148546-99-0

Basic information

• Product Name: 3-(4-Methylpiperazin-1-yl)aniline
• Synonyms: 3-(4-Methylpiperazin-1-yl)aniline ,97%;3-(4-methylpiperazin-1-yl)benzenamine;Benzenamine, 3-(4-methyl-1-piperazinyl)-;3-(4-Methypiperazin-1-yl)anilin;1-(3-Aminophenyl)-4-methylpiperazine;3-(4-Methyl-1-piperazinyl)aniline;3-(4-METHYLPIPERAZIN-1-YL)ANILINE;AKOS BB-8951
• CAS NO: 148546-99-0
• Molecular Formula: C₁₁H₁₇N₃
• Molecular Weight: 191.27
• Product Categories: Amines and Anilines;PIPERIDINE
• Mol File: 148546-99-0.mol

Chemical Properties

• Melting Point: 98-99
• Boiling Point: 353.082 °C at 760 mmHg
• Flash Point: 164.907 °C
• Appearance: /
• Density: 1.093 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 7.88±0.42(Predicted)
• CAS DataBase Reference: 3-(4-Methylpiperazin-1-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Methylpiperazin-1-yl)aniline(148546-99-0)
• EPA Substance Registry System: 3-(4-Methylpiperazin-1-yl)aniline(148546-99-0)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 22-26-36/37/39-45
• RIDADR: 2923
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 148546-99-0(Hazardous Substances Data)

Usage

Chemical Properties

Yellow solid

Upstream product

• 148546-97-8 1‐methyl‐4‐(3‐nitrophenyl)piperazine 
• 109-01-3 1-methyl-piperazine 
• 402-67-5 3-fluoro-1-nitrobenzene 
• 54054-85-2 1-(3-nitrophenyl)piperazine 
• 585-79-5 m-nitrobromobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 645-00-1 m-iodonitrobenzene 

Downstream Products

• 378758-97-5 1-(3'-acetylaminophenyl)-4-methylpiperazine 
• 378759-37-6 1-(3'-benzyloxycarbonylaminophenyl)-4-methylpiperazine 
• 842127-56-4 compound 36 
• 209481-70-9 naphthalene-2-sulfonic acid [3-(4-methylpiperazin-1-yl)phenyl]amide 
• 182618-68-4 (+)-N-[5-Cycloheptyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(N-methyl-N'-piperazinyl)phenyl]urea 
• 1042435-00-6 ethyl 2-[(5-chloro-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]benzoate 
• 1042435-03-9 Ethyl 2-[(5-fluoro-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]benzoate 
• 1042435-05-1 Ethyl 2-[(5-methyl-2-{[3-(4-methyl-1-piperazinyl)phenyl]amino}-4-pyrimidinyl)amino]benzoate 
• 1062073-50-0 C₂₅H₂₅ClN₄O 
• 1006877-92-4 C₂₈H₂₉N₅O₂ 

Relevant articles and documents

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Catalyst-Directed Chemoselective Double Amination of Bromo-chloro(hetero)arenes: A Synthetic Route toward Advanced Amino-aniline Intermediates

A chemoselective sequential one-pot coupling protocol was developed for preparing several amino-anilines in high yield as building blocks for active pharmaceutical ingredients (APIs). Site (Cl vs Br on electrophile) and nucleophile (amine vs imine) selectivity is dictated by the catalyst employed. A Pd-crotyl(t-BuXPhos) precatalyst selectively coupled the Ar-Br of the polyhaloarene with benzophenone imine, even in the presence of a secondary amine, while Pd-based RuPhos or (BINAP)Pd(allyl)Cl coupled the Ar-Cl site with secondary amines.

SAR study on: N 2, N 4-disubstituted pyrimidine-2,4-diamines as effective CDK2/CDK9 inhibitors and antiproliferative agents

Cyclin-dependent kinases (CDKs) are pivotal kinases in cell cycle transition and gene transcription. A series of N2,N4-diphenylpyrimidine-2,4-diamines were previously identified as potent CDK2/CDK9 inhibitors. To explore the SAR of this structural prototype, twenty-four novel N2,N4-disubstituted pyrimidine-2,4-diamines were designed and synthesized. Among them, twenty-one compounds exhibited potent inhibitory activities against both CDK2/cyclin A and CDK9/cyclin T1 systems, and the most potent CDK2 and CDK9 inhibitors, 3g and 3c, showed IC50 values of 83 nM and 65 nM respectively. Most of these compounds displayed significant inhibition against the tested tumor cell lines in the SRB assay, and in particular, remained active against the triple-negative breast cancer (TNBC) cell line MDA-MB-231. Flow cytometer analysis of compounds 2a, 2d and 3b in MDA-MB-231 cells indicated that these compounds induced cell cycle arrest in G2/M phase. Docking studies on compound 3g were performed, which provided conducive clues for further molecular optimization.

DIARYLUREAS AS CB1 ALLOSTERIC MODULATORS

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