92093-23-7

Usage

Uses

Used in Chemical Synthesis:
1,2-ETHANEDIOL-(P-BROMOPHENYL)is used as a reactant in the regioselective palladium-catalyzed O,S rearrangement of cyclic thiocarbonates. This reaction is an important method for the synthesis of complex organic molecules and pharmaceutical compounds, as it allows for the selective formation of specific products with high yields and selectivity.
Used in Pharmaceutical Industry:
1,2-ETHANEDIOL-(P-BROMOPHENYL)is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity enable the development of new drugs with improved therapeutic properties and reduced side effects.
Used in Material Science:
1,2-ETHANEDIOL-(P-BROMOPHENYL)can be used as a building block for the development of new materials with specific properties, such as polymers, coatings, and adhesives. Its versatility in chemical reactions allows for the creation of materials with tailored properties for various applications.

Upstream product

• 32017-76-8 (+/-)-2-(4-bromophenyl)oxirane 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 7500-37-0 2-(4-bromophenyl)-2-oxoethyl acetate 
• 141-78-6 ethyl acetate 
• 34867-87-3 spirocyclobutylmalonoyl peroxide 
• 5195-29-9 4-bromophenylglyoxal 
• 99-90-1 para-bromoacetophenone 
• 20201-26-7 ethyl 4-bromophenylglyoxylate 
• 108-86-1 bromobenzene 
• 57699-28-2 methyl 4-bromophenylglyoxalate 
• 64-17-5 ethanol 
• 3343-45-1 4-bromo-2-hydroxyacetophenone 
• 62566-68-1 (R)-2-(4-bromophenyl)oxirane 
• 148684-05-3 2-(4-bromophenyl)oxirane 

Downstream Products

• 59365-21-8 2-Bromomethyl-4-(4-bromo-phenyl)-2-(2,4-dichloro-phenyl)-[1,3]dioxolane 
• 59362-75-3 2-Bromomethyl-4-(4-bromo-phenyl)-2-phenyl-[1,3]dioxolane 
• 59362-76-4 2-Bromomethyl-4-(4-bromo-phenyl)-2-(4-chloro-phenyl)-[1,3]dioxolane 
• 59365-54-7 2-Bromomethyl-4-(4-bromo-phenyl)-2-(2-chloro-phenyl)-[1,3]dioxolane 
• 32368-06-2 (p-Bromophenyl)-1,2-ethane cyclic carbonate 
• 306282-43-9 (S)-2-methylcarbonyloxy-1-(4-bromophenyl)ethyl acetate 
• 201403-02-3 (+/-)-2-amino-2-(4-bromophenyl)ethanol 
• 387337-83-9 4-(4-bromo-phenyl)-2-phenyl-[1,3]dioxolane 
• 160332-70-7 (S)-(+)-1-(4-bromophenyl)-1,2-ethanediol 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 1407546-34-2 2-(4-bromophenyl)-2-chloroethan-1-ol 

Relevant academic research and scientific papers

Structure-Guided Regulation in the Enantioselectivity of an Epoxide Hydrolase to Produce Enantiomeric Monosubstituted Epoxides and Vicinal Diols via Kinetic Resolution

Structure-guided microtuning of an Aspergillus usamii epoxide hydrolase was executed. One mutant, A214C/A250I, displayed a 12.6-fold enhanced enantiomeric ratio (E = 202) toward rac-styrene oxide, achieving its nearly perfect kinetic resolution at 0.8 M in pure water or 1.6 M in n-hexanol/water. Several other beneficial mutants also displayed significantly improved E values, offering promising biocatalysts to access 19 structurally diverse chiral monosubstituted epoxides (97.1 - ≥ 99% ees) and vicinal diols (56.2-98.0% eep) with high yields.

Method for synthesizing chiral 1,2-diol compound

The invention relates to a method for synthesizing a chiral 1,2-diol compound, which comprises the following steps: sequentially adding a cobalt catalyst, a ligand, alpha-hydroxy ketone, an organic solvent and silane into a reaction system at 20-30 DEG C in a nitrogen atmosphere, then stirring the mixture, and carrying out column chromatography separation on the obtained product to obtain the chiral 1,2-diol compound. The high-yield cobalt catalyst in the earth crust is used, meanwhile, cheap silane (PMHS, 500 g/298 yuan) is used as a reducing agent, the asymmetric reduction reaction of alpha-hydroxy ketone can be efficiently achieved under the mild condition, and the chiral 1,2-diol compound with high yield and optical activity is obtained. Moreover, through the creative labor of the inventor, the reaction yield can reach 99%, and meanwhile, the content of the target product in the generated reaction product is 99% (namely, the yield is 99%, 99% ee).

Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen

We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox-neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2-diols (as a mixture of diastereomers) couple to forge two C?N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co-catalyzed procedure, the first enantioconvergent double amination of racemic 1,2-diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.

Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na2CO3 as the additive, and propylene carbonate as the solvent, instead.

Lewis Base Catalyzed Dioxygenation of Olefins with Hypervalent Iodine Reagents

1,2-Diols are extremely useful building blocks in organic synthesis. Hypervalent iodine reagents are useful for the vicinal dihydroxylation of olefins to give 1,2-diols under metal-free conditions, but strongly acidic promoters are often required. Herein, we report a catalytic vicinal dioxygenation of olefins with hypervalent iodine reagents using Lewis bases as catalysts. The conditions are mild and compatible with various functional groups.

Synthesis and biological evaluation of triazolyl-substituted benzyloxyacetohydroxamic acids as LpxC inhibitors

The bacterial deacetylase LpxC is a promising target for the development of antibiotics selectively combating Gram-negative bacteria. To improve the biological activity of the reported benzyloxyacetohydroxamic acid 9 ((S)-N-hydroxy-2-{2-hydroxy-1-[4-(phenylethynyl)phenyl]ethoxy}acetamide), its hydroxy group was replaced by a triazole ring. Therefore, in divergent syntheses, triazole derivatives exhibiting rigid and flexible lipophilic side chains, different configurations at their stereocenter, and various substitution patterns at the triazole ring were synthesized, tested for antibacterial and LpxC inhibitory activity, and structure-activity relationships were deduced based on docking and binding energy calculations.

Absolute stereochemical determination of 1,2-diols via complexation with dinaphthyl borinic acid

Rapid derivatization of chiral 1,2-diols with dinaphthyl borinic acid (DBA) leads to a cyclic boronate, enabling the absolute stereochemical prediction via exciton-coupled circular dichroic (ECCD) of the naphthyl groups. Aryl- and alkyl-substituted 1,2-diols derivatized with DBA yield a predictable ECCD, which is also in agreement with theoretical predictions derived from computationally minimized structures.

Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds

Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site-directed modification using an “optimized amino acid alphabet” to improve the regioselectivity of epoxide hydrolase from Vigna radiata (VrEH2). The regioselectivity coefficient (r) of variant M263Q for the R-isomer of meta-substituted styrene oxides was improved 40–63-fold, and variant M263V also exhibited higher regioselectivity towards the R-isomer of para-substituted styrene oxides compared with the wild type, which resulted in improved enantioconvergence in hydrolysis of styrene oxide scaffolds. Structural insight showed the crucial role of residue No. 263 in modulating the substrate binding conformation by altering the binding surroundings. Furthermore, increased differences in the attacking distance between nucleophilic residue Asp101 and the two carbon atoms of the epoxide ring provided evidence for improved regioselectivity. Several high-value vicinal diols were readily synthesized (>88% yield, 90%–98% ee) by enantioconvergent hydrolysis using the reprogrammed variants. These findings provide a successful strategy for enhancing the enantioconvergence of native epoxide hydrolases through key single-site mutation and more powerful enzyme tools for the enantioconvergent hydrolysis of styrene oxide scaffolds into single (R)-enantiomers of chiral vicinal diols. (Figure presented.).

Manipulating regioselectivity of an epoxide hydrolase for single enzymatic synthesis of (: R)-1,2-diols from racemic epoxides

Both the activity and regioselectivity of Phaseolus vulgaris epoxide hydrolase were remarkably improved via reshaping two substrate tunnels based on rational design. The elegant one-step enantioconvergent hydrolysis of seven rac-epoxides was achieved by single mutants, allowing green and efficient access to valuable (R)-1,2 diols with high eep (90.1-98.3%) and yields.

Asymmetric ring opening of racemic epoxides for enantioselective synthesis of (S)-β-amino alcohols by a cofactor self-sufficient cascade biocatalysis system

A novel one-pot epoxide hydrolase/alcohol dehydrogenase/transaminase cascade process for the asymmetric ring opening of racemic epoxides to enantiopure β-amino alcohols is reported. The product (S)-β-amino alcohols were obtained in 97-99% ee and 79-99% conversion from readily available racemic epoxides.