873055-35-7

Basic information

• Product Name: 5-amino-2-tert-butylphenol
• Synonyms: 5-amino-2-tert-butylphenol
• CAS NO: 873055-35-7
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• Mol File: 873055-35-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-amino-2-tert-butylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-2-tert-butylphenol(873055-35-7)
• EPA Substance Registry System: 5-amino-2-tert-butylphenol(873055-35-7)

Safety Data

• Hazardous Substances Data: 873055-35-7(Hazardous Substances Data)

Usage

Description

5-amino-2-tert-butylphenol is a chemical compound with the molecular formula C10H15NO. It is a colorless to light yellow liquid with a faint amine odor.

Uses

Used in Pharmaceutical Industry:
5-amino-2-tert-butylphenol is used as an intermediate for the production of pharmaceuticals, contributing to the synthesis of various medicinal compounds.
Used in Dye Industry:
5-amino-2-tert-butylphenol is used as a precursor in the manufacturing of dyes, playing a role in the creation of colorants for different applications.
Used in Polymer Industry:
5-amino-2-tert-butylphenol is used as a component in the production of polymers, aiding in the development of specific polymeric materials.
Used in Organic Synthesis:
5-amino-2-tert-butylphenol is used as an intermediate in organic synthesis, facilitating the creation of a range of organic compounds.
Used in Antioxidant Production:
5-amino-2-tert-butylphenol is used as a precursor in the manufacturing of antioxidants, which are important for preventing oxidative degradation in various products.
Used in UV Stabilizer Manufacturing:
5-amino-2-tert-butylphenol is used in the production of UV stabilizers, which help protect materials from the damaging effects of ultraviolet radiation.
Safety Note:
5-amino-2-tert-butylphenol is considered to be a skin and eye irritant. It should be handled with care using proper protective equipment and stored and used in a well-ventilated area to minimize exposure to harmful fumes.

Upstream product

• 6310-21-0 2-(1,1-dimethylethyl)-benzenamine 
• 442847-11-2 2-(tert-butyl)-5-nitrophenol 
• 103392-84-3 2-tert-Butyl-5-nitro-phenylamine 

Downstream Products

• 1233531-36-6 2-(4-tert-butyl-3-hydroxyphenyl)isoindoline-1,3-dione 
• 1233530-67-0 N-(4-tert-butyl-3-hydroxy-phenyl)-3,4-dihydro-2H-1,4-benzothiazine-2-carboxamide 

Relevant articles and documents

Evaluation of 1,2,3-Triazoles as Amide Bioisosteres In Cystic Fibrosis Transmembrane Conductance Regulator Modulators VX-770 and VX-809

The 1,2,3-triazole has been successfully utilized as an amide bioisostere in multiple therapeutic contexts. Based on this precedent, triazole analogues derived from VX-809 and VX-770, prominent amide-containing modulators of the cystic fibrosis transmembrane conductance regulator (CFTR), were synthesized and evaluated for CFTR modulation. Triazole 11, derived from VX-809, displayed markedly reduced efficacy in F508del-CFTR correction in cellular TECC assays in comparison to VX-809. Surprisingly, triazole analogues derived from potentiator VX-770 displayed no potentiation of F508del, G551D, or WT-CFTR in cellular Ussing chamber assays. However, patch clamp analysis revealed that triazole 60 potentiates WT-CFTR similarly to VX-770. The efficacy of 60 in the cell-free patch clamp experiment suggests that the loss of activity in the cellular assay could be due to the inability of VX-770 triazole derivatives to reach the CFTR binding site. Moreover, in addition to the negative impact on biological activity, triazoles in both structural classes displayed decreased metabolic stability in human microsomes relative to the analogous amides. In contrast to the many studies that demonstrate the advantages of using the 1,2,3-triazole, these findings highlight the negative impacts that can arise from replacement of the amide with the triazole and suggest that caution is warranted when considering use of the 1,2,3-triazole as an amide bioisostere.

Discovery of N -(2,4-Di- tert -butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, Ivacaftor), a potent and orally bioavailable CFTR potentiator

Quinolinone-3-carboxamide 1, a novel CFTR potentiator, was discovered using high-throughput screening in NIH-3T3 cells expressing the F508del-CFTR mutation. Extensive medicinal chemistry and iterative structure-activity relationship (SAR) studies to evaluate potency, selectivity, and pharmacokinetic properties resulted in the identification of N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (VX-770, 48, ivacaftor), an investigational drug candidate approved by the FDA for the treatment of CF patients 6 years of age and older carrying the G551D mutation.

MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR

The present invention relates to modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator, compositions thereof, and methods therewith. The present invention also relates to methods of treating diseases using such CFTR modulators.