135108-48-4

Basic information

• Product Name: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• Synonyms: BUTTPARK 51\09-69;AKOS B029475;5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• CAS NO: 135108-48-4
• Molecular Formula: C₁₀H₇FN₄
• Molecular Weight: 202.19
• Mol File: 135108-48-4.mol
• Article Data: 12

Chemical Properties

• Melting Point: 145.9-146.8 °C(Solv: ethanol (64-17-5))
• Boiling Point: 402.429 °C at 760 mmHg
• Flash Point: 197.182 °C
• Appearance: /
• Density: 1.36
• Storage Temp.: 2-8°C
• PKA: -1.53±0.10(Predicted)
• CAS DataBase Reference: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(135108-48-4)
• EPA Substance Registry System: 5-AMINO-1-(2-FLUOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE(135108-48-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 135108-48-4(Hazardous Substances Data)

Usage

General Description

5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile is a chemical compound that belongs to the pyrazole family. It has the molecular formula C10H7FN4 and a molecular weight of 200.19 g/mol. 5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile is a white to yellow powder that is sparingly soluble in water but soluble in organic solvents such as DMSO and methanol. It is primarily used as an intermediate in the synthesis of pharmaceutical compounds and agrochemicals. Additionally, it has been studied for its potential biological activities, including its anti-inflammatory and anti-cancer properties. 5-Amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile is a versatile chemical with potential applications in the fields of medicine and agriculture.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 2368-80-1 2-fluorophenylhydrazine 
• 109-77-3 malononitrile 
• 2924-15-4 (2-fluorophenyl)hydrazine hydrochloride 
• 123-06-8 Ethoxymethylenemalononitrile 
• 348-54-9 2-Fluoroaniline 

Downstream Products

• 135108-57-5 4-Amino-1-(2-fluoro-phenyl)-5-methyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-6-one 
• 630107-81-2 5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carboxamide 
• 1242015-26-4 1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 1269291-92-0 5-chloro-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile 
• 1293979-10-8 7-(2-fluorophenyl)-3H-pyrazolo[3,4-d][1,2,3]triazin-4(7H)-one 
• 1431459-38-9 5-[1-(2-fluorophenyl)-1H-pyrazole-4-yl]-1H-tetrazole 
• 630107-83-4 4-chloro-1-(2-fluorophenyl)-1H-pyrazolo[3,4-d]pyrimidine 

Relevant articles and documents

Computer-aided molecular design of pyrazolotriazines targeting glycogen synthase kinase 3

Numerous studies have highlighted the implications of the glycogen synthase kinase 3 (GSK-3) in several processes associated with Alzheimer’s disease (AD). Therefore, GSK-3 has become a crucial therapeutic target for the treatment of this neurodegenerative disorder. Hereby, we report the design and multistep synthesis of ethyl 4-oxo-pyrazolo[4,3-d][1–3]triazine-7-carboxylates and their biological evaluation as GSK-3 inhibitors. Molecular modelling studies allow us to develop this new scaffold optimising the chemical structure. Potential binding mode determination in the enzyme and the analysis of the key features in the catalytic site are also described. Furthermore, the ability of pyrazolotriazinones to cross the blood–brain barrier (BBB) was evaluated by passive diffusion and those who showed great GSK-3 inhibition and permeation to the central nervous system (CNS) showed neuroprotective properties against tau hyperphosphorylation in a cell-based model. These new brain permeable pyrazolotriazinones may be used for key in vivo studies and may be considered as new leads for further optimisation for the treatment of AD.

Identification of novel GLUT inhibitors

The compound class of 1H-pyrazolo[3,4-d]pyrimidines was identified using HTS as very potent inhibitors of facilitated glucose transporter 1 (GLUT1). Extensive structure–activity relationship studies (SAR) of each ring system of the molecular framework was established revealing essential structural motives (i.e., ortho-methoxy substituted benzene, piperazine and pyrimidine). The selectivity against GLUT2 was excellent and initial in vitro and in vivo pharmacokinetic (PK) studies are encouraging.

An efficient synthesis of new 5-(1-Aryl-1H-pyrazole-4-yl)-1H-tetrazoles from 1-Aryl-1H-pyrazole-4-carbonitriles via [3 + 2] cycloaddition reaction

A series of new 5-(1-aryl-1H-pyrazole-4-yl)-1H-tetrazoles 4a-l were synthesized via [3 + 2] cycloaddition reaction from 1-aryl-1H-pyrazole-4- carbonitriles 3a-l, sodium azide and ammonium chloride, using dimethylformamide (DMF) as solvent, in good yields: 64-85%. The structures of these newly synthesized compounds were determined from the IR, 1H- and 13C-NMR spectroscopic data and elemental analyses.