5395-08-4

Usage

Uses

Used in Chemical Synthesis:
(dibutoxymethyl)benzene is utilized as a solvent and intermediate in the production of various chemicals and materials. Its solubility in organic solvents and low toxicity make it a suitable candidate for chemical synthesis processes.
Used in Polymer and Resin Production:
(dibutoxymethyl)benzene is also employed in the synthesis of polymers and resins, contributing to the development of a range of materials with diverse applications across different industries.
Used in Pharmaceutical Industry:
(dibutoxymethyl)benzene can be used as a starting material for the synthesis of pharmaceutical compounds, taking advantage of its chemical properties to create new drugs with potential therapeutic benefits.
Used in Environmentally Friendly Applications:
Given its low toxicity and minimal environmental harm, (dibutoxymethyl)benzene can be used in applications where environmental safety is a priority, such as in the development of green chemicals and materials.

Upstream product

• 100-52-7 benzaldehyde 
• 71-36-3 butan-1-ol 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 136-60-7 benzoic acid, butyl ester 
• 4460-46-2 3-chloro-3-phenyl-3H-diazirine 
• 98-87-3 benzylidene dichloride 
• 3999-70-0 potassium n-butoxide 
• 5593-70-4 titanium (IV) butoxide 

Downstream Products

• 106-98-9 1-butylene 
• 136-60-7 benzoic acid, butyl ester 
• 100-52-7 benzaldehyde 
• 588-67-0 benzyl 1-butyl ether 
• 28467-92-7 α-ethylcinnamaldehyde 
• 1755-45-9 (E)-2-benzylidenebutanal 
• 103-37-7 benzyl butanoate 
• 100-51-6 benzyl alcohol 
• 583-03-9 1-Phenyl-1-pentanol 
• 71-36-3 butan-1-ol 
• 109-65-9 1-bromo-butane 
• 1087548-69-3 C₁₄H₂₀O 
• 101-81-5 Diphenylmethane 

Relevant academic research and scientific papers

Graphitic carbon nitride catalysed photoacetalization of aldehydes/ketones under ambient conditions

Graphitic-C3N4 is shown for the first time to catalyse photoacetalization of aldehydes/ketones with alcohols to acetals in high yields using visible light under ambient conditions; transient charge separation over the material is effective to catalyse the reaction in the absence of Lewis or Br?nsted acids, giving a new green alternative catalyst.

A Ta/W mixed addenda heteropolyacid with excellent acid catalytic activity and proton-conducting property

A new HPAs H20[P8W60Ta12(H2O)4(OH)8O236]·125H2O (H-1) which comprises a Ta/W mixed addenda heteropolyanion, 20 protons, and 125 crystalline water molecules has been prepared through ion-exchange method. The structure and properties of H-1 have been explored in detail. AC impedance measurements indicate that H-1 is a good solid state proton conducting material at room temperature with a conductivity value of 7.2×10?3?S?cm?1 (25?°C, 30% RH). Cyclic voltammograms of H-1 indicate the electrocatalytic activity towards the reduction of nitrite. Hammett acidity constant H0 of H-1 in CH3CN is ?2.91, which is the strongest among the present known HPAs. Relatively, H-1 exhibits excellent catalytic activities toward acetal reaction.

Method for synthesizing bis-ether compound by catalyzing benzaldehyde through mixed type heteropoly acid

The invention discloses a method for synthesizing a bis-ether compound by catalyzing benzaldehyde through mixed type heteropoly acid. Benzaldehyde and an alcohol compound are used as raw materials and mixed type heteropoly acid is used as a catalyst, so as to conduct reaction to prepare the bis-ether compound, wherein the alcohol compound is methanol, n-butanol or ethylene glycol, the molecular formula of mixed type heteropoly acid is H20[P8W60Ta12(H2O)4(OH)8O236].125H2O, and mixed type heteropoly acid is formed by one tetrameric Ta/W mixed type heteropoly anion, 20 protons and 125 crystal water molecules. Prepared mixed type heteropoly acid has the strongest acidity in heteropoly acid known at present, and has higher acid catalytic activity due to the strong acidity.

Bronsted instead of lewis acidity in functionalized MIL-101Cr MOFs for efficient heterogeneous (nano-MOF) catalysis in the condensation reaction of aldehydes with alcohols

Porous chromium(III) 2-nitro-, 2-amino-, and nonfunctionalized terephthalate (MIL-101Cr) metal organic frameworks are heterogeneous catalysts for diacetal formation from benzaldehyde and methanol (B-M reaction) as well as other aldehydes and alcohols. MIL-101Cr-NO2 obtained by direct reaction between CrO3 and 2-nitro-terephthalate showed the highest activity with 99% conversion in the B-M reaction in 90 min and turnover numbers of 114. The activity decreased in the order MIL-101Cr-NO2 > MIL-101Cr > MIL-101Cr-NH2. Within different samples of nonfunctionalized MIL-101Cr the activity increased with surface area. Methanol gas sorption of the different MIL materials correlates with the BET surface area and pore volume but not with the diacetalization activity. Benzaldehyde adsorption from heptane showed no significant difference for the different MILs. Gas sorption studies of CD3CN to probe for a higher Lewis acidity in MIL-101Cr-NO2 remained inconclusive. A high B-M catalytic activity of wet MIL-101Cr-NO2 excluded significant contributions from coordinatively unsaturated Lewis-acid sites. pH measurements of methanol dispersions of the MIL materials gave the most acidic pH (as low as 1.9) for MIL-101Cr-NO2, which significantly increased over MIL-101Cr (3.0) to MIL-101Cr-NH2 (3.3). The increase in acidity is of short range or a surface effect to the heterogeneous MIL particles as protons dissociating from the polarized aqua ligands (Cr-OH2) have to stay near the insoluble counteranionic framework. The variation in Bronsted acidity of MIL-101Cr-NO2 > MIL-101Cr ≈ MIL-101Cr-NH2 correlates with the withdrawing effect of NO2 and the diacetalization activity. The catalytic B-M activity of soluble, substitution-inert, and acidic Cr(NO3)3·9H2O supports the Bronsted-acid effect of the MIL materials. Filtration and centrifugation experiments with MIL-101Cr-NO2 revealed that about 2/3 of the catalytic activity comes from nano-MOF particles with a diameter below 200 nm. The MIL-101Cr-NO2 catalysts can be recycled five times with very little loss in activity. The diacetalization activity of MIL-101Cr-NO 2 decreases with the alcohol chain length from methanol over ethanol, n-propanol, n-butanol, to almost inactive n-pentanol, while conversions for benzaldehyde, paratolylaldehyde, 4-chlorobenzaldehyde, and cyclohexanone all reach 90% or more after 90 min.

[Hmim]3PW12O40: A high-efficient and green catalyst for the acetalization of carbonyl compounds

[Hmim]3PW12O40 was developed and used in the acetalization of carbonyl compounds in excellent yields. The ionic liquid-heteropoly acid hybrid compound and reaction medium formed temperature-dependent phase-separation system with the ease of product as well as catalyst separation. The catalyst was recycled more than 10 times without any apparent loss of catalytic activity.

Effect of alkyl group size on the mechanism of acid hydrolyses of benzaldehyde acetals

Hydrolyses of benzaldehyde acetals, PhCH(OR)2, are specific hydrogen-ion catalyzed when R = methyl, n-butyl, but with secondary and tertiary alkyl derivatives, R = i-propyl, s-butyl, t-butyl, t-amyl, hydrolyses are general-acid catalyzed. The Broonsted α values for both secondary and tertiary alkyl groups are in the range: α = 0.57-0.61. A simple iterative procedure was developed to estimate the individual rate constants for general-acid catalysis by the diacid and monoacid forms of succinic acid buffer. Plots of log kobs (at [buffer] = 0 M) against pH are linear for the secondary and tertiary acetals, and plots of log kH for the H3O+-catalyzed reaction, 13C and 1H chemical shifts, and 1JCH coupling constants against the Charton steric parameter, v, for alkoxy groups are linear. The second-order rate constant, kH, increases about 100-fold on going from R = Me to R = t-amyl, indicating the significant role of steric effects on reactivity. Steric effects upon 13C NMR chemical shifts and coupling constants indicate that increasing the bulk of the alkoxy moiety increases the electron density at the carbon reaction center, which accelerates hydrolysis. Analysis of the Jencks-More-O'Ferrall free energy diagram for the reaction provides support for concerted proton transfer and C-O bond breaking in the transition state for hydrolyses of benzaldehyde acetals with secondary and tertiary alkyl groups in contrast to specific hydrogen catalysis with R = Me and n-Bu. All our results are consistent with rate-determining acid hydrolysis of benzaldehyde dialkyl acetals to hemiacetal intermediates that breakdown rapidly to benzaldehyde.

Superacid-Catalyzed Reductive Friedel-Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals

Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethane-sulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph2CHOCH2CH2CH2OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.

TRANSFORMATION OF PHENYLCHLORODIAZIRINES TO 1,3-DIOXOLANES AND A 1,3-DITHIOLANE

Chlorophenylcarbene reacts with bifuncional or polyfuncional alcohols and ethanedithiol to form 2-phenyl-1,3-dioxolanes and 2-phenyl-1,3-dithiolane.

REARRANGEMENT OF SUBSTITUTED AROMATIC ACETALS CATALYSED BY γ-ALUMINA

Aromatic acetals over γ-alumina undergo rearrangement to give the corresponding esters (b) and ethers (c) in good yield.The product distribution varied unusually over the range of reaction temperatures.The effect of substituents has also been felt much in the study.Probable mechanisms have been suggested for the reaction.The catalyst has been characterized by various studies and the specific poisoning of the catalyst has been done with NH3, CO2 and H2S.