Trimethylphosphine

Base Information

• Chemical Name: Trimethylphosphine
• CAS No.: 594-09-2
• Molecular Formula: C3H9P
• Molecular Weight: 76.0782
• Hs Code.: 29319090
• European Community (EC) Number: 209-823-1
• UNII: 5FL6SQK9H3
• DSSTox Substance ID: DTXSID00208120
• Nikkaji Number: J466I
• Wikipedia: Trimethylphosphine
• Wikidata: Q3268860
• Metabolomics Workbench ID: 55231
• Mol file: 594-09-2.mol

Synonyms:trimethyl phosphine

Chemical Property of Trimethylphosphine

Chemical Property:

• Appearance/Colour: colorless liquid
• Vapor Pressure: 7.24 psi ( 20 °C)
• Melting Point: -86 °C(lit.)
• Refractive Index: n20/D 1.428(lit.)
• Boiling Point: 40.5 °C at 760 mmHg
• Flash Point: ?4°F
• PSA: 13.59000
• Density: 0.738 g/cm³
• LogP: 1.35770
• Storage Temp.: 2-8°C
• Sensitive.: Air & Moisture Sensitive
• Water Solubility.: Soluble in water.
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 76.044187285
• Heavy Atom Count: 4
• Complexity: 8

Purity/Quality:

99% ^*data from raw suppliers

Trimethylphosphine >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-36/37/38-67-65-63-48/20-38-17-40-36/37-19
• Safety Statements: 9-16-26-36/37/39-62-36/37-7/9-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: CP(C)C
• Uses: Trimethylphosphine (PMe3) is an electron-rich phosphine ligand used as a reagent in Mitsunobu reaction.It can be used:In transformation of azides into carbamates; aziridines to azidoalcohols; and ketoximes to ketones with 2,2′-dipyridyl diselenide.In Aza-Wittig reaction;, C-H bond activation of imines; cross-coupling reactions.In the preparation of (cyanomethylene) trimethylphosphorane (CMMP) which is used as a reagent in Mitsunobu type reaction.As a reagent in the synthesis of ruthenium trimethylphosphine complexes, which in turn are used as catalysts for hydrogenation of CO2 to formic acid. Trimethylphosphine (PMe3) solution is the suitable reagent used in the synthesis of Fe/Te cluster type complex, Fe6Te8(PMe3)6. It may be employed as a probe to investigate the acid sites in Y-zeolite. It may be used for the synthesis of hexakis(trimethylphosphine)tris-μ-methylene-diruthenium(III). Trimethylphosphine is an electron-rich phosphine ligand used in the Mitsunobu reaction. It participates in the transformation of azides into carbamates, aziridines from azidoalcohols, iminophosphoranes and aza-Wittig reaction. This product is offered as a solution in 2-methyltetrahydrofuran for more convenient handling.

Technology Process of Trimethylphosphine

There total 188 articles about Trimethylphosphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

Re(C5H5)(CO)(NO)(CH3)(P(CH3)3)2 → (η5-C5H5)(CO)(NO)ReCH3 + trimethylphosphane (594-09-2)

Guidance literature:

In acetone; for 1 h; evapd. slowly under vacuo;

DOI:10.1021/ja00539a036

Reference yield: 81.0%

carbon disulfide (75-15-0,12122-00-8) + tetrakis(trimethylphosphine)nickel(0) (28069-69-4) → [nickel(0)(trimethylphosphine)3(η2-SCS)] + trimethylphosphane (594-09-2)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.ica.2012.09.002

Reference yield: 75.0%

trans-MoCl(NO)(PMe3)4 (119998-04-8) → MoCl(η3-S2CPMe3)(NO)(PMe3)2 (119998-14-0) + trimethylphosphane (594-09-2)

Guidance literature:

With CS₂; In tetrahydrofuran; Ar or N2 atmosphere; addn. of 1.4 equiv of CS2 to a soln. of Mo-complex, stirring (24 h at room temp.), pptn.; collection (filtration), washing (Et2O), crystn. (CHCl3), -30°C;

upstream raw materials:

methanol

carbon disulfide

methyl magnesium iodide

methylene chloride

Downstream raw materials:

benzyltrimethyl phosphonium bromide

benzyl-trimethyl-phosphonium; chloride

(2-hydroxyethyl)trimethylphosphonium chloride

Trimethyl-(phenyl-trimethylsilanyloxy-methyl)-phosphonium; chloride

Refernces

Palladium N(CH₂CH₂PiPr₂) ₂-Dialkylamides: Synthesis, structural characterization, and reactivity

10.1021/ic802286u

The study focuses on the synthesis, structural characterization, and reactivity of palladium(II) aminodiphosphine PNP pincer complexes, specifically the dialkylamides [PdR(PNP)] (where R is Cl, Me, Ph; PNP is (NCH2CH2PiPr2)2). These complexes were prepared and characterized to understand their role in C-N coupling reactions, which are significant in cross-coupling reactions like the Hartwig-Buchwald process. The chemicals used include palladium(II) salts, KOBu, AgPF6, TlPF6, MeOTf, PMe3, CNtBu, and various solvents like benzene, THF, and pentane. These reagents and solvents serve various purposes such as deprotonation, chloride abstraction, oxidation, and methylation reactions, as well as solvents for reactions and purification steps. The study aims to provide insights into the molecular structures, basicity (pKa values), and reactivity patterns of these complexes, which are crucial for understanding catalytic mechanisms in C-N bond formation. The results indicate that the palladium PNP dialkylamido complexes are stable, feature pyramidal nitrogen atoms, and exhibit reactivity towards electrophiles and oxidizing agents, with the reactivity being influenced by the nature of the ligands and the palladium-nitrogen bonding.

Hydride and borohydride derivatives of (pentamethylcyclopentadienyl)(tertiary phosphine)ruthenium

10.1021/om00150a032

The research focused on the synthesis and characterization of hydride and borohydride derivatives of (pentamethylcyclopentadienyl)(tertiary phosphine)ruthenium complexes. The purpose of this study was to explore the chemistry of middle- and late-transition-metal polyhydride complexes, which are of interest due to their potential as catalysts for H/D exchange reactions and C-H bond activation. The researchers successfully synthesized a series of trihydride complexes, (q5-C5Me5)RuH3(PR3), and tetrahydroborate complexes, (q5-C5Me5)Ru(PR3)(BH4), using various phosphine ligands (PR3) such as PMe3, PEt3, P(i-Pr)3, PCy3, PPh2Me, and PPh3. The synthesis involved the reaction of NaBH4 with (q5-C5Me5)RuCl2(PR3) in ethanol, and the resulting trihydrides were characterized by IR and 'H NMR spectroscopy. The study also included a single-crystal X-ray diffraction study of (q5-C5Me5)RuH3(PPh3), revealing its pseudo C3 symmetry. Additionally, the research investigated the photoinduced H/D exchange reaction under UV irradiation, which led to the exchange among the hydrides, coordinated phosphine, and solvent. The conclusions of the study provided insights into the structure and reactivity of these ruthenium complexes, contributing to the understanding of their potential applications in catalysis.