39225-17-7

Usage

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

Downstream Products

• 1236-65-3 5-(4-chloro-benzylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene 
• 1229-71-6 9-(4-chlorobenzylidene)-9H-fluorene 
• 57787-10-7 α-chloro-4-chloro-benzyl-phosphonic acid diethyl ester 
• 57787-15-2 1-Chlor-1-(4-chlorphenyl)-3-methyl-1-buten 
• 27980-48-9 5-(4-chloro-benzylidene)-5H-dibenzo[a,d]cycloheptene 
• 57787-12-9 [1-Chloro-1-(4-chloro-phenyl)-ethyl]-phosphonic acid diethyl ester 
• 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 
• 209626-96-0 [(4-Chloro-phenyl)-fluoro-trimethylsilanyl-methyl]-phosphonic acid diethyl ester 
• 209627-02-1 [Chloro-(4-chloro-phenyl)-trimethylsilanyl-methyl]-phosphonic acid diethyl ester 
• 869881-80-1 C₉H₁₁Cl₂O₂P 

Relevant academic research and scientific papers

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.

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.

Tetrahydroquinolinyl phosphinamidates and phosphonamidates enhancing tolerance towards drought stress in crops via interaction with ABA receptor proteins

New phosphorous-containing lead structures against drought stress in crops interacting with RCAR/(PYR/PYL) receptor proteins were identified starting from in-depth SAR studies of related sulfonamide lead structures and protein docking studies. A converging 6-step synthesis via phosphinic chlorides and phosphono chloridates as key intermediates afforded envisaged tetrahydroquinolinyl phosphinamidates and phosphonamidates. Whilst tetrahydroquinolinyl phosphonamidates 13a,b exhibited low to moderate target affinities, the corresponding tetrahydroquinolinyl phosphinamidates 12a,b revealed confirmed strong affinities for RCAR/ (PYR/PYL) receptor proteins in Arabidopsis thaliana on the same level as essential plant hormone abscisic acid (ABA) combined with promising efficacy against drought stress in vivo (broad-acre crops wheat and canola).

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.

TRIARYLAMINE HYDRAZONE DERIVATIVE AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR

PROBLEM TO BE SOLVED: To provide a compound that improves the electric characteristics of electrophotographic photoreceptors. SOLUTION: A triarylamine hydrazone compound is represented by formula (1) or a specific structure (R1 and R2 are halogen, an alkyl group, an alkoxy group, or an aryl group). SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

TRIARYLAMINE DERIVATIVE, ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER, AND METHOD FOR PRODUCING ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER

A triarylamine derivative represented by general formula (1) below. In the general formula (1), R1, R2, R4, R5, R6, R7, R8, and R9 each represent, independently from one another, a hydrogen atom, an optionally substitute alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 14, R3 represents an alkyl group having a carbon number of at least 1 and no greater than 4, X represents an alkylene group having a carbon number of at least 1 and no greater than 6 or an oxygen atom, and n represents an integer of 1 to 3.

TRIARYLAMINE HYDRAZONE COMPOUND AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR

PROBLEM TO BE SOLVED: To provide a compound that improves the electric characteristics of electrophotographic photoreceptors. SOLUTION: A triarylamine hydrazone compound is represented by formula (1) (R1-R6 independently represent halogen, a substituted/unsubstituted C1-6 alkyl group, a C1-6 alkoxy group or a substituted/unsubstituted C6-14 aryl group; a is an integer of 1 to 3 or less; b and c independently represent 0 or 1; d, e, f, g, h and i independently represent an integer of 0-5). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

TRIARYLAMINE HYDRAZONE COMPOUND AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR

PROBLEM TO BE SOLVED: To provide a compound that improves the electric characteristics of electrophotographic photoreceptors. SOLUTION: A triarylamine hydrazone compound is represented by general formula (1) (R1-R6 independently represent a halogen atom, a substituted/unsubstituted C1-6 alkyl group, a substituted/unsubstituted C1-6 alkoxy group or a substituted/unsubstituted C6-14 aryl group; a is an integer of 1 to 3 or less; b-g independently represent an integer of 0-5). SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes

Nrf2, which is a member of the cap'n’ collar family of transcription factors, is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. The importance of inflammation and oxidative stress in many chronic diseases supports the concept that activation of anti-oxidant Nrf2 signaling may have therapeutic potential. A number of Nrf2 activators have entered into clinical trials. Nrf2 exists in the cytosol in complex with its binding partner Keap1, which is a thiol-rich redox-sensing protein. In response to oxidative and electrophilic stress, select cysteine residues of Keap1 are modified, which locks Keap1 in the Nrf2-Keap1 complex and allows newly synthesized Nrf2 to enter the nucleus. Numerous Nrf2-activating chemicals, including a number of natural products, are electrophiles that modify Keap1, often by Michael addition, leading to activation of Nrf2. One concern with the design of Nrf2 activators that are electrophilic covalent modifiers of Keap1 is the issue of selectivity. In the present study, substituted trans stilbenes were identified as activators of Nrf2. These activators of Nrf2 are not highly electrophilic and therefore are unlikely to activate Nrf2 through covalent modification of Keap1. Dose-response studies demonstrated that a range of substituents on either ring of the trans stilbenes, especially fluorine and methoxy substituents, influenced not only the sensitivity to activation, reflected in EC50values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2. The stilbene backbone appears to be a privileged scaffold for development of a new class of Nrf2 activators.