Cyclohexyl chloroformate Property

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

Risk Statements 

23/24/25-34

Safety Statements 

26-36/37/39

RIDADR 

3277

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Cyclohexyl chloroformate Chemical Properties,Usage,Production

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.