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A15619 (1-Ethoxycarbonylethylidene)triphenylphosphorane, 97%

CAS Number
5717-37-3
Synonyms
(1-Carboethoxyethylidene)triphenylphosphorane
Ethyl 2-(triphenylphosphoranylidene)propionate

Stock No. Size Price ($) Quantity Availability
A15619-09 10g 74.80
A15619-14 25g 162.00
A15619-18 50g 288.00
A15619-30 250g 1136.00
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(1-Ethoxycarbonylethylidene)triphenylphosphorane, 97%

MDL
MFCD00009160
EINECS
227-215-4

Chemical Properties

Formula
C23H23O2P
Formula Weight
362.41
Melting point
154-160°
Storage & Sensitivity
Keep Cold. Air Sensitive.
Solubility
Soluble in water.

Applications

(1-Ethoxycarbonylethylidene)triphenylphosphorane is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals. It’s also a Horner-Wadsworth-Emmons reagent. It can be used for olefination. It can also be utilized for the synthesis of more complex compounds, such as (29S,37S)-isomer of malevamide E, a potent ion-channel inhibitor.

Notes

Air sensitive. Avoid contact with oxygen and air. Store away from oxidizing agent. Contains triphenylphosphine oxide.

Literature References

Yasumasa Koyama; Yuichi Fukakusa; Nobuo Kyomura; Saburo Yamagishi; Tadashi Arai. The structure of luteoreticulin, a nitro-containing metabolite of streptomyces luteoreticuli. Tetrahedron Letters. 1969, 10 (5), 355-358.

Vlark F. Beatty; Clive Jennings-White; and Mitchell A. Avery. Stereocontrolled synthesis of (2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the amino acid characteristic of microcystins and nodularin. J. Chem. Soc., Perkin Trans. 1. 1992, (13), 1637-1641.

Stable ylide which reacts with aldehydes to give ß-substituted methacrylic esters. See Appendix 1.

With acyl halides, gives allenic esters: Helv. Chim. Acta, 63, 438 (1980); Org. Synth. Coll., 7, 232 (1990):

Reacts with the carbonyl group of succinic anhydride giving an intermediate useful in the synthesis of 2,2-dialkylcyclopentane-1,3-diones: Synthesis, 845 (1986):

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
757112
Harmonized Tariff Code
2931.39
TSCA
No

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