6640-24-0

Basic information

• Product Name: 3-Chlorophenyl piperazine
• Synonyms: RARECHEM AH CK 0071;N-(3-CHLOROPHENYL)PIPERAZINE;TIMTEC-BB SBB003579;MCPP;1-(3-CHLORPHENYL)-PIPERAZINE;1-(3-CHLOROPHENYL)PIPERAZINE;3-chlorophenyl piperazine;AKOS BBS-00003580
• CAS NO: 6640-24-0
• Molecular Formula: C₁₀H₁₃ClN₂
• Molecular Weight: 196.68
• EINECS: 229-654-7
• Product Categories: Piperazines;PHARMACEUTICAL INTERMEDIATES;Piperidines, Piperidones, Piperazines;Piperaizine;API intermediates;Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;FOR TRAZODONE'S PRODUCTION
• Mol File: 6640-24-0.mol

Chemical Properties

• Melting Point: 210-214°C
• Boiling Point: 105 °C
• Flash Point: 157.2 °C
• Appearance: clear colorless to light yellow oily liquid
• Density: 1.193
• Vapor Pressure: 0.000112mmHg at 25°C
• Refractive Index: 1,598-1,600
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Methanol (Sparingly)
• PKA: 8.85±0.10(Predicted)
• CAS DataBase Reference: 3-Chlorophenyl piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chlorophenyl piperazine(6640-24-0)
• EPA Substance Registry System: 3-Chlorophenyl piperazine(6640-24-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-36
• HazardClass: IRRITANT
• Hazardous Substances Data: 6640-24-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorophenyl piperazine is used as a metabolite in the development and understanding of antidepressant medications, particularly trazodone, nefazodone, and etoperidone. Its unique properties of being a 5-HT2C agonist and a 5-HT2A antagonist make it a valuable compound in the study and treatment of depression.
Used in Antidepressant Efficacy:
3-Chlorophenyl piperazine is used as a key contributor to the antidepressant efficacy of trazodone. Its interaction with the serotonin receptors, specifically the 5-HT2C and 5-HT2A, plays a significant role in the overall effectiveness of the antidepressant treatment.
Used in Research and Development:
3-Chlorophenyl piperazine serves as an important compound in the research and development of new antidepressant drugs. Its properties and interactions with serotonin receptors provide valuable insights into the mechanisms of action and potential improvements in the treatment of depression.

Hazard

A poison.

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

Upstream product

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• 334-22-5 N,N-bis(chloro-2-ethyl)amine 
• 625-99-0 3-iodochlorobenzene 
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• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 
• 108-37-2 1-bromo-3-chlorobenzene 
• 186790-11-4 tert-butyl 4-(3-chlorophenyl)piperazine-1-carboxylate 
• 591-18-4 1-Bromo-3-iodobenzene 

Downstream Products

• 110148-29-3 1-[4-(3-chloro-phenyl)-piperazino]-3-o-tolyloxy-propan-2-ol 
• 110148-38-4 1-[4-(3-chloro-phenyl)-piperazino]-3-(2-methoxy-phenoxy)-propan-2-ol 
• 51941-10-7 2-(4-m-chlorophenyl-piperazino)-ethanol 
• 110148-30-6 1-[4-(3-chloro-phenyl)-piperazino]-3-p-tolyloxy-propan-2-ol 
• 109808-64-2 1-[4-(3-chloro-phenyl)-piperazino]-3-phenylsulfanyl-propan-2-ol 
• 116402-31-4 1-(benzo[1,3]dioxole-5-thiocarbonyl)-4-(3-chloro-phenyl)-piperazine 
• 110146-48-0 1-(2-chloro-phenoxy)-3-[4-(3-chloro-phenyl)-piperazino]-propan-2-ol 
• 112990-77-9 1-[2-(N-ethyl-anilino)-ethyl]-4-(3-chloro-phenyl)-piperazine 
• 141511-13-9 1-acetyl-4-(3-chloro-phenyl)-piperazine 
• 20011-17-0 (4-(3-chlorophenyl)piperazin-1-yl)(phenyl)methanone 
• 116402-29-0 1-(3-chloro-phenyl)-4-(3,4-dimethoxy-thiobenzoyl)-piperazine 
• 39577-43-0 1-(3-chloropropyl)-4-(3-chlorophenyl)piperazine 
• 6323-09-7 1,3-bis-[4-(3-chloro-phenyl)-piperazino]-propane 
• 48167-19-7 3-[4-(3-chlorophenyl)-piperazin-1-yl]-propionitrile 

Relevant articles and documents

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).

Dual demeanour of norcantharidin derived dicarboxamides in acidic media: An insight

The hydrolytic stability of norcantharidine derived conformationally constrained diamides in acidic media is solely governed by the type of amide. Tertiary diamides underwent smooth acid catalyzed hydrolysis due to anchimeric assistance whereas other diamides were stable. This was corroborated from conformational proximity of the amide groups for anchimeric assistance based on single crystal X-ray structure analysis. Theoretical calculations on the diamide structures also predict the similar proximity of the diamides in those conformations. Thus norcantharidine based diamides could probably serve as promising systems for delayed release of certain types of drugs which possess secondary amine component as exemplified by the release of m-chlorophenylpiperazine at a pH range of 1–2.

DUAL NAV1.2/5HT2A INHIBITORS FOR TREATING CNS DISORDERS

Compounds of formula I: I are disclosed, as are pharmaceutical compositions containing such compounds. Methods of treating neurological or psychiatric disorders in a patient in need are also disclosed. Such disorders include depression, bipolar disorder, pain, schizophrenia, obsessive compulsive disorder, addiction, social disorder, attention deficit hyperactivity disorder, an anxiety disorder, autism, a cognitive impairment, or a neuropsychiatric symptom such as apathy, depression, anxiety, psychosis, aggression, agitation, impulse control disorders, and sleep disorders in neurological disorders such as Alzheimer's and Parkinson's diseases.

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.

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.

Efficient copper-catalyzed cross-coupling of 1-Boc-piperazine with aryl iodides and its application in the synthesis of trazodone

A convenient and practical strategy is developed for the cross-coupling of N-Boc protected piperazines with aryl iodides using CuBr/1,1′-bi-2- naphthol as the catalyst and K3PO4 as the base. The protocol affords N-arylated piperazine products in moderate to good yields under the optimized conditions. The application of this catalytic system to the synthesis of trazodone is also successfully demonstrated using commercially available substrates.

4-Substituted-2-phenylquinazolines as inhibitors of BCRP

We investigated several 2-phenylquinazolines with different substitutions at position 4 for their BCRP inhibition. Compounds with phenyl ring attached via an amine-containing linker at position 4 were found to be potent inhibitors of BCRP. In general compounds with meta substitution of phenyl ring at position 4 were found to have higher inhibitory effect, compound 12 being the most potent and selective towards BCRP.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

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.

SUBSTITUTED TRIAZOLOPYRIDINES

Disclosed herein are substituted triazolopyridine serotonin reuptake modulators and/or 5-HT receptor modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.