31166-44-6

Basic information

• Product Name: BENZYL 1-PIPERAZINECARBOXYLATE
• Synonyms: 1-Z-PIPERAZINE;1-(BENZYLOXYCARBONYL)PIPERAZINE;LABOTEST-BB LT00138040;BENZYL 1-PIPERAZINECARBOXYLATE;BENZYL PIPERAZINE-1-CARBOXYLATE;1-Cbz-Piperazine;1-carbobenzoxypiperazine;1-(Benzyloxycarbonyl)piperazine, 1-Cbz-Piperazine, Benzyl piperazine-1-carboxylate
• CAS NO: 31166-44-6
• Molecular Formula: C₁₂H₁₆N₂O₂
• Molecular Weight: 220.27
• EINECS: 1533716-785-6
• Mol File: 31166-44-6.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 158-161 °C1.4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear colorless to yellowish liquid
• Density: 1.142 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.85E-05mmHg at 25°C
• Refractive Index: n20/D 1.546(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 8.44±0.10(Predicted)
• BRN: 179500
• CAS DataBase Reference: BENZYL 1-PIPERAZINECARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 1-PIPERAZINECARBOXYLATE(31166-44-6)
• EPA Substance Registry System: BENZYL 1-PIPERAZINECARBOXYLATE(31166-44-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 31166-44-6(Hazardous Substances Data)

Usage

Description

BENZYL 1-PIPERAZINECARBOXYLATE, also known as 1-Cbz-piperazine, is a chemical compound that serves as an essential intermediate in the synthesis of various pharmaceutical agents. It is a clear colorless to yellowish liquid with significant applications in the development of ligands for specific receptors.

Uses

Used in Pharmaceutical Synthesis:
BENZYL 1-PIPERAZINECARBOXYLATE is used as a key intermediate for the synthesis of serotonin 5-HT6 and dopamine D2 receptor ligands. Its role in the development of these ligands is crucial for creating medications targeting neurological and psychiatric disorders.
Used in Radioligand Synthesis:
BENZYL 1-PIPERAZINECARBOXYLATE is also used for the synthesis of 11-C labelled ligands, which are essential for imaging the vesicular acetylcholine transporter. This application is vital in the field of medical imaging, particularly in the study of neurological conditions and the development of targeted therapies.

InChI:InChI=1/C12H16N2O2/c15-12(14-8-6-13-7-9-14)16-10-11-4-2-1-3-5-11/h1-5,13H,6-10H2

Upstream product

• 110-85-0 piperazine 
• 501-53-1 benzyl chloroformate 
• 121370-60-3 tert-butyl 4-((benzyloxy)carbonyl)piperazine-1-carboxylate 
• 142-63-2 piperazine hexahydrate 
• 1885-14-9 phenyl chloroformate 
• 96452-48-1 benzyl pyridin-2-yl carbonate 
• 1417816-42-2 benzyl 4-pyridyl carbonate 
• 1448041-81-3 C₂₂H₂₀F₆N₂O₄ 
• 93871-69-3 4-(4-nitrobenzenesulfonyl)piperazine-1-carboxylic acid benzyl ester 
• 13795-24-9 benzyl 4-nitrophenyl carbonate 
• 100-51-6 benzyl alcohol 
• 22129-07-3 N-benzyloxycarbonylimidazole 
• 142-64-3 piperazine dihydrochloride 

Downstream Products

• 25539-27-9 4-chlorocarbonyl-piperazine-1-carboxylic acid benzyl ester 
• 588-88-5 benzyl 4-carbamoylpiperazine-1-carboxylate 
• 102477-31-6 4-[(3,4-dimethyl-phenylcarbamoyl)-methyl]-piperazine-1-carboxylic acid benzyl ester 
• 856844-93-4 4-propyl-piperazine-1-carboxylic acid benzyl ester 
• 899-95-6 4-trifluoroacetyl-piperazine-1-carboxylic acid benzyl ester 
• 100876-73-1 4-ethanesulfonyl-piperazine-1-carboxylic acid benzyl ester 
• 46821-51-6 4-methyl-piperazine-1-carboxylic acid benzyl ester 
• 113102-24-2 C₅₀H₆₀N₄O₁₃S 

Relevant articles and documents

Application of triazenes for protection of secondary amines

Use of the phenyldiazenyl group, which serves as a protecting group for secondary amines is described in detail. The triazene protected amine is compatible with oxidative and reductive conditions as well as with strong bases (LDA, tert-butyllithium) and alkylating reagents. The amine is regenerated by action of trifluoroacetic acid and a suitable reducing agent (EtOH or NaH2PO2).

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

Synthesis and Evaluation of Bifunctional Aminothiazoles as Antiretrovirals Targeting the HIV-1 Nucleocapsid Protein

Small molecule inhibitors of the HIV-1 nucleocapsid protein (NC) are considered as promising agents in the treatment of HIV/AIDS. In an effort to exploit the privileged 2-amino-4-phenylthiazole moiety in NC inhibition, here we conceived, synthesized, and tested in vitro 18 NC inhibitors (NCIs) bearing a double functionalization. In these NCIs, one part of the molecule is deputed to interact noncovalently with the NC hydrophobic pocket, while the second portion is designed to interact with the N-terminal domain of NC. This binding hypothesis was verified by molecular dynamics simulations, while the linkage between these two pharmacophores was found to enhance antiretroviral activity both on the wild-type virus and on HIV-1 strains with resistance to currently licensed drugs. The two most interesting compounds 6 and 13 showed no cytotoxicity, thus becoming valuable leads for further investigations.