23755-73-9

Basic information

• Product Name: Triethyl phosphonobromoacetate
• Synonyms: Ethyl 2-bromo-2-(diethoxyphosphoryl)acetate;Triethyl 2-bromophosphonoacetate;TRIETHYL PHOSPHONOBROMOACETATE;Triethyl2-Bromo-2-phosphoacetate
• CAS NO: 23755-73-9
• Molecular Formula: C₈H₁₆BrO₅P
• Molecular Weight: 303.09
• Mol File: 23755-73-9.mol

Chemical Properties

• Boiling Point: 128-131 °C(Press: 1 Torr)
• Appearance: /
• Density: 1.3742 g/cm3
• CAS DataBase Reference: Triethyl phosphonobromoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Triethyl phosphonobromoacetate(23755-73-9)
• EPA Substance Registry System: Triethyl phosphonobromoacetate(23755-73-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 23755-73-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Triethyl phosphonobromoacetate is used as a reagent for various chemical reactions in the field of organic synthesis. Its ability to undergo nucleophilic substitution and ester hydrolysis makes it a valuable compound for creating new organic molecules.
Used in Pharmaceutical Production:
Triethyl phosphonobromoacetate is used as a building block in the production of various pharmaceuticals. Its versatility in chemical reactions allows for the creation of a wide range of drug molecules, contributing to the development of new medications.
Used in Agrochemical Production:
Triethyl phosphonobromoacetate is also used as a building block in the production of agrochemicals. Its chemical properties make it suitable for the synthesis of compounds used in agriculture, such as pesticides and herbicides, to improve crop protection and yield.

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 28845-75-2 triethyl 2,2-dibromophosphonoacetate 

Downstream Products

• 58950-08-6 Ethyl-α-brom-m-nitrocinnamat 
• 91348-52-6 (E)-ethyl 3-(4-nitrophenyl)-2-bromo-2-propenoate 
• 930106-41-5 C₁₇H₂₅BrO₃Si 

Relevant articles and documents

Application of Dually Activated Michael Acceptor to the Rational Design of Reversible Covalent Inhibitor for Enterovirus 71 3C Protease

Targeted covalent inhibitors (TCIs) have attracted growing attention from the pharmaceutical industry in recent decades because they have potential advantages in terms of efficacy, selectivity, and safety. TCIs have recently evolved into a new version with reversibility that can be systematically modulated. This feature may diminish the risk of haptenization and help optimize the drug-target residence time as needed. The enteroviral 3C protease (3Cpro) is a valuable therapeutic target, but the development of 3Cpro inhibitors is far from satisfactory. Therefore, we aimed to apply a reversible TCI approach to the design of novel 3Cpro inhibitors. The introduction of various substituents onto the α-carbon of classical Michael acceptors yielded inhibitors bearing several classes of warheads. Using steady-state kinetics and biomolecular mass spectrometry, we confirmed the mode of reversible covalent inhibition and elucidated the mechanism by which the potency and reversibility were affected by electronic and steric factors. This research produced several potent inhibitors with good selectivity and suitable reversibility; moreover, it validated the reversible TCI approach in the field of viral infection, suggesting broader applications in the design of reversible covalent inhibitors for other proteases.

Visible-Light Organophotoredox-Catalyzed Synthesis of Precursors for Horner-Type Olefinations

A metal-free photoredox-catalyzed α-heteroarylation of 2-bromophosphonoacetic esters allows the synthesis of precursors for Horner-olefinations from indoles in a single step. Numerous functional groups are tolerated in this photoinduced radical coupling u

Enantioselective organocatalytic synthesis of α- cyclopropylphosphonates through a domino michael addition/intramolecular alkylation reaction

An organocatalytic domino reaction consisting of Michael addition/intramolecular alkylation between α,β-unsaturated aldehydes and bromophosphonoacetates was developed. Highly functionalised cyclopropylphosphonates containing three chiral centres, one of them quaternary, were obtained with good diastereoselectivities of up to 83:17 and very high enantioselectivities of up to 99 %. α-Cyclopropylphosphonates with three stereogenic centres were obtained in good yields and high enantio-and diastereocontrol through a "one-pot" domino process catalysed by a chiral pyrrolidine. The highly functionalised cyclopropanes should be versatile starting materials for biologically important compounds. Copyright

Synthesis of 3-alkoxycarbonyl-1β-methylcarbapenem by using the palladium-catalyzed C-N bond-forming reaction between vinyl halide and β-lactam nitrogen

3-Alkoxycarbonyl-1β-methylcarbapenem could be synthesized by using a palladium-catalyzed C-N bond-forming reaction between vinyl halide and β-lactam nitrogen. In this reaction, the use of Pd-(OAc)2 and DPEphos gave a good result, and the generation of Pd(0) from Pd(OAc)2 in the absence of a base is necessary to increase the yield.

Multisubstituted Cyclohexene Construction through Telescoped Radical-Addition Induced Remote Functional Group Migration and Horner–Wadsworth–Emmons (HWE) Olefination

An efficient telescoped method for the rapid assembly of multisubstituted cyclohexenes is presented herein. The whole process nicely merges photoredox-promoted alkene difunctionalization via remote functional group migration with concomitant intramolecular Horner–Wadsworth–Emmons (HWE) olefination. The characteristic feature of this protocol resides in the fact that the follow-up requiring ketone functionality for ring-closing olefination is in situ unveiled from the otherwise inert tertiary alcohol by the preceding alkene difunctionalization.

Visible-Light-Promoted Generation of α-Ketoradicals from Vinyl-bromides and Molecular Oxygen: Synthesis of Indenones and Dihydroindeno[1,2-c]chromenes

Ortho-alkynylated α-bromocinnamates can be converted by a visible-light-mediated photocascade reaction with molecular oxygen into either indenones or dihydroindeno[1,2-c]chromenes. The one-step process features key photochemical steps, that is, the initial activation of vinyl bromides through energy transfer to give α-ketoradicals in a reaction with molecular oxygen, followed by α-oxidation of an arene moiety by 6-π electrocyclization, and subsequent hydroxylation by an electron-transfer process from the same photocatalyst leads to the dihydroindeno[1,2-c]chromenes.

Palladium-Catalyzed Long-Range Deconjugative Isomerization of Highly Substituted α,β-Unsaturated Carbonyl Compounds

The long-range deconjugative isomerization of a broad range of α,β-unsaturated amides, esters, and ketones by an in situ generated palladium hydride catalyst is described. This redox-economical process is triggered by a hydrometalation event and is thermodynamically driven by the refunctionalization of a primary or a secondary alcohol into an aldehyde or a ketone. Di-, tri-, and tetrasubstituted carbon-carbon double bonds react with similar efficiency; the system is tolerant toward a variety of functional groups, and olefin migration can be sustained over 30 carbon atoms. The refunctionalized products are usually isolated in good to excellent yield. Mechanistic investigations are in support of a chain-walking process consisting of repeated migratory insertions and β-H eliminations. The bidirectionality of the isomerization reaction was established by isotopic labeling experiments using a substrate with a double bond isolated from both terminal functions. The palladium hydride was also found to be directly involved in the product-forming tautomerization step. The ambiphilic character of the in situ generated [Pd-H] was demonstrated using isomeric trisubstituted α,β-unsaturated esters. Finally, the high levels of enantioselectivity obtained in the isomerization of a small set of α-substituted α,β-unsaturated ketones augur well for the successful development of an enantioselective version of this unconventional isomerization.

Synthesis of the ABC ring system of jiadifenin via pd-catalyzed cyclizations

An efficient route toward the central ABC system of jiadifenin has been developed using two key Pd-catalyzed cyclizations. A protic solvent-activated Mizoroki-Heck reaction was used to construct the C9 quaternary carbon and the A ring. A cascad

A new general approach to 4-substituted-3-halo-2-quinolones

A general procedure for the preparation of 4-substituted-3-halo-2-quinolones (halo = F, Cl, Br) utilizing 2-halo diethylphosphonoacetic acids (halo = F, Cl, Br) and o-aminophenylketones as the starting materials is described. The title compounds are obtained by an intramolecular Horner-Wadsworth-Emmons olefination of halogen-containing N-acyl-o-aminophenylketones. The transformation process is generally applicable under mild conditions.

Facile access to 2-arylindolines and 2-arylindoles by microwave-assisted tandem radical cyclization

A new route providing access to 2-arylindoles has been developed. The synthesis consists of a tin-mediated tandem radical cyclization of appropriate precursors to form 2,3-disubstituted dihydroindoles, which in turn are oxidized to yield the corresponding 2-arylindoles. The reactions proceed smoothly under microwave irradiation, furnishing the desired products in good yields. Georg Thieme Verlag Stuttgart.