3167-63-3

Usage

Uses

Used in Organic Synthesis:
DIETHYL (CHLOROMETHYL)PHOSPHONATE is used as a reactant for subsequent alkylation after nucleophilic substitution, enabling the formation of a wide range of organic compounds.
Used in One-Pot Alkylation-Boration:
DIETHYL (CHLOROMETHYL)PHOSPHONATE is used as a reactant in one-pot alkylation-boration of α-haloalkylphosphonates, allowing for the efficient synthesis of various organic molecules.
Used in Synthesis of Cyclopentane and Pyrrolidine Derivatives:
DIETHYL (CHLOROMETHYL)PHOSPHONATE is used as a reactant for the synthesis of cyclopentane and pyrrolidine derivatives via regioselective insertion reactions, contributing to the development of complex organic structures.
Used in Phosphorylation Reactions:
DIETHYL (CHLOROMETHYL)PHOSPHONATE is used as a reactant in phosphorylation reactions, leading to the formation of P-containing cyclopropanes and expanding the scope of phosphorus-containing organic compounds.
Used in Wadsworth-Emmons Reactions:
DIETHYL (CHLOROMETHYL)PHOSPHONATE is used as a reactant in Wadsworth-Emmons reactions, facilitating the synthesis of alkenes and providing a valuable method for carbon-carbon bond formation.
Used in Ring Expansion of Zirconacycles:
DIETHYL (CHLOROMETHYL)PHOSPHONATE is used as a reactant in the ring expansion of zirconacycles via carbenoid insertion, allowing for the synthesis of larger ring systems and the development of novel organic compounds.

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 3799, 1987 DOI: 10.1016/S0040-4039(00)96387-1

InChI:InChI=1/C5H12ClO3P/c1-3-8-10(7,5-6)9-4-2/h3-5H2,1-2H3

Upstream product

• 64-17-5 ethanol 
• 1983-26-2 chloromethylphosphonic dichloride 
• 141-52-6 sodium ethanolate 
• 3084-40-0 diethyl (1-hydroxymethyl)phosphonate 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 68027-57-6 bis-p-nitrophenyl (chloromethyl)phosphonate 
• 75-09-2 dichloromethane 
• 2303-76-6 sodium diethyl phosphite 
• 925-93-9 ethyl [2]alcohol 
• 3167-62-2 diethyl (dichloromethyl)phosphonate 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 630-19-3 pivalaldehyde 
• 120-92-3 cyclopentanone 

Downstream Products

• 71790-86-8 ethyl p-nitrophenyl chloromethylphosphonate 
• 1660-94-2 Tetraethyl methylenediphosphonate 
• 54091-78-0 diethyl ((ethylthio)methyl)phosphonate 
• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 75-00-3 chloroethane 
• 58898-13-8 2-(dibromomethylene)-1,3-dimethylcyclohexane 
• 2592-73-6 1,1-dibromo-2,2-diphenylethylene 
• 30094-33-8 l'acide 2-chloro-2-diethylphosphonoacetique 
• 58898-12-7 2-(dibromomethylene)-1,1-dimethylcyclohexane 
• 58898-14-9 2-Dibromomethylene-1,1,4,4-tetramethyl-cyclohexane 
• 1637-16-7 10-ethyl-phenothiazine 
• 18276-82-9 diethyl 2-(p-chlorophenyl)-2-oxo-ethylphosphonate 
• 7436-90-0 2,2-dibromostyrene 
• 3453-00-7 diethyl benzoylmethylphosphonate 

Relevant academic research and scientific papers

A Convenient Synthesis of Diethyl 1-Chloroalkylphosphonates

The title compounds were obtained in high yield by the reaction of diethyl 1-hydroxyalkylphosphonates with triphenylphosphine carbon tetrachloride.

Direct and straightforward transfer of C1 functionalized synthons to phosphorous electrophiles for accessinggem-P-containing methanes

The direct transfer of different α-substituted methyllithium reagents to chlorinated phosphorous electrophiles of diverse oxidation state (phosphates, phosphine oxides and phosphines) is proposed as an effective strategy to synthesize geminal P-containing

SYNTHESIS OF INTERMEDIATES USED IN THE MANUFACTURE OF ANTI-HIV AGENTS

The present invention relates to a process of preparing intermediates of Formula (I). The process comprises of reacting compound of Formula (III) with compound of Formula (V) in the presence of a solvent selected from an alcohol, ether or water to form compound of Formula (I) wherein, R1 is selected from –NH2, Cl, Br, NHCOR", wherein R" is alkyl, aryl, Schiff's base of formula N=CHR', wherein R' is alkyl or aryl; R2 is selected from H, alkyl; R3 and R4, each independently is H; R5 and R6, each independently is H, alkyl; R7 is H, alkyl; and R8 is H, alkyl.

Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: Hemisynthesis of Taxotere through Ru-DIFLUORPHOS asymmetric hydrogenation

The dynamic kinetic resolution (DKR) of racemic α-chloro β-ketoesters and α-chloro β-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding α-chloro β-hydroxyesters and α-chloro β- hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, 13C NMR in chiral oriented solvents was used to investigate the DKR effect.

Reactions of α-boranophosphorus compounds with electrophiles: Alkylation, acylation, and other reactions

(Chemical Equation Presented) The homologation of phosphorus carbenoids with organoboranes leads to α-boranophosphorus compounds, which can be further functionalized through reactions with various electrophiles, either directly or after activation to the

Mild synthesis of organophosphorus compounds: Reaction of phosphorus-containing carbenoids with organoboranes

Organoboranes react with phosphorus-containing carbenoids to produce a variety of functionalized organophosphorus compounds under mild conditions. In some cases, selective migration of one group atached to boron can be observed. Phosphonite-borane complexes are introduced as novel synthons for the synthesis of phosphinic esters.

Synthesis, reactivity and stereochemistry of new phosphorus heterocycles with 5- or 6-membered rings

Syntheses of novel phosphorus heterocycles containing α-amino or α-hydroxyphosphonic or phosphinic acids motifs are developed. 2,3-dihydro-1,3-oxaphospholes (1) and 1,4,2-oxazaphosphinanes (2) exhibit a reactive part, respectively the enolether moiety and the P-H bond, which allows various structural modifications: (i) for 1a, by introduction of amino substituents, (ii) for 2a, by hydroxy- or aminoalkylation, by Michael addition or by P-arylation. These reactions present generally a good or even an excellent kinetic diastereoselectivity which can often be predicted by molecular models of the transition states.

New route to aminomethylphosphonic acid via bis(trifluoroethyl) phosphonate transesterification

Transesterification of bis(trifluoroethyl) chloromethyl- and azidomethyl-phosphonates with alcohols in the presence of catalytic quantities of alcoholates gives dialkyl chloromethyl- and azidomethyl-phosphonates in good yield.This process has been used fo

PREPARATION DE L'ACIDE AMINOMETHYLPHOSPHONIQUE α-DIDEUTERIE

Nucleophilic amination of chloromethylphosphonic esters was studied, α-Dideuteriated aminomethylphosphonic acid was obtained from bis(trifluoroethyl) chloromethylphosphonic ester and sodium azide through substitution of the chlorine, reduction of the azide and acidic hydrolysis.Incorporation of the deuterium was greated than 95percent and overall yields were in the range 55-65percent. Key words: nucleophili amination, chloromethylphosphonic esters, α-dideuteriated chloromethylphosphonic esters, sodium azide, aminomethylphosphonic acid, deuterium oxide, trifluoroethanol d, α-dideuteriated aminomethylphosphonic acid.

Free radical reaction of α-haloalkylphosphonates with alkenes and alkynes: A new approach to modified phosphonates

A new approach to the synthesis of phosphonates 3 functionalized in the α- and γ-phosphonate positions by alkyl, ethoxy, butoxy, acetoxy, acetyl and cyanide groups and allylphosphonate 6 is described. It is based on the radical reaction of α-halosubstituted phosphonates 1 (X = Cl, Br, I) with the terminally unsubstituted alkenes 2 (1-heptene, ethoxyethene, butoxyethene, acetoxyethene, acrylonitrile, methyl vinyl ketone) and alkyne 5 (hept-1-yne). The reaction involving the tin hydride method (Bu3SnH/AIBN) was more effective with alkenes than with alkynes (40-72% versus 20-30%). With electron-rich alkenes, chloro- and bromomethylphosphonates 1 (X = Cl, Br) gave higher yields than iodomethylphosphonate 1 (X = I). Diethyl methylphosphonate 4, as a reduction product of 1, accompanied 3 and 6 in the above reactions. The yield of 4 could be reduced by optimizing the reaction conditions.