13073-25-1

Basic information

• Product Name: 2-Bromo-6-nitrophenol
• Synonyms: TIMTEC-BB SBB008567;2-BROMO-6-NITROPHENOL;6-NITRO-2-BROMOPHENOL;2-Bromo-6-nitropheno;3-Bromo-2-hydroxynitrobenzene;Phenol, 2-broMo-6-nitro-;6-BroMo-2-nitrophenol;2-BroMo-6-nitrophenol, 97+%
• CAS NO: 13073-25-1
• Molecular Formula: C₆H₄BrNO₃
• Molecular Weight: 218
• EINECS: 1308068-626-2
• Product Categories: Fluorobenzene;Aromatic Phenols;Phenol&Thiophenol&Mercaptan;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 13073-25-1.mol

Chemical Properties

• Melting Point: 66-70 °C(lit.)
• Boiling Point: 227.2 °C at 760 mmHg
• Flash Point: 91.2 °C
• Appearance: /
• Density: 1.881 g/cm³
• Vapor Pressure: 0.052mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: Room temperature.
• Solubility: Chloroform; Methanol
• PKA: 5.36±0.24(Predicted)
• CAS DataBase Reference: 2-Bromo-6-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-6-nitrophenol(13073-25-1)
• EPA Substance Registry System: 2-Bromo-6-nitrophenol(13073-25-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 36/37-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13073-25-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Bromo-6-nitrophenol is used as an intermediate in the synthesis of N-Hydroxy Eltrombopag (H825795), which is a derivative compound of Eltrombopag (508000). Eltrombopag is an agonist of the Thrombopoietin (Tpo) receptor and is utilized as a treatment for thrombocytopenia, a condition characterized by a low blood platelet count. The role of 2-Bromo-6-nitrophenol in this synthesis process is crucial, as it contributes to the development of a medication that can help manage and treat thrombocytopenia effectively.

InChI:InChI=1/C6H4BrNO3/c7-4-2-1-3-5(6(4)9)8(10)11/h1-3,9H

Upstream product

• 95-56-7 2-hydroxybromobenzene 
• 64-19-7 acetic acid 
• 88-75-5 2-hydroxynitrobenzene 
• 110-89-4 piperidine 
• 98775-19-0 2-bromo-6-nitrophenyl methyl ether 
• 585-79-5 m-nitrobromobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 100782-02-3 2-bromo-6-nitrophenol t-butylamine salt 
• 7726-95-6 bromine 
• 95-55-6 2-amino-phenol 

Downstream Products

• 15969-09-2 2,4-dibromo-6-nitrophenol 
• 2316-50-9 2-bromo-4,6-dinitrophenol 
• 15969-10-5 2-bromo-4-chloro-6-nitro-phenol 
• 28165-50-6 2-amino-6-bromophenol 
• 688363-73-7 8-bromo-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 853642-87-2 8-bromo-4-(2-fluoro-benzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazine 
• 853642-88-3 4-[4-(2-fluoro-benzenesulfonyl)-2,2-dimethyl-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl]-piperazine-1-carboxylic acid tert-butyl ester 
• 116557-46-1 3-bromo-2-methoxyphenylamine 
• 860584-68-5 2-bromo-6-iodoanisole 
• 55229-71-5 acetic acid-(2-bromo-4,6-dinitro-phenyl ester) 
• 944355-65-1 2-amino-6-bromophenol hydrochloride 
• 98775-19-0 2-bromo-6-nitrophenyl methyl ether 
• 688363-79-3 1-bromo-3-nitro-2-[(phenylmethyl)oxy]benzene 

Relevant articles and documents

Selective nitration of phenols using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid under aprotic conditions

A mild, efficient and regioselective method for the mononitration of phenolic compounds is described using bismuth subnitrate/charcoal in the presence of trichloroisocyanuric acid in CH2Cl2 at room temperature.

Unexpected one pot C (aryl)-N bond cleavage and Questiomycin A formation from the reduction reaction of 2-amino-6-nitrophenol derivatives

2-Amino-6-nitrophenol derivatives 5A and 5B have been prepared from the bromonitro phenol derivative 4 using the Buchwald conditions. While attempting one pot reduction of nitro group and deprotection of phenolic benzyl group of the compounds 5A and 5B separately using Pd/C in methanol under H2 atmosphere, an unexpected C(aryl)-N bond cleavage reaction had occurred which was followed by formation of a known compound Questiomycin A (2-amino-3H-phenoxazin-3-one) 1 from both the compounds. In the present study, the danger of deamination of Buchwald products 5A and 5B under the conditions of catalytic hydrogenation and the simultaneous formation of phenoxazine 1 is disclosed.

Light-Controlled Tyrosine Nitration of Proteins

Tyrosine nitration of proteins is one of the most important oxidative post-translational modifications in vivo. A major obstacle for its biochemical and physiological studies is the lack of efficient and chemoselective protein tyrosine nitration reagents. Herein, we report a generalizable strategy for light-controlled protein tyrosine nitration by employing biocompatible dinitroimidazole reagents. Upon 390 nm irradiation, dinitroimidazoles efficiently convert tyrosine residues into 3-nitrotyrosine residues in peptides and proteins with fast kinetics and high chemoselectivity under neutral aqueous buffer conditions. The incorporation of 3-nitrotyrosine residues enhances the thermostability of lasso peptide natural products and endows murine tumor necrosis factor-α with strong immunogenicity to break self-tolerance. The light-controlled time resolution of this method allows the investigation of the impact of tyrosine nitration on the self-assembly behavior of α-synuclein.

Preparation method of Eltrombopag key intermediate 3'-amino-2'-hydroxybiphenyl-3-carboxylic acid

The invention discloses a preparation method of an Eltrombopag key intermediate 3'-amino-2'-hydroxybiphenyl-3-carboxylic acid. The preparation method comprises the following steps: (1) nitrating o-bromophenol with a nitrating reagent by using water as a s

Novel method for preparing Eltrombopag intermediate

The invention provides a method for preparing a compound shown as the formula I (please see the formula in the description). The method specifically comprises the following steps that 1, a compound shown as the formula (II) (please see the formula in the description) reacts with a compound shown as formula (V) (please see the formula in the description) under the alkaline condition to generate a compound shown as the formula (III) (please see the formula in the description); 2, the compound shown as the formula (III) (please see the formula in the description) reacts with a compound shown as the formula (VI) (please see the formula in the description) under the alkaline condition in the presence of palladium carbon to generate a compound shown as the formula (IV) (please see the formula in the description); 3, the compound shown as the formula (IV) (please see the formula in the description) reacts in the presence of palladium carbon and a hydrogen source under the alkaline condition to generate the compound shown as the formula (I) (please see the formula in the description). According to the method, design is ingenious, protecting group removal, dechlorination and nitro reduction are together completed in the final hydrogenation process, and the purity of the obtained compound shown as the formula (I) (please see the formula in the description) is high; the most important thing is that compared with other Suzuki coupling agents, cost of palladium carbon is lower, a source of palladium carbon is wide and easy to obtain, palladium carbon can be directly recycled and reused after being simply filtered and separated, and therefore the material cost is greatly reduced; meanwhile, emission of three wastes is reduced, and the method is quite suitable for industrialized production.

BICYCLO-SUBSTITUTED PYRAZOLON AZO DERIVATIVES PHARMACEUTCIAL SALTS, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

The present invention relates to bicyclo-substituted pyrazolon azo derivatives pharmaceutical acceptable salts of formula (I), methods for their preparation, pharmaceutical compositions containing the same and their use as a therapeutic agent, especially as thrombopoietin (TPO) mimetics and their use as agonists of thrombopoietin receptor. The definition of substituents in formula (I) are the same as the description.

SALTS OF BICYCLO-SUBSTITUTED PYRAZOLON AZO DERIVATIVES, PREPARATION METHOD AND USE THEREOF

The present invention relates to pharmaceutically acceptable salts of bicycle-substituted pyrazolon azo derivatives represented by general formula (I), methods for their preparation, pharmaceutical compositions comprising the same and their use as a therapeutic agent, especially as thrombopoietin (TPO) mimetics, and their use as agonists of thrombopoietin receptor. The definitions of substituents in general formula (I) are the same as the description.

BICYCLO-SUBSTITUTED PYRAZOLON AZO DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF

The bicyclo-substituted pyrazolon-azo derivatives of formula (I) or pharmaceutical acceptable salts, hydrates or solvates thereof, methods for their preparation, pharmaceutical compositions containing the same and their use as a therapeutic agent, especially as thrombopoietin (TPO) mimetics and their use as agonists of thrombopoietin receptor are disclosed. The definition of substituents in formula (I) are the same as defined in the description.

3,4-Dihydro-2H-benzo[1,4]oxazine derivatives as 5-HT6 receptor antagonists

A series of novel 3,4-dihydro-2H-benzo[1,4]oxazine derivatives has been designed and synthesized as 5-HT6 receptor antagonists. Many of the compounds displayed subnanomolar affinities for the 5-HT6 receptor and good brain penetration in rats. The relationship of structure and lipophilicity to hERG inhibition of this series of compounds is discussed.

Nitration of substituted phenols by different efficient heterogeneous systems

Nitration of substituted phenols were carried out by the mixture of sodium nitrite and wet SiO2 (50% w/w) in the presence of four different efficient heterogeneous systems: 1) oxalic acid dihydrate (I), 2) sodium hydrogen sulphate (II), 3) aluminum hydrogen sulphate (III) and 4) silica sulphuric acid (IV) in CH2Cl2 at room temperature and high yields. Optimum conditions for theses systems and the regioselectivities of the reactions are reported.