3477-33-6

Basic information

• Product Name: Piperazine, 1,4-bis(3-methylphenyl)-
• CAS NO: 3477-33-6
• Molecular Formula: C18H22N2
• Molecular Weight: 266.386
• Mol File: 3477-33-6.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Piperazine, 1,4-bis(3-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 1,4-bis(3-methylphenyl)-(3477-33-6)
• EPA Substance Registry System: Piperazine, 1,4-bis(3-methylphenyl)-(3477-33-6)

Safety Data

• Hazardous Substances Data: 3477-33-6(Hazardous Substances Data)

Usage

General Description

Piperazine, 1,4-bis(3-methylphenyl)-, also known as piperazine or piperazine derivative, is an organic compound with the chemical formula C20H24N2. It is a heteroaromatic compound that is commonly used as a building block in the synthesis of pharmaceuticals and agrochemicals. Piperazine derivatives are known for their antihistamine, antipsychotic, and antimalarial properties, and are also used as intermediates in the production of dyes and pigments. Additionally, they have been investigated for their potential use as molecular scaffolds in drug design due to their diverse chemical reactivity and pharmacological properties.

Upstream product

• 106-93-4 ethylene dibromide 
• 108-44-1 1-amino-3-methylbenzene 
• 110-85-0 piperazine 
• 591-17-3 meta-bromotoluene 
• 108-41-8 1-chloro-3-methylbenzene 
• 107-21-1 ethylene glycol 

Relevant articles and documents

SYNTHESIS AND CRYSTAL STRUCTURE OF A 1:1:1 ADDUCT OF N,N'-DI(m-TOLYL)PIPERAZINE N,N'-DIOXIDE, ACETIC ACID AND WATER

A 1:1:1 adduct of N,N'-di(m-tolyl)piperazine N,N'-dioxide, acetic acid, and water has been synthesized.The crystals are orthorombic, space group Pca21, (No. 29), with a=15.712(3), b=6.018(1), c=19.940(5) Angstroem, V=1885.4(7) , Z=4 and Dc=1.290 g cm-3.The structure has been refined to R=0.076 for 1885 observed Mo Kα reflections.The piperazine ring in the N,N'-dioxide molecule takes the chair form, with two N-O bonds oriented axially in a trans configuration.Proton transfer from the acetic acid molecule to the N,N'-dioxide molecule was found in the adduct.Strong hydrogen bonds, each involving a proton and the oxygen atoms of two N-oxide groups from adjacent N,N'-dioxide molecules, connect the latter into a zigzag chain along the b axis.The acetate ions and the water molecules are alternately linked by hydrogen bonds to form an infinite chain along the b axis.The crystal structure is built up from a lateral stacking of these two types of chain.The length of the novel N-O...H+...O-N hydrogen bond is 2.454(6) Angstroem.

Nickel-catalysed selective N-arylation or N,N′-diarylation of secondary diamines

The selective synthesis of N-aryl or N,N′-diaryl piperazines and trimethylene(bis)piperidines from the corresponding diamines and aryl chlorides using a catalyst combination of Ni(0) associated to 2,2′-bipyridine is described. The Ni/2,2′-bipyridine catalyst is also effective for the sequential arylation of piperazine. The preparation of novel and unsymmetrical 1,4-diaryl piperazines is reported.

Synthesis of N-arylpiperazines from aryl halides and piperazine under a palladium tri-tert-butylphosphine catalyst

A Pd/P(t-Bu), catalyst system has revealed very high activity and selectivity for the amination of N-(hetero)aryl halides with unprotected piperazine. A wide variety of N-(hetero)arylpiperazines could be prepared using this catalyst. Turnover numbers up to 6400mol/mol have been obtained.