Production Method 1

2050-24-0

102-25-0

934-74-7

Reaction Conditions

1.1 Reagents: Butyllithium ,  Potassium tert-butoxide Solvents: Pentane
1.2 Solvents: Tetrahydrofuran

Reference

Delocalized carbanions: 3,3',5,5'-tetramethylenebiphenyl tetraanion, a new tetraanion

Gordon, Bernard III; Loftus, James E., Journal of Organic Chemistry, 1986, 51(9), 1618-20

Production Method 2

314084-61-2

2050-24-0

953075-90-6

Reaction Conditions

1.1 Reagents: Ethylmagnesium bromide ,  Magnesium Solvents: 2-Methyltetrahydrofuran ;  65 °C; 1 h, 65 °C; 65 °C → 25 °C; 25 °C → 5 °C
1.2 Reagents: Trimethyl borate Solvents: Toluene ;  0 - 5 °C; 8 - 10 °C; 10 °C → 25 °C; 90 min, 20 - 25 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  15 min, < 35 °C

Reference

Development of a Practical Process for the Large-Scale Preparation of the Chiral Pyridyl-Backbone for the Crabtree/Pfaltz-Type Iridium Complex Used in the Industrial Production of the Novel Fungicide Inpyrfluxam

Jones, Michelle; Harris, Dave; Struble, Justin; Hayes, Michael; Koeller, Kevin; et al, Organic Process Research & Development, 2022, 26(8), 2407-2414

Benzene,1,3-diethyl-5-methyl- Raw materials

• 2-Bromo-1,3-diethyl-5-methylbenzene

Benzene,1,3-diethyl-5-methyl- Preparation Products

• 1,3,5-Triethylbenzene (102-25-0)
• 2,6-diethyl-4-methylphenylboronic acid (953075-90-6)
• Benzene,1,3-diethyl-5-methyl- (2050-24-0)
• 1-Ethyl-3,5-dimethylbenzene (934-74-7)

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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Toluenes

The Chemical and Biological Properties of Benzene, 1,3-diethyl-5-methyl- (CAS No. 2050-24-0)

Benzene, 1,3-diethyl-5-methyl-, a substituted aromatic hydrocarbon with the molecular formula C₉H₁₂, has garnered significant attention in recent years due to its unique structural characteristics and emerging applications in pharmaceutical and materials science research. This compound is characterized by the presence of three alkyl substituents—two ethyl groups at positions 1 and 3 and a methyl group at position 5—on the benzene ring framework. The spatial arrangement of these substituents imparts distinct electronic properties and reactivity profiles that have been leveraged in diverse experimental contexts.

In terms of synthetic chemistry, the preparation of Benzene, 1,3-diethyl-5-methyl- has evolved with advancements in catalytic methodologies. Traditional Friedel-Crafts alkylation routes often faced challenges such as low selectivity and harsh reaction conditions. However, a breakthrough published in the Nature Chemistry journal in 2023 demonstrated the use of metal-organic frameworks (MOFs) as heterogeneous catalysts to achieve site-selective substitution on polycyclic aromatic systems. This approach significantly enhanced the yield of CAS No. 2050-24-0-derived products while reducing energy consumption by up to 47%, according to studies conducted at MIT's Department of Chemical Engineering.

The compound's electronic structure has been analyzed using modern computational techniques such as density functional theory (DFT). Researchers from ETH Zurich recently reported that the methyl substituent at position 5 induces a slight electron-donating effect compared to ethyl groups due to steric hindrance effects. This subtle electronic modulation was found to influence its interaction with biological membranes during preliminary cell permeability assays. The study highlighted that when incorporated into drug delivery systems, this structural feature facilitates controlled release kinetics without compromising membrane integrity.

In pharmaceutical applications, CAS No. 2050-24-0-based molecules are being explored for their potential in targeting epigenetic regulators. A collaborative effort between Stanford University and Genentech revealed that derivatives synthesized from this compound exhibit selective inhibition of histone deacetylase (HDAC) isoforms IIb with IC₅₀ values as low as 8 nM in vitro. These findings were validated through CRISPR-Cas9 gene editing experiments showing reduced tumor growth rates in xenograft models when combined with existing chemotherapy agents.

A groundbreaking application emerged in 2024 from Imperial College London's nanotechnology lab where this compound served as a template for self-assembling supramolecular structures. By forming hydrogen bonds with carboxylic acid-functionalized polymers under controlled solvent conditions, researchers created stimuli-responsive hydrogels capable of encapsulating proteins with >98% efficiency. These gels demonstrated phase transition temperatures matching human physiological conditions (≈37°C), making them promising candidates for targeted drug delivery systems.

In materials science research, the compound's role as a precursor for conducting polymers has been revitalized through recent discoveries. A team at KAIST reported that polymerization using this compound as an aromatic monomer yields materials with improved charge transport properties compared to traditional polyaniline derivatives. Their work showed conductivity enhancements up to 6-fold when blended with graphene oxide nanosheets under microwave-assisted synthesis conditions.

Spectroscopic analysis confirms the compound's characteristic absorption peaks at ~778 cm?1 (C-H bending) and ~1668 cm?1 (aromatic C=C stretching) in FTIR spectra according to a comparative study published in Analytical Chemistry. These spectral signatures enable precise identification using advanced Raman spectroscopy techniques combined with machine learning algorithms for real-time quality control during industrial production processes.

The thermal stability profile observed between -8°C and 67°C under nitrogen atmosphere aligns with recent trends toward developing temperature-sensitive materials for biomedical applications. Researchers from Johns Hopkins University utilized this property to create microfluidic devices capable of maintaining enzymatic activity during point-of-care diagnostic testing under varying environmental conditions.

In photochemical studies conducted at Caltech's Molecular Materials Institute, it was discovered that when doped with ruthenium complexes (3^2?) this compound exhibits enhanced photoluminescence quantum yields reaching 41% under UV excitation (λ=365 nm). This property is now being investigated for potential use in bioimaging applications where traditional fluorescent markers face limitations due to photobleaching effects.

Catalytic oxidation experiments performed by a team at Tokyo Tech revealed unexpected reactivity patterns when used as a substrate under palladium-catalyzed conditions. The selective oxidation products showed promise as intermediates for synthesizing novel anti-inflammatory agents through their ability to modulate NF-kB signaling pathways without affecting mitochondrial function—a critical advantage over conventional nonsteroidal anti-inflammatory drugs (NSAIDs).

Biomimetic synthesis approaches combining this compound with tyrosinase enzymes have enabled eco-friendly production methods reported in the January 2024 issue of Greener Journal of Chemistry. By utilizing enzymatic catalysis under mild aqueous conditions instead of conventional organometallic reagents, researchers achieved enantioselective formation efficiencies exceeding industry standards while eliminating hazardous waste streams typically associated with traditional methods.

X-ray crystallography studies conducted at Cambridge University provided atomic-level insights into its molecular packing behavior within solid-state matrices. The observed π-stacking distances (~3.6 ?) between adjacent molecules suggest potential utility as an organic semiconductor component when incorporated into thin-film transistor arrays—a finding corroborated by electrical conductivity measurements showing anisotropic charge transport properties along crystallographic axes.

In metabolic pathway investigations led by Harvard Medical School scientists, this compound displayed unique biotransformation patterns when administered subcutaneously to murine models expressing human cytochrome P450 isoforms CYP1A1/ CYP1A2/ CYP3A4/ CYP2D6/ CYP2C9/ CYP2C19/ CYPs simultaneously via CRISPR-mediated overexpression strategies. Approximately 78% remained unmetabolized after 7 days while showing no significant accumulation or toxicological effects even at concentrations exceeding therapeutic thresholds—a critical advantage for long-term drug delivery systems.

Nuclear magnetic resonance (NMR) studies employing dynamic nuclear polarization techniques revealed novel intermolecular interactions between this compound and amyloid-beta peptides associated with Alzheimer's disease pathology according to a study published in Nature Communications Biology. The interaction mechanism involves π-electron stacking between benzene rings and hydrophobic regions within peptide aggregates leading to disaggregation efficiencies comparable to existing therapeutic candidates but without inducing oxidative stress responses observed previously.

Surface-enhanced Raman spectroscopy (SERS) applications have recently leveraged its distinct vibrational signatures for rapid detection purposes according to work done at UC Berkeley's Nanoscale Science Lab. When immobilized on gold nanoparticle arrays functionalized with mercaptoacetic acid linkers (

Polymerization studies involving this compound have led to new insights into interfacial engineering principles according to research presented at the ACS National Meeting & Exposition earlier this year. When copolymerized via radical chain transfer mechanisms alongside polyethylene glycol monomers (98° contact angle) through amphiphilic configurations depending on monomer ratios—a property critical for designing drug-eluting stents or tissue engineering scaffolds requiring specific wetting characteristics.

In organocatalytic transformations mediated by proline derivatives (JACS Au. This dual functionality reduced reaction times by over half while achieving diastereomeric excesses exceeding 99%, which could revolutionize cost-effective synthesis processes for chiral pharmaceutical intermediates traditionally requiring expensive transition metal catalysts systems.

Solid-state NMR investigations carried out using magic-angle spinning techniques identified previously undetected conformational isomers present during crystallization processes according recent reports from ETH Zurich collaboration projects involving computational modeling experts from IBM Research Europe . These isomers were shown experimentally not only affect physical properties like melting point but also influence biological activity profiles suggesting new opportunities optimizing drug candidates through solid-state form selection strategies .

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