33973-48-7

Basic information

• Product Name: DIETHYL 1-PHENYLETHYL PHOSPHONATE
• Synonyms: diethyl(alpha-methylbenzyl)phosphonate;(1-Phenylethyl)phosphonic acid diethyl ester;Brn 2940028;Nsc 220102;Phosphonic acid, (1-phenylethyl)-, diethyl ester (9ci);Phosphonic acid, (alpha-methylbenzyl)-, diethyl ester;(alpha-methylbenzyl)-phosphonicacidiethylester
• CAS NO: 33973-48-7
• Molecular Formula: C₁₂H₁₉O₃P
• Molecular Weight: 242.25
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 33973-48-7.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 130 °C0.6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.082 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000372mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• CAS DataBase Reference: DIETHYL 1-PHENYLETHYL PHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 1-PHENYLETHYL PHOSPHONATE(33973-48-7)
• EPA Substance Registry System: DIETHYL 1-PHENYLETHYL PHOSPHONATE(33973-48-7)

Safety Data

• WGK Germany: 3
• RTECS: SZ9065000
• Hazardous Substances Data: 33973-48-7(Hazardous Substances Data)

Usage

Uses

Reactant for:Carbanion oxidative nucleophilic substitution of hydrogenBase-catalyzed olefination

InChI:InChI=1/C12H19O3P/c1-4-14-16(13,15-5-2)11(3)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

Upstream product

• 585-71-7 (1-bromoethyl)benzne 
• 122-52-1 triethyl phosphite 
• 51346-81-7 (1,1-dichloro-ethyl)-phosphonic acid diethyl ester 
• 23402-69-9 lithium diphenylcuprate 
• 64-17-5 ethanol 
• 100-41-4 ethylbenzene 
• 591-51-5 phenyllithium 
• 25944-64-3 diethyl (1-phenylethenyl)phosphonate 
• 536-74-3 phenylacetylene 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 74-88-4 methyl iodide 
• 98-85-1 1-Phenylethanol 
• 1445-91-6 (S)-1-phenylethanol 
• 1459-14-9 (R)-(1-bromoethyl)benzene 

Downstream Products

• 61470-40-4 1-phenylethylphosphonic acid 
• 115050-50-5 diethyl 1-(4-nitrophenyl)ethylphosphonate 
• 833-81-8 1,2-diphenylpropene 
• 60815-19-2 1-(1'-Phenylethyliden)-4,4-diphenylcyclohexadien-2,5 
• 20615-08-1 1-phenylethylphosphonic dichloride 
• 221655-39-6 N-phenyl-P-(1-phenylethyl)phosphonamidic chloride 
• 102873-85-8 (1-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-ethyl)-phosphonic acid diethyl ester 
• 5470-45-1 (1-{4-[bis-(2-iodo-ethyl)-amino]-phenyl}-ethyl)-phosphonic acid diethyl ester 
• 856997-52-9 [1-(4-amino-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 1043498-97-0 (S)-2,2-dimethyl-4-((E)-2-phenylpropenyl)oxazolidine-3-carboxylic acid tert-butyl ester 
• 1149343-96-3 diethyl α-(2-fluoro-4-nitrophenyl)-α-methylbenzylphosphonate 
• 1149343-94-1 diethyl α-(4-nitrophenyl)-α-methylbenzylphosphonate 
• 1149343-97-4 diethyl α-(3-chloro-4-nitrophenyl)-α-methylbenzylphosphonate 
• 1149343-95-2 diethyl α-(3-fluoro-4-nitrophenyl)-α-methylbenzylphosphonate 

Relevant articles and documents

Selective hydrolysis of phosphorus(v) compounds to form organophosphorus monoacids

An azide and transition metal-free method for the synthesis of elusive phosphonic, phosphinic, and phosphoric monoacids has been developed. Inert pentavalent P(v)-compounds (phosphonate, phosphinate, and phosphate) are activated by triflate anhydride (Tf2O)/pyridine system to form a highly reactive phosphoryl pyridinium intermediate that undergoes nucleophilic substitution with H2O to selectively deprotect one alkoxy group and form organophosphorus monoacids.

Oxidative Dephosphorylation of Benzylic Phosphonates with Dioxygen Generating Symmetrical trans-Stilbenes

Under a dioxygen atmosphere, benzylphosphonates and related phosphoryl compounds can readily produce the corresponding trans-stilbenes in high yields with high selectivity upon treatment with bases. Various functional groups were tolerable under the reaction conditions.

Efficient synthesis of α-substituted ethylphosphonates via CuH-catalyzed conjugate reduction of terminal alkenylphosphonate

An unprecedented approach toward synthesis of α-substituted ethylphosphonates based on CuH-catalyzed conjugate reduction of vinylphosphonates has been successfully developed. This protocol features mild conditions, broad substrate scope, good functional group compatibility, high overall efficiencies, and easy gram-scale synthesis. The Cu-catalyzed reduction takes place in a highly selective manner on the phosphono substituted C[dbnd]C bond in the case of the reaction of alkenylphosphonates bearing both phosphono and alkyl or aryl substituted alkene moieties. Furthermore, the result of competitive reaction indicates that the Cu-catalyzed conjugate reduction of vinylphosphonate is more challenging and reproducible than the corresponding acrylate's reaction.