DIETHYL CYCLOHEXYLAMINOVINYL PHOSPHATE Property

Melting point:

58-61 °C

Boiling point:

151-152 °C(Press: 0.04 Torr)

Density 

1.05±0.1 g/cm3(Predicted)

pka

5.30±0.70(Predicted)

form 

crystalline solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P310Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

DIETHYL CYCLOHEXYLAMINOVINYL PHOSPHATE Chemical Properties,Usage,Production

Uses

Diethyl β-(Cyclohexylimino)ethylphosphonate is used as a reagent for formylalkenation at carbonyl centers.^[1]

Preparation

Preparative Methods of Diethyl β-(Cyclohexylimino)ethylphosphonate: (EtO)2CHCH2P(O)(OEt)2 is prepared by reaction of Triethyl Phosphite with BrCH2CH(OEt)2. Acetal hydrolysis affords diethyl formylmethylphosphonate, which is combined with an equimolar quantity of cyclohexylamine in MeOH. The product is isolated by fractional distillation in the presence of K2CO3, to prevent acid-catalyzed dimerization, and at reduced pressure, followed by crystallization from cold pentane.^[1b] Yields are 65-75%. A modified procedure for imine formation uses MeCN as solvent with isolation of product from Et2O at -40 °C to afford white crystalline material in 70% yield.^[2]

storage

Crystalline material of Diethyl β-(Cyclohexylimino)ethylphosphonate is stable for several months when stored under anhydrous conditions at 0 °C.

Purification Methods

Purification of Diethyl β-(Cyclohexylimino)ethylphosphonate: distillation at reduced pressure. Crystallization from pentane at 0 °C.

References

1. (a) Nagata, W.; Hayase, Y. TL 1968, 4359. (b) Nagata, W.; Wakabayashi, T.; Hayase, Y. OS 1973, 53, 44. (c) Nagata, W.; Wakabayashi, T.; Hayase, Y. OS 1973, 53, 104. (d) Nagata, W.; Hayase, Y. JCS(C) 1969, 460.
2. Farnum, D. G.; Ghandi, M.; Raghu, S.; Reitz, T. JOC 1982, 47, 2598.