253684-21-8

Basic information

• Product Name: methyl 4-(2,2-dibromovinyl)benzoate
• Synonyms: methyl 4-(2,2-dibromovinyl)benzoate
• CAS NO: 253684-21-8
• Molecular Formula: C₁₀H₈Br₂O₂
• Molecular Weight: 320
• Mol File: 253684-21-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: methyl 4-(2,2-dibromovinyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(2,2-dibromovinyl)benzoate(253684-21-8)
• EPA Substance Registry System: methyl 4-(2,2-dibromovinyl)benzoate(253684-21-8)

Safety Data

• Hazardous Substances Data: 253684-21-8(Hazardous Substances Data)

Upstream product

• 1571-08-0 methyl 4-formylbenzoate 
• 558-13-4 carbon tetrabromide 

Downstream Products

• 229174-44-1 methyl 4-[(2-methoxyphenyl)ethynyl]benzoate 
• 1096357-11-7 C₂₀H₁₆N₂O₂ 
• 1096357-13-9 C₁₇H₁₂ClF₃N₂O₂ 
• 727992-64-5 methyl 4-((1H-benzo[d]imidazol-2-yl)methyl)benzoate 
• 1096357-10-6 C₁₆H₁₃BrN₂O₂ 
• 225928-10-9 4-(bromoethynyl)benzoic acid methyl ester 
• 1096357-09-3 C₁₇H₁₆N₂O₂ 
• 1096357-12-8 C₂₂H₁₈N₂O₂ 
• 1232144-42-1 C₁₆H₁₂ClNO₃ 
• 1232144-38-5 C₁₆H₁₃NO₃ 
• 936138-80-6 C₁₆H₁₂N₂O₅ 

Relevant articles and documents

Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis

Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.

Nickel-Catalyzed, Regio- and Enantioselective Benzylic Alkenylation of Olefins with Alkenyl Bromide

A NiH-catalyzed migratory hydroalkenylation reaction of olefins with alkenyl bromides has been developed, affording benzylic alkenylation products with high yields and excellent chemoselectivity. The mild conditions of the reaction preclude olefinic products from undergoing further isomerization or subsequent alkenylation. Catalytic enantioselective hydroalkenylation of styrenes was achieved by using a chiral bisoxazoline ligand.

Selective Rhodium-Catalyzed Hydroformylation of Terminal Arylalkynes and Conjugated Enynes to (Poly)enals Enabled by a π-Acceptor Biphosphoramidite Ligand

The hydroformylation of terminal arylalkynes and enynes offers a straightforward synthetic route to the valuable (poly)enals. However, the hydroformylation of terminal alkynes has remained a long-standing challenge. Herein, an efficient and selective Rh-catalyzed hydroformylation of terminal arylalkynes and conjugated enynes has been achieved by using a new stable biphosphoramidite ligand with strong π-acceptor capacity, which affords various important E-(poly)enals in good yields with excellent chemo- and regioselectivity at low temperatures and low syngas pressures.

A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization

Straightforward access to [1,2]-annulated indoles, key substructures in natural products, is highly desirable yet challenging. Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides is presented, providing a rapid access into [1,2]-annulated indoles by an intermolecular radical addition, intramolecular cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.

Pd-Catalyzed Indole Synthesis via C-H Activation and Bisamination Sequence with Diaziridinone

This work describes an efficient Pd-catalyzed indole synthesis. A wide variety of indoles can be obtained in good yields from readily available vinyl bromides. The reaction likely proceeds through a sequential aryl C-H activation and bisamination of a resulting pallada(II)cycle with diaziridinone.

N -tert-butyl -2 -phenylindole derivative Preparation method and application

The invention belongs to the technical field of organic synthesis, and particularly relates to N - tert-butyl -2 -phenyl indole derivatives as well as a preparation method and application thereof. The preparation method comprises the following steps: (Z)-1 - bromo -1 - phenyl -2 - styrene derivative, N, N - di-tert-butyl diazepinone, palladium catalyst, monophosphine ligand, hydrocarbon activator, base and first solvent, and N -tert-butyl -2 -aryl indole derivatives which can synthesize substituent type diversity, and the prepared N -tert-butyl -2 -aryl indole derivative can be used for preparing biologically active molecules N -2 .

The hydrodebromination of 1,1-dibromoalkenes via visible light catalysis

Vinyl bromides are versatile synthetic intermediates and widely applied in organic synthesis and pharmaceuticals. Herein, a hydrodebromination reaction of 1,1-dibromoalkenes was established via visible light catalysis. A variety of structurally different vinyl bromides were obtained in moderate to excellent yields.

Photostable lysosomal imaging of living cell with hyperspectral stimulated Raman scattering microscopy using a probe based on bisarylbutadiyne

We designed a lysosome-selective Raman probe by conjugating bisphenylbutadiyne with morpholine, a well-known lysosome targeting moiety. This probe, named Lyso-BADY, has a Raman peak 28 times more intense than that of 5-ethynyl-2′-deoxyuridine. Lysosome in

Multicolor Cocktail for Breast Cancer Multiplex Phenotype Targeting and Diagnosis Using Bioorthogonal Surface-Enhanced Raman Scattering Nanoprobes

Early precise diagnosis of cancers is crucial to realize more effective therapeutic interventions with minimal toxic effects. Cancer phenotypes may also alter greatly among patients and within individuals over the therapeutic process. The identification and characterization of specific biomarkers expressed on tumor cells are in high demand for diagnosis and treatment, but they are still a challenge. Herein, we designed three new bioorthogonal surface-enhanced Raman scattering (SERS) nanoprobes and successfully applied the cocktail of them for MDA-MB-231 and MCF-7 breast cancer multiplex phenotype detection. The SERS nanoprobes containing Raman reporters with diynl, azide, or cyano moieties demonstrated apparent Raman shift peaks in 2205, 2120, and 2230 cm-1, respectively, in the biologically Raman-silent region. Three target ligands, including oligonucleotide aptamer (AS1411), arginine-glycine-aspatic acid (RGD) peptide, and homing cell adhesion molecule antibody (anti-CD44), were separately conjugated to the nanoprobes for active recognition capability. The cocktail of the nanoprobes manifested minimal cytotoxicity and simultaneously multiplex phenotype imaging of MDA-MB-231 and MCF-7 cells. Quantitative measurement of cellular uptake by inductively coupled plasma mass spectrometry (ICPMS) verified that MDA-MB-231 cells harbored a much higher expression level of CD44 receptor than MCF-7 cells. For in vivo SERS detection, Raman shift peaks of 2120, 2205, and 2230 cm-1 in the micro-tumor were clearly observed, representing the existence of three specific biomarkers of nucleolin, integrin αvβ3, and CD44 reporter, which could be used for early cancer phenotype identification. The biodistribution results indicated that target ligand modified nanoprobes exhibited much more accumulation in tumors than those nanoprobes without target ligands. The multicolor cocktail of bioorthogonal SERS nanoprobes offers an attractive and insightful strategy for early cancer multiplex phenotype targeting and diagnosis in vivo that is noninvasive and has low cross-talk, unique spectral-molecular signature, high sensitivity, and negligible background interference.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.