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
• Article Data: 16

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

General Description

Triethyl phosphonobromoacetate is a chemical compound with the molecular formula C8H16BrO4P. It is commonly used as a reagent in organic synthesis and as a building block in the production of various pharmaceuticals and agrochemicals. Triethyl phosphonobromoacetate is a phosphonate ester, which means it contains a phosphorus atom bonded to three ethyl groups and a bromoacetate group. Triethyl phosphonobromoacetate is known for its ability to undergo various chemical reactions, such as nucleophilic substitution and ester hydrolysis, making it a versatile and valuable compound in the field of organic chemistry. Triethyl phosphonobromoacetate is often handled with care due to its potential hazards, including irritant properties and toxicity to aquatic organisms.

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 
• 153529-45-4 (E)-diethyl 1-ethoxycarbonyl-2-(4-methylphenyl)-vinylphosphonate 
• 53235-79-3 (E)-diethyl 1-ethoxycarbonyl-2-(4-chlorophenyl)-vinylphosphonate 
• 53235-78-2 E-1-carbethoxy-1-diethoxyphosphoryl-2-(2-chlorophenyl) ethene 
• 53235-80-6 E-1-carbethoxy-1-diethoxyphosphoryl-2-(4-nitrophenyl) ethene 
• 53235-77-1 (E)-3-phenyl-2-(diethoxyphosphoryl)acrylic acid ethyl ester 
• 59106-33-1 ethyl 2-bromo-3-phenylacrylate 
• 59106-33-1 (Z)-ethyl 2-bromo-3-phenylprop-2-enoate 
• 59106-34-2 (E)-ethyl 2-bromo-3-phenylpropenoate 
• 197313-84-1 (2Z,4E)-ethyl 2-bromo-5-phenylpenta-2,4-dienoate 
• 318967-94-1 (Z)-ethyl 2-bromo-3-cyclohexylpropenoate 
• 113324-35-9 3-phenyl-2,3-dipiperidino-propionic acid ethyl ester 
• 477201-91-5 (Z)-2-Bromo-3-(3,6-dimethoxy-2-nitro-phenyl)-acrylic acid ethyl ester 

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

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.

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.