1703-23-7

Basic information

• Product Name: 2-chloro-1-[4-(2-chloroacetyl)piperazin-1-yl]ethanone
• Synonyms: 2-chloro-1-[4-(2-chloroacetyl)piperazin-1-yl]ethanone
• CAS NO: 1703-23-7
• Molecular Formula: C₈H₁₂Cl₂N₂O₂
• Molecular Weight: 239.1
• Mol File: 1703-23-7.mol

Chemical Properties

• Boiling Point: 428.3°Cat760mmHg
• Flash Point: 212.8°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 1.54E-07mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: 2-chloro-1-[4-(2-chloroacetyl)piperazin-1-yl]ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-1-[4-(2-chloroacetyl)piperazin-1-yl]ethanone(1703-23-7)
• EPA Substance Registry System: 2-chloro-1-[4-(2-chloroacetyl)piperazin-1-yl]ethanone(1703-23-7)

Safety Data

• Hazardous Substances Data: 1703-23-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12Cl2N2O2/c9-5-7(13)11-1-2-12(4-3-11)8(14)6-10/h1-6H2

Upstream product

• 110-85-0 piperazine 
• 79-04-9 chloroacetyl chloride 
• 6091-62-9 piperazine dihydrochloride hydrate 

Downstream Products

• 92897-32-0 2H,5H,-6,7-dihydrothiazolo<3,2-a>pyrimidin-3(2H)-one 
• 443735-96-4 C₂₈H₂₆N₂O₄ 
• 97848-35-6 N,N'-di(m-acetamidophenoxy)acetylpiperazine 
• 97848-34-5 N,N'-diacetylpiperazine 
• 133270-11-8 C₄₅H₅₇N₉O₆ 
• 97848-33-4 N,N'-di(o-acetamidophenoxy)acetylpiperazine 
• 134268-74-9 2-(2'-Hydroxy-biphenyl-2-yloxy)-1-{4-[2-(2'-hydroxy-biphenyl-2-yloxy)-acetyl]-piperazin-1-yl}-ethanone 
• 1009-85-4 1,4-bis-(2-chloro-ethyl)-piperazine 

Relevant articles and documents

A new quinoline-based chemosensor in ratiometric sensing of Hg2+ ions

A new quinoline-based chemosensor 1 has been designed and synthesised. Its metal ion-binding properties have been documented in organic and aqueous organic solvents. While chemosensor 1 recognises Hg2+ ions (Ka = 2.15 × 104 M-1) by exhibiting ratiometric change in emission in CHCl3/CH3OH (1:1, v/v), under similar condition both Zn2+ and Cd2+ ions are sensed by significant non-ratiometric increase in emission with measurable red shift. In DMSO/H2O (5:95, v/v), the sensor 1 exhibits a greater selectivity towards Hg2+ ions (Ka = 9.20 × 103 M -1) over the other metal ions examined.

Piperazine-based new sensor: Selective ratiometric sensing of Fe3+, logic gate construction and cell imaging

Newly designed and synthesised chemosensor 1 selectively recognises Fe3+ ions in CHCl3-MeOH (1:1, v/v) by showing ratiometric change in emission and green colouration of the solution under the exposure of UV light. The ensemble 1.Fe3+ selectively detects F- ions over other halides and the phenomenon is useful to construct combinatorial logic gate. Furthermore, the probe 1 can be used for in vitro detection of Fe3+ in human cervical cancer (HeLa) cells.

A benzimidazolium-based new flexible cleft built on the piperazine unit: A case of selective fluorometric sensing of ATP

A benzimidazole-based compound 1 built on the piperazine motif has been designed and synthesized. The chemosensor 1 is highly selective and sensitive towards ATP over ADP and AMP in CH3CN/H2O (1:1, v/v, using 10 mM HEPES buffer, pH 6.4) as evidenced by the significant change in emission. Furthermore, sensor 1 is cell permeable and can detect the presence of ATP in Human cervical cancer cells (HeLa). This journal is

Piperazine-based simple structure for selective sensing of Hg2+ and glutathione and construction of a logic circuit mimicking an INHIBIT gate

A simple chemosensor (1) has been designed and synthesized. The chemosensor selectively recognizes Hg2+ ions in THF-H2O (3:1, v/v) by showing a significant increase in emission and a bluish color of the solution under exposure to UV light. Change of the fluorophore unit in 1 leads to 2, which also shows selective sensing of Hg2+ under similar conditions. Furthermore, while the ensemble of 1 with Hg2+ selectively senses reduced glutathione (GSH) over cysteine and homocysteine, the ensemble of 2 with Hg2+ has been observed to be inefficient to distinguish glutathione from other biothiols. Thus probe 1 and inputs Hg2+ and GSH can be used to develop an INHIBIT logic gate.

Synthesis of N-Heterocyclic Carbine Silver(I) and Palladium(II) Complexes with Acylated Piperazine Linker and Catalytic Activity in Three Types of C—C Coupling Reactions

Two bis-imidazolium salts LH2·Cl2 and LH2·(PF6)2 with acylated piperazine linker and two N-heterocyclic carbene (NHC) silver(I) and palladium(II) complexes [L2Ag2](PF6)2 (1) and [L2Pd2Cl4] (2) were prepared. The crystal structures of LH2·Cl2 and 1 were confirmed by X-ray analysis. In 1, one 26-membered macrometallocycle was generated through two silver(I) ions and two bidentate ligands L. The catalytic activity of 2 was investigated in Sonogashira, Heck-Mizoroki and Suzuki-Miyaura reactions. The results displayed that these C—C coupling reactions can be smoothly carried out under the catalysis of 2.

Synthesis, characterization and study of mesomorphic behavior of new bent and linear core compounds containing heterocyclic rings

The article presents the synthesis and liquid crystalline properties of some of new bent and linear core compounds containing a 1,3,4-oxadiazole, piperazine and thiazolidin-4-one rings as a central core. The new synthesized compounds were characterized by elemental analysis and FTIR, 1HNMR and mass spectroscopy). The liquid crystalline properties were studied by polarized optical microscopy and differential scanning calorimetry. All Schiff bases compounds with 1,3,4-oxadiazole and piprzaine ring in central core presented liquid crystalline properties. The liquid crystallinity of compounds containing 1,3,4-oxadiazole and thiazolidin-4-one rings as a central core were found depending on the type of terminal substituents.

Bi-(2-amidoacetyl)-piperazine amides derivative lubricant additive and preparation method thereof

The invention discloses a novel green multifunctional bi-(2-amidoacetyl)-piperazine amides derivative lubricant additive and a preparation method thereof. The preparation method specifically comprises the following steps: under the action of alkaline, firstly executing the amidation to piperazine and chloroacetyl chloride so as to obtain bi-(chloracetyl)-piperazine amide, and executing the nucleophilic substitution with corresponding amine to obtain a target compound as shown in the formula I. The preparation method is simple, the technological conditions are moderate, the raw materials are easily obtained, the synthesis cost is low, and the yield is high. The novel nitrogen-enriched bi-(2-amidoacetyl)-piperazine amides derivative can be exclusively used as a multifunctional additive of lubricating oil, or compounded to be used as the additive of other lubricating oil. The novel green multifunctional bi-(2-amidoacetyl)-piperazine amides derivative lubricant additive can be used for the general working conditions and the high-temperature working condition environment, is capable of remarkably improving the extreme pressure wear-resistant antifriction property of base oil and effectively improving the corrosion resistance of the base oil, and is a green biodegradable multifunctional lubricant additive.

Amplifying the Sensitivity of Zinc(II) Responsive MRI Contrast Agents by Altering Water Exchange Rates

Given the known water exchange rate limitations of a previously reported Zn(II)-sensitive MRI contrast agent, GdDOTA-diBPEN, new structural targets were rationally designed to increase the rate of water exchange to improve MRI detection sensitivity. These new sensors exhibit fine-tuned water exchange properties and, depending on the individual structure, demonstrate significantly improved longitudinal relaxivities (r1). Two sensors in particular demonstrate optimized parameters and, therefore, show exceptionally high longitudinal relaxivities of about 50 mM-1 s-1 upon binding to Zn(II) and human serum albumin (HSA). This value demonstrates a 3-fold increase in r1 compared to that displayed by the original sensor, GdDOTA-diBPEN. In addition, this study provides important insights into the interplay between structural modifications, water exchange rate, and kinetic stability properties of the sensors. The new high relaxivity agents were used to successfully image Zn(II) release from the mouse pancreas in vivo during glucose stimulated insulin secretion.

TARGETING HUMAN THYMIDYLATE KINASE INDUCES DNA REPAIR TOXICITY IN MALIGNANT TUMOR CELLS

The present invention relates to novel TMPK inhibitor compositions and their methods of use. In particular, it relates to novel TMPK inhibitor compositions and therapeutics that lead to dUTP-mediated DNA repair in tumor cells and acts as a novel chemosensitizer, which are useful in methods for treating or preventing cancers

Design, synthesis and biological evaluation of ambenonium derivatives as AChE inhibitors

Ambenonium (1), an old AChE inhibitor, is endowed with an outstanding affinity and a peculiar mechanism of action that, taken together, make it a very promising pharmacological tool for the treatment of Alzheimer's disease (AD). Unfortunately, the bisquaternary structure of 1 prevents its passage through the blood brain barrier. In a search of centrally active ambenonium derivatives, we planned to synthesize tertiary amines of 1, such as 2 and 3. In addition, to add new insights into the binding mechanism of the inhibitor, we designed constrained analogues of ambenonium by incorporating the diamine functions into cyclic moieties (4-12). The biological evaluation of the new compounds has been assessed in vitro against human AChE and BChE. All tertiary amine derivatives resulted more than 1000-fold less potent than 1 and, unlike prototype, did not show any selectivity between the two enzymes. This result, because of recent findings concerning the role of BChE in AD, makes our compounds, endowed with a well-balanced profile of AChE/BChE inhibition, valuable candidates for further development. To better clarify the interactions that account for the high affinity of 1, docking simulations and molecular dynamics studies on the AChE-1 complex were also carried out.