Introduction：Basic information about Methyl (triphenylphosphoranylidene)acetate CAS 2605-67-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Methyl (triphenylphosphoranylidene)acetate Basic information
| Product Name: | Methyl (triphenylphosphoranylidene)acetate |
| Synonyms: | (TRIPHENYLPHOSPHORANYLIDENE)ACETIC ACID METHYL ESTER;AURORA KA-874;(CARBOMETHOXYMETHYLENE)TRIPHENYLPHOSPHORANE;(METHOXYCARBONYLMETHYLENE)TRIPHENYLPHOSPHORANE;METHYL (TRIPHENYLPHOSPHORANYLIDENE)ACETATE;(2-METHOXY-2-OXOETHYLIDENE)TRIPHENYLPHOSPHORANE;ACETIC ACID, (TRIPHENYLPHOSPHORANYLIDENE)-, METHYL ESTER;Triphenylphosphinideneacetic acid methyl ester |
| CAS: | 2605-67-6 |
| MF: | C21H19O2P |
| MW: | 334.35 |
| EINECS: | 220-018-4 |
| Product Categories: | Wittig Reagents;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction |
| Mol File: | 2605-67-6.mol |
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Methyl (triphenylphosphoranylidene)acetate Chemical Properties
| Melting point | 168-172 °C (lit.) |
| Boiling point | 165～170℃ |
| density | 1.17±0.1 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | Acetonitrile (Slightly), Chloroform (Slightly) |
| form | Powder |
| color | White to off-white |
| Water Solubility | insoluble |
| Sensitive | Air Sensitive |
| BRN | 618430 |
| InChI | InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3 |
| InChIKey | NTNUDYROPUKXNA-UHFFFAOYSA-N |
| SMILES | C(OC)(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 |
| CAS DataBase Reference | 2605-67-6(CAS DataBase Reference) |
| EPA Substance Registry System | Acetic acid, (triphenylphosphoranylidene)-, methyl ester (2605-67-6) |
Safety Information
| Hazard Codes | T,Xi |
| Risk Statements | 36/37/38-25 |
| Safety Statements | 22-24/25-36-26 |
| WGK Germany | 3 |
| Hazard Note | Irritant |
| TSCA | TSCA listed |
| HS Code | 29319090 |
| Storage Class | 11 - Combustible Solids |
Methyl (triphenylphosphoranylidene)acetate Usage And Synthesis
| Chemical Properties | white to off-white powder |
| Uses | - (Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates.
- used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.
- It is used in the preparation of (triphenylphosphoranylidene)-ketene.
- The Wittig reaction we performed in class involved the reaction of 2-nitrobenzaldehyde (1) with methyl (triphenylphosphoranylidene) acetate (2) to produce methyl (2E)-3-(2-nitrophenyl) acrylate (3) with a triphenylphosphine oxide (4) side product, and took place in a silica gel matrix to ensure even product dispersion for chromatography.
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| Uses | (Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Further, it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. It is used in the preparation of (triphenylphosphoranylidene)-ketene. |
| Uses | Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. Also used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine. |
| reaction suitability | reaction type: C-C Bond Formation |
| Purification Methods | Crystallise it by dissolving in it AcOH and adding pet ether (b 40-50o) to give colourless plates. UV max (A 1mm ): 222nm (865) and 268nm (116) [Isler et al. Helv Chim Acta 40 1242 1957]. [Beilstein 16 IV 977.] |
Methyl (triphenylphosphoranylidene)acetate Preparation Products And Raw materials
| Preparation Products | methyl 2-(7-hydroxybenzofuran-3-yl)acetate |
