126058-97-7

Basic information

• Product Name: 4-Amino-2,6-difluorophenol
• Synonyms: 4-AMINO-2,6-DIFLUOROPHENOL;3,5-Difluoro-4-hydroxyaniline;4-amino-2,6-difluoropheneol
• CAS NO: 126058-97-7
• Molecular Formula: C₆H₅F₂NO
• Molecular Weight: 145.11
• Product Categories: pharmacetical;Phenol&Thiophenol&Mercaptan
• Mol File: 126058-97-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: /
• Density: 1.472 g/cm³
• Vapor Pressure: 0.03mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 7.72±0.23(Predicted)
• CAS DataBase Reference: 4-Amino-2,6-difluorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-2,6-difluorophenol(126058-97-7)
• EPA Substance Registry System: 4-Amino-2,6-difluorophenol(126058-97-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 126058-97-7(Hazardous Substances Data)

Usage

General Description

4-Amino-2,6-difluorophenol is a chemical compound with the molecular formula C6H5F2NO. It is a derivative of phenol and contains two fluorine atoms and an amino group. 4-Amino-2,6-difluorophenol is primarily used in the production of pharmaceuticals and dyes. It is also used as an intermediate in the synthesis of various organic compounds. 4-Amino-2,6-difluorophenol has antibacterial and antifungal properties, making it useful in the development of antimicrobial agents. Additionally, it is used in the manufacturing of hair dyes and colorants due to its ability to produce vibrant and long-lasting colors. However, it is important to handle this chemical with care as it can cause irritation to the skin, eyes, and respiratory system if not properly managed.

InChI:InChI=1/C6H5F2NO/c7-4-1-3(9)2-5(8)6(4)10/h1-2,10H,9H2

Upstream product

• 847861-84-1 2-(benzyloxy)-1,3-difluoro-5-nitrobenzene 
• 66684-58-0 3,4,5-trifluoronitrobenzene 
• 18063-03-1 2,6-difluorobenzamide 
• 5509-65-9 2,6-difluoroaniline 
• 28177-48-2 2,6-difluorophenol 
• 658-07-1 2,6-Difluoro-4-nitrophenol 

Downstream Products

• 1115491-38-7 C₁₉H₂₂ClF₂N₃O₂Si 
• 1225278-61-4 4-((2-chloropyridin-4-yl)oxy)-3,5-difluoroaniline 

Relevant articles and documents

N-Substituted pyrrolopyrimidines and purines as p90 ribosomal S6 protein kinase-2 (RSK2) inhibitors

The RSK2 kinase is the downstream effector of the Ras/Raf/MEK/ERK pathway, that is often aberrantly activated in acute myeloid leukemia (AML). Recently, we reported a structure-activity study for BI-D1870, the pan-RSK inhibitor, and identified pteridinones that inhibited cellular RSK2 activity that did not result in concomitant cytotoxicity. In the current study, we developed a series of pyrrolopyrimidines and purines to replace the pteridinone ring of BI-D1870, with a range of N-substituents that extend to the substrate binding site to probe complementary interactions, while retaining the 2,6-difluorophenol-4-amino group to maintain interactions with the hinge domain and the DFG motif. Several compounds inhibited cellular RSK2 activity, and we identified compounds that uncoupled cellular RSK2 inhibition from potent cytotoxicity in the MOLM-13 AML cell line. These N-substituted probes have revealed an opportunity to further examine substituents that extend from the ATP- to the substrate-binding site may confer improved RSK potency and selectivity.

Identification of Diarylurea Inhibitors of the Cardiac-Specific Kinase TNNI3K by Designing Selectivity against VEGFR2, p38α, and B-Raf

A series of diarylurea inhibitors of the cardiac-specific kinase TNNI3K were developed to elucidate the biological function of TNNI3K and evaluate TNNI3K as a therapeutic target for the treatment of cardiovascular diseases. Utilizing a structure-based design, enhancements in kinase selectivity were engineered into the series, capitalizing on the established X-ray crystal structures of TNNI3K, VEGFR2, p38α, and B-Raf. Our efforts culminated in the discovery of an in vivo tool compound 47 (GSK329), which exhibited desirable TNNI3K potency and rat pharmacokinetic properties as well as promising kinase selectivity against VEGFR2 (40-fold), p38α (80-fold), and B-Raf (>200-fold). Compound 47 demonstrated positive cardioprotective outcomes in a mouse model of ischemia/reperfusion cardiac injury, indicating that optimized exemplars from this series, such as 47, are favorable leads for discovering novel medicines for cardiac diseases.

Benzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17Β-HSD10 with implications to Alzheimer’s disease treatment

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymatic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurological diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approximately 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the phenyl ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC50 values of 1–2 μM and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.