N-Cyclohexyl-2-pyrrolidone

Product NameN-Cyclohexyl-2-pyrrolidone
CAS6837-24-7
MFC10H17NO
MW167.25
EINECS229-919-7
MOL File6837-24-7.mol

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	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29337900
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Oral Eye Dam. 1 Skin Corr. 1B

MSDS

Provider	Language
CHP	English
SigmaAldrich	English
ACROS	English
ALFA	English

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

Benzenemethanamine, N-(4-chloro-3-butyn-1-yl)-N-cyclohexyl-

1307661-20-6

6837-24-7

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

Preparation Products And Raw materials

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