Cyclohexyl chloroformate Chemical Properties

Boiling point:

87.5℃

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Hygroscopic, Refrigerator, under inert atmosphere

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

Oil

color 

Colourless

CAS DataBase Reference

13248-54-9(CAS DataBase Reference)

EPA Substance Registry System

Carbonochloridic acid, cyclohexyl ester (13248-54-9)

Safety Information

Risk Statements 

23/24/25-34

Safety Statements 

26-36/37/39

RIDADR 

3277

Cyclohexyl chloroformate Usage And Synthesis

Chemical Properties

transparency liquid

Uses

Cyclohexyl Chloroformate acts as a protecting group for amines and indoles in peptide synthesis.

Synthesis

The Preparative Method of Cyclohexyl Chloroformate: a 1 L round-bottomed flask equipped with a delivery tube extending to the bottom of the flask, a pressure-equalizing addition funnel and a cold-finger condenser cooled with dry ice-acetone were placed in an ice bath. The exit tube of the condenser was connected to a CaCl2 drying tube and a suitable trap for phosgene and HCl. Phosgene was introduced into the flask until 109 g (1.1 mol) had been condensed. The reaction flask was stirred while 100 g (1 mol) of cyclohexyl alcohol was added through the dropping funnel at a rate to keep the mixture in gentle reflux for 1 h. The flask was allowed to stand at room temperature with stirring for 2 h. The solution was then concentrated under reduced pressure at room temperature to remove HCl and the excess phosgene. The residue may be used without further purification.

Precautions

When stored for a prolonged period, it decomposes to CO2 and cyclohexyl chloride. Store in a refrigerator. Bottles may develop pressure and should be cooled before opening. Use in a fume hood. It is irritating to skin, eyes, and mucous membranes.

References

1. Fourneau, M. E.; Montaigne, M.; Puyal, J., J. Anales Soc. Espanol Fis. Quim. 1920, 73, 323.
2. McKay, F. C.; Albertson, N. F., J. Am. Chem. Soc. 1957, 79, 4686.
3. Sakakibara, S.; Shimonishi, Y.; Kishida, Y.; Okada, M.; Sugihara, H., Bull. Chem. Soc. Jpn 1967, 40, 2164.
4. Nishiuchi, Y.; Nishio, H.; Inui, T.; Kimura, T.; Sakakibara, S., Tetrahedron Lett. 1996, 37, 7529.
5. Mez, G.; Mihala, N.; Kóczán, G.; Hudecz, F., Tetrahedron 1998, 54, 6757.

Cyclohexyl chloroformate(13248-54-9)Related Product Information

• Cyclohexanecarboxylic acid
• Cyclohexanecarboxylic acid ethyl ester
• Benzyl chloroformate
• Cyclohexyl acetate
• 4-Nitrophenyl chloroformate
• Benzyl benzoate
• VINYL CHLOROFORMATE
• Isocyanatocyclohexane
• Phenyl chloroformate
• HEXYL CHLOROFORMATE
• 2-Ethylhexyl chloroformate
• 2-CHLOROBENZYL CHLOROFORMATE
• 4-BROMOPHENYL CHLOROFORMATE
• Cyclopentyl chloroformate
• 4-CHLOROPHENYL CHLOROFORMATE
• 2-Chloroethyl chloroformate
• Isopropyl chloroformate
• Isobutyl chloroformate