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| | Cyclohexyl chloroformate Basic information |
| | Cyclohexyl chloroformate Chemical Properties |
| | 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.
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| | Cyclohexyl chloroformate Preparation Products And Raw materials |
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