115761-79-0

Basic information

• Product Name: 1-(2,4-Difluorophenyl)piperazine
• Synonyms: difluorophenylpiperazine;RARECHEM AH CK 0086;1-(2,4-DIFLUOROPHENYL)PIPERAZINE;1-(2,4-Difluorophenyl)piperazine 97%;1-(2,4-Difluorophenyl)piperazine97%;1-(2,4-DIFLUOROPHENYL)-PIPERAZINE >98%;-(2,4-Difluorophenyl)piperazine;Piperazine, 1-(2,4-difluorophenyl)-
• CAS NO: 115761-79-0
• Molecular Formula: C₁₀H₁₂F₂N₂
• Molecular Weight: 198.21
• Product Categories: Piperaizine;piperazines
• Mol File: 115761-79-0.mol

Chemical Properties

• Melting Point: 74-76
• Boiling Point: 100 °C (0.37505 mmHg)
• Flash Point: 108-111°C/0.2mm
• Appearance: white crystals or crystalline powder
• Density: 1.192 g/cm³
• Vapor Pressure: 0.00175mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.75±0.10(Predicted)
• Sensitive: Air Sensitive
• BRN: 8620369
• CAS DataBase Reference: 1-(2,4-Difluorophenyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-Difluorophenyl)piperazine(115761-79-0)
• EPA Substance Registry System: 1-(2,4-Difluorophenyl)piperazine(115761-79-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: UN2928
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 115761-79-0(Hazardous Substances Data)

Usage

Chemical Properties

white crystals or crystalline powder

InChI:InChI=1/C10H12F2N2/c11-8-1-2-10(9(12)7-8)14-5-3-13-4-6-14/h1-2,7,13H,3-6H2/p+1

Upstream product

• 367-25-9 2,4-difluorophenylamine 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 2265-93-2 2,4-difluoro-1-iodobenzene 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 110-85-0 piperazine 
• 348-57-2 2,4-difluorobromobenzene 

Downstream Products

• 760988-94-1 1-(2,4-difluorophenyl)-4-prop-2-ynyl-piperazine 
• 871724-27-5 C₂₄H₂₇F₂N₃O₆S 
• 1197347-60-6 2-[4-(2,4-difluoro-phenyl)-piperazin-1-yl]-N-(3,4-dimethoxy-phenyl)-acetamide 
• 1055347-40-4 C₁₂H₁₃ClF₂N₂O 
• 1369932-21-7 (2,4-diaminoquinazolin-6-yl)methyl 4-(2,4-difluorophenyl)piperazine-1-carbodithioate 
• 1135433-96-3 2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethan-1-amine 
• 1608156-91-7 2-{2-[4-(2,4-difluorophenyl)piperazin-1-yl]ethyl}-2,3-dihydro-1H-isoindole-1,3-dione 

Relevant articles and documents

TRICYCLIC DEGRADERS OF IKAROS AND AIOLOS

Tricyclic cereblon binders for the degradation of Ikaros or Aiolos by the ubiquitin proteasome pathway for therapeutic applications are described.

ADENOSINE RECEPTOR BINDING COMPOUNDS

The present invention relates to pharmaceutical compounds and compositions of Formula (I) and methods of treatment using the compounds and compositions, especially for the treatment and/or prevention of a proliferation disorder, such as cancer. Compounds of Formula (I) as further described herein are shown modulators of the adenosine A2A receptor and exhibit antiproliferative activity. Accordingly, these compounds are useful to treat proliferative disorders such as cancer, and other adenosine receptor-related conditions including an inflammatory disease, renal disease, diabetes, vascular disease, lung disease, or an autoimmune disease.

Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives

We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.

Chrysin-piperazine conjugates as antioxidant and anticancer agents

Synthesis of 7-(4-bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one intermediate treating chrysin with 1,4-dibromobutane facilitated combination of chrysin with a wide range of piperazine moieties which were equipped via reacting the corresponding amines with bis(2-chloroethyl)amine hydrochloride in diethylene glycol monomethyl ether solvent. Free radical scavenging potential of prepared products was analyzed in vitro adopting DPPH and ABTS bioassay in addition to the evaluation of in vitro anticancer efficacies against cervical cancer cell lines (HeLa and CaSki) and an ovarian cancer cell line SK-OV-3 using SRB assay. Bearable toxicity of 7a-w was examined employing Madin-Darby canine kidney (MDCK) cell line. In addition, cytotoxic nature of the presented compounds was inspected utilizing Human bone marrow derived mesenchymal stem cells (hBM-MSCs). Overall, 7a-w indicated remarkable antioxidant power in scavenging DPPH+ and ABTS++, particularly analogs 7f, 7j, 7k, 7l, 7n, 7q, 7v, 7w have shown promising free radical scavenging activity. Analogs 7j and 7o are identified to be highly active candidates against HeLa and CaSki cell lines, whereas 7h and 7l along with 7j proved to be very sensitive towards ovarian cancer cell line SKOV-3. None of the newly prepared scaffolds showed cytotoxic nature toward hBM-MSCs cells. From the structure-activity point of view, nature and position of the electron withdrawing and electron donating functional groups on the piperazine core may contribute to the anticipated antioxidant and anticancer action. Different spectroscopic techniques (FT-IR, 1H NMR, 13C NMR, Mass) and elemental analysis (CHN) were utilized to confirm the desired structure of final compounds.

Binding kinetics of ZM241385 derivatives at the human adenosine A 2A receptor

Classical drug design and development rely mostly on affinity- or potency-driven structure-activity relationships (SAR). Thus far, a given compound's binding kinetics have been largely ignored, the importance of which is now being increasingly recognized. In the present study, we performed an extensive structure-kinetics relationship (SKR) study in addition to a traditional SAR analysis at the adenosine A2A receptor (A 2AR). The ensemble of 24 A2AR compounds, all triazolotriazine derivatives resembling the prototypic antagonist ZM241385 (4-(2-((7-amino-2-(furan-2-yl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-yl)amino) ethyl)phenol), displayed only minor differences in affinity, although they varied substantially in their dissociation rates from the receptor. We believe that such a combination of SKR and SAR analyses, as we have done with the A 2AR, will have general importance for the superfamily of G protein-coupled receptors, as it can serve as a new strategy to tailor the interaction between ligand and receptor. Above and beyond: Insight into the binding kinetics of ZM241385 derivatives at the human adenosine A2A receptor has provided additional information beyond a traditional structure-activity relationship (SAR) analysis. The strategy, combining a structure-kinetics relationship investigation and SAR, can serve as an important tool for more directed medicinal chemistry efforts in the future.

4-Aryl piperazine and piperidine amides as novel mGluR5 positive allosteric modulators

Positive allosteric modulation of metabotropic glutamate receptor 5 (mGluR5) is regarded as a potential novel treatment for schizophrenic patients. Herein we report the synthesis and SAR of 4-aryl piperazine and piperidine amides as potent mGluR5 positive allosteric modulators (PAMs). Several analogs have excellent activity and desired drug-like properties. Compound 2b was further characterized as a PAM using several in vitro experiments, and produced robust activity in several preclinical animal models.

Potent, selective, and orally active adenosine A2A receptor antagonists: Arylpiperazine derivatives of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidines

Antagonism of the adenosine A2A receptor offers great promise in the treatment of Parkinson's disease. Employing the known pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine A2A antagonist SCH 58261 as a starting point, we identified the potent and selective (vs. A1) antagonist 11 h, orally active in the rat haloperidol-induced catalepsy model. We further optimized this lead to the methoxyethoxyethyl ether 12a (SCH 420814), which shows broad selectivity, good pharmacokinetic properties, and excellent in vivo activity.

TRIAZOLO[1,5-A]PYRIMIDINES and PYRAZOLO[1,5-A]PYRIMIDINES AND METHODS OF MAKING AND USING THE SAME

The invention is based on the discovery that compounds of formula (I) possess unexpectedly high affinity for the A2a adenosine receptor, and can be useful as antagonists thereof for preventing and/or treating numerous diseases, including Parkinson's disease. In one embodiment, the invention features a compound of formula (I) .

TRIAZOLO[1,5-C]PYRIMIDINES and PYRAZOLO[1,5-C]PYRIMIDINES AND METHODS OF MAKING AND USING THE SAME

The invention is based on the discovery that compounds of formula (I) possess unexpectedly high affinity for the A2a adenosine receptor, and can be useful as antagonists thereof for preventing and/or treating numerous diseases, including Parkinson's disease. In one embodiment, the invention features a compound of formula (I) .