55513-17-2

Basic information

• Product Name: 1-(3,4-DICHLOROBENZYL)PIPERAZINE
• Synonyms: 1-(3,4-DICHLOROBENZYL)PIPERAZINE;AKOS B014420;ART-CHEM-BB B014420;BUTTPARK 36\08-58;1-(3,4-DICHLORO-BENZYL)-PIERPAZINE;1-(3,4-dichlorobenzyl)piperazine(SALTDATA: FREE);4-Dichlorobenzyl)piperazine;1-(3,4-Dichlorobenzyl)piperazine 2HCl
• CAS NO: 55513-17-2
• Molecular Formula: C₁₁H₁₄Cl₂N₂
• Molecular Weight: 245.15
• Product Categories: API intermediates;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Piperazines;PiperazinesHeterocyclic Building Blocks;Building Blocks;C10 to C11;C11;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 55513-17-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 212-213 °C
• Boiling Point: 124-128 °C0.02 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to yellow/Liquid
• Density: 1.225 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000128mmHg at 25°C
• Refractive Index: n20/D 1.5710(lit.)
• PKA: 9.04±0.10(Predicted)
• CAS DataBase Reference: 1-(3,4-DICHLOROBENZYL)PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-DICHLOROBENZYL)PIPERAZINE(55513-17-2)
• EPA Substance Registry System: 1-(3,4-DICHLOROBENZYL)PIPERAZINE(55513-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 55513-17-2(Hazardous Substances Data)

Usage

General Description

1-(3,4-Dichlorobenzyl)piperazine is a chemical compound that is a derivative of piperazine and contains a benzyl group with two chlorine atoms. It is commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. 1-(3,4-Dichlorobenzyl)piperazine has potential applications in the field of medicinal chemistry, particularly in the development of new drugs for the treatment of neurological disorders and mood-related conditions. Its unique structure and properties make it a valuable building block for the creation of novel chemical compounds with diverse biological activities. Additionally, 1-(3,4-Dichlorobenzyl)piperazine has been studied for its potential toxicity and environmental impact, highlighting the importance of proper handling and disposal of this chemical.

InChI:InChI=1/C11H14Cl2N2/c12-10-2-1-9(7-11(10)13)8-15-5-3-14-4-6-15/h1-2,7,14H,3-6,8H2

Upstream product

• 110-85-0 piperazine 
• 6287-38-3 3,4-dichlorobenzaldehyde 
• 1805-32-9 3,4-dichlorobenzyl alcohol 
• 120-43-4 4-ethoxycarbonylpiperazine 
• 102-47-6 3,4-Dichlorophenylmethyl chloride 
• 18880-04-1 3,4-dichlorobenzyl bromide 

Downstream Products

• 100389-31-9 4-(3,4-dichloro-benzyl)-piperazine-1-carboxylic acid amide 
• 389124-67-8 2(R)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-N-(tert-butoxycarbonyl)pyrrolidine 
• 220772-27-0 1-(3,4-dichlorobenzyl)-4-(2-nitrocyclohexyl)piperazine 
• 220772-20-3 1-(S)-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-N-(tert-butoxycarbonyl)-2-methylpropylamine 
• 850923-47-6 1-[4-(3,4-dichlorobenzyl)piperazin-1-ylcarbonyl]-N-(tert-butoxycarbonyl)-2-methylpropylamine 
• 1218949-60-0 2-[4-(3,4-dichlorobenzyl)piperazin-1-yl]-1-[3,4-dihydro-6,7-dimethoxyisoquinolin-2(1H)-yl]-ethanone 
• 1246384-08-6 2-((4-(3,4-dichlorobenzyl)piperazin-1-yl)methyl)-3-hydroxy-6-(chloromethyl)-4H-pyran-4-one 
• 1038547-98-6 (E)-4-(3,4-dichlorophenylmethyl)-1-[3-(3,5-dimethoxy-4-(4-ethoxyphenylmethoxy)phenyl)-1-oxo-2-propenyl]-piperazine 

Relevant articles and documents

New potent antifungal triazole alcohols containing N-benzylpiperazine carbodithioate moiety: Synthesis, in vitro evaluation and in silico study

A number of 1H-1,2,4-triazole alcohols containing N-(halobenzyl)piperazine carbodithioate moiety have been designed and synthesized as potent antifungal agents. In vitro bioassays against different Candida species including C. albicans, C. glabrata, C. parapsilosis, C. krusei, and C. tropicalis revealed that the N-(4-chlorobenzyl) derivative (6b) with MIC values of 0.063–0.5 μg/mL had the best profile of activity, being 4–32 times more potent than fluconazole. Docking simulation studies confirmed the better fitting of compound 6b in the active site of lanosterol 14α-demethylase (CYP51) enzyme, the main target of azole antifungals. Particularly, the potential of compound 6b against fluconazole-resistant isolates along with its minimal toxicity against human erythrocytes and HepG2 cells make this prototype compound as a good lead for discovery of potent and safe antifungal agents.

Synthesis, biological evaluation, and structure-activity relationship study of novel cytotoxic aza-caffeic acid derivatives

Three series of aza-caffeic acid derivatives with different linkers were designed and synthesized. Each of the synthesized derivatives was then used in cytotoxicity screening on either 8 or 12 human cancer cell lines. The structure-activity relationships on three structural regions A, B, and C are analyzed in detail, indicating that a nine bond linker B, containing a piperazine unit, is the most favorable linker leading to the generation of molecules with potent cytotoxicities. Compound (E)-1-(4-(3,4-dichlorobenzyl) piperazin-1-yl)-3-(4-(4-ethoxybenzyloxy)-3,5-dimethoxyphenyl)prop-2-en-1-one (80) exhibited the most significant and selective cytotoxicity to KB, BEL7404, K562, and Eca109 cell lines, with IC50 values of 0.2, 2.0, 1.7, and 1.1 μM, respectively, stronger than that seen for caffeic acid phenethyl ester (CAPE) and cisplatin (CDDP). Flow cytometric and western blot analysis indicate that compound 80 plays a role in mitochondria-dependent apoptosis activity by suppressing K562 cell proliferation in a concentration- and time-dependent manner.

Use of polymer supported reagents for clean multi-step organic synthesis: Preparation of amines and amine derivatives from alcohols for use in compound library generation

The automated sequential application of polymer supported perruthenate (PSP) and polymer supported cyanoborohydride (PSCBH) in an oxidation-reductive amination procedure allowed the efficient transformation of simple alcohols into more complex amines which can be further derivatised by the use of polymer bound amino sulfonylpyridinium chlorides.