Chemistry:N-Methylpiperazine

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N-Methylpiperazine
N-Methylpiperazine.svg
Names
Preferred IUPAC name
1-Methylpiperazine
Other names
  • 4-Methylpiperazine
  • p-Methylpiperazine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 203-639-5
UNII
UN number 2920
Properties
C5H12N2
Molar mass 100.165 g·mol−1
Melting point −6 °C (21 °F; 267 K)[1]
Boiling point 138 °C (280 °F; 411 K)[1]
Hazards
Safety data sheet FischerSci
GHS pictograms GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Harmful
GHS Signal word Danger
H226, H312, H314, H317, H330, H331, H332
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P301+330+331, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P310, P311, P312, P320, P321, P322
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no codeNFPA 704 four-colored diamond
3
2
1
Related compounds
Related compounds
 Piperazine, 4-methylpyridine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

N-Methylpiperazine is a heterocyclic organic compound.

Uses

N-Methylpiperazine is a common building block used in organic synthesis.[2] For example, N-methylpiperazine is used in the manufacture of various pharmaceutical drugs including cyclizine,[3] meclizine, and sildenafil.

The lithium salt, lithium N-methylpiperazide, is used as a reagent in organic synthesis for protection of aryl aldehydes.[4]

Synthesis

Industrially, N-methylpiperazine is produced by reacting diethanolamine and methylamine at 250 bar and 200 °C.[5][6]

References

  1. ↑ 1.0 1.1 "1-Methylpiperazine". Chemistry Dashboard. Environmental Protection Agency. https://comptox.epa.gov/dashboard/dsstoxdb/results?search=DTXSID4021898. 
  2. ↑ "1-methylpiperazine". European Chemicals Agency. https://echa.europa.eu/brief-profile/-/briefprofile/100.003.309. 
  3. ↑ Vardanyan, Ṛuben & Hruby, Victor J.. Synthesis of Essential Drugs. p. 226. 
  4. ↑ Comins, Daniel L.; Joseph, Sajan P. (2001). "Lithium N-Methylpiperazide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rl128. ISBN 0471936235. 
  5. ↑ "Preparation of N-Methylpiperazine" US patent 4845218, issued 1989-07-04
  6. ↑ "Catalytic synthesis of N-methylpiperazine from diethanolamine and methylamine by cyclodehydration reaction". Indian Journal of Chemical Technology 1 (November): 359–360. 1994. http://nopr.niscair.res.in/bitstream/123456789/31280/1/IJCT%201%286%29%20359-360.pdf. 



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