59276-37-8

Basic information

• Product Name: 3,4,5-TRIMETHOXYBENZALDEHYDE DIMETHYL ACETAL
• Synonyms: 3,4,5-TRIMETHOXYBENZALDEHYDE DIMETHYL ACETAL;1,2,3-Trimethoxy-5-(dimethoxymethyl)benzene
• CAS NO: 59276-37-8
• Molecular Formula: C₁₂H₁₈O₅
• Molecular Weight: 242.27
• Product Categories: Acetals/Ketals/Ortho Esters;Organic Building Blocks;Oxygen Compounds
• Mol File: 59276-37-8.mol

Chemical Properties

• Boiling Point: 180 °C10 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.147 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00324mmHg at 25°C
• Refractive Index: n20/D 1.514(lit.)
• CAS DataBase Reference: 3,4,5-TRIMETHOXYBENZALDEHYDE DIMETHYL ACETAL(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-TRIMETHOXYBENZALDEHYDE DIMETHYL ACETAL(59276-37-8)
• EPA Substance Registry System: 3,4,5-TRIMETHOXYBENZALDEHYDE DIMETHYL ACETAL(59276-37-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 59276-37-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H18O5/c1-13-9-6-8(12(16-4)17-5)7-10(14-2)11(9)15-3/h6-7,12H,1-5H3

Upstream product

• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 149-73-5 trimethyl orthoformate 
• 67-56-1 methanol 

Downstream Products

• 57009-70-8 2-(3,4,5-trimethoxyphenyl)-1,3-dithiane 
• 862847-69-6 2-butyl-5-(hept-1-enyl)-1,3-dimethoxybenzene 
• 862847-63-0 2-butyl-5-((E)-hept-1-enyl)-1,3-dimethoxybenzene 
• 862847-65-2 (R)-1-(4-butyl-3,5-dimethoxyphenyl)heptan-2-ol 
• 862847-66-3 (R)-2-butyl-1,3-dimethoxy-5-(2-methoxyheptyl)benzene 
• 862847-64-1 (1R,2R)-1-(4-butyl-3,5-dimethoxyphenyl)heptane-1,2-diol 
• 862847-67-4 (R)-2-bromo-4-butyl-3,5-dimethoxy-1-(2-methoxyheptyl)benzene 
• 862847-68-5 ethyl (R)-3-butyl-2,4-dimethoxy-6-(2-methoxyheptyl)benzoate 
• 1241896-18-3 α-methoxy-3,4,5-methoxybenzyl-triethylphosphonium bromide 
• 30225-78-6 (3,4,5-Trimethoxyphenyl)methylene diacetate 
• 140464-70-6 3,5-dimethoxy-1-(1,3-dioxolan-2-yl)benzene 
• 140464-79-5 methyl 2,6-dimethoxy-4-dimethoxymethylbenzoate 
• 140464-77-3 1-(4-Dimethoxymethyl-2,6-dimethoxy-phenyl)-2,2-dimethyl-propan-1-ol 
• 140464-78-4 (4-Dimethoxymethyl-2,6-dimethoxy-phenyl)-phenyl-methanone 

Relevant articles and documents

Tropylium salts as efficient organic Lewis acid catalysts for acetalization and transacetalization reactions in batch and flow

Acetalization reactions play significant roles in the synthetically important masking chemistry of carbonyl compounds. Herein we demonstrate for the first time that tropylium salts can act as organic Lewis acid catalysts to facilitate acetalization and transacetalization reactions of a wide range of aldehyde substrates. This metal-free method works efficiently in both batch and flow conditions, prompting further future applications of tropylium organocatalysts in green synthesis.

Acid-catalyzed highly diastereoselective and effective synthesis of 1,3-disubstituted tetrahydropyrano[3,4-b]indoles

We successfully explored for the first time that trifluoroacetic acid (TFA) can effectively catalyze the oxa-Pictet-Spengler reaction of secondary tryptophols and acetals to synthesize 1,3-disubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indoles in high yield (up to >99%) and diastereoselectivity (>20:1). The secondary tryptophols were synthesized from indole-3-acetic acid. The one-pot synthesis of tetrahydropyrano[3,4-b]indoles was successfully developed from secondary tryptophols and in situ prepared acetals from aldehydes and trimethylorthoformate and thus the cost-efficiency of the protocol was effectively enhanced. Finally, the catalytic asymmetric synthesis of the 1,3-disubstituted tetrahydropyrano[3,4-b]indole was also demonstrated after enantioselective achievement of highly enantiopure secondary tryptophols.

Diterpenoid alkaloid lappaconine derivative catalyzed asymmetric α-hydroxylation of β-dicarbonyl compounds with hydrogen peroxide

A new framework derived from the commercially available diterpenoid alkaloid lappaconitine was evaluated as a Bronsted base catalyst for the enantioselective α-hydroxylation of β-dicarbonyl compounds by using 30% hydrogen peroxide as a green and highly practical source of oxygen. This protocol allows convenient access to the corresponding α-hydroxy-β- oxo esters, α-hydroxy-β-oxo amides and (-)-kjellmanianone with up to 98% yield and 92% ee. Copyright

Transformations of several monoterpenoids in the presence of aldehydes in supercritical solvents

The reactivity of verbenol epoxide and isopulegol in supercritical solvents in the presence of aromatic aldehydes was studied using a flow type reactor and a heterogeneous catalyst (Al2O3) or no catalyst. The intramolecular transformations or interactions of reagents with the solvent prevailed in all cases; the yield of the products of intermolecular reactions of terpenoids with aldehydes was up to 1%. The aldehydes did not interact with verbenol epoxide but produced a considerable effect on the distribution of its isomerization products.

New two-step sequence involving a hetero-Diels-Alder and a nonphenolic oxidative coupling reaction: A convergent access to analogs of steganacin

A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans.

SUBSTITUTED ISOQUINOLINES AND THEIR USE AS TUBULIN POLYMERIZATION INHIBITORS

The present invention relates generally to substituted isoquinolines and their use as tubulin polymerization inhibitors. In particular, the invention relates to substituted isoquinolines which possess useful therapeutic activity, use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds

Dichotomous reactivity in the reaction of triethyl- and triphenylphosphane HBr salts with dimethyl acetals: A novel entry to α-alkoxy-functionalized ylides and general synthesis of vinyl ethers and alkoxy dienes

The discovery of dichotomous reactivity in the reaction of trialkyl- vs. triphenylphosphane HBr salts with acetals allows entry to functionalized α-methoxy phosphonium salts and a novel process for tertiary phosphane methylation. The new protocol opens a general entry to the synthesis of vinyl ethers and differentially substituted 1,3-dienes via Wittig reactions of the functionalized ylides derived from the α-methoxy phosphonium salts.

A solvent-controlled highly efficient Pd-C catalyzed hydrogenolysis of benzaldehydes to methylbenzenes via a novel 'acetal pathway'

Pd-C catalyzed hydrogenolysis of benzaldehydes to methylbenzenes has been described to proceed via a 'benzenemethanol pathway'. In this article, a novel 'acetal pathway' was first revealed by a systematic study when lower alcohols were used as solvents and a solvent-controlled highly efficient procedure was established.

Cobalt(II)-catalyzed chemoselective synthesis of acetals from aldehydes

The acetalization of aldehydes has been studied with methanol, ethanol, and 2-propanol using CoCl2 in high yields under reflux conditions. The reaction is simple, efficient, chemoselective and does not involve any other additive.

Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues

Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR p