1829-37-4

Usage

Uses

Used in Agrochemical Synthesis:
1-ACETOXY-2-BROMOBENZENE is used as a chemical intermediate for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique structure allows for the development of new and effective compounds that can help improve crop protection and yield.
Used in Molecular Recognition:
In the field of molecular recognition, 1-ACETOXY-2-BROMOBENZENE is utilized as a key component in the design and synthesis of molecules that can selectively interact with specific biological targets. This selective interaction is crucial for the development of new drugs and diagnostic tools.
Used in Material Science:
1-ACETOXY-2-BROMOBENZENE is also employed in material science as a precursor for the development of novel materials with unique properties. These materials can be used in various applications, such as sensors, electronic devices, and advanced coatings.

InChI:InChI=1/C8H7BrO2/c1-6(10)11-8-5-3-2-4-7(8)9/h2-5H,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 122-79-2 Phenyl acetate 
• 95-56-7 2-hydroxybromobenzene 
• 108-24-7 acetic anhydride 
• 127-09-3 sodium acetate 
• 50-78-2 aspirin 
• 108-86-1 bromobenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 367-12-4 2-fluorophenol 
• 108-95-2 phenol 
• 95-57-8 2-monochlorophenol 
• 90-05-1 2-methoxy-phenol 
• 88-18-6 2-tert-Butylphenol 

Downstream Products

• 136476-27-2 2-acetoxy-α-(trifluoromethyl)styrene 
• 95-56-7 2-hydroxybromobenzene 
• 135449-12-6 2-(2-Furyl)phenyl acetate 
• 183589-09-5 2-(phenylethynyl)phenyl acetate 
• 1391838-53-1 diethyl 3-[(2-acetyloxyphenyl)ethoxyphosphinoyl]propylphosphonate 
• 1218-52-6 8-bromo-2-phenyl-4H-chromen-4-one 
• 68560-81-6 3'-bromo-2'-hydroxychalcone 
• 1836-06-2 3-bromo-4-hydroxyacetophenone 
• 1836-05-1 3’-bromo-2’-hydroxylacetophenone 
• 57486-69-8 methyl 2-(2-bromophenyl)acetate 
• 1774-68-1 2'-Hydroxy-3'-brom-4-dimethylamino-chalkon 
• 1774-58-9 2,2'-Dihydroxy-3',3,5-tribrom-chalkon 
• 1774-69-2 2'-Hydroxy-2,3',4-tribrom-chalkon 

Relevant academic research and scientific papers

Electronic and Steric Optimization of Fluorogenic Probes for Biomolecular Imaging

Fluorogenic probes are invaluable tools for spatiotemporal investigations within live cells. In common fluorogenic probes, the intrinsic fluorescence of a small-molecule fluorophore is masked by esterification until entry into a cell, where endogenous esterases catalyze the hydrolysis of the masking groups, generating fluorescence. The susceptibility of masking groups to spontaneous hydrolysis is a major limitation of these probes. Previous attempts to address this problem have incorporated auto-immolative linkers at the cost of atom economy and synthetic adversity. Here, we report on a linker-free strategy that employs adventitious electronic and steric interactions in easy-to-synthesize probes. We find that X···C = O n→π? interactions and acyl group size are optimized in 2′,7′-dichlorofluorescein diisobutyrate. This probe is relatively stable to spontaneous hydrolysis but is a highly reactive substrate for esterases both in vitro and in cellulo, yielding a bright, photostable fluorophore with utility in biomolecular imaging.

A Unified Approach to Decarboxylative Halogenation of (Hetero)aryl Carboxylic Acids

Aryl halides are a fundamental motif in synthetic chemistry, playing a critical role in metal-mediated cross-coupling reactions and serving as important scaffolds in drug discovery. Although thermal decarboxylative functionalization of aryl carboxylic acids has been extensively explored, the scope of existing halodecarboxylation methods remains limited, and there currently exists no unified strategy that provides access to any type of aryl halide from an aryl carboxylic acid precursor. Herein, we report a general catalytic method for direct decarboxylative halogenation of (hetero)aryl carboxylic acids via ligand-to-metal charge transfer. This strategy accommodates an exceptionally broad scope of substrates. We leverage an aryl radical intermediate toward divergent functionalization pathways: (1) atom transfer to access bromo- or iodo(hetero)arenes or (2) radical capture by copper and subsequent reductive elimination to generate chloro- or fluoro(hetero)arenes. The proposed ligand-to-metal charge transfer mechanism is supported through an array of spectroscopic studies.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes

Although there has been a lot of progress in oxidative arene C–H functionalization reactions catalyzed by Pd(II/IV) system, the non-directed, site-selective functionalization of arene molecules is still challenging. It has been established that ligands play a pivotal role in controlling rate- as well as selectivity-determining step in a catalytic cycle involving well-defined metal-ligand bonding. N-heterocyclic carbene (NHC) ligands have had a tremendous contribution in the recent extraordinary success of achieving high reactivity and excellent selectivity in many catalytic processes including cross-coupling and olefin-metathesis reactions. However, the immense potential of these NHC ligands in improving site-selectivity of non-directed catalytic C–H functionalization reactions of simple arenes is yet to be realized, where overriding the electronic bias on deciding selectivity is a burdensome task. The presented work demonstrated an initiative step in this regard. Herein, a series of well-defined discrete [Pd(NHCR′R)(py)I2] complexes with systematically varied degree of spatial congestion at the Pd centre, exerted through the R and R’ substituents on the NHC ligand, were explored in controlling the activity as well as the site-selectivity of non-directed acetoxylation of representative monosubstituted and disubstituted simple arenes (such as toluene, iodobenzene and bromobenzene, naphthalene and 1,2-dichlorobenzene). The resulting best yields were found to be 75% for toluene and 65% for bromobenzene with [Pd(NHCMePh)(py)I2], 75% for iodobenzene and 79% for naphthalene with [Pd(NHCMeMe)(py)I2], and 41% for 1,2-dichlorobenzene with [Pd(NHCCyCy)(py)I2]. Most importantly, with increasing the bulkiness of the NHC ligand in the complexes, the selectivity of the distal C-acetoxylated products in comparison to the proximal ones, was enhanced to a great extent in all cases. Considering the vast library of NHC ligands, this study underscores the future opportunity to develop more strategies to improve the activity and the crucial site-selectivity of C–H functionalization reactions in simple as well as complex organic molecules.

Iridium-Catalyzed C(sp3)?H Addition of Methyl Ethers across Intramolecular Carbon–Carbon Double Bonds Giving 2,3-Dihydrobenzofurans

Intramolecular addition of an O-methyl C(sp3)?H bond across a carbon-carbon double bond occurs in the iridium-catalyzed reaction of methyl 2-(propen-2-yl)phenyl ethers. The Ir/(S)-DTBM-SEGPHOS catalyst promotes the reaction efficiently in toluene at 110–135 °C to afford 3,3-dimethyl-2,3-dihydrobenzofurans. Enantioselective C(sp3)?H addition is achieved in the reaction of methyl 2-(1-siloxyethenyl)phenyl ethers, affording enantioenriched 3-hydroxy-2,3-dihydrobenzofuran derivatives with up to 96% ee. (Figure presented.).

Synthesis of 8-Bromoflavone and Its Buchwald-Hartwig Reaction with Amines

Simple and convenient synthesis of 8-bromoflavone was achieved, starting from 2-bromophenol through 3′-bromo-2′-hydroxyacetophenone whose preparation was managed to be solved by optimized Fries rearrangement. The Buchwald-Hartwig reaction of 8-bromoflavone with different type of primary and secondary amines was carried out.

Silanediol-Catalyzed Chromenone Functionalization

Promising levels of enantiocontrol are observed in the silanediol-catalyzed addition of silyl ketene acetals to benzopyrylium triflates. This rare example of enantioselective, intermolecular chromenone functionalization with carbonyl-containing nucleophiles has potential applications in the synthesis of bioactive chromanones and tetrahydroxanthones.

Ligand-Promoted Palladium-Catalyzed C?H Acetoxylation of Simple Arenes

The palladium-catalyzed C?H oxidation of simple arenes is an attractive strategy to obtain phenols, which have many applications in the fine chemicals industry. Although some advances have been made in this research area, low reactivity and selectivity are, in general, observed. This report describes a new catalytic system for the efficient C?H acetoxylation of simple arenes based on Pd(OAc)2 and a pyridinecarboxylic acid ligand.

TETRAZOLINONE COMPOUND AND APPLICATIONS THEREOF

Disclosed is a tetrazolinone compound having a high pest control effect and represented by the formula (1): wherein R1, R2, R3, and R11 each represent a halogen atom, a C1-C6 alkyl group, or the like; R4 and R5 each represent a hydrogen atom, a halogen atom, a C1-C3 alkyl group, or the like; R6 represents a C1-C3 alkyl group which may have a halogen atom(s) or the like; R7, R8, and R9 each represent a hydrogen atom, a halogen atom, or the like; R10 represents a C1-C3 alkyl group or the like; R12 represents a C1-C6 alkyl group, a C3-C6 cycloalkyl group, or the like, and R13 represents a C1-C6 alkyl group, a C2-C6 alkenyl group, or the like.

Solventless acetylation of alcohols and phenols catalyzed by supported iron oxide nanoparticles

Supported iron oxide nanoparticles on silicate catalysts were found to be efficient and easily recoverable materials in the acetylation of alcohols and phenols to their corresponding acetyl compounds using acetic anhydride under mild and solvent-less conditions. The supported iron oxide nanoparticles could be easily recovered from the reaction mixture and reused ten times without any loss in activity.