N,N-Dimethylcyclohexylamine
[CAS# 98-94-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: N,N-Dimethylcyclohexylamine
• Synonyms: Dimethylaminocyclohexane; Cyclohexyldimethylamine
• Molecular Formula: C₈H₁₇N
• Molecular Weight: 127.23
• CAS Registry Number: 98-94-2
• EC Number: 202-715-5
• SMILES: CN(C)C1CCCCC1

Properties

• Density: 0.849
• Melting point: -60 °C
• Boiling point: 160 °C
• Refractive index: 1.4525-1.4545
• Flash point: 37 °C
• Water solubility: 10 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07;GHS09 Danger
• Risk Statements: H226-H301+H311+H331-H301-H302-H311-H314-H318-H330-H331-H400-H411-H412
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P261-P262-P264-P264+P265-P270-P271-P273-P280-P284-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P320-P321-P330-P361+P364-P363-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H302
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Acute toxicity	Acute Tox.	2	H310
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335
Substances or mixtures corrosive to metals	Met. Corr.	1	H290

• Transport Information: UN 2264; UN 2266

Discovery and Applications

N,N-Dimethylcyclohexylamine (DMCHA) is a chemical compound that belongs to the class of secondary amines, characterized by a cyclohexane ring with two methyl groups attached to the nitrogen atom. Its molecular formula is C₈H₁₈N, and it features a distinctive structure that contributes to its various properties and applications. The compound was first synthesized in the mid-20th century, during an era of increasing interest in organic chemistry and the development of novel amine compounds for industrial applications.

The synthesis of N,N-dimethylcyclohexylamine typically involves the reaction of cyclohexylamine with formaldehyde and dimethylamine. This reaction results in the formation of DMCHA, which can be purified through standard chemical techniques such as distillation or recrystallization. The compound is recognized for its moderate volatility and solubility in organic solvents, making it a suitable candidate for various applications.

One of the primary applications of N,N-dimethylcyclohexylamine is in the synthesis of surfactants and emulsifiers. Due to its amphiphilic nature, DMCHA can reduce surface tension, making it effective in formulating products such as detergents and personal care items. Additionally, DMCHA has been explored as a corrosion inhibitor in various industrial processes, where it helps protect metal surfaces from oxidation and degradation.

In the realm of pharmaceuticals, N,N-dimethylcyclohexylamine has garnered attention for its potential as a building block in the synthesis of biologically active compounds. Its structural features allow for the modification of various pharmacophores, leading to the development of novel therapeutic agents. Moreover, DMCHA has been studied for its effects on the central nervous system, with research suggesting that it may possess stimulant properties, similar to other amines.

The compound's versatility extends to its use as a reagent in organic synthesis, where it serves as a catalyst in various reactions, including nucleophilic substitutions and reductive aminations. Its ability to facilitate chemical transformations while remaining relatively stable under various conditions highlights its utility in laboratory and industrial settings.

Environmental considerations have also prompted research into the biodegradability and toxicity of N,N-dimethylcyclohexylamine. Studies indicate that while DMCHA is relatively stable in the environment, it can undergo microbial degradation, making it a more environmentally friendly option compared to other amines. However, safety data and regulatory assessments are essential for ensuring its responsible use in industrial applications.

In summary, N,N-dimethylcyclohexylamine is a significant chemical substance with a wide range of applications, particularly in surfactant formulation, pharmaceuticals, and organic synthesis. Its unique properties and versatility continue to inspire research and development in various fields, highlighting its importance in both academic and industrial chemistry.

References

2024. Volumetric, Optical, and Spectroscopic Properties of Three Binary Mixtures of An Amine and Alcohols. Russian Journal of General Chemistry, 94(6).
DOI: 10.1134/s1070363224060161

2023. Combination of switchable hydrophilic solvent liquid-liquid microextraction with QuEChERS for trace determination of triazole fungicide pesticides by GC-MS. Analytical sciences : the international journal of the Japan Society for Analytical Chemistry, 39(3).
DOI: 10.1007/s44211-023-00324-6

1936. über Cyclohexylamin und N-Dimethylcyclohexylamin. Monatshefte für Chemie und verwandte Teile anderer Wissenschaften, 67(1).
DOI: 10.1007/bf01518870