Tetraisopropyl methylenediphosphonate
[CAS# 1660-95-3]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: Tetraisopropyl methylenediphosphonate
• Synonyms: 2-[di(propan-2-yloxy)phosphorylmethyl-propan-2-yloxyphosphoryl]oxypropane
• Molecular Formula: C₁₃H₃₀O₆P₂
• Molecular Weight: 344.32
• CAS Registry Number: 1660-95-3
• EC Number: 216-765-0
• SMILES: CC(C)OP(=O)(CP(=O)(OC(C)C)OC(C)C)OC(C)C

Properties

• Density: 1.08 g/mL (Expl.)
• Boiling point: 155 °C (0.5 mmHg) (Expl.)
• Refractive index: 1.431 (Expl.)
• Flash point: 160 °C (Expl.)

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS09 Danger
• Risk Statements: H301-H302-H311-H312-H318-H319-H331-H335-H411-H412
• Safety Statements: P261-P262-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P319-P321-P330-P337+P317-P361+P364-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H331
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Tetraisopropyl methylenediphosphonate is a chemical compound that contains a methylene group linked to two phosphonic acid ester groups. This molecule belongs to the family of phosphonates, which are widely used in various chemical processes, particularly in industrial and synthetic chemistry. Its unique structure and reactivity make it a versatile intermediate for the preparation of other chemicals and materials with specific applications in both research and industry.

The discovery of tetraisopropyl methylenediphosphonate is part of a broader effort to explore phosphonate compounds due to their stability and ability to coordinate with metal ions. Phosphonates are chemically similar to phosphates, but the phosphorus atom is bonded to a carbon atom rather than an oxygen atom. This subtle difference imparts distinct properties, such as increased stability to hydrolysis, making phosphonates useful in conditions where phosphates might degrade.

One of the main applications of tetraisopropyl methylenediphosphonate is in the field of organic synthesis. It can be used as a reagent or intermediate in the preparation of more complex molecules, especially those that require the introduction of phosphonate groups. Phosphonate groups are valuable in a wide range of reactions, such as nucleophilic substitution, and in the design of molecules with enhanced chemical or biological properties. The methylene bridge in tetraisopropyl methylenediphosphonate allows it to participate in reactions where the phosphonate groups can be selectively modified or used as functional groups in larger molecules.

Tetraisopropyl methylenediphosphonate has also been explored in the synthesis of organophosphorus compounds, which are essential in agriculture, medicine, and materials science. For example, organophosphorus compounds can act as herbicides, pesticides, or flame retardants. The versatility of tetraisopropyl methylenediphosphonate in forming stable phosphorus-containing linkages allows its use in the development of these chemicals, contributing to agricultural productivity and safety.

In addition, tetraisopropyl methylenediphosphonate plays a role in the development of inhibitors for certain enzymes, including those involved in bacterial resistance. Phosphonate-based compounds can act as analogs of phosphate groups, and as such, they can inhibit enzymes that rely on phosphates for their activity. This application has implications in the development of treatments for diseases caused by resistant bacteria, particularly in the design of new antibiotics.

Another area of interest for tetraisopropyl methylenediphosphonate is its potential use in the field of materials science. Phosphonates can be employed to modify the surface properties of materials such as metals, ceramics, and polymers. Tetraisopropyl methylenediphosphonate can be used to create coatings or thin films that improve the durability, corrosion resistance, or functionalization of various materials. This makes it a valuable component in industries that require specialized materials, such as electronics, automotive, and aerospace.

Overall, tetraisopropyl methylenediphosphonate is a significant compound in synthetic chemistry, with a broad range of applications spanning from organic synthesis to industrial manufacturing. Its stability, reactivity, and versatility as a phosphonate reagent make it an essential intermediate in the creation of various functional molecules and materials. As research into phosphonates continues, tetraisopropyl methylenediphosphonate will likely remain a key compound in the development of new technologies and chemical processes.

References

1995. Some phosphonic acid analogs as inhibitors of pyrophosphate-dependent phosphofructokinase, a novel target in Toxoplasma gondii. Biochemical Pharmacology, 49(1), 73-80.
DOI: 10.1016/0006-2952(94)00437-q

2007. Substitution Reactions of α-Haloalkylphosphorus and Related Compounds with Phosphorus Anions or Phosphites (Michaelis-Arbuzov Reaction). Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-030-00527

2010. Extraction of calcium and strontium into nitrobenzene by using a synergistic mixture of hydrogen dicarbollylcobaltate and tetraisopropyl methylene diphosphonate. Journal of Radioanalytical and Nuclear Chemistry, 285(1), 67-72.
DOI: 10.1007/s10967-010-0668-4