39225-17-7

Basic information

• Product Name: DIETHYL 4-CHLOROBENZYLPHOSPHONATE
• Synonyms: Phosphonic acid, [(4-chlorophenyl)methyl]-, diethyl ester;DIETHYL-(4-CHLORBENZYL)-PHOSPHONAT;DIETHYL 4-CHLOROBENZYLPHOSPHATE;DIETHYL 4-CHLOROBENZYLPHOSPHONATE;(4-CHLOROBENZYL)PHOSPHONIC ACID DIETHYL ESTER;Diethyl4-chlorobenzylphosphonate,98+%;NSC 202843;p-(Chlorobenzyl)phosphonic acid diethyl ester
• CAS NO: 39225-17-7
• Molecular Formula: C₁₁H₁₆ClO₃P
• Molecular Weight: 262.67
• EINECS: 254-365-8
• Product Categories: C-C Bond Formation;Horner-Wadsworth-Emmons Reagents;Olefination
• Mol File: 39225-17-7.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 162 °C(lit.)
• Flash Point: 230 °F
• Appearance: Clear colorless/Liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.84E-05mmHg at 25°C
• Refractive Index: n20/D 1.509(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1346690
• CAS DataBase Reference: DIETHYL 4-CHLOROBENZYLPHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 4-CHLOROBENZYLPHOSPHONATE(39225-17-7)
• EPA Substance Registry System: DIETHYL 4-CHLOROBENZYLPHOSPHONATE(39225-17-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 39225-17-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

Reactant for:Preparation of chromenone and chromene derivatives as anti-picornavirus capsid-bindersPreparation of wide band gap monomers and silafluorene copolymers with blue electroluminescence, as emitter layer in organic LEDsAsymmetric synthesis of gamma-nitrophosphonates via Michael addition with nitroalkenesWittig-Horner reactions

InChI:InChI=1/C11H16ClO3P/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

• 637-87-6 1-Chloro-4-iodobenzene 
• 1137728-03-0 C₅H₁₂IO₃PZn 
• 19350-69-7 4-chlorobenzaldehyde p-toluenesulfonylhydrazone 
• 762-04-9 phosphonic acid diethyl ester 
• 104-88-1 4-chlorobenzaldehyde 
• 873-76-7 para-Chlorobenzyl alcohol 
• 122-52-1 triethyl phosphite 
• 622-95-7 4-chlorobenzyl bromide 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 76950-79-3 1-(4-Chloro-benzyl)-2-methylsulfanyl-4,6-diphenyl-pyridinium; iodide 

Downstream Products

• 27980-48-9 5-(4-chloro-benzylidene)-5H-dibenzo[a,d]cycloheptene 
• 130948-88-8 [1-(4-Chloro-phenyl)-cyclohexyl]-phosphonic acid diethyl ester 
• 141544-90-3 1-(4-chlorophenyl)-4-(4-hexyloxyphenyl)buta-1,3-diene 
• 102223-14-3 2-amino-6-(4-chloroxystyryl)-7,8-dihydro-7,7-dimethylpteridin-4(3H)-one 
• 157555-34-5 2-{4-[(E)-2-(4-Chloro-phenyl)-vinyl]-4-methyl-cyclohexyloxy}-tetrahydro-pyran 
• 39225-05-3 p-Chlorbenzylphosphonsaeure 
• 869881-80-1 C₉H₁₁Cl₂O₂P 
• 57787-10-7 α-chloro-4-chloro-benzyl-phosphonic acid diethyl ester 
• 1004794-77-7 diethyl (R,R)-1,2-bis(4-chlorophenyl)-3-nitropropylphosphonate 
• 929290-25-5 E-[2-(4-chloro-phenyl)-vinyl]-3-methyloxymethoxy-benzene 
• 1657-50-7 (E)-1-(4-chlorophenyl)-2-phenylethene 
• 39769-26-1 ClSBF 
• 1657-49-4 1-chloro-4-styrylbenzene 
• 39769-26-1 (E)-1-(4-fluorophenyl)-2-(4-chlorophenyl)ethene 

Relevant articles and documents

Synthesis of α-Aryldiazophosphonates via a Diazo Transfer Reaction

The simple synthetic procedure for preparation of α-aryl-α-diazophosphonates via a diazo transfer reaction is proposed. Benzylphosphonates reacted with tosyl azide (TsN3) in the presence of potassium tert-butoxide (KOtBu) to afford diazophosphonates in a yield up to 79%. The proposed method is general. The reaction uses easily available starting materials, tolerates various functional groups, and may be applied for multi-gram scale synthesis.

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.

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

A strategy for the direct functionalization strategy of inertial dialkyl phosphonates with hydroxy compounds to afford diverse mixed phosphonates with good yields and functional-group tolerance has been developed. Mechanistic investigations involving both NMR studies and DFT studies suggest that an unprecedented highly reactive PV species (phosphoryl pyridin-1-ium salt), a key intermediate for this new synthetic transformation, is generated in situ from dialkyl phosphonate in the presence of Tf2O/pyridine.