38186-51-5

Basic information

• Product Name: DIETHYL 4-BROMOBENZYL PHOSPHONATE
• Synonyms: DIETHYL 4-BROMOBENZYL PHOSPHONATE;4-BROMOBENZYL-PHOSPHONIC ACID DIETHYLESTER;Diethy 4-Bromobenzyl Phosphonate
• CAS NO: 38186-51-5
• Molecular Formula: C₁₁H₁₆BrO₃P
• Molecular Weight: 307.12
• Product Categories: Horner-Emmons Reaction;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Piperidines ,Homopiperidines
• Mol File: 38186-51-5.mol
• Article Data: 66

Chemical Properties

• Boiling Point: 183 °C / 0.6mmHg
• Flash Point: 181.212 °C
• Appearance: /
• Density: 1.37
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5230-1.5270
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIETHYL 4-BROMOBENZYL PHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 4-BROMOBENZYL PHOSPHONATE(38186-51-5)
• EPA Substance Registry System: DIETHYL 4-BROMOBENZYL PHOSPHONATE(38186-51-5)

Safety Data

• Hazardous Substances Data: 38186-51-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Diethyl 4-Bromobenzylphosphonate can be used as a virucide.

InChI:InChI=1/C11H16BrO3P/c1-3-14-16(13,15-4-2)9-10-5-7-11(12)8-6-10/h5-8H,3-4,9H2,1-2H3

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 122-52-1 triethyl phosphite 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 589-87-7 1,4-bromoiodobenzene 
• 78-40-0 triethyl phosphate 
• 106-38-7 para-bromotoluene 
• 873-75-6 4-bromobenzenemethanol 
• 40962-34-3 [(4-bromophenyl)methyl]phosphonic acid 
• 78-39-7 Triethyl orthoacetate 
• 1122-91-4 4-bromo-benzaldehyde 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 
• 589-17-3 p-bromobenzyl chloride 

Downstream Products

• 85137-69-5 1-bromo-4-((E)-2-(4-[(E)-2-(4-bromophenyl)vinyl]phenyl)vinyl)benzene 
• 72436-47-6 diethyl (((diethoxyphosphinyl)methyl)phenyl)phosphonate 
• 209626-97-1 [(4-Bromo-phenyl)-fluoro-trimethylsilanyl-methyl]-phosphonic acid diethyl ester 
• 209627-03-2 [(4-Bromo-phenyl)-chloro-trimethylsilanyl-methyl]-phosphonic acid diethyl ester 
• 18648-66-3 1-bromo-4-(2,2-diphenylvinyl)benzene 
• 336184-06-6 (E)-1-(4-bromophenyl)-2-[2-(3,7-dimethyloctyloxy)-4-methylphenyl]ethene 
• 726-61-4 [(4-ethenylphenyl)methyl]phosphonic acid diethyl ester 
• 380428-42-2 (E)-1-(4-bromophenyl)-2-(2,5-dimethoxyphenyl)ethene 
• 13041-70-8 (E)-4-bromostilbene 
• 861403-99-8 trans-4-bromo-4'-(1,4,7,10,13-pentaoxa-16-azacyclooctadecan-16-yl)stilbene 
• 57082-98-1 1-[(E)-2-(4-chlorophenyl)ethenyl]-4-bromobenzene 
• 144092-35-3 (E)-4-(4-bromostyryl)benzonitrile 
• 862420-05-1 tris-(4-((E)-4-bromostyryl)phenyl)amine 
• 660437-82-1 (E)-1-(4-tertbutylphenyl)-2-(4-bromophenyl)ethene 

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Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.