15715-41-0

Basic information

• Product Name: Methyldiethoxyphosphine
• Synonyms: DIETHOXYMETHYLPHOSPHINE;DIETHYL METHYLPHOSPHONITE;METHYLDIETHOXYPHOSPHINE;O,O-diethyl methylphosphonite;Methyldiethoxyphosphine,99%;METHYL-PHOSPHONOUS ACI DIETHYL ESTER;Methylphosphonous acid diethyl ester;diethoxy(methyl)phosphane
• CAS NO: 15715-41-0
• Molecular Formula: C₅H₁₃O₂P
• Molecular Weight: 136.13
• EINECS: 239-805-9
• Product Categories: Phosphorus compounds
• Mol File: 15715-41-0.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 124.497 °C at 760 mmHg
• Flash Point: 38°C
• Appearance: /Liquid
• Density: 0,9 g/cm3
• Vapor Pressure: 15.4mmHg at 25°C
• Refractive Index: 1.4168
• Storage Temp.: 2-8°C
• Water Solubility: It slowly hydrolyses in water.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: Methyldiethoxyphosphine(CAS DataBase Reference)
• NIST Chemistry Reference: Methyldiethoxyphosphine(15715-41-0)
• EPA Substance Registry System: Methyldiethoxyphosphine(15715-41-0)

Safety Data

• Hazard Codes: Xn
• Statements: 10-36/37/38-22
• Safety Statements: 16-26-36/37/39
• RIDADR: 1993
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 15715-41-0(Hazardous Substances Data)

Usage

Description

Methyldiethoxyphosphine, also known as Dimethyl methylphosphonate, is a phosphonite reagent derived from the chemical synthesis of various organic compounds. It possesses unique chemical properties that make it a versatile building block in the pharmaceutical and chemical industries. Its phosphonite group allows for the formation of phosphinic acid derivatives and its chiral nature makes it a valuable intermediate in the synthesis of complex molecules.

Uses

Used in Pharmaceutical Industry:
Methyldiethoxyphosphine is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its chiral nature and reactivity make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Chemical Synthesis:
Methyldiethoxyphosphine is used as a cyclization reagent in the preparation of 2-substituted penems, a class of β-lactam antibiotics. Its ability to form phosphinic acid derivatives via the Arbuzov reaction makes it a valuable building block in the synthesis of complex organic molecules.
Used in Research and Development:
Methyldiethoxyphosphine is used as a chiral intermediate in the development of new chemical processes and methodologies. Its unique properties and reactivity make it an important tool for researchers in the field of organic chemistry and drug discovery.

InChI:InChI=1/C5H13O2P/c1-4-6-8(3)7-5-2/h4-5H2,1-3H3

Synthetic route

ethanol (64-17-5) + methyldichlorophosphane (676-83-5) → methyldiethoxyphosphine (15715-41-0)

Conditions	Yield
With triethylamine In Petroleum ether at 25 - 60℃; for 1.5h; Time; Flow reactor; Large scale;	98%
Stage #1: ethanol With calcium oxide In 1,3,5-trimethyl-benzene for 2h; Reflux; Stage #2: methyldichlorophosphane In 1,3,5-trimethyl-benzene at 0 - 30℃; for 4h; Temperature; Solvent; Inert atmosphere;	96.7%
at 10 - 120℃; for 0.0833333h; Temperature; Inert atmosphere;	96%

diethyl phosphorylchloridite (589-57-1) + methylmagnesium chloride (676-58-4) → methyldiethoxyphosphine (15715-41-0)

Conditions	Yield
Stage #1: diethyl phosphorylchloridite; methylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 2h; Inert atmosphere; Stage #2: With dibutyl ether; benzylamine In tetrahydrofuran at -5℃; for 10h; Reagent/catalyst; Temperature;	89.3%
In tetrahydrofuran at 0℃; for 2.5h; Temperature;
In tetrahydrofuran at -10 - -5℃; Inert atmosphere;	10.15 g

diethyl phosphorylchloridite (589-57-1) + methyl magnesium iodide (917-64-6) → methyldiethoxyphosphine (15715-41-0)

Conditions	Yield
In diethyl ether	60%

diethyl peroxide (628-37-5) + 1,3,4-trimethyl-Δ3-phospholene (14410-05-0) → methyldiethoxyphosphine (15715-41-0) + Diethyl methylphosphonate (683-08-9) + tetraethoxy-methyl-λ5-phosphane (34736-63-5) + 1,3,4-trimethyl-Δ3-phospholene oxide (15450-80-3) + 1,3,4-trimethyl-2,3-dihydro-1H-phosphole 1-oxide (15450-82-5)

Conditions	Yield
In [D3]acetonitrile for 1.91667h; Rate constant; Product distribution; further reaction times;	A 10 % Spectr. B 6 % Spectr. C 15 % Spectr. D 7 % Spectr. E n/a

diethyl phosphorylchloridite (589-57-1) + methylmagnesium bromide (75-16-1) → methyldiethoxyphosphine (15715-41-0)

Conditions	Yield
In diethyl ether at -12 - 0℃; for 16h;	30.4 g
In diethyl ether -20 deg C then r.t., 1 h;

methylmagnesium bromide (75-16-1) + triethyl phosphite (122-52-1) → methyldiethoxyphosphine (15715-41-0)

diethyl phosphorylchloridite (589-57-1) + methylene chloride (74-87-3) → methyldiethoxyphosphine (15715-41-0)

Conditions	Yield
Stage #1: methylene chloride With magnesium In tetrahydrofuran; toluene for 2h; Stage #2: diethyl phosphorylchloridite In tetrahydrofuran; toluene at 15 - 30℃; for 6h; Solvent; Temperature;

ethanol (64-17-5) + trichloro-methyl-phosphonium; compound of chloride with aluminium chloride → methyldiethoxyphosphine (15715-41-0)

Conditions	Yield
With aluminium at -10 - 150℃; for 2h; Temperature;	71.62 g

methyldiethoxyphosphine (15715-41-0) → ethyl methylphosphinate (16391-07-4)

Conditions	Yield
With water at 22℃; for 17h;	100%
With water at 5 - 20℃; for 18h;
In water at 0 - 22℃; for 17h;
With water; hexadecyltributylammonium chloride; sodium chloride at -5 - 0℃; Inert atmosphere;	8.8 g
With water at 20℃; for 18h; Inert atmosphere;

methyldiethoxyphosphine (15715-41-0) + 1-Chloromethylnaphthalene (86-52-2) → C14H17O2P (936366-26-6)

Conditions	Yield
for 2.5h; Heating;	100%

methyldiethoxyphosphine (15715-41-0) + butan-1-ol (71-36-3) → butyl methylphosphinate (6172-80-1)

Conditions	Yield
Stage #1: methyldiethoxyphosphine; butan-1-ol In water; toluene at 45 - 50℃; for 5h; Inert atmosphere; Stage #2: With tetrabutoxytitanium In water; toluene Reflux;	98.26%
With Amberlyst 15 In water; toluene at 50 - 140℃; Inert atmosphere;	97.9%

ethyl 6-chloro-6-oxohexanoate (1071-71-2) + methyldiethoxyphosphine (15715-41-0) → 5-Ethoxy-adipyl-P-methyl-phosphinsaeure-O-ethylester (115693-04-4)

Conditions	Yield
at 30℃;	98%

methyldiethoxyphosphine (15715-41-0) + [(E)-(R)-4-[(1R,2R,3S,5R)-2-((Z)-6-Bromo-hex-2-enyl)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyloxy]-benzene (380153-45-7) → (6-{3,5-bis(tert-butyldimethylsilanoylxy)-2-[3-(tert-cutyldimethylsilanoylxy)-4-phenoxybut-1-enyl]cyclopentyl}-hex-4-enyl)methylphosphinic acid ethyl ester (380153-32-2)

Conditions	Yield
In toluene at 145℃; for 22h; Arbuzov reaction;	98%

methyldiethoxyphosphine (15715-41-0) + 4-bromomethylphenylboronic acid pinacol ester (138500-85-3) → ethyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphinate (1273492-75-3)

Conditions	Yield
In 1,4-dioxane at 100℃; for 1h; Inert atmosphere;	98%

methyldiethoxyphosphine (15715-41-0) + (S)-tert-butyl 3-((4-(7-bromo-1H-indol-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)piperidine-1-carboxylate → (S)-tert-butyl 3-((4-(7-(ethoxy(methyl)phosphoryl)-1H-indol-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine In N,N-dimethyl-formamide at 130℃; for 0.0833333h; Sealed tube; Microwave irradiation;	98%

methyldiethoxyphosphine (15715-41-0) + tert-Butyl acrylate (1663-39-4) → C10H21O4P

Conditions	Yield
With acetic acid at 70 - 75℃; for 4h; Inert atmosphere;	97.6%

methyldiethoxyphosphine (15715-41-0) + acrylic acid methyl ester (292638-85-8) → methyl 3-(methylethoxyphosphoryl)propionate

Conditions	Yield
With acetic acid at 5 - 20℃; for 2h;	96.3%

methyldiethoxyphosphine (15715-41-0) + 1-bromomethyl-3-methoxy-4-nitrobenzene (23145-65-5) → (3-methoxy-4-nitrobenzyl)-methyl phosphonic acid ethyl ester (1257996-50-1)

Conditions	Yield
In toluene for 16h; Reflux;	96%

methyldiethoxyphosphine (15715-41-0) + ethyl acrylate (140-88-5) → ethyl 3-(ethoxymethylphosphinyl)propionate (15090-27-4)

Conditions	Yield
In ethanol at 5℃; for 2h;	95.8%
With acetic acid at 5 - 25℃; for 2.5h; Inert atmosphere;	95%

pentan-1-ol (71-41-0) + methyldiethoxyphosphine (15715-41-0) → pentyl hydrogen methylphosphonite (87025-52-3)

Conditions	Yield
With sulfuric acid In water at 50℃; Reflux;	95.8%

methyldiethoxyphosphine (15715-41-0) + ethyl 2-iodobenzoate (1829-28-3) → o-ethoxycarbonylphenyl-methylphosphinic acid ethyl ester (57020-81-2)

Conditions	Yield
With nickel dichloride at 170℃;	95%

methyldiethoxyphosphine (15715-41-0) + C26H33BrO3Si (1215320-42-5) → C29H41O5PSi (1215320-44-7)

Conditions	Yield
at 110℃; for 17h; Michaelis-Arbuzov reaction;	95%

ethanol (64-17-5) + methyldiethoxyphosphine (15715-41-0) + acetic anhydride (108-24-7) + acrolein (107-02-8) → 1-acetoxy-1-ethoxy-3-(ethoxy(methyl)phosphinyl)propane

Conditions	Yield
at 25 - 30℃; for 2.33333h; Inert atmosphere;	95%

methyldiethoxyphosphine (15715-41-0) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 2-(ethoxy(methylphosphoryl))acetaldehyde diethyl acetal

Conditions	Yield
In ethanol at 80 - 100℃; for 24h; Solvent;	95%
In toluene at 110℃; for 4h; Arbuzov Reaction;	91%

methyldiethoxyphosphine (15715-41-0) + trimethylammonium methylformamide → O-ethyl-formyl-aminomethyl-methylphosphinate

Conditions	Yield
	94%

methyldiethoxyphosphine (15715-41-0) + 1-bromo-5,9-bis[N-(2-mesitylene)sulfonyl]-12-{N-ethyl-N-[(2-mesitylene)sulfonyl]}amino-5,9-diazadodecane → {4-[{3-[{3-[Ethyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-propyl}-(2,4,6-trimethyl-benzenesulfonyl)-amino]-propyl}-(2,4,6-trimethyl-benzenesulfonyl)-amino]-butyl}-methyl-phosphinic acid ethyl ester

Conditions	Yield
at 125℃; for 3h;	94%

2-bromomethyl-1,3-dioxolane (4360-63-8) + methyldiethoxyphosphine (15715-41-0) → 2-(ethoxy(methylphosphoryl))acetaldehyde ethylene acetal

Conditions	Yield
In toluene at 110℃; for 5h; Inert atmosphere;	93.8%
at 120℃; for 2h; Arbuzov Reaction;	82.6%

4-acetoxy azetidinone (28562-53-0) + methyldiethoxyphosphine (15715-41-0) → O-ethyl(4-oxoazetidin-2-yl)methylphosphinate (84673-24-5)

Conditions	Yield
at 60℃; for 1h;	93%
at 60℃; for 1h;	89%

methyldiethoxyphosphine (15715-41-0) + C9H16ClNO4 → C12H24NO6P

Conditions	Yield
With lanthanum(III) chloride at 140℃; for 10h; Reagent/catalyst; Temperature; Inert atmosphere;	91.3%

1,1-dimethylethyl [4-(bromomethyl)-1,3-thiazol-2-yl]carbamate (1001419-35-7) + methyldiethoxyphosphine (15715-41-0) → C12H21N2O4PS (1001419-75-5)

Conditions	Yield
In tetrahydrofuran at 75℃; for 16h;	91%

methyldiethoxyphosphine (15715-41-0) + C11H20ClNO4 → C14H28NO6P

Conditions	Yield
With tetrabutylammomium bromide; magnesium bromide In water at 140℃; for 15h; Temperature; Solvent; Reagent/catalyst;	90.2%

methyldiethoxyphosphine (15715-41-0) + 4-bromo-2-phthalimidobutyric acid methyl ester (122690-13-5) → METHYL DL-2-(1,3-DIHYDRO-1,3-DIOXO-2H-ISOINDOL-2-YL)-4-(ETHOXYMETHYLPHOSPHINYL)BUTANOATE (109541-73-3)

Conditions	Yield
In toluene at 100℃;	90%

methyldiethoxyphosphine (15715-41-0) + 6-Bromohexanoic Acid Phenylamide (7661-21-4) → methyl-(5-phenylcarbamoyl-pentyl)-phosphinic acid ethyl ester (606092-26-6)

Conditions	Yield
at 120℃; for 10h;	89%
at 120℃; for 10h; Arbuzov reaction;	200 mg

methyldiethoxyphosphine (15715-41-0) + ethyl 2-oxo-3-butenoate (134745-23-6) → ethyl 4-(methylethoxyphosphoryl)-2-oxobutanoate

Conditions	Yield
at 5℃; for 8h; Inert atmosphere;	87.8%

methyldiethoxyphosphine (15715-41-0) + Methyl-3-oxo-pentenoat (108736-44-3) → methyl 4-(methylethoxyphosphoryl)-2-oxobutanoate

Conditions	Yield
In tetrahydrofuran at 5℃; for 6h; Inert atmosphere;	87.1%

methyldiethoxyphosphine (15715-41-0) + 2-decarboxy-2-iodoprostaglandin F2α triacetate (252858-13-2) → 2-decarboxy-2-(O-ethyl-P-methylphosphinico)prostaglandin F2α triacetate (380153-41-3)

Conditions	Yield
In toluene at 100℃; for 6h; Arbuzov reaction;	86%

Upstream product

• 64-17-5 ethanol 
• 676-83-5 methyldichlorophosphane 
• 589-57-1 diethyl phosphorylchloridite 
• 75-16-1 methylmagnesium bromide 
• 122-52-1 triethyl phosphite 
• 676-58-4 methylmagnesium chloride 
• 74-87-3 methylene chloride 
• 628-37-5 diethyl peroxide 
• 14410-05-0 1,3,4-trimethyl-Δ³-phospholene 
• 917-64-6 methyl magnesium iodide 

Downstream Products

• 64654-41-7 Methyl-phosphonic acid (Z)-2-chloro-1-(4-chloro-phenyl)-vinyl ester ethyl ester 
• 64654-38-2 Methyl-phosphonic acid (Z)-2-chloro-1-(2,5-dichloro-phenyl)-vinyl ester ethyl ester 
• 64654-37-1 Methyl-phosphonic acid (E)-2-chloro-1-(2,4,6-trichloro-phenyl)-vinyl ester ethyl ester 
• 58656-46-5 3-(2,6-dimethyl-phenyl)-2,2-diethoxy-2-methyl-2,3-dihydro-2λ⁵-benzo[1,3,2]oxazaphosphole 
• 59986-65-1 Methyl-phosphonic acid (Z)-2-chloro-1-(2,4-dichloro-phenyl)-vinyl ester ethyl ester 
• 58656-52-3 2,2-diethoxy-2-methyl-3-phenyl-2,3-dihydro-2λ⁵-benzo[1,3,2]oxazaphosphole 
• 64654-35-9 Methyl-phosphonic acid 2,2-dichloro-1-(2,4-dichloro-phenyl)-vinyl ester ethyl ester 
• 64654-14-4 Methyl-phosphonic acid (Z)-2-chloro-1-(2,4,5-trichloro-phenyl)-vinyl ester ethyl ester 
• 64654-36-0 Methyl-phosphonic acid 2,2-dichloro-1-(4-chloro-phenyl)-vinyl ester ethyl ester 
• 64654-13-3 Methyl-phosphonic acid 2,2-dichloro-1-(2,5-dichloro-phenyl)-vinyl ester ethyl ester 
• 33032-30-3 C₁₂H₂₁NO₄P₂ 
• 64654-34-8 Methyl-phosphonic acid 2,2-dichloro-1-(2,4,5-trichloro-phenyl)-vinyl ester ethyl ester 
• 64654-33-7 Methyl-phosphonic acid 2,2-dichloro-1-(2,4,6-trichloro-phenyl)-vinyl ester ethyl ester 
• 51276-47-2 DL-homoalanin-4-yl(methyl)phosphinic acid 

Relevant articles and documents

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Synthesis method and synthesis device of diethyl methylphosphite

The invention relates to a synthesis method and a synthesis device of diethyl methylphosphite. The synthesis method comprises the following steps: (1) mixing methyl phosphine dichloride, absolute ethyl alcohol and a solvent to carry out a synthesis reaction; (2) carrying out reduced pressure deacidification treatment on the reaction solution obtained in the step (1); and (3) separating and purifying the deacidified reaction solution obtained in the step (2) to obtain diethyl methylphosphite. According to the synthesis method, an acid-binding agent is not needed, hydrogen chloride gas generatedby the synthesis reaction can be discharged through reduced-pressure deacidification treatment, the generation of solid waste residues containing acid-binding agent hydrochloride is avoided, the separation and treatment of the solid waste residues are reduced, and the dosage of ethanol is reduced by adding a solvent, so that the ethanol does not need to play a role as a solvent, the energy consumption is reduced, the resources are saved, the process is high in yield, simple to operate and environment-friendly, and the atom economy is good.

A method for preparing methyl asia phosphine acid diethyl ester (by machine translation)

The invention discloses a method for preparing methyl asia phosphine acid diethyl ester, aims to solve the problems in the existing method, when using ammonia gas as acid, pH value of the reaction solution in the need to control the 7.0 - 8.5 between, accurate control of the pH value is very difficult, and is lower than the pH value, will produce a large number of methyl inferior phosphine acid ethyl ester by-product, the use of the organic amine do capture, there is caused a large toxicity, high price, the recovery process is tedious, the recovery rate is low. The present invention relates to methyl-phosphine, ethanol and calcium oxide as the main raw material, process for preparing methyl asia phosphine acid diethyl ester is obtained, which is a low-cost, is suitable for the industrial production of methyl asia phosphine acid diethyl ester preparation method. The invention in the preparation of the methyl asia phosphine acid diethyl ester, for the first time the adoption of the calcium oxide to replace the ammonia or organic amine as capture, effectively reduces the production cost, and the calcium oxide is non-toxic, is friendly to the environment, and has a good economic value and social value. (by machine translation)

Methyl asia phosphine acid ester compound synthesis and purification method

The invention relates to a synthesis and purification method of methyl phosphinate compounds. The method concretely comprises the following steps: adding brine to a solution containing a methyldialkyl phosphinate and magnesium chloride mixture in an inert solvent at a low temperature, and separating to obtain methylalkyl phosphinate or methyldialkyl phosphinate. The method solves the post-treatment and purification difficulties of a Grignard reagent method, and has the advantages of industrial production, effective reduction of the generation of methyl phosphonous acid, mild process conditions, and excellent reaction yield and product quality.