| Identification | Back Directory | [Name]
Diethyl cyclohexylaminovinyl phosphate | [CAS]
20061-84-1 | [Synonyms]
Diethyl cyclohexylaminovinyl phosphate
DIETHYL CYCLOHEXYLAMINOVINYLPHOSPHONATE
Diethyl b-(Cyclohexylimino)ethylphosphonate
diethyl 2-(cyclohexylimino)ethylphosphonate
diethyl [2-(cyclohexylamino)vinyl]phosphonate
diethyl (E)-(2-(cyclohexylamino)vinyl)phosphonate
(E)-diethyl (2-(cyclohexylaMino)vinyl) phosphonate
N-[(E)-2-diethoxyphosphorylethenyl]cyclohexanamine
CYCLOHEXYLAMINOETHENEPHOSPHORIC ACID DIETHYL ESTER
[2-(Cyclohexylamino)-vinyl]-phosphonic acid diethyl ester
Phosphonic acid, 2-(cyclohexylamino)ethenyl-, diethyl ester
Phosphonic acid, P-[2-(cyclohexylamino)ethenyl]-, diethyl ester | [EINECS(EC#)]
243-492-4 | [Molecular Formula]
C12H24NO3P | [MDL Number]
MFCD00014287 | [MOL File]
20061-84-1.mol | [Molecular Weight]
261.3 |
| Chemical Properties | Back Directory | [Melting point ]
58-61 °C | [Boiling point ]
151-152 °C(Press: 0.04 Torr) | [density ]
1.05±0.1 g/cm3(Predicted) | [form ]
crystalline solid | [pka]
5.30±0.70(Predicted) |
| Hazard Information | Back Directory | [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.
|
|
|