1660-95-3

Basic information

• Product Name: Tetraisopropyl methylenediphosphonate
• Synonyms: METHYLENEDIPHOSPHONIC ACID TETRAISOPROPYL ESTER;TETRAISOPROPYL(METHYLENE)BISPHOSPHONATE;TETRAISOPROPYL METHYLENEDIPHOSPHONATE;Phosphonic acid, methylenebis-, tetrakis(1-methylethyl) ester;Phosphonic acid, methylenedi-, tetraisopropyl ester;phosphonicacid,methylenebis-,tetrakis(1-methylethyl)ester;tetra-i-Propylmethylenediphosphonate;Methanediphosphonic acid tetraisopropyl ester
• CAS NO: 1660-95-3
• Molecular Formula: C₁₃H₃₀O₆P₂
• Molecular Weight: 344.32
• EINECS: 216-765-0
• Product Categories: Organic Building Blocks;Phosphonates/Phosphinates;Phosphorus Compounds
• Mol File: 1660-95-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 155 °C0.5 mm Hg(lit.)
• Flash Point: 320 °F
• Appearance: Clear colorless to slightly yellow liquid
• Density: 1.08 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.04E-06mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: Insoluble in water.
• BRN: 1080180
• CAS DataBase Reference: Tetraisopropyl methylenediphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: Tetraisopropyl methylenediphosphonate(1660-95-3)
• EPA Substance Registry System: Tetraisopropyl methylenediphosphonate(1660-95-3)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36-39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1660-95-3(Hazardous Substances Data)

Usage

Description

Tetraisopropyl methylenediphosphonate (IPCP) is a tetraisopropyl ester of methylenediphosphonic acid, serving as an electroneutral ligand. It is synthesized from triisopropyl phosphate and is characterized by its clear colorless to slightly yellow liquid appearance. Powder electron paramagnetic resonance (EPR) studies of tris complexes of Cu(II) complexes with IPCP have been analyzed, showcasing its potential in various applications.

Uses

1. Used in Pharmaceutical Industry:
Tetraisopropyl methylenediphosphonate is used as a building block for the preparation of E2-bisphosphonate conjugates, which are potential anti-osteoporosis agents. These conjugates help in the treatment and prevention of osteoporosis by targeting specific enzymes involved in bone resorption.
2. Used in Antiviral Applications:
Tetraisopropyl methylenediphosphonate is utilized in the preparation of AZT 5'-Triphosphate compounds, which exhibit inhibitory effects on HIV-1 reverse transcriptase. This application aids in the development of antiviral drugs to combat HIV and related infections.
3. Used in Chemical Synthesis:
Tetraisopropyl methylenediphosphonate is employed in the synthesis of various compounds, such as tetraisopropyl ethenylidenebisphosphonate, tetraisopropyl 4-acetylthiobutane-1,1-diphosphonate, and tetraisopropyl 2-(3,5-bis(bromomethyl)phenyl)ethane-1,1-diphosphonate. These synthesized compounds can be used in different chemical and industrial applications.
4. Used in Nuclear Industry:
Tetraisopropyl methylenediphosphonate forms a synergistic mixture with hydrogen dicarbollylcobaltate in nitrobenzene, which is used in the extraction of europium and americium. This application is crucial in the nuclear industry for the separation and purification of specific elements.

InChI:InChI=1/C13H30O6P2/c1-10(2)16-20(14,17-11(3)4)9-21(15,18-12(5)6)19-13(7)8/h10-13H,9H2,1-8H3

Upstream product

• 1499-29-2 P,P'-methanediyl-bis-phosphonic acid tetrachloride 
• 67-63-0 isopropyl alcohol 
• 63366-57-4 tetraisopropyl methylenebis 
• 116-17-6 triisopropyl phosphite 
• 74-95-3 1,1-dibromomethane 
• 75-11-6 diiodomethane 
• 75-15-0 carbon disulfide 
• 1809-20-7 diisopropyl hydrogenphosphonate 
• 10596-22-2 tetraisopropyl dichloromethylenebisphosphonate 

Downstream Products

• 104884-06-2 tetraisopropyl 1,1-bisphosphonatecyclohexane 
• 48074-47-1 tetraisopropyl ethenylidenebis(phosphonate) 
• 2404-04-8 NN-dimethyl di-isopropyl-phosphoramidate 
• 87594-23-8 ((E)-2-Dimethylamino-vinyl)-phosphonic acid diisopropyl ester 
• 681-80-1 diisopropyl difluoromethanephosphonate 
• 78715-57-8 fluoromethylenebisphosphonic acid tetraisopropyl ester 
• 78715-59-0 tetraisopropyl (difluoromethylene)bisphosphonate 
• 10596-22-2 tetraisopropyl dichloromethylenebisphosphonate 
• 20107-67-9 tetraisopropyl esters of monochloromethylene bisphosphonic acid 
• 102786-81-2 [(Chloro-difluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester 
• 102786-83-4 [(Dichloro-fluoro-methylsulfanyl)-(diisopropoxy-phosphoryl)-methyl]-phosphonic acid diisopropyl ester 
• 161063-26-9 tetraisopropyl carbonylbisphosphonate 
• 19295-96-6 diisopropyl styrylphosphonate 
• 10038-58-1 Propan-2,2-diphosphonsaeure-tetra-isopropylester 

Relevant articles and documents

METHOD OF THE SYNTHESIS OF DIALKYL HALOALKYLPHOSPHONATES AND DIALKYL HALOALKYLOXYALKYLPHOSPHONATES

The invention deals with the method of the synthesis of dialkyl haloalkylphosphonates and dialkyl haloalkyloxyalkylphosphonates via a microwave-heated Michaelis-Arbuzov reaction of trialkylphosphites with dihaloalkanes or bis(haloalkyl)ethers in a closed vessel, during which the reaction mixture, containing a dihaloalkane or bis(haloalkyl)ether and a trialkylphosphite, is heated with microwave radiation with the standard frequency (2.45 GHz) to reach a reaction temperature which is specific for each individual halogen. In the subsequent reaction of the first dihaloalkane or bis(haloalkyl)ether halogen atom with trialkyl phosphite, the desired dialkyl haloalkylphosphonate or dialkyl haloalkyloxyalkylphosphonate is formed, but the reaction of its halogen atom with the so-far present trialkylphosphite, leading to the creation of the relevant bisphosphonate, no longer takes place. In the case of an inhomogeneous reaction mixture, also the desired product in the amount of 0.1-5 molar % is added to the reaction mixture for its homogenization, which homogenizes it and thus precludes its uncontrollable overheating. The entire process of synthesis is more effective, faster, less expensive and more environmentally friendly than the methods described so far in the literature. The possibility of performing the described procedure also in a continuous-flow microwave reactor allows industrial production with minimal demands on an optimization of the reaction conditions for larger quantities, eliminates some security risks, dramatically reduces the spatial demands in production and reduces the need for the usage of large-tonnage industrial reactors.

Synthesis of methylene bisphosphonates from carbon disulfide and phosphites via desulfurization: A mechanistic study

The reaction of carbon disulfide with an excess of sodium dialkylphosphite in an aprotic solvent led to the formation of the carbanion of methylene bisphosphonate and sodium thiophosphate. The mechanistic study of this unexpected reaction, using both 31P

Preparation of fluorinated compounds

A method for the preparation of a fluorinated Phosphonate having the formula (RO)2PO CFR′R″ comprises treating a phosphonate of the formula (RO)2PO CHR′R″, or a metal salt thereof, with fluorine. R is an alkyl group R′ is hydrogen or alkyl and R″ is hydrogen, alkyl or another group.