39224-65-2

Usage

Uses

Used in Pharmaceutical Industry:
4,5-Dichloro-2-nitrophenol is used as a key intermediate in the synthesis of dimethylpropanthioates, which are known as Cholesteryl Ester Transfer Protein (CETP) inhibitors. These inhibitors play a crucial role in modulating the transfer of cholesteryl esters between lipoproteins, thus potentially influencing the treatment of conditions related to lipid metabolism, such as atherosclerosis and hyperlipidemia.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4,5-dichloro-2-nitrophenol is utilized in the improved synthesis of hydroxyindoles. Hydroxyindoles are important building blocks for the creation of various pharmaceuticals, agrochemicals, and other specialty chemicals. The use of 4,5-dichloro-2-nitrophenol in this process enhances the efficiency and selectivity of the synthesis, leading to better yields and more cost-effective production of these valuable compounds.

InChI:InChI=1/C6H3Cl2NO3/c7-3-1-5(9(11)12)6(10)2-4(3)8/h1-2,10H

Upstream product

• 95-77-2 3,4-dichlorophenol 
• 89-69-0 2,4,5-Trichloronitrobenzene 
• 99-54-7 3,4-dichloronitrobenzene 
• 6306-39-4 1,2-dichloro-4,5-dinitrobenzene 

Downstream Products

• 28443-57-4 2-amino-4,5-dichlorophenol 
• 98141-37-8 4-chloro-6-nitro-resorcinol 
• 842117-32-2 1-benzyloxy-4,5-dichloro-2-nitrobenzene 
• 1413929-68-6 C₁₄H₁₀Cl₃NO₃ 
• 1413929-97-1 C₂₂H₁₅Cl₄NO₅ 
• 1413929-83-5 C₁₄H₁₀Cl₃NO₂S 
• 1413930-00-3 C₁₄H₈Cl₃NO₂ 
• 1413929-90-4 C₁₄H₁₀Cl₃NO₂S 
• 1413930-05-8 C₁₄H₈Cl₃NO₂ 

Relevant academic research and scientific papers

The reaction of 1,2-dichloro-4,5-dinitrobenzene with hydroxide ion: Roles of meisenheimer complexes and radical pairs

The reaction of 1,2-dichloro-4,5-dinitrobenzene (DCDNB) with aqueous OH- produces (after acidification) 2-nitro-4,5-dichlorophenol with loss of NO 2. Nevertheless, with > 2 mol L-1 OH-, only DCDNB was recovered due to the

ANTIBIOTIC COMPOUNDS

The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.

COVALENT INHIBITORS OF KRAS G12C

Irreversible inhibitors of G12C mutant K-Ras protein are provided. Also disclosed are methods to modulate the activity of G12C mutant K-Ras protein and methods of treatment of disorders mediated by G12C mutant K-Ras protein.

Synthesis and in vitro antimycobacterial and isocitrate lyase inhibition properties of novel 2-methoxy-2′-hydroxybenzanilides, their thioxo analogues and benzoxazoles

A new series of 2-methoxy-2′-hydroxybenzanilide derivatives and their thioxo analogues have been synthesised and characterised by IR, NMR and elemental analysis. These compounds were investigated for their in vitro antimycobacterial activities against Mycobacterium tuberculosis 331/88, Mycobacterium avium 330/88, Mycobacterium kansasii 235/80, clinically isolated M. kansasii 6509/96 and the ability to act as in vitro isocitrate lyase inhibitors. The best ICL inhibitors were two compounds from the thiobenzanilide group (8f, 8m), which exhibited an inhibition potential that was equal to the standard compound, 3-nitropropionic acid. In addition, the best antimycobacterial properties were exhibited by benzanilide derivatives 6h, 6k and 6l with 5-Cl and 4′ or 5′ Cl/Br substitution. For all the thiobenzanilide derivatives tested, two conformers were observed in the NMR spectra, which is most likely due to the hindered rotation of the C-N bond.

Synthesis and biological evaluation of 1-(2,4,5-trisubstituted phenyl)-3-(5-cyanopyrazin-2-yl)ureas as potent Chk1 kinase inhibitors

Based on the X-ray crystallography of our lead compound 1-(5-chloro-2,4-dimethoxyphenyl)-3-(5-cyanopyrazin-2-yl)urea in the checkpoint kinase 1 (Chk1) enzyme, we modified R4, and to a lesser extent, R2, and R5 of the phenyl ring, and made a variety of N-aryl-N′-pyrazinylurea Chk1 inhibitors. Enzymatic activity less than 20 nM was observed in 15 of 41 compounds. Compound 8i provided the best overall results in the cellular assays as it abrogated doxorubicin-induced cell cycle arrest (IC50 = 1.7 μM) and enhanced doxorubicin cytotoxicity (IC50 = 0.44 μM) while displaying no single agent activity.

HETEROARYL UREA DERIVATIVES USEFUL FOR INHIBITING CHKl

Substituted urea compounds useful in the treatment of diseases and conditions related to DNA damage or lesions in DNA replication are disclosed. Methods of making the compounds, and their use as therapeutic agents, for example, in treating cancer and other diseases characterized by defects in DNA replication, chromosome segregation, or cell division, also are disclosed.

An improved synthesis of hydroxyindoles

An improved synthetic procedure for the synthesis of 6- and 7-hydroxyindoles is described. In this method, the addition of two chlorine atoms in 1-benzyloxy-4,5-dichloro-2-nitrobenzene (3) and 1-benzyloxy-2,6- dichloro-3-nitrobenzene (9) facilitated the subsequent cyanomethylation step to give substituted cyanomethyl-dichloronitrobenzenes 4 and 10, leading to an overall increase in the yield of the hydroxyindoles 6 and 12.

Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen

Rhone-Poulenc Polska Ltd., ul. Grzybowska 80/82, 00-844 Warszawa, Poland Garbo- and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.

Facile rearrangements of alkynylamino heterocycles with noble metal cations

A number of 2-(alkynylamino)-substituted heterocycles have been synthesized. These heterocycles rearrange in the presence of silver(I) and gold(I) salts to give novel 2H-pyrimido[2,1-b]benzoxazoles, 2H-pyrimido[2,1-b]benzothiazoles, and a 2H-pyrimido[2,1-b]benzoselenazole. Two of the the 2H-pyrimido[2,1-b]benzoxazoles were isolated in good yield. The kinetics of the silver tetrafluoroborate-catalyzed rearrangements of selected (alkynylamino)benzoxazoles and benzothiazoles have been examined by 1H NMR in CD3CN. Factors affecting the electron densities of the triple bond and of the nitrogen atom in the heterocycle are important in influencing the rate of rearrangement.

Thieno[3,4-b][1,5]benzoxazepin-10-ones and thieno[3,4-b][1,5]benzothiazepin-10-ones

This disclosure describes novel substituted thieno[3,4-b][1,5]benzoxazepin-10 (9H)-ones and thieno[3,4-b][1,5]benzothiazepin-10(9H)-ones which are useful as intermediates for the preparation of 10-[4-(substituted)-1-piperazinyl]thieno[3,4-b][1,5]benzoxaze