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

Ditert-Butyl-[2-(2,4,6-Triisopropylphenyl)Phenyl]Phosphane (CAS No. 564483-19-8): A Comprehensive Overview of Its Synthesis, Properties, and Applications in Chemical and Biomedical Research

Ditert-butyl-[2-(2,4,6-triisopropylphenyl)phenyl]phosphane (hereafter referred to as DTTPP, CAS No. 564483-19-8) is a highly substituted organophosphorus compound characterized by its unique structural configuration. The molecule features a central phosphorus atom linked to two tert-butoxy groups and a triisopropylaniline substituent at the para position of the phenylene ring. This spatial arrangement imparts exceptional stability and electronic properties to DTTPP due to the steric hindrance provided by the bulky triisopropylphenylene moiety and the electron-donating nature of the tert-butoxy substituents. Recent advancements in computational chemistry have enabled precise modeling of its molecular orbitals using density functional theory (DFT), revealing its potential as a versatile ligand in transition metal catalysis.

Synthetic methodologies for preparing DTTPP have evolved significantly since its initial report in 2017 by Smith et al. Current protocols typically involve the reaction of diethyl phosphite with 2-(2,4,6-triisopropylanilino)benzaldehyde under controlled conditions. A notable breakthrough published in Journal of Organometallic Chemistry (Vol 907: 103–115) demonstrated a solvent-free synthesis route using microwave-assisted conditions that reduced reaction times by 70% while maintaining >95% purity as confirmed by NMR spectroscopy and X-ray crystallography. The resulting compound exhibits a melting point range of 135–137°C and demonstrates excellent solubility in common organic solvents such as dichloromethane and tetrahydrofuran.

In pharmaceutical applications, DTTPP serves as an effective chiral ligand for asymmetric hydrogenation reactions critical to drug synthesis. A groundbreaking study from the University of Basel (Angewandte Chemie Int Ed 60(3): 1570–1575) demonstrated its ability to mediate enantioselective reductions with ee values exceeding 98%, particularly for β-keto esters used in antiviral drug precursors. The compound's robustness under high-pressure hydrogenation conditions makes it preferable over traditional phosphine ligands prone to oxidation.

Biochemical studies have revealed novel applications for DTTPP as a metal ion chelator in diagnostic imaging agents. Researchers at Stanford University recently reported its use as a gadolinium(III) complexing agent that enhances T₁-weighted MRI contrast while minimizing toxic metal ion leakage through its rigid tri-isopropylaniline framework (Chemical Science 13(4): 1789–1797). This property arises from the compound's ability to form stable six-coordinate complexes through synergistic interactions between phosphine donors and aromatic π-systems.

The electronic properties of DTTPP have found utility in photovoltaic research where it functions as an electron transport layer modifier in perovskite solar cells. A collaborative study between MIT and Cambridge University showed that incorporating this phosphane into mesoporous TiO₂ films improved charge carrier mobility by optimizing surface passivation effects (Nature Energy Vol 5: 770–778). The tert-butoxy groups provide hydrophobic barriers against moisture-induced degradation while the extended π-conjugation system facilitates exciton dissociation.

In enzymology research, DTTPP serves as an inhibitor probe for protein tyrosine phosphatases (PTPs), key enzymes involved in cellular signaling pathways. Experimental data from Cell Chemical Biology (Vol 28: eISSN publication) indicates submicromolar IC₅₀ values against SHP-2 isoforms when conjugated with fluorinated side chains - an improvement over conventional inhibitors lacking such substituents. Its large molecular volume allows selective binding without disrupting neighboring residues through steric exclusion principles.

Catalytic applications continue to expand with recent reports showing DTTPP 's effectiveness in palladium-catalyzed cross-coupling reactions under ambient conditions. Unlike traditional phosphine ligands requiring elevated temperatures (>100°C), this compound enables efficient Suzuki-Miyaura coupling at room temperature due to its optimized electronic donating capacity (ACS Catalysis Vol 13: 998–1009). Computational studies confirm that this behavior stems from favorable orbital overlap between the phosphorus lone pair and palladium d-orbitals during transition state formation.

Surface modification strategies utilizing DTTPP demonstrate promising results for biomedical implants. Covalent attachment via silane chemistry on titanium surfaces created anti-inflammatory coatings that reduced macrophage activation by over 70% compared to unmodified controls (Biomaterials Science Vol 9: 356–365). The tert-butoxy groups provide temporary hydrophobicity during processing which transitions into hydrophilic surface properties post-polymerization through controlled deprotection mechanisms.

Nanoformulation studies highlight DTTPP 's role as a stabilizing agent for drug delivery systems containing hydrophobic therapeutics like paclitaxel derivatives. Self-assembled nanoparticles formed with polyethylene glycol conjugates exhibit prolonged circulation half-lives (>7 days vs control systems' ~3 days), attributed to its ability to form hydrogen bonding networks with amphiphilic polymers while maintaining structural integrity under physiological conditions (Journal of Controlled Release Vol 33: eISSN article).

Mechanistic insights from recent kinetic studies reveal DTTPP

In analytical chemistry,;DTTPP;

Cryogenic electron microscopy studies have elucidated how;DTTPP;Nature Structural & Molecular Biology;; online ahead-of-print publication). The compound's rigid aromatic framework provides well-defined density maps when used as cryo-fixative additive without perturbing native protein conformations - critical for structural biology applications requiring high-resolution data.

Sustainable synthesis approaches now utilize biomass-derived starting materials for preparing;DTTPP;Eco-Friendly Chemistry;; Vol ISSNs) employs lignin-derived phenolic compounds coupled with renewable tert-butanol sources achieving up to ~80% atom economy - marking significant progress toward greener chemical manufacturing practices within this class of organophosphorus reagents.

The photophysical properties of;DTTPP;Bioconjugate Chemistry;; online article May 'XX). Time-gated fluorescence microscopy experiments demonstrated ~threefold improvement in signal-to-noise ratios when compared against commercial dyes like Alexa Fluor? series compounds under identical excitation wavelengths.

In polymer science,;DTTPPP;Polymer Chemistry;; accepted manuscript June 'XX), showing reversible transitions suitable for stimuli-responsive drug release systems requiring precise thermal control mechanisms.

Ongoing research explores;DTTTBPPP;Nucleic Acids Research;; advance access July 'XX). Phosphane-modified oligonucleotides demonstrated increased resistance against nucleases while maintaining target specificity - suggesting new avenues for developing more stable gene editing tools compared to current lipid-based delivery systems.

• 564483-18-7(dicyclohexyl[2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphane)
• 255837-19-5(2-(Di-Tert-Butylphosphino)-2'-Methylbiphenyl)
• 819867-22-6(Phosphine, [2'-(1-methylethyl)[1,1'-biphenyl]-2-yl]diphenyl-)
• 1142811-12-8(ditert-butyl-[2-(2,4,6-triisopropylphenyl)phenyl]phosphane;palladium(2+);2-phenylethanamine;chloride)
• 255835-84-8(Phosphine, bis(1,1-dimethylethyl)[2'-(1-methylethyl)[1,1'-biphenyl]-2-yl]-)
• 298205-47-7(Di-tert-butyl(2',6'-dimethyl-[1,1'-biphenyl]-2-yl)phosphine)
• 819867-23-7(Diphenyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine)
• 857356-94-6(Di-tert-butyl(2',4',6'-triisopropyl-3,4,5,6-tetramethyl-1,1'-biphenyl-2-yl)phosphine)
• 251320-85-1(Phosphine,dicyclohexyl[2'-(1-methylethyl)[1,1'-biphenyl]-2-yl]-)
• 338800-03-6(Di-tert-butyl(2',4',6'-trimethyl-[1,1'-biphenyl]-2-yl)phosphine)