105175-00-6

Basic information

• Product Name: 3-Bromo-5-(2-hydroxyethyl)isoxazole
• Synonyms: 3-Bromo-5-(2-hydroxyethyl)isoxazole;2-(3-Bromo-isoxazol-5-yl)-ethanol;5-Isoxazoleethanol, 3-bromo-;2-(3-bromo-1,2-oxazol-5-yl)ethanol
• CAS NO: 105175-00-6
• Molecular Formula: C5H6BrNO2
• Molecular Weight: 192
• Mol File: 105175-00-6.mol

Chemical Properties

• Boiling Point: 308.608°C at 760 mmHg
• Flash Point: 140.441°C
• Appearance: /
• Density: 1.715g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.545
• PKA: 14.34±0.10(Predicted)
• CAS DataBase Reference: 3-Bromo-5-(2-hydroxyethyl)isoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-(2-hydroxyethyl)isoxazole(105175-00-6)
• EPA Substance Registry System: 3-Bromo-5-(2-hydroxyethyl)isoxazole(105175-00-6)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 105175-00-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-5-(2-hydroxyethyl)isoxazole is used as a key intermediate in the synthesis of N-(2-Benzoylphenyl)-L-tyrosine analogs, which are peroxisome proliferator-activated receptor gamma (PPARγ) agonists. PPARγ agonists play a crucial role in regulating cellular differentiation, development, and metabolism, and are particularly relevant in the treatment of type 2 diabetes and other metabolic disorders.
Additionally, due to its reactive functional groups and structural features, 3-Bromo-5-(2-hydroxyethyl)isoxazole can be further modified or used in the development of new drug candidates with potential applications in various therapeutic areas, such as inflammation, cardiovascular diseases, and oncology. Its versatility as a synthetic building block makes it an important compound in medicinal chemistry and drug discovery processes.

InChI:InChI=1/C5H6BrNO2/c6-5-3-4(1-2-8)9-7-5/h3,8H,1-2H2

Upstream product

• 927-74-2 3-Butyn-1-ol 
• 74213-24-4 N-dibromomethylidenehydroxylamine 

Relevant articles and documents

COMPOUNDS AND USES THEREOF

The present disclosure features compounds useful for the treatment of BAF complex-related disorders.

(4-HYDROXYPYRROLIDIN-2-YL)-HYDROXAMATE COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to bifunctional compounds, which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands.

(4-HYDROXYPYRROLIDIN-2-YL)-HETEROCYCLIC COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to bifunctional compounds of formula (I), which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds which contain on one end a VHL ligand moiety, which binds to the VHL E3 ubiquitin ligase, and on the other end a moiety that binds a target protein such that degradation of the target protein/polypeptide is effectuated. Also disclosed are VHL ligands of formula (III).

HETERO-BIFUNCTIONAL DEGRADER COMPOUNDS AND THEIR USE AS MODULATORS OF TARGETED UBIQUINATION (VHL)

The present disclosure relates to bifunctional compounds, which can be used as modulators of targeted ubiquitination. In particular, the present disclosure is directed to compounds that contain on one end a VHL ligand moiety, which binds to the VHL ubiqui

COMPOUNDS AND METHODS FOR THE TARGETED DEGRADATION OF BROMODOMAIN-CONTAINING PROTEINS

The present invention relates to bifunctional compounds, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the present invention is directed to compounds, which contain on one end a VHL ligand which binds to the ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. The present invention exhibits a broad range of pharmacological activities associated with compounds according to the present invention, consistent with the degradation/inhibition of targeted polypeptides.

Process for the preparation of 3,5-disubstituted isoxazoles

A novel process for the preparation of 3-bromo- and 3-chloro-5-substituted isoxazoles is provided. Dibromo- or dichloro-formaldoxime is reacted with an excess of an 1-alkyne derivative of the formula where R is hydrogen, phenyl or 1-6 C alkyl optionally substituted by halogen, OH, OR', CHO, COR', COOR', CONH2, CONR'R" or NHCOR' where, in turn, R' and R", which may be the same or different, are a 1-6 C alkyl or haloalkyl, in the presence of (i) at least an equimolecular amount, with respect to the dibromo- or dichloro-formaldoxime, of an alkaline base selected from the class consisting of sodium and potassium carbonate and bicarbonate and (ii) an inert solvent in which the 1-alkyne is soluble at room temperature.