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Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Phosphonic acid, [[4-(trifluoromethyl)phenyl]methyl]-, diethyl ester is used as a key building block in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new drugs and pesticides.
Used in Materials Science:
Phosphonic acid, [[4-(trifluoromethyl)phenyl]methyl]-, diethyl ester is also used in the field of materials science for the development of new materials. Its high chemical stability and potential as a chelating agent for metal ions make it a promising candidate for creating innovative materials with unique properties.
Used in Organic Chemistry:
Phosphonic acid, [[4-(trifluoromethyl)phenyl]methyl]-, diethyl ester is utilized in organic chemistry for its reactivity and stability. It can be employed in various organic synthesis processes, contributing to the development of new organic compounds and reactions.

Upstream product

• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 122-52-1 triethyl phosphite 
• 762-04-9 phosphonic acid diethyl ester 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 6140-17-6 4-methylbenzotrifluoride 
• 939-99-1 4-trifluoromethylbenzyl chloride 

Downstream Products

• 146780-15-6 4-Trifluoromethylbenzylphosphonic acid 
• 145838-97-7 1-methoxy-4-((1E,3E)-4-(4-(trifluoromethyl)phenyl)buta-1,3-dien-1-yl)benzene 
• 42134-74-7 (E)-1,2-bis(4-trifluoromethylphenyl)ethene 
• 835595-61-4 tert-butyl 4-[4-(trifluoromethyl)benzylidene]piperidine-1-carboxylate 
• 847186-66-7 (E,E)-p,p'-bistrifluoromethyl-1,4-diphenyl-1,3-butadiene 
• 1027335-55-2 (E)-2-(4-(trifluoromethyl)styryl)pyridine 

Relevant academic research and scientific papers

A new insight into the push-pull effect of substituents via the stilbene-like model compounds

In this paper, authors report on 1-pyridyl-2-arylethenes, 1-furyl-2-arylethylenes, 1,2-diphenylpropylenes and substituted cinnamyl anilines as stilbene-like model compounds to investigate the factors dominating the push-pull effect of substituents via usi

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.

Transition metal-free access to 3,4-dihydro-1,2-oxaphosphinine-2-oxides from phosphonochloridates and chalcones through tandem Michael addition and nucleophilic substitution

A novel and transition metal-free synthesis of 3,4-dihydro-1,2-oxaphosphinine 2-oxides was developed. LiHMDS-mediated tandem Michael addition and nucleophilic substitution of readily available phosphonochloridates and chalcones afforded a variety of valuable 3,4-dihydro-1,2-oxaphosphinine 2-oxides bearing diverse functionalities in excellent yields and satisfactory to good diastereoselectivity (up to 99% yield and up to 99?:?1 dr).

Identification of novel non-nucleoside vinyl-stilbene analogs as potent norovirus replication inhibitors with a potential host-targeting mechanism

Norovirus (NV), is the most common cause of acute gastroenteritis worldwide. To date, there is no specific anti-NV drug or vaccine to treat NV infections. In this study, we evaluated the inhibitory effect of different stilbene-based analogs on RNA genome replication of human NV (HNV) using a virus replicon-bearing cell line (HG23). Initial screening of our in-house chemical library against NV led to the identification of a hit containing stilbene scaffold 5 which on initial optimization gave us a vinyl stilbene compound 16c (EC50 = 4.4 μM). Herein we report our structure-activity relationship study of the novel series of vinyl stilbene analogs that inhibits viral RNA genome replication in a human NV-specific manner. Among these newly synthesized compounds, several amide derivatives of vinyl stilbenes exhibited potent anti-NV activity with EC50 values ranging from 1 to 2 μM. A trans-vinyl stilbenoid with an appended substituted piperazine amide (18k), exhibited potent anti-NV activity and also displayed favorable metabolic stability. Compound 18k demonstrated an excellent safety profile, the highest suppressive effect, and was selective for HNV replication via a viral RNA polymerase-independent manner. Its potential host-targeting antiviral mechanism was further supported by specific activation of heat shock factor 1-dependent stress-inducible pathway by 18k. These results suggest that 18k might be a promising lead compound for developing novel NV inhibitors with the novel antiviral mechanism.

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.

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.

Influence of the methyl group at C=C bridging bond of stilbene on the longest wavelength maximum in ultraviolet absorption spectra

The compounds stilbenes XArCH=CHArY(XSBY) and 1,2-diphenylpropylenes XArC(Me)=CHArY(XSMBY) have bridging groups CH=CH and C(CH3)=CH, respectively, in which the C(CH3)=CH has a side-group CH3 at the carbon-carbon double bond. A series of XSMBY were synthesized, and their longest wavelength maximum λmax (nm) in ultraviolet absorption spectra were measured in this work. We investigated the change regularity of the νmax (cm-1, νmax?=?1/λmax) of XSMBY and compared it with that of XSBY. The results indicate that (1) there is no good linear relationship between the νmax of XSMBY and that of XSBY. (2) Because of the influence of the side-group CH3, in case of the same couple of groups X and Y, the λmax of XSMBY is shorter than that of XSBY, that is, it has a blue shift. (3) The cross-interaction between the side-group CH3 and Y has an important effect on the νmax of XSMBY, while the cross-interaction between the side-group CH3 and X has a little effect on the νmax and can be ignored. (4) The specific cross-interaction between X and Y has important effect on the νmax of XSMBY, whereas it has no important effect on the νmax of XSBY.

Swivel-cruciform stilbenes based on bithiophene

Bithiophene-based cruciforms with different stilbenoid arms at the 3,3′- and 5,5′-positions have been synthesized by various combinations of Suzuki and Horner-Wadsworth-Emmons (HWE) reactions. According to DFT calculations, the steric hindrance between th

Bulk photovoltaic effect in an organic polar crystal

Organic polar crystals from the donor-acceptor substituted 1,4-diphenybutadiene 1 can generate a short-circuit photocurrent and a photovoltage upon illumination with near UV light. The photocurrent and photovoltage are attributed to a bulk photovoltaic effect. The bulk photovoltaic effect has been known for inorganic polar crystals for decades and can now also be demonstrated for organic polar crystals. This journal is the Partner Organisations 2014.