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:

98%,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

[Me₃PPPh₂][Cl]

Refernces

• 1、 Alt, Helmut G.,Schwind, Karl-Heinz,Rausch, Marvin D.,Thewalt, Ulf. "Formation and reactivity of the ethylene complex Cp2TiC2H4. The crystal structure of (Cp2TiEt)2O". . p. C7 - C10. Retrieved 1988.
• 2、 Abe, Naoya,Abe, Takayuki,Gunji, Takahiro,Nakashima, Satoru,Tsukada, Satoru,Yamamoto, Kazuki. "Benzenedithiolate-bridged MoFe complexes: Structures, oxidation states, and reactivities". . p. 9048 - 9056. Retrieved 2020.
• 3、 Rehbein, Steven M.,Kania, Matthew J.,Neufeldt, Sharon R.. "Experimental and Computational Evaluation of Tantalocene Hydrides for C-H Activation of Arenes". . p. 2666 - 2677. Retrieved 2021.
• 4、 Kurtikyan, Tigran S.,Hovhannisyan, Astghik A.,Ford, Peter C.. "Six-Coordinate Ferrous Nitrosyl Complex FeII(TTP)(PMe3)(NO) (TTP = meso-Tetra-p-tolylporphyrinato Dianion)". . p. 9517 - 9520. Retrieved 2016.
• 5、 Casey, Charles P.,Jones, William D.. "". . p. 6154 - 6156. Retrieved 1980.
• 6、 García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.. "A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics". supporting information. . Retrieved 2022/01/04.