21655-48-1

Basic information

• Product Name: 2,6-DIMETHYLPIPERAZINE
• Synonyms: cis-2,6-DiMethylpiperazine , 98.0%(GC&T;2,6DIMETHYLPIPRAZINE;cis-2,6-Dimethylpiperazine;cis-2,6-Dimethylpiperazine 98+%;2,6-Dimethylpiperazi;(2S,6R)-rel-2,6-DiMethylpiperazine;cis-3,5-DiMethylpiperazine;cis-2,6-DiMethylpiper
• CAS NO: 21655-48-1
• Molecular Formula: C₆H₁₄N₂
• Molecular Weight: 114.19
• EINECS: 203-588-9
• Mol File: 21655-48-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 108-111 °C(lit.)
• Boiling Point: 162 °C(lit.)
• Flash Point: 113 °F
• Appearance: /
• Density: 0.9140 (estimate)
• Vapor Pressure: 2.31mmHg at 25°C
• Refractive Index: 1.4628 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 9.38±0.60(Predicted)
• Water Solubility: Completely soluble in water
• Sensitive: Light Sensitive & Hygroscopic
• CAS DataBase Reference: 2,6-DIMETHYLPIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIMETHYLPIPERAZINE(21655-48-1)
• EPA Substance Registry System: 2,6-DIMETHYLPIPERAZINE(21655-48-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 26-36-24/25
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• F: 3-8-10-34
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 21655-48-1(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow to Light Yellow Solid.

Uses

cis-2,6-Dimethylpiperazine is a very versatile reagent used in the preparation of biologically active compounds such as antibacterial agents.

Synthesis

A method for the synthesis of cis-2,6-dimethylpiperazine:diisopropanolamine reacts with ammonia in the presence of a catalyst.

Solubility in water

Completely soluble.

InChI:InChI=1/C6H14N2/c1-5-3-7-4-6(2)8-5/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1

Upstream product

• 110-97-4 diisopropanolamine 
• 56-81-5 glycerol 
• 108-50-9 2,6-dimethylpyrazine 
• 57-55-6 propylene glycol 
• 78-90-0 1,2-diaminopropan 
• 115893-42-0 (β-hydroxy-isopropyl)-(2-hydroxy-propyl)-amine 
• 2294-46-4 bis(2-hydroxy-1-methylethyl)amine 
• 6168-72-5 2-Amino-1-propanol 
• 592-20-1 Acetol acetate 

Downstream Products

• 59794-54-6 1,4-dibenzoyl-2,6-dimethyl-piperazine 
• 1123-66-6 1,2,4,6-Tetramethyl-piperazin 
• 129779-30-2 (3S,5R)-3,5-dimethylpiperazine-1-carboxylic acid tert-butyl ester 
• 110871-86-8 sparfloxacin 
• 113617-63-3 1-cyclopropyl-5,6,8-trifluoro-7-(cis-3,5-dimethyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 157402-75-0 7-(benzyloxy)-10-cyclopropyl-2-(cis-3,5-dimethylpiperazin-1-yl)-3-fluoro-6,7,8,10-tetrahydropyrido<2',3':4,5>imidazo<1,2-c>pyrimidine-6,8-dione 
• 20350-26-9 2,4-dinitrophenolate 
• 14609-74-6 p-nitrophenolate 
• 191543-36-9 1-((3S,5R)-3,5-dimethylpiperazin-1-yl)ethanone 
• 654071-78-0 2,6-dimethyl-piperazine-1-carboxylic acid dimethylamide 
• 262295-71-6 (+/-)-cis-4-(3,5-dimethylpiperazin-1-yl)-2-(trifluoromethyl)benzonitrile 
• 866538-93-4 (3R,5S)-1-(2-fluoro-4-nitrophenyl)-3,5-dimethylpiperazine 

Relevant articles and documents

Iridium-catalyzed condensation of amines and vicinal diols to substituted piperazines

A straightforward procedure is described for the synthesis of piperazines from amines and 1,2-diols. The heterocyclization is catalyzed by [Cp*IrCl2]2 and sodium hydrogen carbonate and can be achieved with either toluene or water as solvent. The transformation does not require any stoichiometric additives and only produces water as the byproduct. The reaction can be performed between a 1,2-diamine and a 1,2-diol or by a double condensation between a primary alkylamine and a 1,2-diol. At least one substituent is required on the piperazine ring to achieve the cyclization in good yield. The mechanism is believed to involve dehydrogenation of the 1,2-diol to the α-hydroxy aldehyde, which condenses with the amine to form the α-hydroxy imine. The latter rearranges to the corresponding α-amino carbonyl compound, which then reacts with another amine followed by reduction of the resulting imine. Piperazines are prepared by [Cp*IrCl 2]2-catalyzed heterocyclization of 1,2-diols with either 1,2-diamines or primary alkylamines. The reaction is performed in toluene or water and requires no stoichiometric additive. The key step in the mechanism is believed to be the isomerization of an α-hydroxy imine to the corresponding α-amino carbonyl compound. Copyright

Process for preparing Cis-2,6-dimethylpiperazine

This invention relates to a process for the selective preparation of cis-2,6-dimethylpiperazine by reacting (i) a diisopropanolamine mixture comprising compounds having the formulas HN(CH2CH(OH)CH3)2, HN(CH(CH3)CH2OH)2, and HN(CH(CH3)CH2OH)(CH2CH(OH)CH3) or (ii) 1,2-diaminopropane with ammonia and hydrogen in the presence of a hydrogenation catalyst.

Reduction of Heterocycles with Nickel-Aluminum Alloy

Pyrazines, pyridazines, isoxazoles, oxazole, 4-methylpyrimidine, and indole are reduced by nickel-aluminum alloy in potassium hydroxide solution.The reaction is simple to carry out and does not require special apparatus or hydrogen atmospheres.The products were the fully hydrogenated species although benzene rings were not attacked. 4-Methylpyrimidine gave 1,3-diaminobutane and oxazole gave 2-(methylamino)ethanol.It was found that the reaction frequently exhibited an induction period.