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

• 63057-72-7 2-benzyloxy-5-bromoanisole 
• 132532-64-0 4-bromo-2-methoxy-1-methoxymethylenoxybenzene 
• 81258-24-4 acide(bromo-4 methoxy-2 phenoxy-1)-3 propionique 
• 2380-78-1 homovanillyl alcohol 
• 35857-70-6 2,3-dihydroxybenzene-1-sulfonic acid 
• 120-80-9 benzene-1,2-diol 
• 352019-92-2 2-allyl-4-bromo-6-methoxyphenol 
• 431879-38-8 4-(tert-butyldiphenylsilanoxy)-3-methoxybromobenzene 
• 37055-79-1 4-hydroxy-3-methoxybiphenyl 
• 876514-71-5 2-methoxy-4-(trimethylsilylethynyl)phenol 
• 875654-33-4 4-isopropoxy-3-methoxyphenylboronic acid 
• 875654-30-1 7-isopropoxy-1-(4-isopropoxy-3-methoxyphenyl)-3-[2-(3-isopropoxy-4-methoxyphenyl)ethyl]-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-4(3H)-one 
• 660396-67-8 3,11-diisopropoxy-14-(4-isopropoxy-3-methoxyphenyl)-2,12-dimethoxy-6H-chromeno[4′,3′:4,5]pyrrolo[2,1-a]-isoquinolin-6-one 
• 875654-39-0 dimethyl 3-(4-isopropoxy-3-methoxyphenyl)-1-[2-(3-isopropoxy-4-methoxyphenyl)ethyl]-4-(trifluoromethanesulfonyloxy)pyrrole-2,5-dicarboxylate 

Relevant articles and documents

Synthesis method 5 - halogeno-veratraldehyde

The invention belongs to the field of organic chemistry, and in particular relates 5 - to a method for synthesizing halogenated O-veratraldehyde by using 4 - halogenoylguaiacol as a raw material to obtain 2 -hydroxy -3 - methoxy -5 -halogenated mandelic a

Synthesis and Photoswitching Properties of Bioinspired Dissymmetric I-Pyrone, an Analogue of Cyclocurcumin

Cyclocurcumin (CC), a turmeric curcuminoid with potential therapeutic properties, is also a natural photoswitch that may undergo E/Z photoisomerization under UV light. To be further exploited in relevant biological applications, photoactivation under near-infrared (NIR) irradiation is required. Such requirement can be met through opportune chemical modifications, by favoring two-photon absorption (TPA) probability. Herein, a general and efficient synthesis of a biomimetic 2,6-disubstituted-δ-pyrone analogue of CC is described, motivated by the fact that molecular modeling previews an order of magnitude increase of its NIR TPA compared to CC. Three retrosynthetic pathways have been identified (i) via an aryl-oxazole intermediate or via aryl-diynone through (ii) a bottom-up or (iii) a top-down approach. While avoiding the passage through unstable synthons or low-yield intermediate reactions, only the latest approach could conveniently afford the 2,6-disubstituted-I-pyrone analogue of CC, in ten steps and with an overall yield of 18%. The photophysical properties of our biomimetic analogue have also been characterized showing an improved photoisomerization yield over the parent natural compound. The potentially improved nonlinear optical properties, as well as enhanced stability, may be correlated to the enforcement of the planarity of the pyrone moiety leading to a quadrupolar D-π-A-π-D system.

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.