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

Description

DIETHYL 4-CHLOROBENZYLPHOSPHONATE is a clear colorless liquid that serves as a versatile reactant in various chemical processes and applications. It is known for its ability to contribute to the synthesis of a range of compounds with diverse properties and uses.

Uses

Used in Pharmaceutical Industry:
DIETHYL 4-CHLOROBENZYLPHOSPHONATE is used as a reactant for the preparation of chromenone and chromene derivatives, which act as anti-picornavirus capsid-binders. These compounds are essential in the development of antiviral medications targeting picornaviruses, such as the common cold virus.
Used in Electronics Industry:
In the electronics industry, DIETHYL 4-CHLOROBENZYLPHOSPHONATE is utilized as a reactant for the preparation of wide band gap monomers and silafluorene copolymers with blue electroluminescence. These materials are crucial for the development of emitter layers in organic light-emitting diodes (OLEDs), which are used in various display and lighting applications.
Used in Chemical Synthesis:
DIETHYL 4-CHLOROBENZYLPHOSPHONATE is employed as a reactant in asymmetric synthesis of gamma-nitrophosphonates via Michael addition with nitroalkenes. This process is significant in the production of various chemical compounds with potential applications in different industries, including pharmaceuticals and materials science.
Used in Organic Chemistry:
DIETHYL 4-CHLOROBENZYLPHOSPHONATE is also used in Wittig-Horner reactions, which are essential for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and natural products. These reactions contribute to the development of new molecules with potential applications in various fields.

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

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

Downstream Products

• 81795-79-1 4,4'-((2,5-dimethoxy-1,4-phenylene)bis(ethene-2,1-diyl))bis(chlorobenzene) 
• 251107-35-4 4-(4-chloro-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester 
• 57787-10-7 α-chloro-4-chloro-benzyl-phosphonic acid diethyl ester 
• 209627-02-1 [Chloro-(4-chloro-phenyl)-trimethylsilanyl-methyl]-phosphonic acid diethyl ester 
• 209626-96-0 [(4-Chloro-phenyl)-fluoro-trimethylsilanyl-methyl]-phosphonic acid diethyl ester 
• 79177-63-2 diethyl α-fluoro-4-chlorobenzylphosphonate 
• 869881-97-0 2-[(4-chloro-benzyl)-ethoxy-phosphinoyloxy]-benzoic acid methyl ester 
• 869882-00-8 3-(4-chloro-phenyl)-2-ethoxy-2-oxo-2,3-dihydro-2λ⁵-benzo[e][1,2]oxaphosphinin-4-one 
• 869881-80-1 C₉H₁₁Cl₂O₂P 
• 39225-05-3 p-Chlorbenzylphosphonsaeure 

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.

Determination and application of the excited-state substituent constants of pyridyl and substituted phenyl groups

Thirty six 1-pyridyl-2-arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2-pyridyl, 3-pyridyl and 4-pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1-substituted phenyl-2-arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited-state substituent constants (Formula presented.) of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve-fitting method. Taking the λmax values of 358 samples of bi-arylethene derivatives as a data set and 126 samples of bi-aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained (Formula presented.) as a parameter, and good results were obtained for the two data sets. The reliability of the obtained (Formula presented.) values was verified. The results of this paper can provide excited-state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.

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.