1-Pyrrolidino-1-cyclohexene Chemical Properties

Melting point:

113 °C

Boiling point:

114-115 °C/15 mmHg (lit.)

Density 

0.94 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5217(lit.)

Flash point:

103 °F

storage temp. 

2-8°C

pka

8.91±0.20(Predicted)

form 

Liquid

color 

Clear light yellow

Sensitive 

Air Sensitive

BRN 

114797

CAS DataBase Reference

1125-99-1(CAS DataBase Reference)

NIST Chemistry Reference

Pyrrolidine, 1-(1-cyclohexen-1-yl)-(1125-99-1)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

10-36/37/38-20/21/22

Safety Statements 

16-26-36/37/39

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29339980

MSDS

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

1-Pyrrolidino-1-cyclohexene Usage And Synthesis

Chemical Properties

clear light yellow liquid

Uses

1-Pyrrolidino-1-cyclohexene is a cyclic enamine that is used as an electron-rich dienophile in synthetic reactions.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 16, p. 1466, 1968 DOI: 10.1248/cpb.16.1466

Reactivity Profile

The enamine nitrogen and its β-carbon atom are nucleophilic, undergoing substitution or conjugate addition; they can take part in 1,2- or 1,4-cycloadditions; iminium salts act as electrophiles.

Synthesis

The most commonly used preparation method for these enamines is the acid-catalyzed condensation of a secondary amine with cyclohexanone. An example is the reaction of Pyrrolidine with cyclohexanone (eq 1). Using a preformed Titanium(IV) Chloride-amine complex with cyclohexanone greatly decreases the reaction time while maintaining high yields. This technique is also effective with functionalized cyclohexanones. When unsymmetrical tin(II) amides are allowed to react with cyclohexanone, good yields of enamines result.

Precautions

Readily reacts with water or atmospheric oxygen; should be stored under dry nitrogen.

1-Pyrrolidino-1-cyclohexene(1125-99-1)Related Product Information

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