34-3 ethyl 3,3-dimethoxy-2-methyl-3-phenylpropanoate 
• 87986-37-6 2,3-Dimethoxy-3-phenyl-butyric acid ethyl ester 
• 134692-19-6 1-(1-Methoxy-1-phenyl-ethyl)-1H-benzotriazole 
• 78905-88-1 2-methoxymethylbenzyl-2-cyclohexenone 
• 116594-36-6 2,3,2',3',4',6'-hexa-O-benzyl-4,6-O-(S)-(1-phenylethylidene)-α,α-trehalose 
• 129144-57-6 (2R,5S) 2-phenyl-2,5-dimethyl-1,3-dioxolan-4-one 
• 129144-54-3 (2S,5S) 2-phenyl-2,5-dimethyl-1,3-dioxolan-4-one 
• 104333-83-7 (4R,5R)-2-phenyl-2-methyl-4,5-bis(methoxycarbonyl)-1,3-dioxolane 
• 42237-98-9 isopropyl 1-phenylvinyl ether 
• 4316-26-1 acetophenone diisopropyl acetal 

Relevant academic research and scientific papers

Ring Substituent Effects on Acetophenone Dimethyl Acetal Formation. 1. Dual-Parameter Treatment of Equilibrium Data in Methanol, Water, and Dodecane

For substituted acetophenones, the ketone to acetal equilibrium constants, Kx, measured by a water concentration jump method, are reported.Ketone and acetal partition coefficients, P, for the water-dodecane and methanol-dodecane solvent systems provide Gibbs free energies of transfer from methanol to dodecane and from methanol to water.Both sets of results make it possible to calculate Kx values in water and dodecane; these values are compared with those directly measured in methanol and with equilibrium constants reported for other reactions involving the trigonal to tetrahedral conversion of the carbonyl carbon atom.Substituent effects tor the three solvents are examined by means of the usual dual-parameter Gibbs free energy relationships.The Young-Jencks modified Yukawa-Tsuno equation, log Kx = ρn?n + ρr(?+-?n) + i, gives ρn = 1.73, 1.81, and 0.99 for methanol, dodecane, and water, respectively, but ρr ca. 1 whatever the solvent.It is concluded that the through-ring conjugation effects are solvent independent.In contrast, the Taft-Lewis equation, log Kx = ρI?I + ρ+R?+R + i, gives ρI and ρ+R values that are both solvent dependent.The substituent effects on relative solubilities in methanol, dodecane, and water are examined by means of the equation ΠX(Y) = log PX(Y) - log PH(Y) where Y is the carbonyl or the acetal group and X is the substituent.It is shown that log PX(Y) deviates from additivity (ΠX(Y) ΠX(H) and is Y dependent) because of the effects of X on carbonyl and acetal solvation.These effects are particularly large for solvation of acetals by water molecules.Therefore, substituent effects on Kx are interpreted as being mainly due to (a) an inductive effects of the sustituted ring on ketone stability, (b) a solvent-independent through-ring conjugation effect within the ketone, and (c) a specific inhibition of acetal solvation by water molecules.

Synthesis and thermal properties of salts comprising cationic bis(oxazoline)-AuIII complexes and fluorinated anions

Salts comprising cationic bis(oxazoline) (box)-AuIII complexes and fluorinated anions were synthesized and their thermal properties were investigated. Cations that contain box ligands with butyl substituents (butyl-box) were used with either achiral-(R,S) ([1]+) or chiral-(S,S) ([2]+) configurations. [1][Tf2N] (Tf2N- = bis(trifluoromethanesulfonyl)amide) is a solid that can also be classified as an ionic liquid (Tm = 62 °C, Tg = -11 °C). [1]X and [2]X (X = SbF6- and BF4-) exhibit melting points higher than 100 °C, where [1]X exhibits a higher melting point than [2]X. A salt with an ethyl-box ligand ([3][SbF6]) exhibits no melting up to its decomposition temperature of 267 °C. Crystal structure determination revealed that the achiral cation in [1][BF4] has a bent structure. The potential utility of [1][Tf2N] for catalysis was demonstrated by the catalytic formation of an acetal from an alkyne.

Conjugate addition of acetal-derived benzyl radicals generated from low-valent titanium-mediated CO bond cleavage

A new method for the generation of benzyl radicals from acetals via low-valent titanium-mediated homolytic CO bond cleavage is presented. The low cost and availability of the developed titanium reagent enable efficient access to α-alkoxy carbon radical species via the developed reaction.

P-Anisaldehyde-Photosensitized Sulfonylcyanation of Chiral Cyclobutenes: Enantioselective Access to Cyclic and Acyclic Systems Bearing All-Carbon Quaternary Stereocenters

The photosensitized p-Anisaldehyde-mediated addition of sulfonylcyanides onto the I -system of cyclobutenes is shown to afford highly functionalized cyclobutanes in high yields and diastereocontrol. The homochiral cyclobutene precursors are accessible on multigram scale in two steps through an asymmetric [2 + 2] cycloaddition/vinyl thioether reduction sequence. The enantiopure cyclobutylnitriles can be elaborated further through SmI2-mediated ring opening or converted into new enantiopure cyclobutenes through base-mediated sulfone elimination.

Photocatalytic Reductive Formation of α-Tertiary Ethers from Ketals

A general photocatalytic reductive strategy for the construction of unsymmetrical α-tertiary dialkyl ethers is reported. By merging Lewis acid-mediated ketal activation and visible-light photocatalytic reduction, in situ-generated α-alkoxy radicals were found to engage in addition reactions with a variety of olefinic partners. Good reaction efficiency is demonstrated with a range of ketals of aromatic and aliphatic ketones. Extension to acetal substrates is also described, demonstrating the overall synthetic utility of this methodology for complex ether synthesis.

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.

Utilization of hexabromoacetone for protection of alcohols and aldehydes and deprotection of acetals, ketals, and oximes under UV irradiation

Hexabromoacetone (HBA) was efficiently used for the protection of alcohols and aldehydes and deprotection of benzaldehyde dimethyl acetal, solketal, and other acetals and ketals. In only 10?min, the protection of glycerol yielded 90% of solketal and protection of benzaldehyde gave 95% of benzaldehyde dimethyl acetal. The deprotection of benzaldehyde dimethyl acetal under UV irradiation gave over 90% yield of benzaldehyde within 15?s using only 2.5?mol% of HBA. HBA was also successfully used for deoximation. Solvent was found to play an important role in the efficiency of HBA for these reactions.

Hierarchical porous organic polymer as an efficient metal-free catalyst for acetalization of carbonyl compounds with alcohols

An efficient melamine-porous organic polymer (M-POP) as N-functionalized organic polymer catalyst was synthesized with melamine and terephthalaldehyde by a facile microwave-assisted method. The synthesized M-POP exhibited a high specific surface area with hierarchical pore structure of both mesoporosity and microporosity. The rich N-moieties namely, C[dbnd]N and N–H from the melamine precursor were found to show hydrogen-bonding ability with various organic molecules such as carbonyl compounds. This was illustrated in the acetalization of aldehydes and ketones with methanol or ethylene glycol under mild conditions as a metal-free H-bonding catalyst with high product selectivity. The superior catalytic performance of M-POP was attributed to the availability of a large number of H-bonding sites both as H-donor and H-acceptor between the reactants and the catalyst.

Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates

The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.

A fluorinated cobalt(III) porphyrin complex for hydroalkoxylation of alkynes

A fluorinated cobalt(III) porphyrin complex [Co(TPFPP)-NTf2·2C2H5OH, where TPFPP=5,10,15,20-tetrakis(penta-fluorophenyl)porphyrin, Tf=CF3SO2] promotes hydroalkoxylation of alkynes to give acetals in good to excellent yields. The acetals can be directly functionalized with nucleophiles in a one-pot procedure.