128833-03-4

Basic information

• Product Name: DIETHYL 3-BROMOBENZYLPHOSPHONATE
• Synonyms: DIETHYL 3-BROMOBENZYLPHOSPHONATE;Phosphonic acid, [(3-broMophenyl)Methyl]-, diethyl ester;[(3-Bromophenyl)methyl]phosphonic acid diethyl ester;Diethyl m-bromobenzylphosphonate;1-bromo-3-(diethoxyphosphorylmethyl)benzene
• CAS NO: 128833-03-4
• Molecular Formula: C₁₁H₁₆BrO₃P
• Molecular Weight: 307.12
• Mol File: 128833-03-4.mol

Chemical Properties

• Boiling Point: 376.023 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.343 g/mL at 25 °C
• Refractive Index: n20/D1.523
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: DIETHYL 3-BROMOBENZYLPHOSPHONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 3-BROMOBENZYLPHOSPHONATE(128833-03-4)
• EPA Substance Registry System: DIETHYL 3-BROMOBENZYLPHOSPHONATE(128833-03-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 128833-03-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL 3-BROMOBENZYLPHOSPHONATE is used as a reagent for the synthesis of various pharmaceutical compounds. Its ability to convert benzylic and allylic alcohols to phosphonates makes it a valuable tool in the development of new drugs and medicinal agents.
Used in Chemical Research:
In the field of chemical research, DIETHYL 3-BROMOBENZYLPHOSPHONATE is employed as a reagent to study the reactivity and properties of benzylic and allylic alcohols. This helps researchers to understand the underlying mechanisms of various chemical reactions and develop new synthetic routes for the production of complex organic molecules.
Used in Organic Synthesis:
DIETHYL 3-BROMOBENZYLPHOSPHONATE is used as a reagent in organic synthesis for the preparation of phosphonate derivatives. These derivatives are important intermediates in the synthesis of various organic compounds, including agrochemicals, dyes, and specialty chemicals.
Used in Material Science:
In material science, DIETHYL 3-BROMOBENZYLPHOSPHONATE can be used as a reagent to modify the properties of certain materials. The introduction of phosphonate groups can enhance the stability, solubility, or reactivity of these materials, making them suitable for various applications, such as catalysts, sensors, or coatings.
Overall, DIETHYL 3-BROMOBENZYLPHOSPHONATE is a versatile reagent with applications in various industries, including pharmaceuticals, chemical research, organic synthesis, and material science. Its ability to convert benzylic and allylic alcohols to phosphonates makes it a valuable tool for the development of new compounds and materials.

Upstream product

• 823-78-9 meta-bromobenzyl bromide 
• 122-52-1 triethyl phosphite 
• 591-17-3 meta-bromotoluene 
• 15852-73-0 (3-Bromophenyl)methanol 
• 762-04-9 phosphonic acid diethyl ester 
• 78-40-0 triethyl phosphate 
• 78-39-7 Triethyl orthoacetate 
• 3132-99-8 m-bromobenzoic aldehyde 

Downstream Products

• 263165-27-1 Diethyl [3-(diethoxyphosphoryl)phenyl]methylphosphonate 
• 282724-83-8 8β-tert-butyldimethylsilyloxy-(17E)-[1-(3-bromophenyl)methylidene]-de-A,B-androstane 
• 268232-20-8 3-bromo-[2-(3-ethoxymethoxy-5-ethoxymethoxymethylphenyl)vinyl]phenyl 
• 869070-21-3 2-[2-(3-bromo-phenyl)-vinyl]-benzoic acid 
• 18951-48-9 (E)-4-<2-(3-bromophenyl)ethenyl>phenol 
• 23958-26-1 trans-1,2-bis(3-bromophenyl)ethene 
• 198707-81-2 2-(3-bromophenethyl)benzoic acid 
• 4890-85-1 o-phenethylbenzoic acid 
• 869070-31-5 2-phenyl-10,11-dihydro-dibenzo[a,d]cyclohepten-5-one 
• 198707-82-3 2-bromo-10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-one 
• 14064-45-0 (E)-3-bromostilbene 
• 307318-52-1 (17E)-1α-tert-butyldimethylsilyloxy-20-[3-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether 
• 307318-57-6 (17Z)-1α-tert-butyldimethylsilyloxy-20-[3-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether 
• 307318-51-0 (17E)-1α-tert-butyldimethylsilyloxy-20-[3-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether 

Relevant articles and documents

The preparation of heterobiaryl phosphonates via the Stille coupling reaction

The Stille cross-coupling reaction between various heteroarylstannanes and substituted bromo-benzylphosphonates was used to prepared heterobiaryl phosphonates in moderate to good yields.

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.

Selective esterification of phosphonic acids

Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.

Novel phenanthrene compounds, a method of making the same and organic electronic devices using the same

The present invention relates to novel phenanthrene compounds having excellent luminous efficiency and lifespan, a manufacturing method thereof, and an organic electronic device including the novel phenanthrene compounds. The novel phenanthrene compounds according to the present invention can form steric conformation, can improve performance through improvement of electronic density, also can improve performance by regulating the molecular weight and position of a functional group because the molecular weight of the compounds is low, and can minutely regulate luminous wavelength and improve performance according to types of the functional groups. As the result, the organic electronic device including the novel phenanthrene compounds has high brightness, excellent thermal resistance, long lifespan, and high efficiency.

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 conversion of benzylic and allylic alcohols to phosphonates

Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth- Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI2.

Synthesis and evaluation of stilbene derivatives as a potential imaging agent of amyloid plaques

Fluorescence probes that can detect Aβ (β-amyloid peptide) plaque are important tools for diagnosis of Alzheimer's disease (AD), and 4-N-methylamino-4′-hydroxystilbene (SB-13) is one of the promising candidate molecules. We report here the synthesis of SB-13 derivatives that consist of various electron donating/withdrawing moieties and distinct size of N-substituents. The synthesized compounds were screened for detection of Aβ40 fibrils in vitro. Four compounds exhibited more than sixfold intensity increase, and they were further analyzed for detail bindings and Aβ plaque imaging. Among these molecules, compound 42 meets two critical requirements for imaging agent; high fluorescence responsiveness and strong binding affinity. This compound showed more than 25-fold increase with the dissociation constant of 1.13 ± 0.37 μM. In AD mouse brain tissue, 42 selectively stained Aβ plaque, more specifically peripheral regions of Aβ plaque. This finding demonstrated its potential use as brain-imaging agents for AD studies.

Dual Pharmacophores - PDE4-Muscarinic Antagonistics

The present invention is directed to novel compounds of Formula (I) and pharmaceutically acceptable salts thereof, pharmaceutical compositions and their use as dual chromaphores having inhibitory activity against PDE4 and muscarinic acetylcholine receptors (mAChRs), and thus being useful for treating respiratory diseases.

Novel Compounds, Their Preparation and Use

Novel compounds of the general formula (I), the use of these compounds as pharmaceutical compositions, pharmaceutical compositions comprising the compounds and methods of treatment employing these compounds and compositions. The present compounds may be useful in the treatment and/or prevention of conditions mediated by Peroxisome Proliferator-Activated Receptors (PPAR), in particular the PPARδ subtype.

Studies on a series of potent, orally bioavailable, 5-HT1 receptor ligands-Part II

A series of 5-(piperidinylethyloxy)quinoline 5-HT1 receptor ligands have been studied by elaboration of the series of dual 5-HT1-SSRIs reported previously. These new compounds display a different in vitro pharmacological profile with potent affinity across the 5-HT1A, 5-HT1B and 5-HT1D receptors and selectivity against the serotonin transporter. Furthermore, they have improved pharmacokinetic profiles and CNS penetration.