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A14020 (Methoxycarbonylmethylene)triphenylphosphorane, 98%

CAS Number
2605-67-6
Synonyms
(Carbomethoxymethylene)triphenylphosphorane
Methyl (triphenylphosphoranylidene)acetate

Stock No. Size Price ($) Quantity Availability
A14020-14 25g 92.20
A14020-22 100g 265.00
A14020-36 500g 1001.00
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(Methoxycarbonylmethylene)triphenylphosphorane, 98%

MDL
MFCD00008455
EINECS
220-018-4

Chemical Properties

Formula
CH3O2CCH=P(C6H5)3
Formula Weight
334.36
Melting point
165-169°
Storage & Sensitivity
Air Sensitive. Store under Nitrogen. Ambient temperatures.
Solubility
Soluble in chloroform. Slightly soluble in ethanol and terahydrofuran. Insoluble in water.

Applications

(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.

Notes

Air sensitive. Incompatible with strong oxidizing agents.

Literature References

Stable ylide which undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. See also (Ethoxycarbonyl­methyl­ene)­triphenyl­phosphorane, A12896 and Appendix 1. For a detailed study of the reaction with benzaldehyde, see J. Org. Chem., 59, 1126 (1994). For use of high pressure to increase the yield and trans-selectivity of reaction with aromatic aldehydes, see: Liebigs Ann. Chem., 2135 (1983).

For tandem Wittig reaction and Cope rearrangement, see: J. Chem. Soc., Chem. Commun., 381 (1995):

Strong base, for example Na bis(TMS)amide, brings about elimination of methanol, giving ketenylidenetriphenylphosphorane, which reacts with ɑ-hydroxy-ketones, e.g. in the steroid series, to give butenolides, by acylation and Wittig cyclization: Chem. Ber., 113, 2038 (1980):

Review of phosphacumulene ylides: Angew. Chem. Int. Ed., 16, 349 (1977).

Dierkes, G.; Bongartz, A.; Guth, H.; Hayen, H. Quality Evaluation of Olive Oil by Statistical Analysis of Multicomponent Stable Isotope Dilution Assay Data of Aroma Active Compounds. J. Agric. Food Chem., 2012, 60 (1), 394-401.

Mears, P. R.; Thomas, E. J. Difluoroallylation using a 2-bromomethyl-1,1-difluoroalk-1-ene. Tetrahedron Lett. 2015, 56 (26), 3980-3981.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H315-H319-H335

Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
618430
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2931.39
TSCA
Yes

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