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
• Article Data: 7

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

Description

Tris(pyrrolidinophosphine) oxide, also known as Tris(N,N-tetramethylene)phosphoric Acid Triamide, is a clear light yellow liquid with unique chemical properties. It is a versatile compound that has found applications in various fields due to its ability to act as a competitive inhibitor of horse serum butyrylcholinesterase.

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

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.

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.

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.