39539-66-7

Basic information

• Product Name: 4-Methylpiperazine-1-carbonyl chloride
• Synonyms: METHYL PIPERAZINE CARBAMOYL CHLORIDE;4-METHYL-1-PIPERAZINECARBONYL CHLORIDE;4-METHYL-1-CHLOROCARBONYL PIPERAZINE;4-METHYLPIPERAZINE-1-CARBONYL CHLORIDE;4-METHYLPIPERAZINECARBONYL CHLORIDE;1-Piperazinecarbonyl chloride, 4-methyl- (6CI,9CI);4-Methylpierazine-1-carbonylchloride;4-Methyl-1-piperazinecarbonyl chloride 97%
• CAS NO: 39539-66-7
• Molecular Formula: C₆H₁₁ClN₂O
• Molecular Weight: 162.62
• Product Categories: ACIDHALIDE;Piperazine derivates;API intermediates;Building Blocks;Heterocyclic Building Blocks;Piperazines;Building Blocks;C4 to C8;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 39539-66-7.mol
• Article Data: 16

Chemical Properties

• Melting Point: 225-228 °C(lit.)
• Boiling Point: 278-279 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless to brown/Liquid
• Density: 1.200 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0256mmHg at 25°C
• Refractive Index: n20/D 1.4980(lit.)
• Storage Temp.: 2-8°C
• PKA: 6.61±0.10(Predicted)
• CAS DataBase Reference: 4-Methylpiperazine-1-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylpiperazine-1-carbonyl chloride(39539-66-7)
• EPA Substance Registry System: 4-Methylpiperazine-1-carbonyl chloride(39539-66-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 39539-66-7(Hazardous Substances Data)

Usage

General Description

4-Methyl-1-piperazinecarbonyl chloride can be synthesized from 1-methylpiperazine by reacting with phosgene.

InChI:InChI=1/C6H11ClN2O/c1-8-2-4-9(5-3-8)6(7)10/h2-5H2,1H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 75-44-5 phosgene 
• 67-66-3 chloroform 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 58226-19-0 1-Piperazinecarboxylic acid, 4-methyl- 
• 55112-42-0 4-methylpiperazine-1-carbonyl chloride monohydrochloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 62226-74-8 1-benzyl-4-methylpiperazine 

Downstream Products

• 68061-02-9 1-Methyl-4-[N-(3,4,5-trimethoxyphenyl)-carbamoyl]piperazine (hydrochloride) 
• 53788-34-4 2-acetylamino-7-chloro-1,8-naphthyridine 
• 43200-80-2 zopiclon 
• 244154-66-3 tert-butyl (S)-1-(chloromethyl)-5-((4-methylpiperazine-1-carbonyl)oxy)-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 

Relevant articles and documents

RAS INHIBITORS

The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.

Synthesis and Biological Evaluation of Celastrol Derivatives with Improved Cytotoxic Selectivity and Antitumor Activities

Cdc37 associates kinase clients to Hsp90 and promotes the development of cancers. Celastrol, a natural friedelane triterpenoid, can disrupt the Hsp90-Cdc37 interaction to provide antitumor effects. In this study, 31 new celastrol derivatives, 2a - 2d , 3a - 3g , and 4a - 4t , were designed and synthesized, and their Hsp90-Cdc37 disruption activities and antiproliferative activities against cancer cells were evaluated. Among these compounds, 4f , with the highest tumor cell selectivity (15.4-fold), potent Hsp90-Cdc37 disruption activity (IC50= 1.9 μM), and antiproliferative activity against MDA-MB-231 cells (IC50= 0.2 μM), was selected as the lead compound. Further studies demonstrated 4f has strong antitumor activities both in vitro and in vivo through disrupting the Hsp90-Cdc37 interaction and inhibiting angiogenesis. In addition, 4f exhibited less toxicity than celastrol and showed a good pharmacokinetics profile in vivo. These findings suggest that 4f may be a promising candidate for development of new cancer therapies.

Synthesis of 3- and 29-substituted celastrol derivatives and structure-activity relationship studies of their cytotoxic activities

A series of 3-carbamate and 29-ester celastrol derivatives (compounds 1–26) were designed and synthesized. These analogues were evaluated for their cytotoxic activities against several cancer cell lines. Cytotoxicity data revealed that the properties of substituents and substitution position had important influence on cytotoxic activity. Modification of C-3 hydroxyl with size-limited groups did not reduce the activity obviously. The introduction of polarity group like piperazine could improve the solubility. Compound 23 was chosen to further evaluate anti-tumor efficacy in vivo. It showed higher inhibition rate and better safety than celastrol during in vivo experiment by intragastric administration. The preliminary antitumor studies of compound 23 in vivo showed that it might be promising for the development of new antitumor agents.