39512-50-0

Basic information

• Product Name: 1-(2-Chlorophenyl)piperazine
• Synonyms: TIMTEC-BB SBB003581;1-(2-CHLORPHENYL)-PIPERAZINE;1-(2-CHLOROPHENYL)PIPERAZINE;AKOS BBS-00006438;LABOTEST-BB LT00077031;1-(2-Chlorophenyl)piperazine 98%;1-(2-CHLOROPHENYL)PIPERAZINE 98+%;1-(o-Chlorophenyl)piperazine
• CAS NO: 39512-50-0
• Molecular Formula: C₁₀H₁₃ClN₂
• Molecular Weight: 196.68
• EINECS: 254-480-3
• Product Categories: Piperidines, Piperidones, Piperazines;Piperazines
• Mol File: 39512-50-0.mol

Chemical Properties

• Melting Point: 152-154 °C
• Boiling Point: 102-104°C 0,2mm
• Flash Point: 145.7 °C
• Appearance: white to yellow crystalline mass or oil
• Density: 1.18
• Vapor Pressure: 0.000387mmHg at 25°C
• Refractive Index: 1.5810-1.5850
• PKA: 8.81±0.10(Predicted)
• CAS DataBase Reference: 1-(2-Chlorophenyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chlorophenyl)piperazine(39512-50-0)
• EPA Substance Registry System: 1-(2-Chlorophenyl)piperazine(39512-50-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 39512-50-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Chlorophenyl)piperazine is used as a therapeutic agent for the treatment of cardiovascular and cerebrovascular diseases. Its application is based on its ability to target and alleviate the symptoms associated with these conditions, thereby improving the overall health and well-being of patients suffering from such diseases.

InChI:InChI=1/C10H13ClN2/c11-9-3-1-2-4-10(9)13-7-5-12-6-8-13/h1-4,12H,5-8H2/p+1

Upstream product

• 110-85-0 piperazine 
• 694-80-4 2-bromo-1-chlorobenzene 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 95-51-2 o-chloroaniline 
• 95-50-1 1,2-dichloro-benzene 
• 348-51-6 1-chloro-2-fluorobenzene 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 41202-32-8 1-(2-chlorophenyl)piperazine hydrochloride 
• 111-42-2 2,2'-iminobis[ethanol] 

Downstream Products

• 40004-62-4 1-(2-hydroxyethyl)-4-(2-chlorophenyl)piperazine 
• 110148-33-9 1-[4-(2-chloro-phenyl)-piperazino]-3-p-tolyloxy-propan-2-ol 
• 116402-30-3 1-(benzo[1,3]dioxole-5-thiocarbonyl)-4-(2-chloro-phenyl)-piperazine 
• 110145-77-2 1-(2-chloro-phenoxy)-3-[4-(2-chloro-phenyl)-piperazino]-propan-2-ol 
• 7556-52-7 1-(2-chlorophenyl)-4-methylpiperazine 
• 101260-30-4 5-[4-(2-chloro-phenyl)-piperazino]-pentylamine 
• 109339-57-3 6-[4-(2-chloro-phenyl)-piperazino]-hexan-1-ol 
• 150557-82-7 1-(4-(2-chlorophenyl)piperazin-1-yl)ethan-1-one 
• 116402-32-5 1-(2-chloro-phenyl)-4-phenylthioacetyl-piperazine 
• 116402-33-6 1-(2-chloro-phenyl)-4-thiobenzoyl-piperazine 
• 20386-34-9 (4-(2-chlorophenyl)piperazin-1-yl)(phenyl)methanone 
• 91494-87-0 [4-(2-chloro-phenyl)-piperazin-1-yl]-acetonitrile 
• 52536-36-4 1-(2-chlorophenyl)-4-(3-chloropropyl)-piperazine 
• 115098-05-0 1,3-bis-[4-(2-chloro-phenyl)-piperazino]-propane 

Relevant articles and documents

Discovery of Selective Toxoplasma gondii Dihydrofolate Reductase Inhibitors for the Treatment of Toxoplasmosis

A safer treatment for toxoplasmosis would be achieved by improving the selectivity and potency of dihydrofolate reductase (DHFR) inhibitors, such as pyrimethamine (1), for Toxoplasma gondii DHFR (TgDHFR) relative to human DHFR (hDHFR). We previously reported on the identification of meta-biphenyl analog 2, designed by in silico modeling of key differences in the binding pocket between TgDHFR and hDHFR. Compound 2 improves TgDHFR selectivity 6.6-fold and potency 16-fold relative to 1. Here, we report on the optimization and structure-activity relationships of this arylpiperazine series leading to the discovery of 5-(4-(3-(2-methoxypyrimidin-5-yl)phenyl)piperazin-1-yl)pyrimidine-2,4-diamine 3. Compound 3 has a TgDHFR IC50 of 1.57 ± 0.11 nM and a hDHFR to TgDHFR selectivity ratio of 196, making it 89-fold more potent and 16-fold more selective than 1. Compound 3 was highly effective in control of acute infection by highly virulent strains of T. gondii in the murine model, and it possesses the best combination of selectivity, potency, and prerequisite drug-like properties to advance into IND-enabling, preclinical development.

MONOACYLGLYCEROL LIPASE INHIBITORS

Provided are compounds of formula (I), or a pharmaceutically acceptable salt or solvate thereof: Also provided are compositions comprising compounds of formula (I). The compounds and compositions are also provided for use as medicaments, for example as medicaments useful in the treatment of a condition modulated by monoacylglycerol lipase (MAGL). Also provided are the use of compounds and compositions for the inhibition of monoacylglycerol lipase (MAGL).

Preparation method of diaryl sulfide amine compound

The invention relates to a preparation method for a diaryl thioether amine compound. Specifically, the invention relates to a preparation method for 1-[2-(2,4-dimethylphenylsulfalkyl)phenyl]piperazine derivative as shown in a formula I which is described in the specification. The preparation method comprises the following steps: subjecting a compound as shown in a formula V and a compound as shown in a formula IV to cyclization, condensation or introduction of an amino protective group; carrying out further condensation; etc. Thus, the target compound is obtained. Compared with other methods, the preparation method provided by the invention has the advantages of good process reproducibility and easy operation and the characteristics of high yield, low cost and high product purity, is more suitable for industrial production and has higher economic benefits.

Pd-Catalyzed Synthesis of Piperazine Scaffolds under Aerobic and Solvent-Free Conditions

A facile Pd-catalyzed methodology providing an efficient synthetic route to biologically relevant arylpiperazines under aerobic conditions is reported. Electron donating and sterically hindered aryl chlorides were aminated to afford yields up to 97%, with examples using piperazine as solvent, illustrating an ecofriendly, cost-effective synthesis of these privileged structures.

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.

Microwave-assisted amination from fluorobenzenes without catalyst and strong base

A facile and versatile amination of fluorobenzenes has been developed in good to excellent yields under microwave irradiation in N-methylpyrrolidinone (NMP) without strong base and catalyst. The presence of additional halogen atom(s) enhanced the leaving ability of fluorine and meta fluorine gave higher activation than the ortho. It is remarkable that 1,2,3-trifluorobenzene, 1,2,4-trifluorobenzene and 1,2,4,5-tetrafluorobenzene can produce the regioselective mono-substituted products.

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.

Discovery and Initial SAR of Arylsulfonylpiperazine Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1)

High-throughput screening of a small-molecule compound library resulted in the identification of a series of arylsulfonylpiperazines that are potent and selective inhibitors of human 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1). Optimization of the initial lead resulted in the discovery of compound (R)-45 (11β-HSD1 IC50 = 3 nM).

Arylpiperazines displaying preferential potency against chloroquine-resistant strains of the malaria parasite Plasmodium falciparum

Arylpiperazines in which the terminal secondary amino group is unsubstituted were found to display a mefloquine-type antimalarial behavior in being significantly more potent against the chloroquine-resistant (W2 and FCR3) strains of Plasmodium falciparum than against the chloroquine-sensitive (D10 and NF54) strains. Substitution of the aforementioned amino group led to a dramatic drop in activity across all strains as well as abolition of the preferential potency against resistant strains that was observed for the unsubstituted counterparts. The data suggest that unsubstituted arylpiperazines are not well-recognized by the chloroquine resistance mechanism and may imply that they act mechanistically differently from chloroquine. On the other hand, 4-aminoquinoline-based heteroarylpiperazines in which the terminal secondary amino group is also unsubstituted, were found to be equally active against the chloroquine-resistant and chloroquine-sensitive strains, suggesting that chloroquine cross-resistance is not observed with these two 4-aminoquinolines. In contrast, two 4-aminoquinoline-based heteroarylpiperazines are positively recognized by the chloroquine resistance mechanism. These studies provide structural features that determine the antimalarial activity of arylpiperazines for further development, particularly against chloroquine-resistant strains.

Fused heterocyclic compounds and pharmaceutical applications thereof

The present invention relates to a fused heterocyclic compound of the formula (I) wherein each symbol is as defined in the specification, an optical isomer thereof, a pharmaceutically acceptable salt thereof, a pharmaceutical composition containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive, and a medicament containing a compound of the formula (I), an optical isomer thereof or a pharmaceutically acceptable salt thereof. The compound of the present invention is a useful antipsychotic agent effective not only for positive symptoms centering on hallucination and delusion characteristic of the acute stage of schizophrenia, but also negative symptoms of apathy, abulia and autism. The inventive compound is expected to make a highly safe antipsychotic agent associated with less side effects, such as extrapyramidal symptoms and endocrine disturbance, which are observed when a conventional antipsychotic agent having a D2receptor blocking action is administered. Therefore, the inventive compound can be used as a therapeutic agent for the diseases such as schizophrenia.