7333-63-3

Usage

Uses

Used in Organic Synthesis:
(4-Bromobutyl)triphenylphosphonium bromide is used as a reactant in various organic synthesis processes, including azidification, C-H activation and β-elimination to produce an eight-membered ring system, and 1,3-dipolar cycloaddition of azides onto alkenes. Its reactivity and stability make it a valuable component in the synthesis of complex organic molecules.
Used in Stereoselective SmI2-mediated Coupling:
In the field of stereoselective reactions, (4-Bromobutyl)triphenylphosphonium bromide is used as a reactant in SmI2-mediated coupling of unsaturated carbonyl compounds and aldehydes. This application allows for the formation of specific stereoisomers, which is crucial in the development of enantioselective synthetic routes.
Used in Synthesis of D-labeled Methylenecyclobutane:
(4-Bromobutyl)triphenylphosphonium bromide is also utilized in the synthesis of D-labeled methylenecyclobutane, a valuable intermediate in the production of various pharmaceuticals and agrochemicals. Its involvement in this synthesis process highlights its versatility and importance in the field of organic chemistry.
Used in Coupling Reactions:
As a reactant in coupling reactions, (4-Bromobutyl)triphenylphosphonium bromide plays a crucial role in the formation of new chemical bonds and the synthesis of a wide range of compounds. Its ability to participate in various coupling reactions further demonstrates its utility in organic synthesis.
Used in the Synthesis of Cell-Penetrating Peptoids with Cationic Side Chains:
(4-Bromobutyl)triphenylphosphonium bromide is used in the synthesis of cell-penetrating peptoids with cationic side chains, which have potential applications in the delivery of therapeutic agents and diagnostic tools. Its role in the development of these peptoids underscores its importance in the field of medicinal chemistry and drug development.

InChI:InChI=1/C22H23BrP/c23-18-10-11-19-24(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22/h1-9,12-17H,10-11,18-19H2/q+1

Upstream product

• 110-52-1 1,4-dibromo-butane 
• 603-35-0 triphenylphosphine 

Downstream Products

• 15546-42-6 [1,1'-(butane-1,4-diyl)bis(triphenylphosphonium)] dibromide 
• 884495-97-0 1-cyclobutylidenemethyl-4-methyl-benzene 
• 884495-99-2 p-chlorophenylmethylenecyclobutane 
• 884496-00-8 1-bromo-4-cyclobutylidenemethyl-benzene 
• 117962-25-1 diphenyl-(5,9,13-trimethyl-tetradeca-4t,8t,12-trienyl)-phosphine 
• 121599-30-2 (4-diphenylphosphinoyl-butyl)-triphenyl-phosphonium; bromide 
• 4151-27-3 1,4-bis(diphenylphosphinyl)butane 
• 168423-31-2 (4-mercaptobutyl)triphenylphosphonium bromide 
• 1256380-50-3 (4-aminobutyl)(triphenyl)phosphonium bromide 

Relevant academic research and scientific papers

A diketopyrrolopyrrole-based fluorescent probe for investigating mitochondrial zinc ions

We demonstrate a strategy to asymmetrically introduce a Zn2+ chelator (MeO-DPEN) and a mitochondrial-targeting group (TPP) at the N-positions of both lactam moieties of diketopyrrolopyrrole (DPP) fluorophore. And two probes DPP-Mito and DPP-C2

Synthesis and characterization of novel positively charged organocobaloximes as catalysts for the fixation of CO2 to cyclic carbonates

A series of cobaloxime complexes (1-6) and corresponding to positively charged phosphonium linked cobaloximes (called cobaloximes-PCPL) (1a-6a) have been prepared in high yields and characterized by means of NMR (1H, 13C, and 31

A mitochondria-targeted thiazoleorange-based photothermal agent for enhanced photothermal therapy for tumors

Organic small molecules with near-infrared (NIR) absorption hold great promise as the phototheranostic agents for clinical translation by virtue of their inherent merits such as well-defined chemical structure, high purity and good reproducibility. Probes

A long-linker conjugate of fluorescein and triphenylphosphonium as mitochondria-targeted uncoupler and fluorescent neuro- and nephroprotector

Background Limited uncoupling of oxidative phosphorylation is known to be beneficial in various laboratory models of diseases. Linking a triphenyl-phosphonium cation to fluorescein through a decyl (C10) spacer yields a fluorescent uncoupler, co

Fluorescent Probe HKSOX-1 for imaging and detection of endogenous superoxide in live cells and in vivo

Superoxide anion radical (O2-) is undoubtedly the most important primary reactive oxygen species (ROS) found in cells, whose formation and fate are intertwined with diverse physiological and pathological processes. Here we report a highly sensitive and selective O2- detecting strategy involving O2- cleavage of an aryl trifluoromethanesulfonate group to yield a free phenol. We have synthesized three new O2- fluorescent probes (HKSOX-1, HKSOX-1r for cellular retention, and HKSOX-1m for mitochondria-targeting) which exhibit excellent selectivity and sensitivity toward O2- over a broad range of pH, strong oxidants, and abundant reductants found in cells. In confocal imaging, flow cytometry, and 96-well microplate assay, HKSOX-1r has been robustly applied to detect O2- in multiple cellular models, such as inflammation and mitochondrial stress. Additionally, our probes can be efficiently applied to visualize O2- in intact live zebrafish embryos. These probes open up exciting opportunities for unmasking the roles of O2- in health and disease.

Synthesis, crystal and structural characterization, Hirshfeld surface analysis and DFT calculations of three symmetrical and asymmetrical phosphonium salts

Three stable phosphonium salts of 1,4-butanediylebis(triphenylphosphonium) dibromide I, butane-4?bromo-1-(triphenylphosphonium) bromide II and 1,3-propanediylbis(triphenylphosphonium) tetrahydroborate III were synthesized and structurally characterized. Single crystal X-ray diffraction analysis, spectroscopic methods and thermal analysis methods were used for the characterization of titled compounds. Crystallographic data showed that compound I crystallized in the triclinic crystal system with Pī space group and compound II crystallized in the monoclinic crystal system with P21/c space group. The crystal packing structures of I and II were stabilized by various intermolecular interactions, especially of C–H···π contacts. The molecular Hirshfeld surface analysis and 2D fingerprint revealed that the C···H contacts have 24.3% and 18.4% contributions in the crystal packings of compounds I and II, respectively. In addition, the H···Br (28.5%) contact has a considerable contribution to the crystal architecture of compound II. Theoretical studies were performed by DFT method to investigate the structural properties of the titled compounds. The isotopic ratio of boron in tetrahydroborate anion of compound III calculated by 1H NMR spectroscopy. The isotopic ratio for 10B/11B was 19.099 / 80.900%. Reduction of some carbonyl compounds to corresponding alcohols was performed by compound III and the optimum conditions were determined.

Two Are Better Than One: A Design Principle for Ultralong-Persistent Luminescence of Pure Organics

Because of their innate ability to store and then release energy, long-persistent luminescence (LPL) materials have garnered strong research interest in a wide range of multidisciplinary fields, such as biomedical sciences, theranostics, and photonic devices. Although many inorganic LPL systems with afterglow durations of up to hours and days have been reported, organic systems have had difficulties reaching similar timescales. In this work, a design principle based on the successes of inorganic systems to produce an organic LPL (OLPL) system through the use of a strong organic electron trap is proposed. The resulting system generates detectable afterglow for up to 7 h, significantly longer than any other reported OLPL system. The design strategy demonstrates an easy methodology to develop organic long-persistent phosphors, opening the door to new OLPL materials.

Organic super-long room-temperature phosphorescent material, triple anti-counterfeiting organic ink and application

The invention discloses an organic super-long room-temperature phosphorescent material which is an organic phosphonium salt prepared by taking triphenylphosphine as a raw material, the compound can still continuously emit light for a period of time after

A SET OF MITOCHONDRIA-TARGETED COMPOUNDS

Here are described SkQ compounds containing cations of various types: alkyl(triphenyl)phosphonium cation, quaternary ammonium cations, including pH -dependent and permanent cations of rhodamines, berberine and palmatine alkaloids.

BODIPY-based high-sensitivity fluorescent probe and synthesis method and application thereof

The invention relates to a BODIPY-based high-sensitivity fluorescent probe and a synthesis method and application thereof. A structural general formula of the probe is shown as (I), wherein Trigger is stimulant triggering groups, R1 and R2 are groups for regulating and controlling fluorescent transmission wavelength of the probe and introducing organelle targeting, and R1 and R2 are defined in the description. By the probe, detection of different substrates can be realized without changing mother nucleus structure of the probe by only changing different Trigger groups. In addition, according to different needs on wavelength and targeting, the mother nucleus structure of the probe can be quickly modified. By changing R1 and R2, maximum fluorescent emission wavelength of the probe can be changed, and the probe can target mitochondrion to realize detection of active substances in the mitochondrion. The probe has good biocompatibility, thereby being applicable to detecting biological systems. Application value of the fluorescent probe in the aspect of detecting bioactive molecules and protease over-expressed in inflammatory or tumor tissue has potential social benefit and economic benefit.