80526-44-9

Basic information

• Product Name: 2-AMINO-4-CHLORO-6-METHYL-PHENOL
• Synonyms: 2-AMINO-4-CHLORO-6-METHYL-PHENOL
• CAS NO: 80526-44-9
• Molecular Formula: C₇H₈ClNO
• Molecular Weight: 157.59752
• Mol File: 80526-44-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-AMINO-4-CHLORO-6-METHYL-PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-CHLORO-6-METHYL-PHENOL(80526-44-9)
• EPA Substance Registry System: 2-AMINO-4-CHLORO-6-METHYL-PHENOL(80526-44-9)

Safety Data

• Hazardous Substances Data: 80526-44-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-AMINO-4-CHLORO-6-METHYL-PHENOL is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 2-AMINO-4-CHLORO-6-METHYL-PHENOL is used as a building block for the creation of diverse organic compounds, leveraging its reactive functional groups.
Used in Medicinal Chemistry Research:
2-AMINO-4-CHLORO-6-METHYL-PHENOL is utilized as a subject of study in medicinal chemistry, where its biological activities are explored for potential therapeutic applications.
Safety Measures:
When handling 2-AMINO-4-CHLORO-6-METHYL-PHENOL, it is crucial to follow proper safety protocols to prevent health risks associated with exposure to this chemical compound.

Upstream product

• 1760-71-0 4-chloro-2-methyl-6-nitrophenol 
• 1570-65-6 4,6-dichloro-2-methylphenol 
• 95-48-7 ortho-cresol 

Downstream Products

• 93794-45-7 5-chloro-2-mercapto-7-methylbenzoxazole 
• 1186814-42-5 2-chloro-N-(5-chloro-2-hydroxy-3-methylphenyl)-2-phenylacetamide 
• 944356-43-8 2-bromo-N-(5-chloro-2-hydroxy-3-methylphenyl)-3-methylbutyramide 
• 103502-90-5 (6-chloro-8-methyl-2-oxo-2,3-dihydro-benz[1,4]oxazin-4-yl)-acetic acid 

Relevant articles and documents

SYNTHESIS OF 2-AMINOBENZOXAZOLE COMPOUNDS

A method for forming an optionally substituted 2-aminobenzoxazole compound includes: contacting an optionally substituted 2-aminophenol compound with (1) an amine of the formula NHR2R3, wherein R2 and R3 are each independently selected from H, an optionally substituted alkyl group or an optionally substituted aryl group, or R2 and R3, taken together with the nitrogen atom to which they are attached, form an optionally substituted heterocyclic ring; and (2) a reactant selected from the group consisting of: (a) C(OR)4, wherein R represents an alkyl group; (b) C(OAr)4, wherein Ar represents an aryl group; and (c) CCl2(OAr)2, wherein Ar represents an aryl group, in combination with a base; thereby forming the optionally substituted 2-aminobenzoxazole compound.

Synthesis of new carbon-11 labeled benzoxazole derivatives for PET imaging of 5-HT3 receptor

5-HT3 receptor is an attractive target for the development of therapeutic agents for use in brain, heart and cancer diseases, and imaging agents for use in biomedical imaging technique PET. Benzoxazole derivatives are a novel class of 5-HT3 receptor partial agonists with high binding affinity. Carbon-11 labeled benzoxazole derivatives have been synthesized as new potential PET radioligands for imaging 5-HT3 receptor. The target tracers were prepared by N-[11C]methylation of their corresponding precursors using [11C]CH3OTf and isolated by HPLC purification procedure in 40-50% radiochemical yields, which were decay corrected to the end of bombardment (EOB), based on [11C]CO2. The overall synthesis time was 20-25 min from EOB. The radiochemical purity was >99%, and specific activity was in a range of 74-111 GBq/μmol at the end of synthesis (EOS).

Regulatory molecules for the 5-HT3 receptor ion channel gating system

Substituted benzoxazole derivatives which possess a nitrogen-containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor.

Carboxylic Acid Compounds and Use Thereof

Provision of a superior URAT1 activity inhibitor effective for the treatment and the like of a pathology involving uric acid, such as hyperuricemia, gouty tophus, acute gouty arthritis, chronic gouty arthritis, gouty kidney, urinary lithiasis, renal dysfunction, coronary heart disease, ischemic cardiac diseases and the like. A URAT1 activity inhibitor containing a compound represented by the following formula [1] or a pharmaceutically acceptable salt thereof, or a solvate thereof as an active ingredient: [image] wherein each symbol is as defined in the specification.

Orally active benzoxazole derivative as 5-HT3 receptor partial agonist for treatment of diarrhea-predominant irritable bowel syndrome

During our search for therapeutic agents to treat diarrhea-predominant IBS, we found that 2-substituted benzoxazole derivatives have a characteristic 5-HT3 receptor partial agonist activity with high affinity. Some of these compounds showed high in vitro metabolical stability, and 6g showed marked antidiarrhetic activity with little side effect of constipation in in vivo tests. Our results indicate that 5-HT3 receptor partial agonists might be superior as therapeutic agents to the drugs currently used for IBS treatment.

Benzoxazole derivatives as novel 5-HT3 receptor partial agonists in the gut

A series of benzoxazoles with a nitrogen-containing heterocyclic substituent at the 2-position was prepared and evaluated for 5-HT3 partial agonist activity on isolated guinea pig ileum. The nature of the substituent at the 5-position of the benzoxazole ring affected the potency for the 5-HTs receptor, and the 5-chloro derivatives showed increased potency and lowered intrinsic activity. 5-Chloro-7-methyl-2-(4-methyl-1- homopiperazinyl)benzoxazole (6v) exhibited a high binding affinity in the same range as that of the 5-HT3 antagonist granisetron, and its intrinsic activity was 12% of that of 5-HT. Compound 6v inhibited 5-HT-evoked diarrhea but did not prolong the transition time of glass beads in the normal distal colon even at a dose of 100 times the ED50 for diarrhea inhibition in mice. Compounds of this type are expected to be effective for the treatment of irritable bowel syndrome without the side effect of constipation.