N,N-Dicyclohexylmethylamine Chemical Properties

Melting point:

193-194 °C

Boiling point:

265 °C(lit.)

Density 

0.912 g/mL at 25 °C(lit.)

vapor pressure 

7.52Pa at 25℃

refractive index 

n20/D 1.49(lit.)

Flash point:

231 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

clear liquid

pka

11.03±0.20(Predicted)

color 

Colorless to Light orange to Yellow

Water Solubility 

740mg/L at 25℃

BRN 

2074991

LogP

3.71 at 25℃

CAS DataBase Reference

7560-83-0(CAS DataBase Reference)

NIST Chemistry Reference

Cyclohexanamine, N-cyclohexyl-N-methyl-(7560-83-0)

EPA Substance Registry System

Cyclohexanamine, N-cyclohexyl-N-methyl- (7560-83-0)

Safety Information

Hazard Codes 

C

Risk Statements 

22-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2735 8/PG 2

WGK Germany 

2

RTECS 

HY4190000

F 

10-34

HazardClass 

8

PackingGroup 

III

HS Code 

29213000

Hazardous Substances Data

7560-83-0(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

N,N-Dicyclohexylmethylamine Usage And Synthesis

Uses

N,N-Dicyclohexylmethylamine is used as a reagent in the base preparation of 13C2- and 2H phenethylamines as internal standards for IDMS by Pd-catalyzed double carbonylation of aryl iodides in the presence of amine nucleophiles followed by deoxygenation.

Uses

N,N-Dicyclohexylmethylamine has been employed as:

• catalyst during O-phenylation of tertiary alcohol with organobismuth(V) compounds
• base during Pd-catalyzed 5-endo-trig cyclization of 1-(o-bromophenyl)-2-methylprop-2-en-1-ol

Definition

ChEBI: N-Cyclohexyl-N-methylcyclohexanamine is an amine.

Application

N,N-Dicyclohexylmethylamine has uses similar to those of the other cyclohexylamines, e.g., as a urethane foam catalyst.

Preparation

N,N-Dicyclohexylmethylamine is prepared by methylating dicyclohexylamine with dimethyl sulfate or by the Leuckart – Wallach reaction.

Synthesis

The general procedure for the synthesis of N-methyldicyclohexylamine from the compound (CAS:88374-60-1) is as follows: phenylboronic acid (1.0 equiv. for aliphatic N-oxides and 1.5 equiv. for pyridine N-oxides) was mixed with tertiary amine N-oxide (1 mmol) in dichloroethane (2 mL) at 80 °C and stirred. Subsequently, the reaction mixture was transferred to a pressure tube and the reaction was continued at 120 °C. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate and washed sequentially with water and sodium hydroxide solution (1 equiv., 3 x 5 mL). The organic layer was dried with anhydrous sodium sulfate and the solvent was evaporated and purified by column chromatography to afford the target product, N-methyl dicyclohexylamine.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 10, p. 909 - 913

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