|
| (ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE Basic information |
| (ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE Chemical Properties |
Melting point | 203-205 °C (lit.) | Boiling point | 478.5±28.0 °C(Predicted) | density | 1.14 | storage temp. | Inert atmosphere,Room Temperature | solubility | Soluble in chloroform. Slightly soluble in methanol. | form | Powder | color | White to off-white | Sensitive | Air Sensitive | BRN | 750077 | Stability: | Stable. Combustible. Incompatible with strong oxidizing agents. | InChI | InChI=1S/C21H19OP/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-17H,1H3 | InChIKey | KAANTNXREIRLCT-UHFFFAOYSA-N | SMILES | C(=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)C | CAS DataBase Reference | 1439-36-7(CAS DataBase Reference) |
Risk Statements | 22-36/37/38 | Safety Statements | 22-24/25 | WGK Germany | 3 | RTECS | UC3900000 | HS Code | 29319090 |
| (ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE Usage And Synthesis |
Chemical Properties | white to light beige crystalline powder | Uses | (Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes. | reaction suitability | reaction type: C-C Bond Formation | Synthesis |
The preparative method of (Acetylmethylene)triphenylphosphorane: treatment of Triphenylphosphine with chloro- or Bromoacetone provides the phosphonium salt (eq 1). Deprotonation with a weak base such as bicarbonate in cold water provides the crude ylide which may by isolated by filtration.
| storage |
Handling, Storage, and Precautions: may be handled in atmosphere for short periods; will decompose in water at pH > 9.
|
| (ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE Preparation Products And Raw materials |
|