16001-93-7

Basic information

• Product Name: TETRAMETHYL METHYLENEDIPHOSPHONATE
• Synonyms: TETRAMETHYL METHYLENEDIPHOSPHONATE;(Dimethoxy-phosphorylmethyl)-phosphonicaciddimethylester;Tetramethyl methylenediphosphonate, 98+%;Tetramethyl methylenediphosphonatedisc 6/01;tetramethyl methylenebis(phosphonate)
• CAS NO: 16001-93-7
• Molecular Formula: C₅H₁₄O₆P₂
• Molecular Weight: 232.11
• Mol File: 16001-93-7.mol

Chemical Properties

• Boiling Point: 152-154°C 2,5mm
• Flash Point: 152-154°C/2.5mm
• Appearance: /
• Density: 1.255g/cm³
• Vapor Pressure: 0.00203mmHg at 25°C
• Refractive Index: 1.4550
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• Water Solubility: Miscible with water.
• Stability: Moisture Sensitive
• BRN: 1874756
• CAS DataBase Reference: TETRAMETHYL METHYLENEDIPHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAMETHYL METHYLENEDIPHOSPHONATE(16001-93-7)
• EPA Substance Registry System: TETRAMETHYL METHYLENEDIPHOSPHONATE(16001-93-7)

Safety Data

• Statements: 22
• Safety Statements: 23-36/37/39
• RIDADR: 3278
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 16001-93-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Tetramethyl methylenediphosphonate is used as a synthetic intermediate for the preparation of phosphonate analogues of biologically important molecules. It serves as a key building block in the synthesis of various phosphonic acid derivatives, which have potential applications in pharmaceuticals, agrochemicals, and other industries.
Used in the Preparation of Ribose-1-Phosphate Analogues:
Specifically, Tetramethyl methylenediphosphonate is used in the preparation of phosphonate analogues of ribose-1-phosphate. Ribose-1-phosphate is an important intermediate in the biosynthesis of nucleotides and other biomolecules. The phosphonate analogues synthesized using TMP can be used for studying the mechanisms of enzymatic reactions and as potential inhibitors of enzymes involved in these processes.

InChI:InChI=1/C5H14O6P2/c1-8-12(6,9-2)5-13(7,10-3)11-4/h5H2,1-4H3

Upstream product

• 75-15-0 carbon disulfide 
• 868-85-9 Dimethyl phosphite 
• 1984-15-2 Methylenediphosphonic acid 
• 149-73-5 trimethyl orthoformate 
• 1660-95-3 Tetraisopropyl methylenediphosphonate 
• 186581-53-3 diazomethane 

Downstream Products

• 877760-75-3 tetramethyl [3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylofuranos-6,6'-diyl]bisphosphonate 
• 871116-41-5 [(3R,4R,5S,6S)-4,5-Bis-benzyloxy-3-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-ylmethyl]-phosphonic acid dimethyl ester 
• 753020-09-6 dimethyl (3S,4S,5S)-3-N,N-dibenzylamino-4,5-dibenzyloxy-6-octadecyn-(1E)-enephosphonate 
• 363619-54-9 ((3aS,4S,6R,7R,7aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl)-phosphonic acid dimethyl ester 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 133918-47-5 tetrabenzyl methylenediphosphonate 
• 161722-31-2 (Z)-(dimethoxy-phosphoryl)-2-<2-(trityl-amino)-thiazol-4-yl>-acrylic acid 2,3,4,5,6-pentafluoro-phenyl ester 

Relevant articles and documents

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.

Diketopyrrolopyrrole Bis-Phosphonate Conjugate: A New Fluorescent Probe for In Vitro Bone Imaging

The synthesis of a conjugate molecule between an unusual red-fluorescent diketopyrrolopyrrole (DPP) unit and a bis-phosphonate (BP) precursor by a click-chemistry strategy to target bone tissue and monitor the interaction is reported. After thorough investigation, conjugation through a triazole unit between a γ-azido rather than a β-azido BP and an alkyne-functionalized DPP fluorophore group turned out to be the winning strategy. Visualization of the DPP-BP conjugate on osteoclasts and specific antiresorption activity were successfully demonstrated.

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

SYNTHESIS OF α-HALOGENATED METHANEDIPHOSPHONATES

Methanediphosphonate (MDP) anions can exhibit anti-viral activity, inhibit bone resorption, and act as ligands in radiopharmaceuticals. α-Halo-substitution provides MDP derivatives (XYMPD, where X = H, F, Cl or Br; Y = F, Cl or Br) with modified acid-base, steric and other properties.These compounds are conveniently made from the corresponding α-halogenated XYMDP esters (RO)2P(O)CXYP(O)(OR)2.Detailed procedures are given for synthesis of R4XYMDP for R = Pri and X, Y = H, Cl; Cl, Cl; H, Br; Br, Br; F, Cl; F, Br and Cl, Br in 88-96percent yield; for R = Et and X, Y = H, Cl; Cl, Cl; H, Br; Br, Br and Cl, F in 81-94percent yield; and for R = Me and X, Y = Cl, Cl and Br, Br in 72-80percent yield.NMR data (1H, 31P,13C, (19F)) are presented for the products obtained.The XYMDP acids (X, Y = H, Cl; Cl, Cl; H, Br; Br, Br; F, Cl; F, Br and Cl, Br) were prepared by HCl hydrolysis of a corresponding ester and characterized as tris(dicyclohexylammonium) salts by elemental analyses and 31P NMR.