151657-72-6

Basic information

• Product Name: Piperazine, 1-methyl-4-(3-methylphenyl)- (9CI)
• Synonyms: Piperazine, 1-methyl-4-(3-methylphenyl)- (9CI);1-METHYL-4-(3-METHYLPHENYL)PIPERAZINE
• CAS NO: 151657-72-6
• Molecular Formula: C₁₂H₁₈N₂
• Molecular Weight: 190.28472
• Product Categories: PIPERIDINE
• Mol File: 151657-72-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Piperazine, 1-methyl-4-(3-methylphenyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Piperazine, 1-methyl-4-(3-methylphenyl)- (9CI)(151657-72-6)
• EPA Substance Registry System: Piperazine, 1-methyl-4-(3-methylphenyl)- (9CI)(151657-72-6)

Safety Data

• Hazardous Substances Data: 151657-72-6(Hazardous Substances Data)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 352-32-9 p-fluorotoluene 
• 106-38-7 para-bromotoluene 
• 108-41-8 1-chloro-3-methylbenzene 
• 55-86-7 mechlorethamine hydrochloride 
• 108-44-1 1-amino-3-methylbenzene 
• 591-17-3 meta-bromotoluene 

Relevant articles and documents

Buchwald-Hartwig reactions in water using surfactants

Examination of the scope and limitation of the Buchwald-Hartwig cross-coupling reaction in micellar medium is reported. An array of aryl or heteroaryl halides were coupled to diverse nitrogen coupling partners using a combination of [(allyl)PdCl]2 and cBRIDP to afford the corresponding products in moderate to excellent yields. 30 examples are reported, including polar solid and fairly water-soluble organic substrates/reagents.

Structure-affinity relationships of a unique nicotinic ligand: N1-dimethyl-N4-phenylpiperazinium iodide (DMPP)

DMPP is a well-known nicotinic agonist that does not fit any proposed pharmacophore for nicotinic binding and represents a unique ligand among the hundreds of nicotinic agonists studied in the past decades. A systematic modulation of the chemical structure of DMPP, aimed to establish its structure-affinity relationships, is reported. The research has allowed to identify molecules such as 11c, 13c, 14c, and 28c, with affinities for α4β2 receptors in the low nanomolar range, some 2 orders of magnitude lower than the lead compound. The agonistic properties of the most interesting compounds have been assessed by measuring their analgesic activity on mice (hot-plate test). Another result of the research was the identification of DMPP analogues, such as 3a (Ki = 90 nM) and 14b (Ki = 180 nM), that maintain affinity for the central nicotinic receptor when the ammonium function is changed into an aminic one and are therefore possible leads for drug development in neurodegenerative diseases.

Direct Substitution of Aromatic Ethers by Lithium Amides. A New Aromatic Amination Reaction

Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution.Especially with lithiated secondary amines high conversions and selectivities are achieved.Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates.The scope and mechanistic implications of this novel nucleophilic amination reaction are described.