7040-52-0

Usage

Uses

Used in Micro-Nano Electronic Materials:
Cyclohexyl methyl methylphosphonate is used as a component in micro-nano electronic materials to create extended self-assembled monolayers (SAMs). It allows for the expansion of substrate choices for SAM preparation by altering the chemical functionalities in film-forming molecules through the introduction of phosphate or phosphonate groups.
Used in Surface Modification for SAMs:
In the field of surface modification, Cyclohexyl methyl methylphosphonate is used as a film-forming molecule to create self-assembled monolayers (SAMs) on diverse metal-oxide surfaces. These surfaces include Al2O3, Ta2O5, NbO5, ZrO2, and TiO2. The polar acidic nature of the compound enables it to interact with these surfaces, resulting in films with a similar degree of ordering as alkyl thiol SAMs on gold.

InChI:InChI=1/C8H17O3P/c1-10-12(2,9)11-8-6-4-3-5-7-8/h8H,3-7H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 329-99-7 GF 
• 108-93-0 cyclohexanol 
• 186581-53-3 diazomethane 
• 676-97-1 methylphosphonic acid dichloroanhydride 
• 1932-60-1 methylphosphonic acid monocyclohexyl ester 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 175352-88-2 Phosphorous acid cyclohexyl ester dimethyl ester 
• 74-88-4 methyl iodide 
• 1066-52-0 methyl methylphosphonochloridate 
• 22096-22-6 sodium cyclohexanolate 

Downstream Products

• 1932-60-1 methylphosphonic acid monocyclohexyl ester 

Relevant academic research and scientific papers

Synthesis of alkyl methylphosphonic acid esters

A synthesis and isolation scheme is described for producing mono alkyl esters of methylphosphonic acid based upon stoichiometric addition of alcohol to methylphosphonic dichloride. Solvent extraction is applied to the reaction mixture to separate the mono

Preparation, derivatization with trimethylsilyldiazomethane, and GC/MS analysis of a "pool" of alkyl methylphosphonic acids for use as qualitative standards in support of counterterrorism and the chemical weapons convention

There are hundreds of nerve agents in the class of alkyl methylphosphonofluoridates covered by Schedule 1 of the CWC (Chemical Weapons Convention). Hydrolysis of these sarin-like nerve agents results in an equal number of alkyl methylphosphonic acids. These alkyl methylphosphonic acids are persistent and provide good evidence of specific agent production or use. In order to support the CWC and counterterrorism activities, it is desirable to have ready access to each of these hydrolysis products for use as qualitative standards. A means for simultaneously producing multiple alkyl methylphosphonates from methylphosphonic acid and the corresponding alcohols was developed. Derivatization of these alkyl methylphosphonic acids with trimethylsilyldiazomethane yields the corresponding methyl esters which are suitable for GC/MS analysis.

Synthesis of alkyl- and arylphosphonic acid monoesters by direct esterification of dibasic phosphonic acids in the presence of an arsonic acid catalyst

Partial hydrolysis of a diester, hydrolysis of the monochloro monoester, or alcoholysis of a phosphonic acid anhydride generally is used to prepare monoesters of alkyl- and arylphosphonic acids. Limited cases have been reported for the esterification of a dibasic phosphonic acid to yield the monoester, and none of these methods are as simple as the analogous method for preparing carboxylic acid esters, in which the carboxylic acid is esterified with an alcohol in the presence of an acid catalyst. Described is a method for preparing monoesters of alkyl- and arylphosphonic acids by direct esterification with an alcohol in the presence of a catalytic amount of phenylarsonic acid. The water formed during the reaction is removed azeotropically. For example, methylphosphonic acid was esterified in good yield to give its isopropyl, butyl, cyclohexyl, bornyl, and octadecyl monoesters. Similarly prepared are the ethyl, butyl, hexyl, and 2-(ethylthio)ethyl monoesters of phenylphosphonic acid, as well as 2-isopropoxyethyl hydrogen ethylphosphonate and 2-methoxyethyl hydrogen benzylphosphonate.

Organophosphorus chemistry. Part 1: The synthesis of alkyl methylphosphonic acids

Several alkyl hydrogen methylphosphonates of structure RO(HO)P(O)Me were synthesised by a three-stage route [R =i-Pr, n-Bu, i-Bu, s-Bu, pinacolyl Me3C-CH(Me)-, cyclopentyl and cyclohexyl]. Trimethyl phosphite was transesterified with alcohols in the presence of sodium catalyst to give the mixed phosphites (MeO)2POR in 6-64% yield. Treatment of these with methyl iodide gave alkyl methyl methylphosphonates RO(MeO)P(O)Me in 66-95% yield. Selective demethylation of these compounds by bromotrimethylsilane, followed by methanolysis of the phosphorus silyl esters RO(Me3SiO)P(O)Me, gave the hydrogen phosphonates in 60-97% yield.

Inhibition of plasma cholinesterase by O-alkylfluorophosphonates

Inhibition of plasma cholinesterase by three methylfluorophosphonates (MFF), sarin, soman and cyclosin, and by the products of their hydrolysis and alcoholysis was examined. Inhibition by phosphonic acids and by methyl esters derived from MFF was purely competitive while that by MFF was irreversible. The rate of phosphorylation of cholinesterase by MFF differs, depending on the structure of the alkoxy group in the MFF and decreases in the sequence soman-sarin-cyclosin. The affinity values of MFF, phosphonic acids and methyl esters of phosphonic acid for cholinesterase are comparable. The in vitro kinetic parameters suggest that plasma cholinesterase might act as a natural detoxicating agent in cases of poisoning with the above inhibitors of acetylcholinesterase.