Introduction：Basic information about (ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE CAS 1439-36-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE Basic information
| Product Name: | (ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE |
| Synonyms: | (METHYLCARBONYLMETHYLENE)TRIPHENYLPHOSPHORANE;(ACETYLMETHYLENE)TRIPHENYLPHOSPHORANE;1-TRIPHENYLPHOSPHANYLIDENE-PROPAN-2-ONE;1-(TRIPHENYLPHOSPHORANYLIDENE)-2-PROPANONE;triphenylphosphoranylidene-2-propanon;AURORA KA-1177;(Triphenylphosphoranylidene)acetone 98%;triphenylphosphoranylidene-2-propanone |
| CAS: | 1439-36-7 |
| MF: | C21H19OP |
| MW: | 318.35 |
| EINECS: | 215-878-2 |
| Product Categories: | Wittig Reagents;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction |
| Mol File: | 1439-36-7.mol |
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(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) |
Safety Information
| Risk Statements | 22-36/37/38 |
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
| RTECS | UC3900000 |
| HS Code | 29319090 |
| Storage Class | 11 - Combustible Solids |
(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.
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| 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
| Raw materials | Phosphonium, (2-oxopropyl)triphenyl-, iodide (1:1)-->Phosphonium, methyltriphenyl-, inner salt-->(TRIMETHYLSILYLMETHYL)TRIPHENYLPHOSPHONIUM IODIDE-->ACETONYLTRIPHENYLPHOSPHONIUM CHLORIDE-->ACETONYL TRIPHENYLPHOSPHONIUM BROMIDE-->BROMOACETONE |
| Preparation Products | (E)-6-Methyl-3,5-heptadien-2-one-->1-CYCLOPROPYL-PROPAN-2-ONE-->3-DECEN-2-ONE-->3-Hepten-2-one, 5-methyl--->E-(2-ETHOXY-PROPENYL)-TRIPHENYL-PHOSPHONIUM IODIDE SALT-->Acridin-3-ol |
