LITHIUM DICYCLOHEXYLAMIDE Property

solubility 

Partially soluble in benzene and hexanes; soluble in THF.

Safety

Hazard Codes 

F,C

Risk Statements 

17-34

Safety Statements 

16-26-27-36/37/39-45

RIDADR 

UN 3393 4.2/PG 1

WGK Germany 

3

HazardClass 

4.2

PackingGroup 

I

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H250Catches fire spontaneously if exposed to air

H261In contact with water releases flammable gas

H314Causes severe skin burns and eye damage

Precautionary statements

P231+P232Handle under inert gas. Protect from moisture.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P370+P378In case of fire: Use … for extinction.

LITHIUM DICYCLOHEXYLAMIDE Chemical Properties,Usage,Production

Uses

Lithium Dicyclohexylamide is used in processes for preparing 2-Dihalo-ribolactones as synthons for antiviral nucleosides via coupling reaction.

Reactivity Profile

Lithium Dicyclohexylamide performs as a strong base, allowing deprotonation of ketones, esters, aryl and allyl halides, alkyl dihalides, allenes, alkyl boron reagents, azulene and methylazulenes; used for the formation of formamides, glyoxylamides, oxomalonamides, and tartronamides.

Synthesis

Lithium Dicyclohexylamide could be prepared from the reaction of dicyclohexylamine with n-Butyllithium in hexanes and benzene at 0 °C; the solvent can then be removed under reduced pressure, and the resulting free-flowing solid can be dissolved in THF.
Both solution and solid are pyrophoric and air- and moisture-sensitive; also, the solid is spontaneously flammable in air. The reagent is corrosive and extremely destructive to tissues of the mucous membranes and the upper respiratory tract, eyes, and skin. Note that dicyclohexylamine is a suspected carcinogen and may cause chemical pneumonitis and pulmonary edema. Use in a fume hood.

References

1. Wilson, J. W.; Pelter, A.; Garad, M. V.; Pardasani, R. T 1993, 49, 2979.
2. Aldrich Chemical Co.; Material Safety Data Sheet.
3. Furlong, J. J. P.; Lewkowicz, E. S.; Nudelman, N. S. JCS(P2) 1990, 1461.