N,N-Dicyclohexylmethylamine
[CAS# 7560-83-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amine salt (ammonium salt)
• Name: N,N-Dicyclohexylmethylamine
• Synonyms: N-Methyldicyclohexylamine
• Molecular Formula: C₁₃H₂₅N
• Molecular Weight: 195.34
• CAS Registry Number: 7560-83-0
• EC Number: 231-453-4
• SMILES: CN(C1CCCCC1)C2CCCCC2

Properties

• Density: 0.912
• Boiling point: 265 °C
• Refractive index: 1.49
• Flash point: 110 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07;GHS09 Danger
• Risk Statements: H301-H302-H311-H314-H318-H411
• Safety Statements: P260-P262-P264-P264+P265-P270-P273-P280-P301+P316-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P361+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1C	H314

• Transport Information: UN 2735

Discovery and Applications

N,N-Dicyclohexylmethylamine, commonly referred to as DCMA, is a chemical compound with notable applications in organic synthesis and industrial chemistry. Its structure consists of a central methylamine group with two cyclohexyl groups attached to the nitrogen atom. This configuration endows DCMA with distinctive properties that make it valuable in various chemical processes.

The discovery of N,N-Dicyclohexylmethylamine can be traced back to the need for versatile amines in synthetic chemistry. Researchers identified DCMA as an effective reagent due to its ability to stabilize reactive intermediates and interact with various electrophiles. Its unique combination of steric and electronic effects, provided by the cyclohexyl groups, enhances its utility in numerous chemical transformations.

One of the primary applications of N,N-Dicyclohexylmethylamine is as a reagent in organic synthesis. It functions as a base in various chemical reactions, particularly in the formation of amides, esters, and other functional groups. The compound’s bulky cyclohexyl groups provide steric hindrance that can influence the reactivity and selectivity of chemical processes. For instance, DCMA is used in the preparation of N,N-dicyclohexylurea, which is an important intermediate in pharmaceutical and agrochemical synthesis.

In addition to its role in organic synthesis, N,N-Dicyclohexylmethylamine is employed as a catalyst in certain chemical reactions. Its ability to form stable complexes with various substrates makes it a useful catalyst for reactions such as cyclization and polymerization. The compound's catalytic properties contribute to improved yields and selectivity in these processes, making it valuable in both research and industrial applications.

N,N-Dicyclohexylmethylamine is also used in the development of specialty chemicals and materials. Its chemical properties allow it to act as a stabilizing agent or an additive in the formulation of various products. For example, it is utilized in the synthesis of specialty polymers and resins, where its presence can enhance the physical properties and performance of the final materials.

Moreover, DCMA's applications extend to the field of pharmaceuticals, where it is used in the synthesis of complex molecules and drug intermediates. The compound’s ability to interact with various functional groups and stabilize reactive intermediates makes it an important tool in the development of new drug candidates.

Overall, N,N-Dicyclohexylmethylamine is a versatile compound with significant applications in organic synthesis, catalysis, and material science. Its unique chemical properties and reactivity make it a valuable reagent and catalyst in various chemical processes, contributing to advancements in both research and industrial chemistry.

References

2003. The Extremely High Specificity of N-Methyldicyclohexylamine for the Production of the Large-Pore Microporous AFI Material. Catalysis Letters, 88(3-4).
DOI: 10.1023/a:1024053504331

2008. 1,3-Dicyclo-hexyl-1-isonicotinoylurea monohydrate. Acta crystallographica. Section E, Structure reports online, 64(8).
DOI: 10.1107/s1600536808019430

2018. Metal-Substituted Microporous Aluminophosphates. Structure and Reactivity of Metals in Zeolite Materials.
DOI: 10.1007/430_2018_25