15764-16-6

Basic information

• Product Name: 2,4-Dimethylbenzaldehyde
• Synonyms: M-XYLENE-4-CARBOXALDEHYDE;2,4-dimethyl-benzaldehyd;2,4-Dimethylbenzenecarboxaldehyde;FEMA 3427;2,4-xylylaldehyde;2,4-DIMETHYLBENZALDEHYDE;1-formyl-2,4-dimethyl benzene;2,4-DIMETHYLBENZALDEHYDE, TECH., 90%
• CAS NO: 15764-16-6
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• EINECS: 239-856-7
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Benzaldehyde;Aldehydes;C9;Carbonyl Compounds;Alphabetical Listings;C-D;Flavors and Fragrances
• Mol File: 15764-16-6.mol

Chemical Properties

• Melting Point: −9 °C(lit.)
• Boiling Point: 102-103 °C14 mm Hg(lit.)
• Flash Point: 192 °F
• Appearance: Clear colorless/Liquid
• Density: 0.962 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.112mmHg at 25°C
• Refractive Index: n20/D 1.549(lit.)
• Storage Temp.: Store below +30°C.
• Sensitive: Air Sensitive
• CAS DataBase Reference: 2,4-Dimethylbenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethylbenzaldehyde(15764-16-6)
• EPA Substance Registry System: 2,4-Dimethylbenzaldehyde(15764-16-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-52/53-41-37/38
• Safety Statements: 24/25-39-26
• WGK Germany: 3
• Hazardous Substances Data: 15764-16-6(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
2,4-Dimethylbenzaldehyde is used as a flavoring agent for its distinct naphthyl, cherry, almond, spice, and vanilla taste characteristics. Its ability to impart these flavors makes it a valuable addition to the flavor and fragrance industry.
Used in Pharmaceutical Industry:
2,4-Dimethylbenzaldehyde serves as a pharmacological intermediate, playing a crucial role in the synthesis of various drugs and medicinal compounds. Its chemical properties make it a versatile building block for creating new pharmaceuticals.
Used in Chemical Synthesis:
As a clear colorless liquid with a mild, sweet, and bitter-almond odor, 2,4-Dimethylbenzaldehyde can be utilized in chemical synthesis for creating a wide range of products, including specialty chemicals and additives.
Manufacturing Process:
2,4-Dimethylbenzaldehyde can be manufactured through the reaction between m-xylene and CO under the catalysis of powdery and anhydrous AlCl3, providing a reliable method for producing this valuable compound.

References

Yu-Long, W. U. "Study on the Synthesizing of 2,4-Dimethylbenzaldehyde." Chemical Intermediates (2008). Yu-Long, W. U. "Study on Reaction Mechanism of Carbonylating Synthesis of 2,4-Dimethylbenzaldehyde from Meta-xylene." Technology & Development of Chemical Industry (2011). Spicer, By, and V. Denise. "The effects of protein concentration and temperature on flavor delivery and volatility of 2,4-Dimethylbenzaldehyde and Ethyl butyrate in whey protein isolate solutions."

Preparation

By passing HCl into a mixture of o-xylole, aluminum chloride, sodium cyanide at 100°C.

InChI:InChI=1/C9H10O/c1-7-3-4-9(6-10)8(2)5-7/h3-6H,1-2H3

Upstream product

• 95-47-6 o-xylene 
• 16308-92-2 2,4-dimethylbenzyl alcohol 
• 106-42-3 para-xylene 
• 95-63-6 1,2,4-Trimethylbenzene 
• 871898-22-5 4-dichloromethyl-1,4-dimethyl-cyclohexa-2,5-dienol 
• 776279-83-5 2-oxo-2-(2,4-dimethylphenyl)acetic acid 
• 74-90-8 hydrogen cyanide 
• 108-38-3 m-xylene 
• 50-00-0 formaldehyd 
• 824-55-5 2,4-dimethyl-benzyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 74-88-4 methyl iodide 
• 4885-02-3 Dichloromethyl methyl ether 
• 201230-82-2 carbon monoxide 

Downstream Products

• 528-44-9 1,2,4-benzene tricarboxylic acid 
• 61052-15-1 (E)-ethyl 3-(2,4-dimethylphenyl)acrylate 
• 74381-57-0 3-(2,4-dimethyl-phenyl)-2,3-epoxy-propionic acid ethyl ester 
• 1685-80-9 3-(2,4-Dimethylphenyl)-propensaeure 
• 138753-48-7 N-[(2,4-dimethylphenyl)methylene]benzeneamine 
• 70233-10-2 (E)-4-(2,4-dimethylphenyl)but-3-en-2-one 
• 16308-92-2 2,4-dimethylbenzyl alcohol 
• 28042-78-6 2,4-Dimethylbenzaldehyd-azin 
• 91061-51-7 (rac)-2-(2,4-dimethylphenyl)-2-hydroxyacetic acid 
• 1685-79-6 2-(2',4'-dimethylphenyl)amino methylene urea 
• 611-01-8 2,4-dimethyl-benzoic acid 
• 13495-27-7 Acetyl-<2,4-dimethyl-benzoyl>-peroxid 
• 1432-96-8 1-<2,4-Dimethyl-phenyl>-2-nitro-aethylenlorbenzol 
• 21464-56-2 3-Amino-3-(2.4-xylyl)-propionsaeure-ethylester 

Relevant articles and documents

Influence of Protonation on Gattermann-Koch Formylation Rate of Alkylbenzene in CF3SO3H-SbF5

The influence of the protonation on Gattermann-Koch formylation rate of alkylbenzenes was studied in CF3SO3H-SbF5.From the kinetic study of m-xylene formylation using various SbF5:m-xylene molar ratios in CF3SO3H, it is revealed that the formylation rate is explained with the equations which take into account the protonation equilibrium of m-xylene, and the apparent formylation rate is decreased by the protonation.The decrease of the apparent formylation rate by the protonation is proportional to the ratio of protonated alkylbenzene to form the ?-complex; therefore, the apparent relative formylation rate of alkylbenzenes is not consistent with their relative basicity under strong acidic conditions such as in CF3SO3H-SbF5.

A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant

A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).

A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2

A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

Magnetic crosslinked copoly(ionic liquid) nanohydrogel supported palladium nanoparticles as efficient catalysts for the selective aerobic oxidation of alcohols

Nowadays it is still a great sustainable processes challenge to produce efficient, selective and easy magnetic recovery and recycling catalysts for oxidation of alcohols using air as the oxidant. In this work, a new magnetic nanohydrogel comprising [DABCO-allyl][Br] ionic liquid, allyl alcohol and N,N’-methylenebis(acrylamide) is used for stabilization of small and highly uniform palladium nanoparticles of 3–4 nm size MXCPILNHG@Pd. This material has been characterized by Fourier-transform infrared spectroscopy (FTIR), atomic adsorption spectroscopy (AAS), thermogravimetric analysis (TGA), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), SEM-Map, energy-dispersive X-ray spectroscopy (EDX), X-ray photoelectron spectra (XPS), vibrating-sample magnetometer (VSM) and dynamic light scattering (DLS). According to optimization of cross-linking degree and ratio of DABCO-IL, MXCPILNHG-2@Pd is found as a highly selective catalyst in oxidations of primary alcohols to the corresponding aldehydes in toluene and to acids in water. Furthermore, secondary alcohols were reacted efficiently to the corresponding ketones in both toluene and water. Catalyst is magnetically recovered and recycled for several times in both toluene and water and the reused catalysts are characterized by TEM and XPS.

Simple formylation of aromatic compounds using a sodium formate/triphenylphosphine ditriflate system

A new procedure was developed for formylation of arenes to produce aromatic aldehydes using a sodium formate/triphenylphosphine ditriflate system in ethanol at room temperature in good yields. The simplicity of the procedure, short reaction times, and mild reaction conditions are the other advantages of this metal- and carbon monoxide-free protocol.

Oxygenation of Methylarenes to Benzaldehyde Derivatives by a Polyoxometalate Mediated Electron Transfer-Oxygen Transfer Reaction in Aqueous Sulfuric Acid

The synthesis of benzaldehyde derivatives by oxygenation of methylarenes is of significant conceptual and practical interest because these compounds are important chemical intermediates whose synthesis is still carried out by nonsustainable methods with very low atom economy and formation of copious amounts of waste. Now an oxygenation reaction with a 100% theoretical atom economy using a polyoxometalate oxygen donor has been found. The product yield is typically above 95% with no "overoxidation" to benzoic acids; H2 is released by electrolysis, enabling additional reaction cycles. An electrocatalytic cycle is also feasible. This reaction is possible through the use of an aqueous sulfuric acid solvent, in an aqueous biphasic reaction mode that also allows simple catalyst recycling and recovery. The solvent plays a key role in the reaction mechanism by protonating the polyoxometalate thereby enabling the activation of the methylarenes by an electron transfer process. After additional proton transfer and oxygen transfer steps, benzylic alcohols are formed that further react by an electron transfer-proton transfer sequence forming benzaldehyde derivatives. (Chemical Equation Presented).

Formylation of electron-rich aromatic rings mediated by dichloromethyl methyl ether and TiCl4: Scope and limitations

Here the aromatic formylation mediated by TiCl4 and dichloromethyl methyl ether previously described by our group has been explored for a wide range of aromatic rings, including phenols, methoxy- and methylbenzenes, as an excellent way to produce aromatic aldehydes. Here we determine that the regioselectivity of this process is highly promoted by the coordination between the atoms present in the aromatic moiety and those in the metal core.

Photooxidative cleavage of aromatic alkenes into aldehydes using catalytic iodine and molecular oxygen under visible light irradiation

We report a method for the photooxidative cleavage of aromatic alkenes to give aldehydes using molecular oxygen as the terminal oxidant, visible light, a catalytic amount of iodine and trifluoroacetic acid.

Morphology dependant oxidation of aromatic alcohols by new symmetrical copper(II) metallatriangles formed by self-assembly of a shared bis-benzimidazolyl diamide ligand

A new bis-benzimidazole-based diamide ligand N2,N 2′-bis((1H-benzo[d]imidazol-2-yl)methyl)-[1,1′-biphenyl] -2,2′-dicarboxamide, L and its three Cu(II) metallatriangles of general formula [Cu3(L)3X3]·3X·nH 2O (where X = Cl, Br, NO3) have been synthesized and one of them is structurally characterized. X-ray diffraction work reveals that the metallatriangle [Cu3(L)3Cl3] ·3Cl·15H2O crystallizes in trigonal R3? space group with two independent molecules in the asymmetric unit. The asymmetric unit contains only one-third of the molecules and the rest are generated by the crystallographic 3? axis. Each copper(II) ion adopts a highly distorted square pyramidal geometry. The copper(II) metallatriangles are used as catalyst to carry out the oxidation of substituted benzyl alcohols heterogeneously, in the presence of tert-butyl hydroperoxide. Interestingly, the ratio of product profile and the percentage conversion of the products changes with the surface morphology of the metallatriangle employed as a catalyst. A kite type morphology is found to be highly selective to the formation of acid product over the aldehyde, while a hexagonal type morphology results in a mixed acid + aldehyde product. The initial rate of formation of the aldehyde is found to be almost independent of the amount of catalyst employed.

Oxidative cleavage of C=C bond of styrene and its derivatives with H 2O2 using vanadyl (IV) acetylacetonate anchored SBA-15 catalyst

Cleavage of C=C bond of styrene and its derivatives into two carbonyl compounds with H2O2 is accomplished at mild conditions using Vanadyl(IV) acetylacetonate anchored SBA-15 catalyst, which is prepared and characterized by BET surface area, low angle XRD and FT-IR. It is a highly efficient, recyclable and reusable catalyst.