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Phosphonic acid, (4-methylbenzoyl)-, diethyl ester, also known as 4-Methylbenzoylphosphonic acid diethyl ester, is a chemical compound with the molecular formula C11H15O4P. It is a colorless liquid with a density of 1.19 g/cm3 and a boiling point of 320°C. Phosphonic acid, (4-methylbenzoyl)-, diethyl ester is an organophosphorus compound, which is a type of compound that contains carbon-phosphorus bonds. It is used as a reagent in the synthesis of various pharmaceuticals and agrochemicals, particularly in the production of herbicides and insecticides. Due to its potential toxicity and environmental impact, it is important to handle this chemical with care and in accordance with safety regulations.

2942-54-3

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2942-54-3 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 2942-54-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,9,4 and 2 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 2942-54:
(6*2)+(5*9)+(4*4)+(3*2)+(2*5)+(1*4)=93
93 % 10 = 3
So 2942-54-3 is a valid CAS Registry Number.

2942-54-3Relevant academic research and scientific papers

A convenient and mild protocol for preparation of α – trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide

Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.

, (2021/10/05)

A convenient and mild protocol was developed for the trimethylsilylation of α-hydroxyphosphonates using hexamethyldisilazane as the silylating agent in the presence of sulfamic acid (SA) as a heterogeneous solid acid catalyst in dichloromethane as the rea

Enantioselective vinylogous aldol reaction of acylphosphonates with 3-alkylidene oxindoles

Jaiswal, Manish K.,Singh, Ravi P.,Singh, Sanjay

supporting information, p. 7861 - 7866 (2021/09/28)

A simple strategy for yielding chiral tertiary α-hydroxy phosphonates that integrates two highly biologically relevant scaffolds namely 3-alkylidene-2-oxindoles and phosphonates has been described. The hydrogen bonding ability of the bifunctional thiourea catalyst allows simultaneous dual activation of a vinylogous oxindole nucleophile and an acylphosphonate electrophile, affording hydroxyphosphonato-3-alkylidene-2-oxindoles as aldol adducts in high yields (up to 92%) with excellent stereocontrol (up to 99% ee).

Highly efficient and extremely simple protocol for the oxidation α-hydroxyphosphonates to α-ketophosphonates using Dess-Martin periodinane

Kupwade, Ravindra V.,Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.

, p. 50 - 58 (2021/02/26)

Dess-Martin periodinane has been demonstrated for the first time to be an efficient reagent in metal - free oxidation of α-hydroxyphosphonates to α-ketophosphonates under ambient conditions. Acquiescent reaction conditions and a simple isolation procedure

Visible photocatalysis of novel oxime phosphonates: Synthesis of β-aminophosphonates

Li, Yong-Hong,Wang, Chun-Hai,Gao, Su-Qian,Qi, Feng-Ming,Yang, Shang-Dong

supporting information, p. 11888 - 11891 (2019/10/11)

A novel type of oxime phosphonate was synthesized and used in the intermolecular cascade radical addition reaction of alkenes to access β-aminophosphonates via visible-light-driven N-centered iminyl radical-mediated and redox-neutral selective C-P single-bond cleavage in an active phosphorus radical route. The procedure is characterized by its ability to achieve the construction of Csp3-P and Csp3-N bonds without the requirement for oxidants and bases.

Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates

Sun, Jun,He, Fangcheng,Wang, Zhongyao,Pan, Dingwu,Zheng, Pengcheng,Mou, Chengli,Jin, Zhichao,Chi, Yonggui Robin

supporting information, p. 6040 - 6043 (2018/06/18)

A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between α,β-unsaturated aldehydes and α-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection.

Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates

Kayal, Satavisha,Mukherjee, Santanu

supporting information, p. 5508 - 5511 (2015/11/18)

A cascade aldol-cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction

Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides

Lian, Zhong,Yin, Hongfei,Friis, Stig D.,Skrydstrup, Troels

supporting information, p. 7831 - 7834 (2015/05/13)

The first transition-metal catalysed carbonylation with a phosphorus nucleophile is presented. This transformation provides efficient and mild access to aroylphosphonates under mild conditions, thus ensuring a broad substrate scope. The utility of aroylph

Synthesis of acylphosphonates by a palladium-catalyzed phosphonocarbonylation reaction of aryl iodides with phosphites

Masuda, Yusuke,Ishida, Naoki,Murakami, Masahiro

supporting information, p. 321 - 324 (2015/02/05)

Acylphosphonates are conveniently synthesized from aryl iodides by a palladium-catalyzed reaction with dialkyl phosphites under an atmospheric pressure of carbon monoxide. The reaction demonstrates the first example of the use of phosphorus nucleophiles in related metal-catalyzed carbonylation reactions.

Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst

Jang, Ki Po,Hutson, Gerri E.,Johnston, Ryne C.,McCusker, Elizabeth O.,Cheong, Paul H.-Y.,Scheidt, Karl A.

supporting information, p. 76 - 79 (2014/01/23)

A highly selective NHC-catalyzed synthesis of γ-butyrolactones from the fusion of enals and α-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enanti

Rational design of selective organoruthenium inhibitors of protein tyrosine phosphatase 1B

Ong, Jun Xiang,Yap, Chun Wei,Ang, Wee Han

, p. 12483 - 12492 (2013/01/15)

Protein tyrosine phosphatases (PTPs) belong to a large family of important regulatory enzymes involved in vital mammalian signaling pathways. Selective inhibitors of PTPs are highly valuable from a therapeutic standpoint given their association with various pathological conditions. One such target is PTP-1B which has previously been linked to diabetes and cancer. However, developing a selective inhibitor against PTP-1B has proven to be daunting because the enzyme shares a high degree of structural homology with TC-PTP, an essential PTP involved in modulating immune functions. To address this challenge, a series of organoruthenium complexes was developed to bind at the PTP substrate-binding site while simultaneously target the peripheral structural space. By capitalizing on the potential difference in the structural environment proximal to the active site between different PTPs, selectivity toward PTP-1B over TC-PTP was improved, paving the way for organoruthenium complexes as selective PTP-1B metalloinhibitors.

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