115551-33-2

Basic information

• Product Name: 6-AMINO-2 3-DIFLUOROPHENOL
• Synonyms: 2-Hydroxy-3,4-difluoroaniline;2-Amino-5,6-difluorophenol
• CAS NO: 115551-33-2
• Molecular Formula: C₆H₅F₂NO
• Molecular Weight: 145.1068
• Product Categories: Benzene series
• Mol File: 115551-33-2.mol

Chemical Properties

• Boiling Point: 229.4 °C at 760 mmHg
• Flash Point: 92.5 °C
• Appearance: /
• Density: 1.472 g/cm³
• Vapor Pressure: 0.0463mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.50±0.15(Predicted)
• CAS DataBase Reference: 6-AMINO-2 3-DIFLUOROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AMINO-2 3-DIFLUOROPHENOL(115551-33-2)
• EPA Substance Registry System: 6-AMINO-2 3-DIFLUOROPHENOL(115551-33-2)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 115551-33-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
6-Amino-2,3-difluorophenol is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
6-AMINO-2 3-DIFLUOROPHENOL also serves as an intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural products to enhance crop protection and yield.
Used in Dye and Pigment Manufacturing:
6-Amino-2,3-difluorophenol is employed in the manufacturing process of dyes and pigments due to its chemical properties, which enable the creation of a wide range of colors and shades for various industries.
Used in Organic Compound Synthesis:
As an intermediate, 6-Amino-2,3-difluorophenol plays a crucial role in the synthesis of other organic compounds, expanding its applications across different chemical and industrial sectors.

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

Upstream product

• 441713-58-2 2-benzyloxy-3,4-difluoro-1-nitrobenzene 
• 868735-81-3 1-(benzyloxy)-2.3-difluoro-4-nitrobenzene 
• 771-69-7 2,3,4-trifluoronitrobenzene 
• 144298-04-4 (3,4-difluorophenyl)-carbamic acid-tert-butyl ester 
• 82419-26-9 2,3-difluoro-6-nitrophenol 

Downstream Products

• 371914-74-8 1-(3-chloro-4-fluoro-phenyl)-3-(3,4-difluoro-2-hydroxy-phenyl)-thiourea 
• 371914-71-5 1-(3,4-difluoro-2-hydroxy-phenyl)-3-(2,4-difluoro-phenyl)-thiourea 
• 509147-86-8 6,7-difluoro-1,3-benzoxazol-2(3H)-one 
• 85741-74-8 diethyl 2-(((3,4-difluoro-2-hydroxyphenyl)amino)methylene)malonate 
• 921590-87-6 5-[4-(benzyloxy)phenyl]-1-(2,4-dichlorophenyl)-N-(3,4-difluoro-2-hydroxyphenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 124532-06-5 2,3-Difluoro-6-(2,2-diethoxycarbonylethenyl)amino-{[(R)-2-hydroxypropyl]oxy}benzene 
• 124409-86-5 diethyl [3,4-difluoro-2-(2-hydroxypropyloxy)anilinyl]methylenemalonate 
• 100986-86-5 (R)-ofloxacin 

Relevant articles and documents

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.

BACTERIAL TOPOISOMERASE I INHIBITORS WITH ANTIBACTERIAL ACTIVITY

The present invention provides compounds as bacterial topoisomerase inhibitors with antibacterial activity. The present invention also provides pharmaceutical compositions comprising at least one of the compounds and methods of using the compounds and pharmaceutical compositions as antibacterial agents for treating infectious diseases.

Synthesis, evaluation, and CoMFA study of fluoroquinophenoxazine derivatives as bacterial topoisomerase IA inhibitors

New antibacterial agents with novel target and mechanism of action are urgently needed to combat problematic bacterial infections and mounting antibiotic resistances. Topoisomerase IA represents an attractive and underexplored antibacterial target, as such, there is a growing interest in developing selective and potent topoisomerase I inhibitors for antibacterial therapy. Based on our initial biological screening, fluoroquinophenoxazine 1 was discovered as a low micromolar inhibitor against E.?coli topoisomerase IA. In the literature, fluoroquinophenoxazine analogs have been investigated as antibacterial and anticancer agents, however, their topoisomerase I inhibition was relatively underexplored and there is little structure-activity relationship (SAR) available. The good topoisomerase I inhibitory activity of 1 and the lack of SAR prompted us to design and synthesize a series of fluoroquinophenoxazine analogs to systematically evaluate the SAR and to probe the structural elements of the fluoroquinophenoxazine core toward topoisomerase I enzyme target recognition. In this study, a series of fluoroquinophenoxazine analogs was designed, synthesized, and evaluated as topoisomerase I inhibitors and antibacterial agents. Target-based assays revealed that the fluoroquinophenoxazine derivatives with 9-NH2and/or 6-substituted amine functionalities generally exhibited good to excellent inhibitory activities against topoisomerase I with IC50s ranging from 0.24 to 3.9?μM. Notably, 11a bearing the 6-methylpiperazinyl and 9-amino motifs was identified as one of the most potent topoisomerase I inhibitors (IC50?=?0.48?μM), and showed broad spectrum antibacterial activity (MICs?=?0.78–7.6?μM) against all the bacteria strains tested. Compound 11g with the 6-bipiperidinyl lipophilic side chain exhibited the most potent antituberculosis activity (MIC?=?2.5?μM, SI?=?9.8). In addition, CoMFA analysis was performed to investigate the 3D-QSAR of this class of fluoroquinophenoxazine derivatives. The constructed CoMFA model produced reasonable statistics (q2?=?0.688 and r2?=?0.806). The predictive power of the developed model was obtained using a test set of 7 compounds, giving a predictive correlation coefficient r2predof 0.767. Collectively, these promising data demonstrated that fluoroquinophenoxazine derivatives have the potential to be developed as a new chemotype of potent topoisomerase IA inhibitors with antibacterial therapeutic potential.

Synthesis and fluorescent properties of 2-styryl-6,7-difluoro-8- hydroxyquinoline and its Zn(II) complex

A synthetic approach to 2-methyl-6,7-difluoro-8-hydroxyquinoline, a key intermediate, has been developed. 6,7-Difluoro derivative of 2-styryl substituted 8-hydroxyquinoline and its Zn(II) complex have been obtained. Effects of fluorine atoms in the benzen

NOVEL PYRIDINE DERIVATIVE AND PYRIMIDINE DERIVATIVE (3)

A compound represented by the following formula, a salt thereof or a hydrate of the foregoing has an excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibits anti-tumor activity, angiogenesis inhibitory activity and cancer metastasis inhibitory activity. [R1 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; R2 and R3 represent hydrogen; R4, R5, R6, and R7 may be the same or different and each represents hydrogen, halogen, C1-6 alkyl or the like; R8 represents hydrogen or the like; R9 represents a 3- to 10-membered non-aromatic heterocyclic group or the like; n represents an integer of 1 or 2; X represents -CH=, nitrogen or the like.]

Monocyclic heterocycles as kinase inhibitors

The present invention is directed to compounds having the formula and methods for using them for the treatment of cancer.

IL-8 RECEPTOR ANTAGONISTS

The present invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease states mediated by the chemokine Interleukin-8 (IL-8).

An efficient synthesis of ofloxacin and levofloxacin from 3,4- difluoroaniline

The functionalization at either C-2 or C-3 of N-(tert-butoxycarbonyl)- 3,4-difluoroaniline based on its ortho-deprotonation under different experimental conditions is described. This kind of products can be readily applied to the synthesis of ofloxacin, levofloxacin and related compounds.

IL-8 RECEPTOR ANTAGONISTS

This invention relates to the novel use of phenyl ureas in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).

IL-8 RECEPTOR ANTAGONISTS

This invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease scates mediated by the chemokine, Interleukin-8 (IL-8). In particular, this invention relates to the novel compounds of Formula (Ia) and their use in treating chemokine mediated diseases wherein the chemokine binds to an IL-8 a or b receptor. Compounds of Formula (Ia) are represented by the structure: STR1 wherein interalia, X is oxygen or sulfur;Rb is NR 6 R. sub.7, alkcyl, aryl, arylC 1-4 alkyl, aryl C 2-4 alkenyl, heteroaryl, heteroarylC 1-4 alkyl, heteroarylC 2-4 alkenyl, heterocyclic or heterocyclic C 1-4 alkyl, or a heterocyclic C 2-4 alkenyl moiety, camphor, all of which may be optionally substituted; R 1 is independently selected from hydrogen; halogen; nitro; cyano; C 1-10 alkyl; halosubstituted C 1-10 alkyl; C 2-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR. sub.8 R 8)q S(O) t R 4 ; hydroxy; hydroxy substituted C 1-4 alkyl; aryl; aryl C 1-4 alkyl; aryl C 2-10 alkenyl; aryloxy; aryl C 1-4 alkyloxy; heteroaryl; heteroarylalkyl; heteroaryl C 2-10 alkenyl; heteroaryl C 1-4 alkyloxy; heterocyclic; heterocyclic C 1-4 alkyl; heterocyclicC 1-4 alkyloxy; heterocyclic C 2-10 alkenyl; q is 0 or an integer having a value of 1 to 10; n is an integer having a value of 1 to 3;m is an integer having a value of 1 to 3; Y is hydrogen; halogen; nitro; cyano; halosubstituted C 1-10 alkyl; C 1-10 alkyl; C 2-10 alkenyl C. sub.1-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR 8 R. sub.8)qS(O) t R 4, (CR 8 R 8)qOR 4 ; hydorxy; hydroxy substituted C. sub.1-4 alkyl; aryl; aryl C 1-4 alkyl; aryloxy; arylC. sub.1-4 alkyloxy; aryl C 2-10 alkenyl; heteroaryl; heteroarylalkyl; heteroaryl C 1-4 alkyloxy; heteroaryl C 2-10 alkenyl; heterocyclic, heterocyclic C 1-4 alkyl; heterocyclicC 2-10 alkenyl;or a pharmaceutically acceptable salt thereof.