593-54-4

Usage

Uses

Used in Chemical Industry:
Methylphosphin is used as a chemical intermediate for the production of agricultural chemicals, pharmaceuticals, and flame retardants. Its reactivity and ability to form stable compounds with other elements contribute to its wide range of applications in this industry.
Used in Catalysts:
Methylphosphin is used as a catalyst in various chemical reactions. Its ability to facilitate and speed up chemical processes without being consumed in the reaction makes it a valuable component in the production of various chemicals and materials.
Used in Organic Synthesis:
Methylphosphin is used as a reagent in organic synthesis. Its unique chemical properties allow it to participate in a variety of organic reactions, enabling the synthesis of complex organic compounds and molecules.
Safety Precautions:
Due to its toxic and flammable nature, methylphosphin should be handled with caution and appropriate safety measures. Proper handling, storage, and disposal protocols must be followed to minimize the risk of exposure and accidents.

InChI:InChI=1/CH5P/c1-2/h2H2,1H3

Upstream product

• 74-87-3 methylene chloride 
• 67-66-3 chloroform 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 
• 3167-63-3 diethyl chloromethylphosphonate 
• 7803-51-2 phosphan 
• 10419-85-9 diphenyl (chloromethyl)phosphonate 
• 41948-89-4 Dimethyl-<α-(ethoxy)-ethyliden>-ammonium-Ion 
• 756-79-6 dimethyl methane phosphonate 
• 121-45-9 phosphorous acid trimethyl ester 
• 67-56-1 methanol 
• 1660-95-3 Tetraisopropyl methylenediphosphonate 
• 17579-99-6 methyltriphenoxyphosphonium iodide 
• 108-88-3 toluene 

Downstream Products

• 5573-52-4 Bis-diethylamino-(methyl-phosphino)-methyl-silan 
• 10103-00-1 (2-Chloro-1,1,3,3-tetrafluoro-allyl)-methyl-phosphane 
• 54772-60-0 1-[Methyl-(2-phosphanyl-ethyl)-phosphanyl]-2-phosphanyl-ethane 
• 5573-48-8 Bis--methyl-phosphin 
• 5573-53-5 Diaethylamino-dimethyl--silan 
• 5573-54-6 Bis--methyl-phosphin 
• 5573-50-2 Bis--methyl-phosphin 
• 67373-54-0 [Dimethyl-(1,1,2-trimethyl-propyl)-silanyl]-methyl-phosphane 
• 67373-55-1 1,1,2,3,3-Pentamethyl-1,3-bis-(1,1,2-trimethyl-propyl)-disilaphosphane 
• 63578-31-4 1,1,7,7-tetra(dimethylamino)-4-methyl-1,4,7-phospha-heptane 
• 75877-14-4 1,2,2,3,3,4,4,5,5-Nonamethyl-[1,2,3,4,5]phosphatetrasilolane 
• 75877-12-2 1,2,2,3,3,4,4,5,5,6,6,7,7-Tridecamethyl-[1,2,3,4,5,6,7]phosphahexasilepane 
• 75877-13-3 1,2,2,3,3,4,4,5,5,6,6-Undecamethyl-[1,2,3,4,5,6]phosphapentasilinane 
• 73727-00-1 Diphenyl<3-(methylphosphino)propyl>phosphin 

Relevant academic research and scientific papers

Gas-Phase Chemistry of H2P(-)

The gas-phase ion-molecule chemistry of H2P(-) has been investigated by using the flowing afterglow technique.Generated by proton abstraction from PH3 by H2N(-) or OH(-), H2P(-) reacts with N2O, CO2, OCS, CS2, O2, NO2, SO2, CH3X, and (CH3)3SiCl to yield a variety of ion products.Products usually arise from initial nucleophilic attack of H2P(-) on the neutral, followed by intramolecular proton transfer and/or expulsion of a neutral fragment.Many of the reactions are similar to those for H2N(-), though differences are attributable to the weaker nucleophilicity of H2P(-).Product branching ratios and reaction rate constants are reported, and possible mechanistic pathways are discussed.

ANTI-BACTERIAL COMPOUNDS BASED ON AMINO-GOLD PHOSPHINE COMPLEXES

A compound of formula (I) for use in the prevention or treatment of a bacterial infection wherein: PX is selected from the group consisting of (P1), (P2) and (P3).

Synthesis, photoelectron spectroscopy and quantum chemical study of kinetically unstabilized phosphines complexed by borane

Ethynyl- and allenylphosphine-boranes have been prepared by addition at low temperature of borane on the free phosphine. Purification was performed by selective trapping in vacuo and the complexes were characterized by NMR and infrared spectroscopy and ma

The Ever-surprising chemistry of boron: Enhanced acidity of phosphine·boranes

The gas-phase acidity of a series of phosphines and their corresponding phosphine·borane derivatives was measured by FT-ICR techniques. BH 3 attachment leads to a substantial increase of the intrinsic acidity of the system (from 80 to 110 kJ mol-1). This acidity-enhancing effect of BH3 is enormous, between 13 and 18 orders of magnitude in terms of ionization constants. This indicates that the enhancement of the acidity of protic acids by Lewis acids usually observed in solution also occurs in the gas phase. High- level DFT calculations reveal that this acidity enhancement is essentially due to stronger stabilization of the anion with respect to the neutral species on BH3 association, due to a stronger electron donor ability of P in the anion and better dispersion of the negative charge in the system when the BH3 group is present. Our study also shows that deprotonation of ClCH2PH2 and ClCH 2PH2·BH3 is followed by chloride departure. For the latter compound deprotonation at the BH3 group is found to be more favorable than PH2 deprotonation, and the subsequent loss of Cl- is kinetically favored with respect to loss of Cl - in a typical SN2 process. Hence, ClCH2PH 2·BH3 is the only phosphine·borane adduct included in this study which behaves as a boron acid rather than as a phosphorus acid.

More user-friendly phosphines? Molecular structure of methylphosphine and its adduct with borane, studied by gas-phase electron diffraction and quantum chemical calculations

The molecular structures of methylphosphine (CH3PH2) and methylphosphine-borane (CH3PH2?BH3) have been determined from gas-phase electron diffraction data and rotational constants, employing the SARACEN method. The experimental geometric parameters generally showed a good agreement with those obtained using ab initio calculations and previous microwave spectroscopy studies. In order to assess the accuracy of the calculated structures a range of ab initio methods were used, including the CCSD(T) method, with correlation-consistent basis sets. The structural environment around the phosphorus atom was found to change significantly upon complexation with borane, with the P-C bond length shortening and the bond angles widening. The Royal Society of Chemistry 2008.

B(C6F5)3-catalyzed silylation versus reduction of phosphonic and phosphinic esters with hydrosilanes

HSiR3/cat-B(C6F)3 induced dealkylation or reduction of esters of phosphorus at 20°C. A specific conversion to silylesters occurred by reaction with tertiary silanes. In contrast, free phosphines were observed in the reaction with mono- or disubstituted silanes. A mechanism was proposed to rationalize these results.

Reaction of dichlorophosphines with glycidol. New data on the transformations of cyclic phosphonates

Reaction of dichlorophosphines with glycidol yields 2-R-4-chloromethyl-1,3,2-dioxaphospholanes as primary products, which under the reaction conditions or under the action of HC1 surprisingly readily undergo redox transformations yielding 2-R-4-chloromethyl-1,3,2-dioxaphospholane 2-oxides, dichloropropyl R-phosphinates, bis(dichloropropyl) R-phosphonates, and phosphines RPH2.

P-H bond activation of primary phosphine-boranes: Access to α-hydroxy and α,α′-dihydroxyphosphine-borane adducts by uncatalyzed hydrophosphination of carbonyl derivatives

Primary P-phenyl and P-methyl phosphine-boranes 1 and 2 are prepared by complexation of the free phosphines with BH3 · SMe2. They are stable and can be purified by distillation. Under basic conditions, they lead selectively to secondary alkylphosphine-boranes and under neutral conditions to the corresponding mono- and bis-hydroxyphosphine-boranes 5 and 6. All these new compounds are purified by chromatography on silica gel. A competitive hydroboration induced by the decomplexation of BH3 is observed as a minor process. Conditions for the decomplexation of phosphine-borane adducts are presented.

Synthesis of Primary and Secondary Phosphines by Selective Alkylation of PH3 under Phase Transfer Conditions

Primary phosphines, RPH2, may be synthesized selectively by alkylation of phosphine, PH3, with alkyl halides RX (R = Me, Et, n-Bu, 2-Bu, C16H33, CH2=CH-CH2, Ph-CH2, 2-Py-CH2-CH2; X = Cl, Br) and concentrated aqueous KOH as auxilliary base in dimethylsulfoxide as a solvent or in two phase systems employing phase transfer catalysts.Under more rigorous conditions secondary phosphines R2PH (R = Me, n-Bu, CH2=CH-CH2) are also acessible in good yields.Using 1,3-dibromo(chloro)-propane or -butane diprimary phosphines H2P-(CH2)2-CHR-PH2 (R = H, Me) are obtaines, while 1,4-dibromopentane in a high yield cyclization reaction leads to 2-methylphospholane (12) with a chiral C-atom in α-position.

SYNTHESIS OF PRIMARY α-CHLOROPHOSPHINES BY A CHEMOSELECTIVE REDUCTION OF α-CHLOROPHOPHONATES

Reduction of chloromethylphosphonates with lithium aluminium hydride gave a mixture of chloromethylphosphine and methylphosphine, characterized by NMR, IR and mass spectra.Reduction of the same compounds by AlH3 gave chloromethylphosphine as nearly the only product.Extension of this reaction to the C-substituted derivatives gave the correspondeng α-chlorophosphines with good chemoselectivity.Keywords: Reduction of phosphonates; aluminium hydride; chemoselectivity; primary phosphines.