6415-07-2

Basic information

• Product Name: Tris(pyrrolidinophosphine) oxide
• Synonyms: LABOTEST-BB LT00847654;PHOSPHORIC ACID TRIPYRROLIDIDE;TRIS(PYRROLIDINO)PHOSPHINE OXIDE;TRIS(N,N-TETRAMETHYLENE)PHOSPHORIC ACID TRIAMIDE;TRIPYRROLIDINOPHOSPHINE OXIDE;Tri(N,N-tetra-Methylene) Phosphor Amide;TRIS(N N-TETRAMETHYLENE)PHOSPHORIC ACID TRIAMIDE 98+%;1,1',1''-Phosphinylidynetripyrrolidine
• CAS NO: 6415-07-2
• Molecular Formula: C₁₂H₂₄N₃OP
• Molecular Weight: 257.31
• EINECS: 229-118-2
• Mol File: 6415-07-2.mol

Chemical Properties

• Boiling Point: 140-142 °C0.1 mm Hg(lit.)
• Flash Point: 113 ºC
• Appearance: /
• Density: 1.120 g/mL at 20 °C(lit.)
• Vapor Pressure: 2.76E-06mmHg at 25°C
• Refractive Index: n20/D 1.514
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.89±0.20(Predicted)
• CAS DataBase Reference: Tris(pyrrolidinophosphine) oxide(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(pyrrolidinophosphine) oxide(6415-07-2)
• EPA Substance Registry System: Tris(pyrrolidinophosphine) oxide(6415-07-2)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 6415-07-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Tris(pyrrolidinophosphine) oxide is used as a competitive inhibitor for horse serum butyrylcholinesterase, which plays a crucial role in the regulation of neurotransmitter acetylcholine. By inhibiting this enzyme, it can potentially be used in the development of drugs targeting neurological disorders and conditions related to the cholinergic system.
Used in Chemical Research:
As a clear light yellow liquid with distinct chemical properties, Tris(pyrrolidinophosphine) oxide can be utilized in various chemical research applications. It may serve as a reagent, catalyst, or intermediate in the synthesis of other complex molecules, contributing to the advancement of chemical science and technology.
Used in Analytical Chemistry:
Due to its ability to inhibit horse serum butyrylcholinesterase, Tris(pyrrolidinophosphine) oxide can be employed in analytical chemistry for the development of assays and tests to measure the activity of this enzyme. This can be particularly useful in studying the effects of various compounds on the cholinergic system and in the development of new drugs targeting this system.

InChI:InChI=1/C12H24N3OP/c16-17(13-7-1-2-8-13,14-9-3-4-10-14)15-11-5-6-12-15/h1-12H2

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 128625-52-5 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 
• 875639-86-4 5-bromo-2-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-nicotinic acid 
• 124-40-3 dimethyl amine 
• 124-38-9 carbon dioxide 
• 161118-67-8 tert-butylimino-tri(pyrrolidino)phosphorane 
• 918871-51-9 3-(triisopropylsilyl)prop-2-yn-1-amine 
• 554-95-0 benzene-1,3,5-tricarboxylic acid 
• 132705-51-2 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 
• 4530-20-5 BOC-glycine 
• 123-75-1 pyrrolidine 

Downstream Products

• 132705-51-2 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 
• 139098-05-8 {UCl₃(tris(pyrrolidinyl)phosphine oxide)3}{Ph₄B} 
• 128625-52-5 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 

Relevant articles and documents

Enantioselective Total Synthesis and Structural Revision of Dysiherbol A

A 12-step total synthesis of the natural product dysiherbol A, a strongly anti-inflammatory and anti-tumor avarane meroterpene isolated from the marine sponge Dysidea sp., was elaborated. As key steps, the synthesis features an enantioselective Cu-catalyzed 1,4-addition/enolate-trapping opening move, an Au-catalyzed double cyclization to build up the tetracyclic core-carbon skeleton, and a late installation of the C5-bridgehead methyl group via proton-induced cyclopropane opening associated with spontaneous cyclic ether formation. The obtained pentacyclic compound (corresponding to an anhydride of the originally suggested structure for dysiherbol A) showed identical spectroscopic data as the natural product, but an opposite molecular rotation. CD-spectroscopic measurements finally confirmed that both the constitution and the absolute configuration of the originally proposed structure of (+)-dysiherbol A need to be revised.

SAR Matrices Enable Discovery of Mixed Efficacy μ-Opioid Receptor Agonist Peptidomimetics with Simplified Structures through an Aromatic-Amine Pharmacophore

We previously described the development of potent μ-opioid receptor (MOR)-agonist/?-opioid receptor (DOR)-antagonist peptidomimetic ligands as an approach toward effective analgesics with reduced side effects. In this series, a tetrahydroquinoline (THQ) or substituted phenyl is employed to link two key pharmacophore elements, a dimethyltyrosine amino acid and typically an aromatic pendant. Using new and previously reported analogues, we constructed a structure-activity relationship (SAR) matrix that probes the utility of previously reported amine pendants. This matrix reveals that the MOR-agonist/DOR-antagonist properties of these ligands do not change when a tetrahydroisoquinoline (THIQ) pendant is used, despite removal of substituents on the core phenyl ring. Based on this observation, we retained the THIQ pendant and replaced the phenyl core with simpler aliphatic chain structures. These simpler analogues proved to be potent MOR-agonists with high variability in their effects at the DOR and the κ-opioid receptor (KOR). These data show that the amine of the THIQ pendant may be a novel pharmacophore element that favors high MOR-efficacy, whereas the aromatic ring of the THIQ pendant may produce high MOR-potency. Combined, the two pharmacophores within the THIQ pendant may be a structurally efficient means of converting opioid peptides and peptidomimetics into potent and efficacious MOR-agonists.

Rapid Analysis of Tetrakis(dialkylamino)phosphonium Stability in Alkaline Media

Hydroxide-stable organic cations are crucial components for ion-transport processes in electrochemical energy systems, and the tetrakis(dialkylamino)phosphonium cation is a promising candidate for this application. These phosphoniums are known to be highly resistant to alkaline media; however, very few investigations have systematically evaluated how these cations decompose in the presence of hydroxide or alkoxide anions. The excellent stability of several tetraaminophosphoniums in 2 M KOH/CH3OH at 80 °C led us to design experiments for the rapid assessment of phosphonium degradation in homogeneous solution and under phase-transfer conditions. The analysis illustrated how substituents around the cation core affect both degradation pathways and rates. β-H elimination and direct attack at the phosphorus atom are the most common degradation pathways observed in an alcoholic solvent, while α-H abstraction and direct attack are observed under phase-transfer conditions (PhCl and 50 wt % NaOH/H2O). The collected data provided a relative stability comparison for this family of cations to enable future design improvements and illustrated the utility of using multiple tests for degradation studies.

The development of a versatile trifunctional scaffold for biological applications

We describe the synthesis of a trifunctional scaffold constructed from a planar core of trimesic acid derivatized with three propargylamine moieties. The scaffold was attached to a solid-phase resin through the carboxylic group of a fluorinated alkyl spacer arm. The orthogonal protection of two of the alkyne groups with triethylsilyl and triisopropylsilyl moieties enabled modular and efficient derivatization of the scaffold with three different azides by using solid-phase synthesis on amphiphilic ChemMatrix resin. We showed that a fluorine label can be used to quantify the content of fluorine-containing compounds by 19F NMR spectroscopic analysis after cleavage from the resin. We have thus designed a versatile and convenient tool that could be useful for simple and rapid solid-phase syntheses of combinatorial libraries of the scaffold-based compounds, for example as new protein binders. The development of a trifunctional scaffold derivatized with three orthogonally protected alkyne moieties that is useful for the solid-phase synthesis of combinatorial libraries is described.

Phosphazenes: Efficient organocatalysts for the catalytic hydrosilylation of carbon dioxide

Phosphazene superbases are efficient organocatalysts for the metal-free catalytic hydrosilylation of carbon dioxide. They react with CO2 to form the respective phosphine oxides, but in the presence of hydrosilanes, CO2 can be selectively reduced to silyl formates, which can in turn be reduced to methoxysilanes by addition of an extra loading of silanes. Activities reach a TOF of 32 h-1 with a TON of 759. It is also shown that unexpectedly, N,N-dimethylformamide can reduce CO2 to a mixture of silyl formates, acetals and methoxides in the absence of any catalyst.

Pyrrolo-pyridine kinase modulators

The present invention provides novel pyrrolo-pyridine kinase modulators and methods of using the novel pyrrolo-pyridine kinase modulators to treat diseases mediated by kinase activity.

Coupling N-Methylated Amino Acids Using PyBroP and PyCloP Halogenophosphonium Salts: Mechanism and Fields of Application

PyBroP (1) and PyCloP (2), two halotripyrrolidinophosphonium hexafluorophosphates, are peptidecoupling reagents highly efficient for coupling N-methylated amino esters, in contrast with PyBOP (3), the hydroxybenzotriazolyl analogue.These halogenophosphonium salts 1 and 2 are convenient (one-pot reactions) stable solids soluble in conventional solvents.Use of them gave an excellent peptide yield with essentially no epimerization.Activation with these reagents probably involves the formation of an (acyloxy)phosphonium, as shown in the case of 2,4,6-trimethylbenzoic acid activation.In the case of reagents 1 and 2, oxazolone and/or a symmetrical anhydride were intermediates which were rapidly aminolyzed.In contrast, the benzotriazolyl ester intermediate which was formed with PyBOP (3) was poorly reactive with N-methylated amino esters.PyBroP (1) and PyCloP (2) were less efficient in the coupling of some Boc-amino acids because of N-carboxyanhydride formation; this was particularly the case when Boc-Val-OH or Boc-MeVal-OH was coupled with MeVal-OMe.