Tetraethyl methylenediphosphonate

Base Information

• Chemical Name: Tetraethyl methylenediphosphonate
• CAS No.: 1660-94-2
• Molecular Formula: C9H22O6P2
• Molecular Weight: 288.218
• Hs Code.: 29319090
• European Community (EC) Number: 216-764-5
• NSC Number: 133889
• UNII: WT3D5Q9EPC
• DSSTox Substance ID: DTXSID60937146
• Nikkaji Number: J40.747J
• Wikidata: Q72505017
• Mol file: 1660-94-2.mol

Synonyms:Tetraethyl methylenediphosphonate;1660-94-2;tetraethyl methylenebis(phosphonate);Tetraethyl methanediphosphonate;Methylenebis(diethylphosphonate);Phosphonic acid, methylenebis-, tetraethyl ester;Tetraethyl methylenebisphosphonate;Tetraethyl diphosphonomethane;1-[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxyethane;Methylenebis(diethoxyphosphine oxide);Methylenebisphosphonic acid, tetraethyl ester;Methylenedi(phosphonic acid) tetraethyl ester;PHOSPHONIC ACID, METHYLENEDI-, TETRAETHYL ESTER;NSC 133889;Tetraethyl (methylene)bisphosphonate;EINECS 216-764-5;WT3D5Q9EPC;Tetraethyl methanediylbis(phosphonate);BRN 1813241;Bis(diethoxyphosphinyl)methane;Methylenediphosphonic acid tetraethyl ester;Phosphonic acid, P,P'-methylenebis-, P,P,P',P'-tetraethyl ester;MFCD00039887;NSC-133889;Methylenediphosphonic acid, tetraethyl ester;diethyl [(diethoxyphosphoryl)methyl]phosphonate;4-01-00-03071 (Beilstein Handbook Reference);C9H22O6P2;UNII-WT3D5Q9EPC;bis-(diethylphosphono)methane;bis(diethoxyphosphoryl)methane;SCHEMBL282472;tetraethyl methylene-diphosphonate;DTXSID60937146;tetraethyl(methylene)bisphosphonate;tetraethylmethylenebis(phosphonate);Tetraethyl Methylidenebisphosphonate;STR02519;(EtO)2P(O)CH2P(O)(OEt)2;BBL100008;C9-H22-O6-P2;Methylenebis(phosphonic acid diethyl);NSC133889;STL510915;AKOS003600075;WLN: 2OPO&O2&1PO&O2&O2;CS-W017776;Tetraethyl methylenediphosphonate, 97%;Methanediphosphonic acid tetraethyl ester;SY019507;LS-106681;methylene diphosphonic acid tetraethyl ester;FT-0628883;methylene bisphosphonic acid, tetraethyl ester;EN300-207836;methanediyl-bis-phosphonic acid tetraethyl ester;A810692;J-010254;1-[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxyethan;(diethoxy-phosphorylmethyl)-phosphonic acid diethyl ester;(diethoxy-phosphorylmethyl)phosphonic acid diethyl ester;Tetraethyl methylenediphosphonate, purum, >=97.0% (GC)

Chemical Property of Tetraethyl methylenediphosphonate

Chemical Property:

• Appearance/Colour: clear yellow to yellow-brown liquid
• Vapor Pressure: 0.000616mmHg at 25°C
• Refractive Index: n20/D 1.442(lit.)
• Boiling Point: 319.894 °C at 760 mmHg
• Flash Point: 185.911 °C
• PSA: 90.68000
• Density: 1.149 g/cm³
• LogP: 3.47610
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Slightly miscible with water.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 288.08916241
• Heavy Atom Count: 17
• Complexity: 245

Purity/Quality:

99% ^*data from raw suppliers

TetraethylMethylidenebisphosphonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: CCOP(=O)(CP(=O)(OCC)OCC)OCC
• Uses: Tetraethyl methylidenebisphosphonate, can be used in the synthesis of tetrazoloquinoline-based mono- and bisphosphonate esters as potent anti-inflammatory agents. It is also an intermediate for the synthesis of new bisphosphonate and bisphosphonic acid derivatives with anticancer and antischistosomal activity. Reactant for synthesis of: Dual substrate-site inhibitors of 3-deoxy-D-arabino-heptulosonate 7-phosphate synthaseUnnatural alpha-amino acid derivatives containing gem-biphosphonatesBiphenyl sulfonylamino Me bisphosphonic acids as inhibitors of matrix metalloproteinases and bone resorptionLycopene via Wittig-Horner reactionAlkylaminoethylbisphosphinic acids to target farnesyl diphosphate synthaseAromatic bisphosphonates for use as inhibitors of geranylgeranyl diphosphate synthasePrecursor for synthesis of dendritic polyglycerol anions used toward L-selectin inhibition

Technology Process of Tetraethyl methylenediphosphonate

There total 44 articles about Tetraethyl methylenediphosphonate 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: 85.0%

triethyl phosphite (122-52-1) + 1,1-dibromomethane (74-95-3) → Tetraethyl methylenediphosphonate (1660-94-2)

Guidance literature:

at 150 ℃; for 120h;

DOI:10.1002/ejic.200600615

Reference yield: 83.0%

tetraethyl methylenebisphosphonate lithium salt (73778-55-9) → Tetraethyl methylenediphosphonate (1660-94-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; from -50 deg C to room temperature;

DOI:10.1016/0022-328X(86)80147-4

Reference yield: 83.0%

O,O-diethyl diethoxyphosphinomethylphosphonate (74992-34-0) → Tetraethyl methylenediphosphonate (1660-94-2)

Guidance literature:

With furfural; at 100 ℃; for 10h;

upstream raw materials:

diethyl chloromethylphosphonate

sodium diethyl phosphite

diethyl iodomethanephosphonate

triethyl phosphite

Downstream raw materials:

Methylenediphosphonic acid

P,P'-methanediyl-bis-phosphonic acid tetrachloride

tetraethyl 2-(4-nitrophenyl)ethene-1,1-diyldiphosphonate

tetraethyl 2-(4-methoxyphenyl)ethene-1,1-diyldiphosphonate

Refernces

• 1、 Vepsaelaeinen, Jouko,Nupponen, Heikki,Pohjala, Esko,Ahlgren, Markku,Vainiotalo, Pirjo. "Bisphosphonic Compounds. Part 3. Preparation and Identification of Tetraalkyl Methylene- and (α-Halomethylene)bisphosphonates by Mass Spectrometry, NMR Spectroscopy and X-Ray Crystallography". . p. 835 - 842. Retrieved 1992.
• 2、 Ezquerra,Yruretagoyena,Moreno-Manas,Roglans. "Improved preparation of diethyl bromomethylphosphonate and diiodomethane-catalyzed triethylphosphite Michaelis-Arbuzov isomerization". . p. 191 - 194. Retrieved 1995.
• 3、 Chaleix, Vincent,Lecouvey, Marc. "Synthesis of novel phosphonated tripodal ligands for actinides chelation therapy". . p. 703 - 706. Retrieved 2007.
• 4、 Penczek, Stanislaw,Kaluzynski, Krzysztof,Pretula, Julia. "Bisphosphonate units in the main polymer chain: The first synthesis". . p. 3030 - 3038. Retrieved 2012.
• 5、 Baldeschwieler et al.. "". . p. 4454. Retrieved 1962.
• 6、 Schwarzenbach,Zurc. "-". . p. 202,206. Retrieved 1950.
• 7、 Hossain, Khohinur,Florean, Luca,Del Tedesco, Anna,Cattaruzza, Elti,Geppi, Marco,Borsacchi, Silvia,Canton, Patrizia,Benedetti, Alvise,Riello, Pietro,Scarso, Alessandro. "Modification of Amorphous Mesoporous Zirconia Nanoparticles with Bisphosphonic Acids: A Straightforward Approach for Tailoring the Surface Properties of the Nanoparticles". supporting information. p. 17941 - 17951. Retrieved 2021/11/20.
• 8、 Chiminazzo, Andrea,Borsato, Giuseppe,Favero, Alessia,Fabbro, Chiara,McKenna, Charles E.,Dalle Carbonare, Luca Giuseppe,Valenti, Maria Teresa,Fabris, Fabrizio,Scarso, Alessandro. "Diketopyrrolopyrrole Bis-Phosphonate Conjugate: A New Fluorescent Probe for In Vitro Bone Imaging". supporting information. p. 3617 - 3626. Retrieved 2019/02/19.