35447-78-0

Usage

Uses

Used in Organic Synthesis:
3-(4-NITROPHENYL)-2,3-DIBROMOPROPIONIC ACID is used as a synthetic intermediate for the creation of various organic compounds. Its unique structure allows it to be a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(4-NITROPHENYL)-2,3-DIBROMOPROPIONIC ACID is used as a key component in the development of new drugs. Its chemical properties make it suitable for the synthesis of molecules with potential therapeutic applications, contributing to the advancement of novel treatments for various diseases.
Used in Agrochemical Industry:
3-(4-NITROPHENYL)-2,3-DIBROMOPROPIONIC ACID is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its unique chemical structure can be exploited to create compounds with enhanced efficacy and selectivity, leading to more effective and environmentally friendly products.
Used in Chemical Research:
In the field of chemical research, 3-(4-NITROPHENYL)-2,3-DIBROMOPROPIONIC ACID serves as a valuable compound for studying various reaction mechanisms and exploring new synthetic routes. Its unique properties make it an interesting subject for academic and industrial research, potentially leading to the discovery of new chemical processes and applications.

InChI:InChI=1/C9H7Br2NO4/c10-7(8(11)9(13)14)5-1-3-6(4-2-5)12(15)16/h1-4,7-8H,(H,13,14)

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 882-06-4 4-nitro-trans-cinnamic acid 
• 619-89-6 p-nitrocinnamic acid 
• 7726-95-6 bromine 

Downstream Products

• 13161-29-0 p-nitrocinnamyl bromide 
• 619-89-6 p-nitrocinnamic acid 
• 2216-24-2 3-(4-nitrophenyl)-2-propynoic acid 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 18462-34-5 (Z)-1-(2-bromovinyl)-4-nitrobenzene 
• 28000-04-6 α-Brom-p-amino-styrol 
• 14235-81-5 4-Ethynylaniline 
• 18462-35-6 (E)-1-[2-bromovinyl]-4-nitrobenzene 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs

Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.

Chloro/bromotrimethylsilane-Cu(NO3)2·3H2O: Safe and efficient reagent system for the decarboxylative ipso-nitration and dibromination of cinnamic acids

Further synthetic potential of halotrimethylsilane-nitrate salt mixture is revealed. A mixture of TMSX-Cu(NO3)2·3H2O system is found to be an efficient reagent system for both the decarboxylative nitration (ipso-nitration) when X?=?Cl, and dibromination of cinnamic acids, with X?=?Br, under mild conditions. The reactions are safe and simple, affording the corresponding products (E)-β-nitrostyrenes, and anti-2,3-dibromo-3-phenylpropanoic acids in high yields with high selectivity in a relatively short time. Use of hazardous and toxic nitrating systems such as acetyl nitrate and brominating agents such as molecular bromine can be avoided.

Convenient synthesis of terminal alkynes from anti-3-aryl-2,3- dibromopropanoic acids using a K2CO3/DMSO system

A convenient, efficient, and generally applicable method was developed for the synthesis of terminal alkynes from anti-3-aryl-2,3-dibromopropanoic acids in the presence of DMSO and K2CO3.

Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in a Et3N/DMF system. A one-pot synthesis of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed by microwave-induced reaction.

Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time (0.2-1.0 min) by microwave irradiation of the corresponding 2,3-dibromoalkanoic acids in DMF in the presence of triethylamine.

Synthesis of the Substituted Z-1-Bromo-1-alkenes and Arylacetylenes from 2,3-Dibromocarboxylic Acids

Stereoselectivity was studied of simultaneous debromination-decarboxylation of dibrominated cinnamic and acrylic acids. The best selectivity in formation of Z-vinyl bromides was achieved with the use of organic nitrogen bases. The 1-bromo-1-alkenes were converted into the corresponding acetylenes.