214614-81-0

Basic information

• Product Name: 2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL
• Synonyms: AKOS PAO-0968;AKOS B024012;2-(4-BROMO-PYRAZOL-1-YL)-ETHANOL;2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL;ART-CHEM-BB B024012;Albb-003673;2-(4-bromo-1H-pyrazol-1-yl)ethanol(SALTDATA: FREE);4-BroMo-1-(2-hydroxyethyl)pyrazole
• CAS NO: 214614-81-0
• Molecular Formula: C₅H₇BrN₂O
• Molecular Weight: 191.03
• Product Categories: Building Blocks;Pyrazole
• Mol File: 214614-81-0.mol

Chemical Properties

• Boiling Point: 299.235 °C at 760 mmHg
• Flash Point: 134.773 °C
• Appearance: /
• Density: 1.743 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.30±0.10(Predicted)
• CAS DataBase Reference: 2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL(214614-81-0)
• EPA Substance Registry System: 2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL(214614-81-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 214614-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL is used as a key intermediate in the synthesis of more complex pharmaceutical compounds. Its bromine atom allows for further functionalization and modification, making it a versatile building block for the development of new drugs with potential therapeutic applications.
Used in the Synthesis of T302675:
Specifically, 2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL is utilized in the synthesis of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-ethanol (T302675), a compound with potential applications in the treatment of various medical conditions. The synthesis of T302675 involves the use of 2-(4-BROMO-1H-PYRAZOL-1-YL)ETHANOL as a starting material, highlighting its importance in the development of novel pharmaceuticals.

InChI:InChI=1/C5H7BrN2O/c6-5-3-7-8(4-5)1-2-9/h3-4,9H,1-2H2

Upstream product

• 2075-45-8 4-bromo-1H-pyrazole 
• 540-51-2 2-bromoethanol 
• 96-49-1 [1,3]-dioxolan-2-one 
• 1072-53-3 ethyleneglycol sulfate 

Downstream Products

• 1040377-08-9 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]ethanol 

Relevant articles and documents

Design, (Radio)Synthesis, and in Vitro and in Vivo Evaluation of Highly Selective and Potent Matrix Metalloproteinase 12 (MMP-12) Inhibitors as Radiotracers for Positron Emission Tomography

Dysregulated levels of activated matrix metalloproteinases (MMPs) are linked to different pathologies, such as cancer, atherosclerosis, neuroinflammation, and arthritis. Therefore, imaging of MMPs with positron-emission tomography (PET) represents a powerful tool for the diagnosis of MMP-associated diseases. Moreover, to distinguish between the distinct functions and roles of individual MMPs in particular pathophysiological processes, their specific imaging must be realized with radiolabeled tracers, such as fluorine-18-labeled MMP inhibitors (MMPIs). Therefore, fluorinated dibenzofuransulfonamide-based MMPIs showing excellent inhibition of MMP-12 and selectivity for MMP-12 over other MMPs were prepared. MMP-12 is a key enzyme in diseases such as chronic obstructive pulmonary disease (COPD) and atherosclerosis. Because of their promising in vitro properties, three candidates (4, 9, and 19) were selected from this library, and radiofluorinated analogues ([18F]4, [18F]9, and [18F]19) were successfully synthesized. Initial in vitro serum stability and in vivo biodistribution studies of the radiolabeled MMPIs with PET demonstrated their potential benefit for preferable MMP-12 imaging.

Synthesis and biological evaluation of 2-amino-5-aryl-3-benzylthiopyridine scaffold based potent c-Met inhibitors

A series of 2-amino-N-benzylpyridine-3-carboxnamides, 2-amino-N- benzylpyridine-3-sulfonamides and 2-amino-3-benzylthiopyridines against c-Met were designed by means of bioisosteric replacement and docking analysis. Optimization of the 2-amino-3-benzylthiopyridine scaffold led to the identification of compound (R)-10b displaying c-Met inhibition with an IC 50 up to 7.7 nM. In the cytotoxic evaluation, compound (R)-10b effectively inhibited the proliferation of c-Met addictive human cancer cell lines (IC50 from 0.19 to 0.71 μM) and c-Met activation-mediated cell metastasis. At a dose of 100 mg/Kg, (R)-10b evidently inhibited tumor growth (45%) in NIH-3T3/TPR-Met xenograft model. Of note, (R)-10b could overcome c-Met-activation mediated gefitinib-resistance, which indicated its potential use for drug combination. Taken together, 2-amino-3-benzylthiopyridine scaffold was first disclosed and exhibited promising pharmacological profiles against c-Met, which left room for further exploration.

KINASE INHIBITOR COMPOUNDS

Pyridine and pyridazine derivatives have unexpected drug properties as inhibitors of protein kinases and are useful in treating disorders related to abnormal protein kinase activities such as cancer.

PYRAZOLE-SUBSTITUTED AMINOHETEROARYL COMPOUNDS AS PROTEIN KINASE INHIBITORS

Compounds of formula (1) are provided, as well as methods for their synthesis and use. Preferred compounds are potent inhibitors of the c-Met protein kinase, and are useful in the treatment of abnormal cell growth disorders, such as cancers.