108655-63-6

Basic information

• Product Name: 5-Isoxazolamine,3-(trifluoromethyl)-(9CI)
• Synonyms: 5-Isoxazolamine,3-(trifluoromethyl)-(9CI);3-TRIFLUOROMETHYL-5-AMINOISOXAZOLE;3-(Trifluoromethyl)-5-isoxazolamine;3-(TrifluoroMethyl)isoxazol-5-aMine;3-(Trifluoromethyl)-1,2-oxazol-5-amine, 5-Amino-3-(trifluoromethyl)-1,2-oxazole;5-Amino-3-(trifluoromethyl)isoxazole;3-Trifluoromethyl-isoxazol-5-ylamine
• CAS NO: 108655-63-6
• Molecular Formula: C₄H₃F₃N₂O
• Molecular Weight: 152.08
• Product Categories: OXAZOLE
• Mol File: 108655-63-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 53-55°
• Boiling Point: 216.072°C at 760 mmHg
• Flash Point: 84.478°C
• Appearance: /
• Density: 1.502g/cm³
• Vapor Pressure: 0.143mmHg at 25°C
• Refractive Index: 1.424
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: -2.65±0.10(Predicted)
• CAS DataBase Reference: 5-Isoxazolamine,3-(trifluoromethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isoxazolamine,3-(trifluoromethyl)-(9CI)(108655-63-6)
• EPA Substance Registry System: 5-Isoxazolamine,3-(trifluoromethyl)-(9CI)(108655-63-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 108655-63-6(Hazardous Substances Data)

Usage

General Description

5-Isoxazolamine,3-(trifluoromethyl)-(9CI) is a chemical compound that belongs to the class of isoxazoles, which are five-membered heterocyclic compounds containing an oxygen atom and a nitrogen atom at adjacent positions. The addition of a trifluoromethyl group to the isoxazolamine structure adds three fluorine atoms to the molecule, increasing its electron-withdrawing power and altering its chemical properties. 5-Isoxazolamine,3-(trifluoromethyl)-(9CI) may have potential applications in pharmaceutical and agrochemical industries, as well as in materials science and organic synthesis. Further research and development may be needed to explore its full range of potential uses and properties.

InChI:InChI=1/C4H3F3N2O/c5-4(6,7)2-1-3(8)10-9-2/h1H,8H2

Upstream product

• 108655-61-4 methyl 5-amino-3-(trifluoromethyl)isoxazole-4-carboxylate 
• 110234-78-1 4,4,4-trifluoro-3-methoxybut-2-enenitrile 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 151-50-8 potassium cyanide 
• 117341-57-8 3-bromo-1,1,1-trifluoropropan-2-one oxime 
• 108655-62-5 5-Amino-3-trifluoromethylisoxazole-4-carboxamide 

Downstream Products

• 110411-51-3 3-trifluoromethyl-5-hydroxyisoxazole 

Relevant articles and documents

Identification of 1-(3-(6,7-dimethoxyquinazolin-4-yloxy)phenyl)-3-(5-(1,1, 1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)urea hydrochloride (CEP-32496), a highly potent and orally efficacious inhibitor of V-RAF murine sarcoma viral oncogene homologue B1 (BRAF) V600E

The Ras/RAF/MEK/ERK mitogen-activated protein kinase (MAPK) signaling pathway plays a central role in the regulation of cell growth, differentiation, and survival. Expression of mutant BRAFV600E results in constitutive activation of the MAPK pathway, which can lead to uncontrolled cellular growth. Herein, we describe an SAR optimization campaign around a series of quinazoline derived BRAFV600E inhibitors. In particular, the bioisosteric replacement of a metabolically sensitive tert-butyl group with fluorinated alkyl moieties is described. This effort led directly to the identification of a clinical candidate, compound 40 (CEP-32496). Compound 40 exhibits high potency against several BRAFV600E-dependent cell lines and selective cytotoxicity for tumor cell lines expressing mutant BRAFV600E versus those containing wild-type BRAF. Compound 40 also exhibits an excellent PK profile across multiple preclinical species. In addition, significant oral efficacy was observed in a 14-day BRAFV600E-dependent human Colo-205 tumor xenograft mouse model, upon dosing at 30 and 100 mg/kg BID.

3-perfluoroalkyl-5-hydroxyisoxazoles

A novel compound useful as an intermediate for synthesizing pesticides and medicine of the formula: STR1 in which: R is perfluoroalkyl, R1 is hydrogen, alkyl or optionally substituted phenyl, or a salt thereof.

Synthesis and Reaction of 5-Amino-3-trifluoromethylisoxazole and -pyrazole-4-carboxylic Acids

5-Amino-3-trifluoromethylisoxazole- and -pyrazole-4-carboxylic acids were prepared by the reactions of trifluoroacetonitrile oxide or -imines with cyanoacetic acid derivatives, respectively.The behavior of thus obtained aminoazole-4-carboxylic acids towar