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Piperazine

Piperazine
Piperazine Structural Formula V1.svg
Piperazine-3D-balls-B.png
Names
Preferred IUPAC name
Piperazine
Other names
Hexahydropyrazine
Piperazidine
Diethylenediamine
1,4-Diazinane
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.003.463
KEGG
PubChem CID
UNII
Properties
C4H10N2
Molar mass 86.136 g/mol
Appearance White crystalline solid
Melting point 106 °C (223 °F; 379 K)
Boiling point 146 °C (295 °F; 419 K) Sublimates
Freely soluble
Acidity (pKa) 9.8
Basicity (pKb) 4.19
-56.8·10−6 cm3/mol
Pharmacology
P02CB01 (WHO)
Pharmacokinetics:
60-70%
Hazards
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Piperazine (/paɪˈpɛrəziːn/) is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste.

The piperazines are a broad class of chemical compounds, many with important pharmacological properties, which contain a core piperazine functional group.

Piperazines were originally named because of their chemical similarity with piperidine, part of the structure of piperine in the black pepper plant (Piper nigrum). It is important to note, however, that piperazines are not derived from plants in the Piper genus.

Piperazine is freely soluble in water and ethylene glycol, but insoluble in diethyl ether. It is a weak base with two pKbs of 5.35 and 9.73 at 25 °C.; the pH of a 10% aqueous solution of piperazine is 10.8-11.8. Piperazine readily absorbs water and carbon dioxide from the air. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol.


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