7368-78-7

Basic information

• Product Name: 4-Bromo-2-methoxyphenol
• Synonyms: 4-BROMOGUAIACOL;4-BROMO-2-METHOXYPHENOL;AKOS 225-06;2-Methoxy-4-Bromophenol;4-Bromo-2-methoxyphenol,4-Bromoguaiacol;4-Bromo-2-methoxyphenol 98%;4-Bromoguaiacol, 5-Bromo-2-hydroxyanisole;4-Bromo-o-guaiacol, 5-Bromo-2-hydroxyanisole
• CAS NO: 7368-78-7
• Molecular Formula: C₇H₇BrO₂
• Molecular Weight: 203.03
• Product Categories: blocks;Bromides;Benzene series;Miscellaneous;Building Blocks;C6 to C8;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;Phenols
• Mol File: 7368-78-7.mol
• Article Data: 52

Chemical Properties

• Melting Point: 34-37 °C(lit.)
• Boiling Point: 129-132°C 12mm
• Flash Point: >230 °F
• Appearance: Colorless to white to pale brown/Low Melting Solid or Crystalline Solid
• Density: 1.585 g/cm³
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 9.40±0.18(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 2045286
• CAS DataBase Reference: 4-Bromo-2-methoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-methoxyphenol(7368-78-7)
• EPA Substance Registry System: 4-Bromo-2-methoxyphenol(7368-78-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 7368-78-7(Hazardous Substances Data)

Usage

Description

4-Bromo-2-methoxyphenol is an organic compound that serves as a crucial intermediate in the synthesis of various substituted phenyl products and polyfunctionalized bicyclic systems. It is characterized by the presence of a bromine atom at the 4-position and a methoxy group at the 2-position on a phenol ring.

Uses

Used in Organic Synthesis:
4-Bromo-2-methoxyphenol is used as a key intermediate for the synthesis of substituted phenyl products, which are essential building blocks in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Bromo-2-methoxyphenol is utilized as a vital raw material and intermediate in the development of new drugs and medicinal compounds.
Used in Agrochemical Industry:
4-Bromo-2-methoxyphenol is employed as an important ingredient and intermediate in the synthesis of agrochemicals, such as pesticides and herbicides, to improve agricultural productivity and crop protection.
Used in Dye Industry:
In the dye industry, 4-Bromo-2-methoxyphenol is used as a key intermediate for the production of various dyes and pigments, contributing to the coloration and appearance of textiles, plastics, and other materials.
Additionally, 4-Bromo-2-methoxyphenol has been studied for its potential applications in palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides, as well as in an expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols, as demonstrated in the following references:
A. Schoenberg; R. F. Heck. Palladium-catalyzed formylation of aryl, heterocyclic, and vinylic halides. J. Am. Chem. Soc. 1974, 96 (25), 7761-7764.
Joel S. Freundlich; Howard E. Landis. An expeditious aqueous Suzuki-Miyaura method for the arylation of bromophenols. Tetrahedron Letters. 2006, 47(25), 4275-4279.

InChI:InChI=1/C7H7BrO2/c1-10-7-4-5(8)2-3-6(7)9/h2-4,9H,1H3

Upstream product

• 90-05-1 2-methoxy-phenol 
• 63057-72-7 2-benzyloxy-5-bromoanisole 
• 138505-27-8 4-bromo-1-isopropoxy-2-methoxy-benzene 
• 54145-18-5 4-bromo-2-methoxyphenyl acetate 
• 6689-37-8 1-methoxy-2-trimethylsilyloxybenzene 
• 151-10-0 1,3-Dimethoxybenzene 
• 376396-10-0 4-bromo-6,6-dimethoxy-2,4-cyclohexadien-1-one 

Downstream Products

• 824-46-4 methoxyhydroquinone 
• 70978-61-9 4-bromo-2-methoxy-6-nitrophenol 
• 54145-18-5 4-bromo-2-methoxyphenyl acetate 
• 63057-72-7 2-benzyloxy-5-bromoanisole 
• 132532-64-0 4-bromo-2-methoxy-1-methoxymethylenoxybenzene 
• 25141-17-7 2-(4-bromo-2-methoxyphenoxy)acetic acid 
• 2859-78-1 4-Bromoveratrole 
• 168985-93-1 4-Bromo-6-tert-butyl-2-methoxyphenol 
• 81258-24-4 acide(bromo-4 methoxy-2 phenoxy-1)-3 propionique 
• 65854-87-7 (4-Bromo-2-methoxy-phenoxy)-trimethyl-silane 
• 2380-78-1 homovanillyl alcohol 
• 35857-70-6 2,3-dihydroxybenzene-1-sulfonic acid 
• 120-80-9 benzene-1,2-diol 
• 111047-58-6 (+/-)-1-bromo-4-(1-ethoxyethyl)-3-methoxybenzene 

Relevant articles and documents

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

A synthetic preparation method for small carbags hydrochloric acid

The present invention belongs to the field of organic chemistry, relates to a method of synthesizing berberine hydrochloride, comprising: S1: with 5-halo-o-quinoastearaldehyde and piperine ethylamine to obtain N- [2-(3,4-dimethoxyphenyl-5-yl) ethyl] -1- (5-halo-2,3-dimethoxybenzyl) methylimide; S2: to obtain 2- (3,4-diimoxyphenyl) -N- (5-bromo-2,3-dimethoxybenzyl) ethylamine; S3: to obtain 2-(3,4-dimethoxyphenyl) -N- (5-bromo-2 S4: to obtain 12-halogenated berberine derivative; S5: to obtain berberine. The present invention is free from the application of the by-product o-vanillin synthesis of o-resveratal raw material constraints, synthesis of 5- substitute o-resveratal and piperine ethylamine, and the use of the two preparation of berberine hydrochloride, with raw materials readily available, mild reaction conditions, easy to operate, high chemical yield, low cost and other advantages.

Structure-based design, docking and binding free energy calculations of a366 derivatives as spindlin1 inhibitors

The chromatin reader protein Spindlin1 plays an important role in epigenetic regulation, through which it has been linked to several types of malignant tumors. In the current work, we report on the development of novel analogs of the previously published lead inhibitor A366. In an effort to improve the activity and explore the structure–activity relationship (SAR), a series of 21 derivatives was synthesized, tested in vitro, and investigated by means of molecular modeling tools. Docking studies and molecular dynamics (MD) simulations were performed to analyze and rationalize the structural differences responsible for the Spindlin1 activity. The analysis of MD simulations shed light on the important interactions. Our study highlighted the main structural features that are required for Spindlin1 inhibitory activity, which include a positively charged pyrrolidine moiety embedded into the aromatic cage connected via a propyloxy linker to the 2-aminoindole core. Of the latter, the amidine group anchor the compounds into the pocket through salt bridge interactions with Asp184. Different protocols were tested to identify a fast in silico method that could help to discriminate between active and inactive compounds within the A366 series. Rescoring the docking poses with MM-GBSA calculations was successful in this regard. Because A366 is known to be a G9a inhibitor, the most active developed Spindlin1 inhibitors were also tested over G9a and GLP to verify the selectivity profile of the A366 analogs. This resulted in the discovery of diverse selective compounds, among which 1s and 1t showed Spindlin1 activity in the nanomolar range and selectivity over G9a and GLP. Finally, future design hypotheses were suggested based on our findings.