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N,N'-Dimethylpiperazine
[CAS# 106-58-1]

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Identification
ClassificationPharmaceutical intermediate >> Heterocyclic compound intermediate >> Piperazine
NameN,N'-Dimethylpiperazine
Synonyms1,4-Dimethyl-piperazine
Molecular StructureCAS # 106-58-1, N,N'-Dimethylpiperazine
Molecular FormulaC6H14N2
Molecular Weight114.19
CAS Registry Number106-58-1
EC Number203-412-0
SMILESCN1CCN(CC1)C
Properties
Density0.844
Melting point-1 °C
Boiling point130-133 °C
Refractive index1.4453-1.4473
Flash point21.5 °C
Water solubilitymiscible
Safety Data
Hazard Symbolssymbol symbol symbol   GHS02;GHS05;GHS07 Danger  Details
Risk StatementsH225-H226-H302-H314-H318  Details
Safety StatementsP210-P233-P240-P241-P242-P243-P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P330-P363-P370+P378-P403+P235-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Acute toxicityAcute Tox.4H302
Flammable liquidsFlam. Liq.2H225
Serious eye damageEye Dam.1H318
Skin corrosionSkin Corr.1CH314
Skin corrosionSkin Corr.1BH314
Skin corrosionSkin Corr.1H314
Flammable liquidsFlam. Liq.3H226
Acute toxicityAcute Tox.3H311
Chronic hazardous to the aquatic environmentAquatic Chronic3H412
Transport InformationUN 2924
SDSAvailable
up Discovery and Applications
N,N'-Dimethylpiperazine is an organic compound with the molecular formula C6H14N2. It belongs to the class of piperazine derivatives, characterized by a piperazine ring where two methyl groups are attached to the nitrogen atoms. The compound appears as a colorless to pale yellow liquid with a faint amine-like odor. N,N'-Dimethylpiperazine plays a crucial role in various chemical processes, particularly in pharmaceuticals, agrochemicals, and polymer chemistry.

The discovery of N,N'-dimethylpiperazine dates back to the mid-20th century during a period of extensive research into piperazine derivatives. Piperazine itself was first synthesized in 1888 and has since been recognized for its diverse biological and chemical properties. The dimethylated derivative was developed to enhance the pharmacological properties of piperazine, leading to its exploration in various synthetic applications. The synthesis of N,N'-dimethylpiperazine typically involves the reaction of piperazine with formaldehyde and methyl iodide, resulting in the formation of the dimethylated product.

One of the primary applications of N,N'-dimethylpiperazine is in the pharmaceutical industry. It serves as an important intermediate in the synthesis of various drugs, including antihistamines, antidepressants, and anti-anxiety medications. Its ability to enhance the solubility and bioavailability of active pharmaceutical ingredients (APIs) makes it a valuable component in drug formulation. Researchers have also explored the compound's potential as a ligand in metal-catalyzed reactions, further expanding its role in medicinal chemistry.

In addition to its pharmaceutical applications, N,N'-dimethylpiperazine is utilized in the agrochemical industry. It acts as a key intermediate in the synthesis of herbicides and insecticides, contributing to improved crop protection. The compound’s ability to enhance the efficacy of agrochemicals has made it an essential ingredient in agricultural formulations, helping to increase agricultural productivity while minimizing the impact of pests and weeds.

Moreover, N,N'-dimethylpiperazine is employed in the production of specialty chemicals and polymers. It is used as a curing agent in epoxy resins and as a stabilizer in polyurethane formulations. The incorporation of N,N'-dimethylpiperazine into polymer systems can enhance their thermal and mechanical properties, making them suitable for a wide range of applications, including coatings, adhesives, and composite materials.

Despite its beneficial applications, N,N'-dimethylpiperazine poses potential health and safety risks. It is classified as a hazardous substance, and exposure may lead to skin irritation, respiratory issues, and other health effects. Therefore, regulatory guidelines have been established to ensure safe handling and usage in industrial settings. Proper safety measures, including personal protective equipment and adequate ventilation, are essential to mitigate the risks associated with this compound.

In conclusion, N,N'-dimethylpiperazine is a significant organic compound with diverse applications in pharmaceuticals, agrochemicals, and polymer chemistry. Its role as a chemical intermediate underscores its importance in the synthesis of various products, contributing to advancements in drug development, agricultural practices, and materials science. As ongoing research continues to explore its potential, N,N'-dimethylpiperazine is expected to remain a relevant substance in the field of organic chemistry and industrial applications.

References

2024. Tandem asymmetric propargylic amination/carboxylative cyclization reaction to chiral 5-methylidene-2-oxazolidinones using CO2 as C1 synthon. Science China Chemistry, 67, 1-10.
DOI: 10.1007/s11426-024-2346-4

2017. Screening of additives and other chemicals in polyurethanes by direct analysis in real time mass spectrometry (DART-MS). Analytical and Bioanalytical Chemistry, 409(23), 5503-5512.
DOI: 10.1007/s00216-017-0553-x

2015. Synthesis, Structure, Property of a Templated Borate [Hdmpip][B5O6(OH)4]. Journal of Cluster Science, 26(4), 1237-1245.
DOI: 10.1007/s10876-015-0863-0
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