206872-01-7

Basic information

• Product Name: 2-Amino-6-bromo-4-methoxyphenol
• Synonyms: 2-AMINO-6-BROMO-4-METHOXYPHENOL;2-Amino-6-Bromo-4-Methoxypheno;2-amino-4-methoxy-6-bromophenol;2-Amino-6-bromo-4-methoxybenzenol;3-Bromo-2-hydroxy-5-methoxyaniline, 3-Amino-5-bromo-4-hydroxyanisole
• CAS NO: 206872-01-7
• Molecular Formula: C₇H₈BrNO₂
• Molecular Weight: 218.05
• Product Categories: Aromatic Halides (substituted);Amines;Phenyls & Phenyl-Het;heterocyclic/Aliphatic series;Phenyls & Phenyl-Het
• Mol File: 206872-01-7.mol

Chemical Properties

• Melting Point: 99°C
• Boiling Point: 294.4 °C at 760 mmHg
• Flash Point: 131.8 °C
• Appearance: /
• Density: 1.673 g/cm³
• Vapor Pressure: 0.000926mmHg at 25°C
• Refractive Index: 1.636
• Storage Temp.: 2-8°C
• PKA: 8.72±0.23(Predicted)
• CAS DataBase Reference: 2-Amino-6-bromo-4-methoxyphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-bromo-4-methoxyphenol(206872-01-7)
• EPA Substance Registry System: 2-Amino-6-bromo-4-methoxyphenol(206872-01-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 206872-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-6-bromo-4-methoxyphenol is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
2-Amino-6-bromo-4-methoxyphenol is used as a building block in organic synthesis for creating a variety of organic compounds, leveraging its unique functional groups to form diverse chemical structures.
Used in Dye and Pigment Production:
2-Amino-6-bromo-4-methoxyphenol is used as a precursor in the production of various dyes and pigments, taking advantage of its chemical properties to create a range of colorants for different applications.
Used in Antibacterial and Antifungal Applications:
2-Amino-6-bromo-4-methoxyphenol is studied for its potential as an antibacterial and antifungal agent, exploring its ability to inhibit the growth of harmful microorganisms, which could lead to new treatments and preventive measures in medicine and related fields.

InChI:InChI=1/C7H8BrNO2/c1-11-4-2-5(8)7(10)6(9)3-4/h2-3,10H,9H2,1H3

Upstream product

• 115929-59-4 6-bromo-4-methoxy-2-nitrophenol 
• 1568-70-3 4-methoxy-2-nitrophenol 

Downstream Products

• 544704-74-7 2-bromo-6-[(3-fluoro-4-methoxybenzoyl)amino]-4-methoxyphenyl-3-fluoro-4-methoxybenzoate 
• 544704-73-6 7-bromo-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol 
• 544704-75-8 7-bromo-2-(3-fluoro-4-methoxyphenyl)-5-methoxy-1,3-benzoxazole 
• 524684-52-4 prinaberel 
• 544705-42-2 7-(2-bromo-1-fluoroethyl)-2-(3-fluoro-4-hydroxyphenyl)-1,3-benzoxazol-5-ol 
• 544704-84-9 4-[5-(acetyloxy)-1,3-benzoxazol-2-yl]-7-vinyl-2-fluorophenyl acetate 
• 688363-47-5 8-bromo-6-methoxy-4H-benzo[1,4]oxazin-3-one 
• 544704-71-4 2-bromo-4-methoxy-6-[(4-methoxybenzoyl)amino]phenyl 4-methoxybenzoate 
• 544705-24-0 2-Bromo-4-methoxy-6-{[4-methoxy-3-(trifluoromethyl)benzoyl]amino}phenyl 4-methoxy-3-(trifluoromethyl)benzoate 
• 440123-54-6 5-oxo-pyrrolidine-2-carboxylic acid (3-bromo-2-hydroxy-5-methoxy-phenyl)-amide 
• 1443533-27-4 7-bromo-2-(6-benzyloxypyridin-3-yl)-5-methoxy-1,3-benzoxazole 
• 1092352-82-3 7-bromo-5-methoxy-2-methyl-1,3-benzoxazole 

Relevant articles and documents

THERAPEUTIC AGENT FOR INFLAMMATORY DISEASES, AUTOIMMUNE DISEASES, FIBROTIC DISEASES, AND CANCER DISEASES

A therapeutic agent for treating at least one disease selected from the group consisting of inflammatory diseases, autoimmune diseases, fibrotic diseases, and cancer diseases, comprising: at least one selected from the group consisting of a compound represented by the following general formula (1) and pharmacologically acceptable salts thereof as an active ingredient. [In the formula (1), R1 and R2 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a carboxy group, a cyano group, an optionally substituted C1-6 alkyl group et al.; R3 represents a hydrogen atom; R4 represents an optionally substituted 4- to 10-membered monocyclic heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom; X represents a group represented by the following formula: -CH2-, - CH2-CH2-, -CH2-CH2-CH2-, or -CH2-O-CH2-; and Z represents a hydrogen atom or a hydroxyl group.]

NOVEL COMPOUND AND PHARMACOLOGICALLY ACCEPTABLE SALT THEREOF

A compound represented by the general formula (1) below or a pharmacologically acceptable salt thereof: [In the formula (1), R1 and R2 may be the same or different and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a carboxy group, a cyano group, an optionally substituted C1-6 alkyl group et al.; R3 represents a hydrogen atom; R4 represents an optionally substituted 4- to 10-membered monocyclic heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom; X represents a group represented by the following formula: —CH2—, —CH2—CH2—, —CH2—CH2—CH2—, or —CH2—O—CH2—; and Z represents a hydrogen atom or a hydroxyl group.]

Synthesis of substituted 2-heteroarylbenzazol-5-ol derivatives as potential ligands for estrogen receptors

Exposure to estrogen is associated with increased risk of breast and other types of human cancer. One therapeutic goal would be the creation of new molecules that would retain hormonal potency while incorporating features to retard or prevent quinone toxicity. Hence, new structures closely related to ERB-041, a known ERβ selective agonist, were synthesized whereas the phenol ring is substituted with non-quinone forming rings such as pyrazole, 2-pyrimidine-2(1H)-one or pyridine-2(1H)-one. 2-Methyl-5-methoxy-1,3- benzoxazoles (or 1,3-benzothiazole) are key intermediates for the production of the pyrazole and pyrimidine-2(1H)-one analogs. The required 1,3-benzoxazoles were synthesized starting from reduction of 2-nitro-4-methoxyphenols, followed by condensation with trimethyl orthoacetate. Then, the diiminium perchlorate intermediates were prepared from the latter compounds by Vilsmeier-Haack reaction. The reaction of the resulting intermediates with hydrazine hydrate and guanidium chloride afforded the title pyrazole and pyrimidine-2(1H)-ones, respectively. The pyridine analogs were synthesized starting from the reaction of 2-amino-4-methoxyphenols with 6-bromopyridine-3-carboxaldehyde followed by oxidation with DDQ to afford bromopyridines. These compounds were next treated with benzyl alcohol in the presence of potassium tert-butoxide to afford 2-benzyloxypyridine, which in subsequent dealkylation with boron tribromide produced the title pyridine-2-(1H)-ones.

An efficient method for aryl nitro reduction and cleavage of azo compounds using iron powder/calcium chloride

A novel, efficient Fe/CaCl2 system is revealed for the reduction of nitroarenes and reductive cleavage of azo compounds by catalytic transfer hydrogenation (CTH). The selective reduction of nitro compounds in the presence of sensitive functional groups including halides, carbonyl, hydroxyl, aldehyde, methyl, methoxy, acetyl, nitrile, and ester substituents with an excellent yields is reported. The simple experimental procedure and easy purification make the protocol advantageous

Aryl nitro reduction with iron powder or stannous chloride under ultrasonic irradiation

The selective reduction of aryl nitro compounds in the presence of sensitive functionalities, including halide, carbonyl, nitrile, and ester substituents, under ultrasonic irradiation at 35 kHz is reported in yields of 39-98%. Iron powder proved superior to stannous chloride with high tolerance of sensitive functional groups and high yields of the desired aryl amines in relatively short reaction times. Simple experimental procedure and purification also make the iron reduction of aryl nitro compounds advantageous over other methods of reduction. Copyright Taylor & Francis Group, LLC.

Prodrug substituted benzoxazoles as estrogenic agents

This invention provides estrogen receptor modulators of formula I, having the structure wherein Q, Q2, R1, R2, R2a, R3, R3a, and X as defined in the specification, or a pharmaceutically acceptable salt thereof.

Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-β ligands

New diphenolic azoles as highly selective estrogen receptor-β agonists are reported. The more potent and selective analogues of these series have comparable binding affinities for ERβ as the natural ligand 17β-estradiol but are > 100-fold selective over ERα. Our design strategy not only followed a traditional SAR approach but also was supported by X-ray structures of ERβ cocrystallized with various ligands as well as molecular modeling studies. These strategies enabled us to take advantage of a single conservative residue substitution in the ligand-binding pocket, ERα Met421 → ERβ Ile373, to optimize ERβ selectivity. The 7-position-substituted benzoxazoles (Table 5) were the most selective ligands of both azole series, with ERB-041 (117) being >200-fold selective for ERβ. The majority of ERβ selective agonists tested that were at least sim;50-fold selective displayed a consistent in vivo profile: they were inactive in several models of classic estrogen action (uterotrophic, osteopenia, and vasomotor instability models) and yet were active in the HLA-B27 transgenic rat model of inflammatory bowel disease. These data suggest that ERβ-selective agonists are devoid of classic estrogenic effects and may offer a novel therapy to treat certain inflammatory conditions.

Substituted benzoxazoles as estrogenic agents

This invention provides estrogen receptor modulators of formula I, having the structure wherein R1, R2, R2a, R3, R3a, and R4, and X as defined in the specification, or a pharmaceutically acceptable salt thereof.