N-Cyclohexyl-2-pyrrolidone Chemical Properties

Melting point:

12 °C

Boiling point:

154 °C7 mm Hg(lit.)

Density 

1.007 g/mL at 25 °C(lit.)

vapor pressure 

0.05 mm Hg ( 25 °C)

refractive index 

n20/D 1.499(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

pka

-0.49±0.20(Predicted)

color 

Colorless to Orange to Green

Water Solubility 

Soluble

BRN 

121832

InChI

InChI=1S/C10H17NO/c12-10-7-4-8-11(10)9-5-2-1-3-6-9/h9H,1-8H2

InChIKey

PZYDAVFRVJXFHS-UHFFFAOYSA-N

SMILES

N1(C2CCCCC2)CCCC1=O

CAS DataBase Reference

6837-24-7(CAS DataBase Reference)

EPA Substance Registry System

2-Pyrrolidinone, 1-cyclohexyl- (6837-24-7)

Safety Information

Hazard Codes 

Xn,T+,C

Risk Statements 

22-36/37/38-26-21/22-34

Safety Statements 

23-24/25-45-38-36/37/39-28A-26

RIDADR 

UN 2810 6.1/PG 2

WGK Germany 

1

RTECS 

UY5748450

TSCA 

Yes

HazardClass 

8

PackingGroup 

III

HS Code 

29337900

MSDS

• Language:English Provider:CHP
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-Cyclohexyl-2-pyrrolidone Usage And Synthesis

Uses

N-Cyclohexylpyrrolidone possesses excellent properties such as high boiling point, high solubility, and improved fabric leveling, and is safe and non-toxic to humans. Due to its superior performance, N-cyclohexylpyrrolidone products are widely used in fabric leveling agents, polymer solvents, and ink dispersants. Currently, N-cyclohexylpyrrolidone exhibits excellent leveling and dispersibility, strong solubility for polymers (especially polyimide compounds, mainly used as encapsulants for mobile phone screen protectors and high-speed rail motors), and can be used as a solvent during polymerization.

Chemical Properties

clear liquid

Safety Profile

Poison by ingestion. Moderately toxic by inhalation and slun contact. A severe skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Bis[(4-chlorophenyl)methyl](4-chloro-3-butynyl)amine (5) (31.8 mg, 0.090 mmol) was used as a raw material and reacted with rhodium trifluoroacetate dimer (Rh2(tfa)4, 1.18 mg, 0.018 mmol) under argon protection in a mixed solvent of toluene (1.0 mL) and water (0.01 mL) at a heated reflux for 10 hr. After the reaction was completed, the mixture was cooled down. After completion of the reaction, the mixture was cooled to room temperature and filtered through a short diatomaceous earth pad assisted with ethyl acetate. The filtrates were combined and concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane-ethyl acetate mixed solvent) to give N-cyclohexylpyrrolidone (15.5 mg, 82% yield) as a final oil. The structure of the product was confirmed by 1H NMR, 13C NMR and IR: 1H NMR (δ, ppm): 2.01 (quintuple peak, J = 7.7 Hz, 2H), 2.45 (t, J = 7.7 Hz, 2H), 3.26 (t, J = 7.7 Hz, 2H), 4.42 (s, 2H), 7.18 (d, J = 8.4 Hz, 2H), 7.30 ( d, J = 8.4 Hz, 2H); 13C NMR (δ, ppm): 17.78, 30.81, 46.02, 66.60, 128.87 (2C), 129.51 (2C), 133.51, 135.22, 174.97; IR (pure, cm-1): 3060, 3049, 2926, 1682 (C=O) , 1493, 1093, 1016, 802.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 19, p. 2458 - 2461

N-Cyclohexyl-2-pyrrolidone(6837-24-7)Related Product Information

• Povidone iodine
• 2-Pyrrolidinone
• Polyvinylpyrrolidone
• N-Vinyl-2-pyrrolidone
• Isocyanatocyclohexane
• N-Methyl-2-pyrrolidone
• N-CYCLOHEXYLFORMAMIDE
• N-Cyanoimido-S,S-dimethyl-dithiocarbonate
• N-Cyanoethyl-N-methylaniline
• N-Cyanoethyl-hydroxyethyl aniline
• CHES
• N-Cyclohexyl-4-methylbenzenesulfonamide
• N-Cyclohexylmaleimide
• 3-Cyclohexylaminopropanesulfonic Acid
• METHYL-2-PYRROLIDONE
• N-(CYCLOHEXYL)SUCCINIMIDE
• ALPHA-PYRIDOIN
• 3A-METHYL-DECAHYDRO-BENZO[D]PYRROLO[1,2-A]-IMIDAZOL-1-ONE