1449-91-8

Basic information

• Product Name: Ethylidynetris(methyleneoxy)phosphine
• Synonyms: 4-Methyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane;4-Methyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane;Ethylidynetris(methyleneoxy)phosphine;Trimethylolethane cyclic phosphite
• CAS NO: 1449-91-8
• Molecular Formula: C₅H₉O₃P
• Molecular Weight: 148.1
• Mol File: 1449-91-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 122.7°C at 760 mmHg
• Flash Point: 25.1°C
• Appearance: /
• Vapor Pressure: 16.6mmHg at 25°C
• CAS DataBase Reference: Ethylidynetris(methyleneoxy)phosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Ethylidynetris(methyleneoxy)phosphine(1449-91-8)
• EPA Substance Registry System: Ethylidynetris(methyleneoxy)phosphine(1449-91-8)

Safety Data

• Hazardous Substances Data: 1449-91-8(Hazardous Substances Data)

Usage

Description

Ethylidynetris(methyleneoxy)phosphine, also known as ethylidene triphosphoramide, is a phosphine oxide with the molecular formula C5H15O3P. It is a versatile chemical compound that is known for its ability to form stable complexes with various metal ions. This unique property, along with its use as a ligand in the synthesis of organometallic and coordination compounds, makes Ethylidynetris(methyleneoxy)phosphine an important chemical in both inorganic and organic chemistry.

Uses

Used in Inorganic Chemistry:
Ethylidynetris(methyleneoxy)phosphine is used as a ligand for the synthesis of organometallic and coordination compounds. Its ability to form stable complexes with various metal ions makes it a valuable component in the development of new inorganic compounds with potential applications in various fields.
Used in Organic Synthesis:
Ethylidynetris(methyleneoxy)phosphine is used as a reagent in organic synthesis, particularly in the preparation of phosphorus-containing compounds. Its unique structure and reactivity contribute to the synthesis of a wide range of organic compounds, expanding the scope of chemical research and development.
Used in Pharmaceutical Industry:
Ethylidynetris(methyleneoxy)phosphine, due to its ability to form stable complexes with metal ions, can be used in the development of metal-based pharmaceuticals. Its potential applications in drug design and synthesis can lead to the discovery of new therapeutic agents with improved efficacy and selectivity.
Used in Material Science:
The unique properties of Ethylidynetris(methyleneoxy)phosphine, such as its ability to form stable complexes with metal ions, can be utilized in the development of advanced materials with specific properties. These materials can find applications in various industries, including electronics, energy storage, and catalysis.

InChI:InChI=1/C5H9O3P/c1-5-2-6-9(7-3-5)8-4-5/h2-4H2,1H3

Upstream product

• 77-85-0 2-(hydroxymethyl)-2-methylpropane-1,3-diol 
• 122-52-1 triethyl phosphite 
• 100277-68-7 C₂₃H₂₁O₉P₃ 
• 4579-03-7 2,6,7-trioxa-1,4-diphospha-bicyclo[2.2.2]octane 

Downstream Products

• 78-40-0 triethyl phosphate 
• 1449-89-4 4-methyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane 1-oxide 
• 3196-56-3 1-methyl-4-phospha-3,5,8-trioxa-bicyclo<2,2,2>octane-4-sulfide 
• 14095-06-8 Ni(CO)3P(OCH₂)3CCH₃ 
• 115889-91-3 fac-(4-methyl-2,6,7-trioxa-1-phodphabicyclo{2.2.2}octane)-1,2-bis(diphenylphosphino)ethaneMo(CO)3 
• 117119-84-3 {Cp*Re(CO)(P(OCH₂)3CMe)(p-N₂C₆H₄OMe)}{BF₄} 
• 14709-09-2 Ni(CO){P(OCH₂)3CCH₃}3 
• 139344-45-9 fac-(cis-1,5-bis((diphenylphosphino)-methyl)-3-oxabicyclo{3.3.0}octane-P,P')tricarbonyl(1-methyl-4-phospha-3,5,8-trioxabicyclo{2.2.2}octane-P)tungsten 
• 139344-46-0 fac-(cis-1,5-bis((diphenylphosphino)-methyl)-3-oxabicyclo{3.3.0}octane-P,P')tricarbonyl(1-methyl-4-phospha-3,5,8-trioxabicyclo{2.2.2}octane-P)tungsten 
• 85134-91-4 Fe(P(C₆H₅)3)(CH₃C(CH₂O)3P)(CO)2(C₆H₅NSO) 
• 85115-73-7 [Fe(MeC(CH₂O)3P)2(CO)2(4-NO₂C₆H₄NSO)] 

Relevant articles and documents

Visible light-induced homolytic cleavage of perfluoroalkyl iodides mediated by phosphines

In an effort to explain the experimentally observed variation of the photocatalytic activity of tBu3P, nBu3P and (MeO)3P in the blue-light regime [Helmecke et al., Org. Lett. 21 (2019) 7823], we have explored the absorption characteristics of several phosphine– and phosphite–IC4F9 adducts by means of relativistic density functional theory and multireference configuration interaction methods. Based on the results of these computational and complementary experimental studies, we offer an explanation for the broad tailing of the absorption of tBu3P-IC4F9 and (MeO)3P-IC4F9 into the visible-light region. Larger coordinate displacements of the ground and excited singlet potential energy wells in nBu3P-IC4F9, in particular with regard to the P–I–C bending angle, reduce the Franck–Condon factors and thus the absorption probability compared to tBu3P-IC4F9. Spectroscopic and computational evaluation of conformationally flexible and locked phosphites suggests that the reactivity of (MeO)3P may be the result of oxygen lone-pair participation and concomitant broadening of absorption. The proposed mechanism for the phosphine-catalyzed homolytic C–I cleavage of perfluorobutane iodide involves S1 ←S0 absorption of the adduct followed by intersystem crossing to the photochemically active T1 state.

A Study of the Polarities, Anisotropic Polarisabilities and Carbonyl Infrared Vibrational Frequencies of the Complexes > (M=Cr, Mo or W) and the Crystal Structure of >: Evidence for ?-Acceptor Behaviour in Co-ordinated Phosphorus

Studies of electric dipole moments, electric birefringences, carbonyl infrared frequencies and interatomic bond distances provide mutually reinforcing evidence for ?-acid behaviour of the bicyclic phosphite ligand in > complexes (M = Cr, Mo or W).Molecular optical anisotropies and directional polarisabilities from experiment are analysed to show strong polarisability enhancement along the molecular symmetry axis and concomitant diminution of polarisability perpendicular to that axis, relative to a hypothetical ?-bonded P-M model.The results provide evidence for a highly deformable ?-component in the phosphorus-metal bonding and for a ?-delocalised P-M-CO(trans) system.Comparisons are made with other compounds where L = quinuclidine, PMe3 or PCl3.The crystal structure of > is reported and bond dimensions are compared with those of related molybdenum complexes.

Effects of Molecular Structure on basicity. Gas-Phase Proton Affinities of Cyclic Phosphites

The proton affinities of several monocyclic and bicyclic phosphite esters are determined by ion cyclotron resonance spectroscopy.The order of proton affinities is identical with the solution basicity order reported earlier.Thus, increasing steric constraint decreases the proton affinity of the phosphorus lone pair in phosphites.Moreover, the phosphorus lone pair in monocyclic six-membered-ring phosphites is more basic in the axial than in the equatorial position.Adiabatic ionization potentials are obtained from photoelectron spectra of the phosphites.Increases in ionization potential are found to parallel decreases in proton affinity.This relationship between the ionization potential and proton affinity suggests that the first ionization potential of the phosphites corresponds to ionization from the phosphorus lone pair orbital.These trends are rationalized in terms of changes in the interactions of the oxygen lone pair orbitals with the phosphorus lone pair and ?-bonding orbitals.

NOVEL HIGH-YIELD TRANSESTERIFICATION AND TRANSAMINATION ROUTES TO P(OCH2)3CCH3 AND P3CCH3, RESPECTIVELY

High yields (93-96percent) in a one-step syntheses of CH3C(CH2OP(o-O2C6H4))3 (3), (4) and (5) are reported.Compounds 4 and 5 at 100-110o give P(OCH2)3CCH3 (2) and P(N(CH3)CH2)3CCH3 (7) in 97 and 96percent yield, respectively, plus the diphosphite (CH3)2C(CH2O)2POCH2C(CH3)2CH2OP(OCH2)2C(CH3)2 (8).Compound 8 was also characterized as its dithiophosphate derivative.Experiments designed to synthesize the adamantane-like P(OCH)3(CH2)3 (9) and P(CH2O)3P (10) in an analogous manner met with only partial success.The tris-phosphate analogue of 4 was also synthesized but it did not thermolyze to OP(OCH2)3CCH3 under the conditions used for 4 and 5 even after prolonged heating.