1660-94-2

Usage

Uses

Used in Pharmaceutical Industry:
TETRAETHYL METHYLENEDIPHOSPHONATE is used as a synthetic intermediate for the development of tetrazoloquinoline-based monoand bisphosphonate esters, which are potent anti-inflammatory agents. It also plays a role in the synthesis of new bisphosphonate and bisphosphonic acid derivatives with anticancer and antischistosomal activities.
Used in Chemical Synthesis:
TETRAETHYL METHYLENEDIPHOSPHONATE is used as a reactant for the synthesis of various compounds, including:
1. Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase.
2. Unnatural alpha-amino acid derivatives containing gem-biphosphonates.
3. Biphenyl sulfonylamino Me bisphosphonic acids, which act as inhibitors of matrix metalloproteinases and bone resorption.
4. Lycopene via the Wittig-Horner reaction.
5. Alkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthase.
6. Aromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthase.
7. Precursor for the synthesis of dendritic polyglycerol anions used toward L-selectin inhibition.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1865, 1990 DOI: 10.1080/00397919008053112Tetrahedron Letters, 34, p. 1515, 1993 DOI: 10.1016/S0040-4039(00)60333-7

InChI:InChI=1/C9H22O6P2/c1-5-12-16(10,13-6-2)9-17(11,14-7-3)15-8-4/h5-9H2,1-4H3

Upstream product

• 3167-63-3 diethyl chloromethylphosphonate 
• 2303-76-6 sodium diethyl phosphite 
• 10419-77-9 diethyl iodomethanephosphonate 
• 122-52-1 triethyl phosphite 
• 75-11-6 diiodomethane 
• 66197-72-6 diethyl (bromomethyl)phosphonate 
• 1660-95-3 Tetraisopropyl methylenediphosphonate 
• 122-51-0 orthoformic acid triethyl ester 
• 1984-15-2 Methylenediphosphonic acid 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 109-72-8 n-butyllithium 
• 19928-97-3 (dichloromethylene)bisphosphonic acid, tetraethyl ester 
• 75-09-2 dichloromethane 
• 63366-56-3 methylene bis phosphonate de diethyle 

Downstream Products

• 1984-15-2 Methylenediphosphonic acid 
• 1499-29-2 P,P'-methanediyl-bis-phosphonic acid tetrachloride 
• 19928-97-3 (dichloromethylene)bisphosphonic acid, tetraethyl ester 
• 54552-70-4 ((E)-2-{4-[(E)-2-(Diethoxy-phosphoryl)-vinyl]-phenyl}-vinyl)-phosphonic acid diethyl ester 
• 5849-51-4 1,4-Bis--benzol 
• 53359-85-6 tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate 
• 53235-92-0 tetraisopropyl 2-phenylethene-1,1-diyldiphosphonate 
• 95601-03-9 [1-(diethoxyphosphoryl)-2-phenyl-vinyl]-phosphonic acid diethyl ester 
• 5849-49-0 styrylphosphonic acid ethylester 
• 20408-33-7 diethyl (E)-(2-phenylethenyl)phosphonate 
• 53235-90-8 tetraethyl 2-(4-methoxyphenyl)ethene-1,1-diyldiphosphonate 
• 5849-50-3 4-Phenyl-buta-1,3-dien-1-phosphonsaeure-monoaethylester 
• 36892-91-8 diethyl 4-phenylbutadienephosphonate 
• 37465-31-9 1,1-bis(diethylphosphono)ethylene 

Related news

The structure and spectroscopic characterization of UO22+ complexes with TETRAETHYL METHYLENEDIPHOSPHONATE (cas 1660-94-2) in solution and in solid state09/07/2019

The crystal structure of UO22+ complex with tetraethyl methylenediphosphonate, CH2[P(O)(OCH2CH3)2]2, POPO, and its spectroscopic characterization in solution and in solid state are discussed. The complex was also characterized by CHN microanalytical procedures, infrared, absorption and luminesce...detailed

Relevant academic research and scientific papers

Functional bisphosphonate synthesis for the development of new anti-resorption bone drug candidates

Herein we present the synthesis of β-mono and β-bis-substituted vinylidenebisphosphonate esters bearing a carboxylic ester moiety to be used as building blocks for further functionalizations. Reactions of these new bisphosphonate scaffolds through hydrogenation of the unsaturated CC bond and through metal mediated addition of aryl boronic acids and indoles provide a wide range of new bisphosphonate products as potential leads to contrast osteoporosis.

Bisphosphonic Compounds. Part 3. Preparation and Identification of Tetraalkyl Methylene- and (α-Halomethylene)bisphosphonates by Mass Spectrometry, NMR Spectroscopy and X-Ray Crystallography

The preparation and identification of tetraalkyl methylenebisphosphonates (XYC2; X = Y = H, Cl or Br and R = alkyl) have been studied.Detailed procedures are given for the synthesis of XYC2 (X = Y = H; R = hexyl; X = Y = Cl or Br and R = Me). 1H, 13C and 31P NMR data are reported including 1JCH, 2JCP', 3JCP and 2JPP coupling constants.The fragmentation of 19 XYC2 has been studied in the gas phase.The solid state structures are given for two compounds (X = Y = Cl, R = Pri and X = Y = Br, R = Me).

One-Pot, Highly Regioselective 1,3-Dipole Cycloaddition Promoted by Montmorillonite for the Synthesis of Spiro[indole-pyrrolizine], Spiro[indole-indolizine], and Spiro[indole-pyrrolidine] gem -Bisphosphonates

Various spiro[indole-pyrrolizine], spiro[indole-indolizine], and spiro[indole-pyrrolidine] gem-bisphosphonates were prepared by multicomponent reactions between isatins, tetraethyl vinylidenebis(phosphonate), and amino acids in the presence of montmorillonite. The one-pot reactions proceeded by 1,3-dipole cycloadditions of azomethine ylides formed in a decarboxylative manner. The proposed mechanism is in line with experimental data that confirmed that the azomethine ylide is formed in a decarboxylative manner; this provides new insight into the underlying mechanisms of such cycloadditions. The method has many notable features, such as a broad substrate scope, high efficiency, and high regioselectivity.

Improved preparation of diethyl bromomethylphosphonate and diiodomethane-catalyzed triethylphosphite Michaelis-Arbuzov isomerization

An improved method to prepare diethyl bromomethylphosphonate and a new method for the isomerization of triethyl phosphite into diethyl ethylphosphonate are reported.

An efficient and facile access to substituted 1e,3e-dienylphosphonates via horner-wadsworth-emmons olefination of α,β-unsaturated aldehydes with tetraethyl methylenebisphosphonate

An operationally simple and high-yielding synthetic method for 1E,3E-dienylphosphonates has been developed through the Horner-Wadsworth-Emmons olefination of α,β-unsaturated aldehydes with tetraethyl methylenebisphosphonate, in heterogeneous medium, in th

Synthesis of novel phosphonated tripodal ligands for actinides chelation therapy

Efficient synthetic routes for preparation of a new family of aldehyde-bisphosphonate conjugates were presented. These compounds appeared as promising intermediates for incorporation of bisphosphonate moiety in various substrates under mild conditions. We report here a first application to the synthesis of a series of three phosphonated tripods designed for actinides chelation therapy.

One-pot alkylidenediphosphorylation of nucleophiles

Direct phosphonylalkylidenephosphinylation of nucleophiles is achieved by one-pot mono dialkylphosphonoalkylation of dichlorophosphates or methylphosphonic dichloride followed, in situ, by nucleophilic substitution of the chlorine atom of the alkylidenediphosphorylated intermediate.

Bisphosphonate units in the main polymer chain: The first synthesis

Radical copolymerization of tetraethyl vinylidene phosphonate (B) with vinyl monomers has been described for the first time. In copolymerization with vinyl acetate (V) strictly alternating copolymer was formed even when [V] 0/[B]0 was equal to 80. In copolymerization with acrylic acid (A) copolymers of the general structure -[(B)1A x)]n- were formed. The number of A units (x) was shown to depend on the [A]0/[B]0 ratio in the monomers feed. The reactivity ratio rA was determined as equal to 2.1 and on this basis, the distribution of x as a function of [A]0/[B]0 was found. Bisphosphonic units were deblocked and the corresponding polyacids were analyzed by NMR spectra. Mn > 0.5 × 106 were measured by SEC for copolymers of B with A.

High yield synthesis of tetraethyl alkylenediphosphonates via the Michaelis-Arbuzov reaction

A high-yield synthesis of tetraethyl alkylenediphosphonates was achieved via the Michaelis-Arbuzov reaction. Application of optimized reaction conditions for a series of homologous alkylenediphosphonates establishes the generality of the approach.

Challenging synthesis of bisphosphonate derivatives with reduced steric hindrance

An alternative approach is reported for the synthesis of methyl ester protected bisphosphonate building blocks, such as methylene bisphosphonate, vinylidenebisphosphonate and aryl substituted prochiral vinylidenebisphosphonates, that cannot be obtained directly from dimethyl phosphite and dichloromethane.