16015-71-7

Basic information

• Product Name: 1-(3-Methoxyphenyl)piperazine
• Synonyms: RARECHEM AH CK 0127;TIMTEC-BB SBB003619;AKOS BBS-00003611;1-(3-METHOXYPHENYL)PIPERAZINE;N-(3-methoxyphenyl)piperazine;1-(3-m-Methoxyphenyl)piperazine;1-(3-Methyoxyphenyl)-piperazine;1-(3-Methoxyphenyl)piperazine 97%
• CAS NO: 16015-71-7
• Molecular Formula: C₁₁H₁₆N₂O
• Molecular Weight: 192.26
• EINECS: 240-154-8
• Product Categories: Piperaizine;Building Blocks;Heterocyclic Building Blocks;Piperazines
• Mol File: 16015-71-7.mol

Chemical Properties

• Melting Point: 201-204°C
• Boiling Point: 150 °C0.5 mm Hg(lit.)
• Flash Point: 195 °F
• Appearance: white to grey or pinkish crystalline powder
• Density: 1.114 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.8E-05mmHg at 25°C
• Refractive Index: n20/D 1.5815(lit.)
• PKA: 8.98±0.10(Predicted)
• CAS DataBase Reference: 1-(3-Methoxyphenyl)piperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-Methoxyphenyl)piperazine(16015-71-7)
• EPA Substance Registry System: 1-(3-Methoxyphenyl)piperazine(16015-71-7)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3267 8/PG 3
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 16015-71-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Methoxyphenyl)piperazine is used as an active pharmaceutical ingredient for the development of various medications, particularly those targeting the central nervous system. Its unique chemical structure allows it to interact with specific receptors, making it a promising candidate for the treatment of neurological disorders.
Used in Research and Development:
1-(3-Methoxyphenyl)piperazine is used as a research compound to study its interactions with various biological targets, such as receptors and enzymes. This helps in understanding its potential therapeutic applications and in the development of new drugs with improved efficacy and safety profiles.
Used in Forensic Applications:
1-(3-Methoxyphenyl)piperazine is used as a reference standard in forensic analysis, particularly in the identification and quantification of piperazine derivatives in biological samples. This aids in the investigation of drug-related crimes and the assessment of drug abuse patterns.
Used in Chemical Synthesis:
1-(3-Methoxyphenyl)piperazine serves as a key intermediate in the synthesis of various chemical compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile chemical properties make it a valuable building block for the development of new molecules with diverse applications.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 4463, 1996 DOI: 10.1016/0040-4039(96)00877-5

InChI:InChI=1/C11H16N2O/c1-14-11-4-2-3-10(9-11)13-7-5-12-6-8-13/h2-4,9,12H,5-8H2,1H3

Upstream product

• 110-85-0 piperazine 
• 2398-37-0 3-methoxyphenyl bromide 
• 766-85-8 3-methoxy-1-iodobenzene 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 16015-70-6 4-(3-methoxyphenyl) piperazine hydrochloride 
• 536-90-3 m-Anisidine 
• 507263-18-5 tert-butyl 4-(3-methoxylphenyl)piperazine-1-carboxylate 
• 334-22-5 N,N-bis(chloro-2-ethyl)amine 
• 6163-58-2 tris-(o-tolyl)phosphine 
• 821-48-7 bis-(2-chloroethyl)amine hydrochloride 

Downstream Products

• 90125-97-6 1-(3-Methoxy-phenyl)-4-(2-pyridin-2-yl-ethyl)-piperazine; compound with (E)-but-2-enedioic acid 
• 83767-49-1 1-(3-chloropropyl)-4-(3-methoxyphenyl)piperazine 
• 1025969-94-1 1-Chloro-3-[4-(3-methoxy-phenyl)-piperazin-1-yl]-propan-2-ol 
• 208537-55-7 4-[4-(3-Methoxy-phenyl)-piperazin-1-yl]-benzonitrile 
• 714911-38-3 1-benzo[b]thiophen-3-yl-3-[4-(3-methoxy-phenyl)-piperazin-1-yl]-propan-1-one 
• 475596-06-6 1-[(1,2-diphenyl-1H-imidazol-4-yl)carbonyl]-4-(3-methoxyphenyl)piperazine 
• 952592-60-8 C₂₃H₃₁N₃O₄ 
• 898533-22-7 4-[4-(3-methoxyphenyl)piperazin-1-yl]butanenitrile 
• 1192490-65-5 1-(3-bromopropyl)-4-(3-methoxyphenyl)piperazine 

Relevant articles and documents

Synthesis of arylpiperazines via palladium-catalyzed aromatic amination reaction with unprotected piperazines

A series of arylpiperazines were synthesized in moderate to good yields by palladium-catalyzed coupling reaction of aryl halides with unprotected piperazines. Very high regioselectivities were observed when using 2-methyl or 2,6-dimethylpiperazine.

Nickel-mediated amination chemistry. Part 2: Selective N-arylation or N,N'-diarylation of piperazine

The 2,2'-bipyridine liganded Ni catalyst has revealed a good selectivity in the mono arylation of piperazine starting from aryl chlorides allowing a selective and efficient synthesis of N-arylpiperazines using stoichiometric amounts of reagents. The preparation of N,N'-diaryl substituted piperazines is also described. (C) 2000 Elsevier Science Ltd.

Synthesis of arylpiperazines via nucleophilic aromatic substitution of (η6-fluoroarene)tricarbonylchromium complexes

A one-pot, high yield preparation procedure for the synthesis of arylpiperazines using a nucleophilic aromatic substitution of (η6-fluoroarene)tricarbonylchromium complexes (including those bearing electron donating groups) is described. A new, easy and fast decomplexation procedure, in DMSO as solvent, is also presented.

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).

Design, synthesis, and biological evaluation of structurally constrained hybrid analogues containing ropinirole moiety as a novel class of potent and selective dopamine D3 receptor ligands

Two series of hybrid analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined (using the method of radioligand binding assay). Compared to comparator agent BP897, compounds 2a and 2c were found to demonstrate a considerable binding affinity and selectivity for D3 receptor, and especially compound 2h was similarly potent and more selective D3R ligand than BP897, a positive reference. Thus, they may provide valuable information for the discovery and development of highly potent dopamine D3 receptor ligands with outstanding selectivity.

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.

Multifunctional D2/D3 agonist D-520 with high in vivo efficacy: Modulator of toxicity of alpha-synuclein aggregates

We have developed a series of dihydroxy compounds and related analogues based on our hybrid D2/D3 agonist molecular template to develop multifunctional drugs for symptomatic and neuroprotective treatment for Parkinson"s disease (PD). The lead compound (-)-24b (D-520) exhibited high agonist potency at D2/D3 receptors and produced efficacious activity in the animal models for PD. The data from thioflavin T (ThT) assay and from transmission electron microscopy (TEM) analysis demonstrate that D-520 is able to modulate aggregation of alpha-synuclein (αSN). Additionally, coincubation of D-520 with αSN is able to reduce toxicity of preformed aggregates of αSN compared to control αSN alone. Finally, in a neuroprotection study with dopaminergic MN9D cells, D-520 clearly demonstrated the effect of neuroprotection from toxicity of 6-hydroxydopamine. Thus, compound D-520 possesses properties characteristic of multifunctionality conducive to symptomatic and neuroprotective treatment of PD.

NOVEL CATALYSTS

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

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.

A general and convenient synthesis of N-aryl piperazines

A general and convenient synthesis of N-aryl piperazines from bis(2-chloroethyl)amine hydrochloride and a broad range of anilines in diethylene glycol monomethyl ether is described.