2077-19-2

Usage

Uses

Used in Organic Synthesis:
2-(4-Bromophenyl)propan-2-ol is used as a key intermediate in the synthesis of various organic compounds. Its bromine atom can be easily replaced by other functional groups, making it a versatile building block for the creation of a wide range of molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-Bromophenyl)propan-2-ol is used as a crucial intermediate for the development of new drugs. Its unique structure allows for the formation of various medicinally relevant compounds, contributing to the advancement of drug discovery and development.
Used in Agrochemicals:
2-(4-Bromophenyl)propan-2-ol is also utilized in the agrochemical industry as a starting material for the synthesis of various agrochemical products. Its reactivity and structural properties make it suitable for the development of new pesticides, herbicides, and other agricultural chemicals.
Used in Dyestuffs:
In the dyestuffs industry, 2-(4-Bromophenyl)propan-2-ol is employed as an important raw material for the production of various dyes and pigments. Its ability to form a wide range of derivatives makes it a valuable component in the synthesis of colorants for various applications, including textiles, plastics, and printing inks.
Used as a Medicine Intermediate:
2-(4-Bromophenyl)propan-2-ol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structural features enable the development of new drugs with potential therapeutic applications, making it an essential component in the pharmaceutical industry's efforts to create novel and effective medications.

Upstream product

• 5798-75-4 Ethyl 4-bromobenzoate 
• 75-16-1 methylmagnesium bromide 
• 99-90-1 para-bromoacetophenone 
• 917-64-6 methyl magnesium iodide 
• 106-37-6 1.4-dibromobenzene 
• 67-64-1 acetone 
• 917-54-4 methyllithium 
• 6888-79-5 4-bromo-α-methylstyrene 
• 1261174-44-0 C₁₅H₁₅BrS 
• 32454-35-6 2-(4-bromophenyl)-2-methylpropionic acid 
• 586-61-8 4-iso-propylbromobenzene 
• 64-19-7 acetic acid 
• 676-58-4 methylmagnesium chloride 
• 619-42-1 4-methoxycarbonylphenyl bromide 

Downstream Products

• 6888-79-5 4-bromo-α-methylstyrene 
• 14276-98-3 2-(4-bromophenyl)-2-chloropropane 
• 35658-88-9 tert-butyl p-bromo-α,α-dimethylbenzyl peroxide 
• 88519-64-6 2,5-dimethyl-2,5-bis(p-bromo-α,α-dimethylbenzylperoxy)-3-hexyne 
• 106-41-2 4-bromo-phenol 
• 90862-23-0 p-Tolyl-carbamic acid 1-(4-bromo-phenyl)-1-methyl-ethyl ester 
• 90862-25-2 Carbonic acid 1-(4-bromo-phenyl)-1-methyl-ethyl ester phenyl ester 
• 61776-65-6 1-bromo-4-(2-bromopropan-2-yl)benzene 
• 775352-57-3 2-(4-bromophenyl)-2-[(2-trimethylsilylethoxy)methoxy]propane 
• 917024-62-5 [1-(4-bromo-phenyl)-1-methyl-ethoxy]-trimethyl-silane 
• 35338-65-9 2,4-di(4'-bromophenyl)-4-methyl-pent-1-en 
• 119027-36-0 1-bromo-4-(2-methoxypropan-2-yl)benzene 
• 1200131-44-7 (1-(4-bromophenyl)-1-methylethoxy)-tert-butyldimethylsilane 
• 857293-81-3 1-bromo-4-(1-fluoro-1-methylethyl)benzene 

Relevant academic research and scientific papers

Stepwise benzylic oxygenation via uranyl-photocatalysis

Stepwise oxygenation at the benzylic position (1°, 2°, 3°) of aromatic molecules was comprehensively established under ambient conditions via uranyl photocatalysis to produce carboxylic acids, ketones, and alcohols, respectively. The accuracy of the stepwise oxygenation was ensured by the tunability of catalytic activity in uranyl photocatalysis, which was adjusted by solvents and additives demonstrated through Stern–Volmer analysis. Hydrogen atom transfer between the benzylic position and the uranyl catalyst facilitated oxygenation, further confirmed by kinetic studies. Considerably improved efficiency of flow operation demonstrated the potential for industrial synthetic application.

Palladium-Aminopyridine Catalyzed C?H Oxygenation: Probing the Nature of Metal Based Oxidant

A mechanistic study of direct selective oxidation of benzylic C(sp3)?H groups with peracetic acid, catalyzed by palladium complexes with tripodal amino-tris(pyriylmethyl) ligands, is presented. The oxidation of arylalkanes having secondary and tertiary benzylic C?H groups, predominantly yields, depending on the substrate and conditions, either the corresponding ketones or alcohols. One of the three 2-pyriylmethyl moieties, which is pending in the starting catalyst, apparently, facilitates the active species formation and takes part in stabilization of the high-valent Pd center in the active species, occupying the axial coordination site of palladium. The catalytic, as well as isotopic labeling experiments, in combination with ESI-MS data and DFT calculations, point out palladium oxyl species as possible catalytically active sites, operating essentially via C?H abstraction/oxygen rebound pathway. For the ketones formation, O?H abstraction/в-scission mechanism has been proposed.

To Rebound or...Rebound? Evidence for the "alternative Rebound" mechanism in Ca'H Oxidations by the systems nonheme Mn Complex/H2O2/carboxylic acid

In this work, it has been shown that aliphatic Ca'H oxidations by bioinspired catalyst systems Mn aminopyridine complex/H2O2/carboxylic acid in acetonitrile afford predominantly a mixture of the corresponding alcohol and the ester. The alcohol/ester ratio is higher for catalysts bearing electron-donating groups at the aminopyridine core. Isotopic labeling studies witness that the oxygen atom of the alcohol originates from the H2O2molecule, while the ester oxygen comes exclusively from the acid. Oxidation of ethylbenzene in the presence of acetic acid affords enantiomerically enriched 1-phenylethanol and 1-phenyl acetate, with close enantioselectivities and the same sign of absolute chirality. Experimental data and density functional theory calculations provide evidence in favor of the rate-limiting benzylic H atom abstraction by the high-spin (S = 1) [LMnV(O)OAc]2+active species followed by competitive OH/OC(O)R rebound. This mechanism has been unprecedented for Ca'H oxidations catalyzed by bioinspired Mn complexes. The trends governing the alcohol/ester ratios have been rationalized in terms of steric properties of the catalyst, acid, and substrate. copy; 2021 American Chemical Society.

Efficient and selective oxidation of tertiary benzylic C[sbnd]H bonds with O2 catalyzed by metalloporphyrins under mild and solvent-free conditions

The direct and efficient oxidation of tertiary benzylic C[sbnd]H bonds to alcohols with O2 was accomplished in the presence of metalloporphyrins as catalysts under solvent-free and additive-free conditions. Based on effective inhibition on the unselective autoxidation and deep oxidation, systematical investigation on the effects of porphyrin ligands and metal centers, and apparent kinetics study, the oxidation system employing porphyrin manganese(II) (T(2,3,6-triCl)PPMn) with bulkier substituents as catalyst, was regarded as the most promising and efficient one. For the typical substrate, the conversion of cumene could reach up to 57.6% with the selectivity of 70.5% toward alcohol, both of them being higher than the current documents under similar conditions. The superiority of T(2,3,6-triCl)PPMn was mainly attributed to its bulkier substituent groups preventing metalloporphyrins from oxidative degradation, its planar structure favoring the interaction between central metal with reactants, and the high efficiency of Mn(II) in the catalytic transformation of hydroperoxides to alcohols.

Method for synthesizing tertiary alcohol by catalytically oxidizing benzyl tertiary C-H bonds of aromatic hydrocarbon through metalloporphyrin

The invention discloses a method for synthesizing tertiary alcohol by catalytically oxidizing benzyl tertiary C-H bonds of aromatic hydrocarbon through metalloporphyrin. The method comprises the following steps: dispersing metalloporphyrin (1*10-1%, mol/mol) into aromatic hydrocarbon; sealing the reaction system, heating to 40-120 DEG C while stirring, introducing an oxidant (0.10-1.0 MPa), keeping the set temperature and pressure, carrying out reactions for 3.0-24.0 hours under stirring, and carrying out after-treatment on the reaction solution to obtain the product aromatic benzyl tertiary alcohol. The method has the advantages of shortest conversion path, highest atom economy, lower reaction temperature, lower environmental influence and the like, and the selectivity of aromatic benzyl tertiary alcohol is high. In addition, the content of aromatic hydrocarbon hydroperoxide is low, and the safety coefficient is high. The invention provides an efficient, feasible and safe method for synthesizing aromatic benzyl tertiary alcohol through selective catalytic oxidation of benzyl tertiary C-H bonds of aromatic hydrocarbon.

Isopropanol as a hydrogen source for single atom cobalt-catalyzed Wacker-type oxidation

The first example of a heterogeneous cobalt catalytic system for Wacker-type oxidation catalyzed by a single atom dispersed Co-N/C catalyst using alcohol as the hydrogen source under an oxygen atmosphere is presented. By combining a well-designed, controlled experiment and various methods of characterization, we determined that single atom cobalt was the active center rather than nanoparticle or oxide counterparts.

Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group

Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.

Method for selectively oxidizing cumene compounds

The invention relates to a method for selectively oxidizing cumene compounds, and the method comprises the following steps: placing cumene compounds shown in a formula (I), an iron porphyrin catalyst,an oxidant and a dispersant into a ball milling tank, sealing the ball milling tank, performing ball milling for 3 to 24 hours at a rotating speed of 100 to 800 rpm at room temperature, stopping ballmilling once every 1 to 3 hours in the ball milling process, discharging gases in the ball milling tank, finishing the reaction, and performing post-treatment on a reaction mixture to obtain product2-phenyl-2-propanol compound shown in a formula (II); according to the invention, the oxidation conversion of the cumene and derivatives thereof is realized through solid-phase ball milling, the reaction mode is novel, the operation is convenient, and the energy consumption is low; the method needs no organic solvent, thus effectively avoiding the use of toxic and harmful organic solvents and being green and environment-friendly; has low peroxide content and high safety factor, and high 2-phenyl-2-propanol and derivative selectivity and meets the social requirements of the current green chemical process, environmental compatibility chemical process and biological compatibility chemical process.

Hindered dialkyl ether synthesis with electrogenerated carbocations

Hindered ethers are of high value for various applications; however, they remain an underexplored area of chemical space because they are difficult to synthesize via conventional reactions1,2. Such motifs are highly coveted in medicinal chemistry, because extensive substitution about the ether bond prevents unwanted metabolic processes that can lead to rapid degradation in vivo. Here we report a simple route towards the synthesis of hindered ethers, in which electrochemical oxidation is used to liberate high-energy carbocations from simple carboxylic acids. These reactive carbocation intermediates, which are generated with low electrochemical potentials, capture an alcohol donor under non-acidic conditions; this enables the formation of a range of ethers (more than 80 have been prepared here) that would otherwise be difficult to access. The carbocations can also be intercepted by simple nucleophiles, leading to the formation of hindered alcohols and even alkyl fluorides. This method was evaluated for its ability to circumvent the synthetic bottlenecks encountered in the preparation of 12 chemical scaffolds, leading to higher yields of the required products, in addition to substantial reductions in the number of steps and the amount of labour required to prepare them. The use of molecular probes and the results of kinetic studies support the proposed mechanism and the role of additives under the conditions examined. The reaction manifold that we report here demonstrates the power of electrochemistry to access highly reactive intermediates under mild conditions and, in turn, the substantial improvements in efficiency that can be achieved with these otherwise-inaccessible intermediates.

COMPOUNDS AND THEIR METHODS OF USE

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including Dravet syndrome or epilepsy are also provided herein.