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A11709 (Formylmethylene)triphenylphosphorane, 97%, may cont. up to ca 3% water

CAS Number
2136-75-6
Synonyms
(Triphenylphosphoranylidene)acetaldehyde

Stock No. Size Price ($) Quantity Availability
A11709-09 10g 59.00
A11709-14 25g 136.00
A11709-22 100g 449.00
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(Formylmethylene)triphenylphosphorane, 97%, may cont. up to ca 3% water

MDL
MFCD00006994
EINECS
218-375-6

Chemical Properties

Formula
(C6H5)3P=CHCHO
Formula Weight
304.33
Melting point
183-188°
Storage & Sensitivity
Keep Cold. Air Sensitive.
Solubility
Soluble in Chloroform, Methanol.

Applications

(Formylmethylene)triphenylphosphorane is used as Wittig reagent. It is also used as Pharmaceutical Intermediates. It is employed as raw material in organic Synthesis, Agrochemicals.

Notes

Air Sensitive. Store at -20°C. Incompatible with strong oxidizing agents.

Literature References

Kenji Kumazawa; Yoshiyuki Wada and Hideki Masuda. Characterization of Epoxydecenal Isomers as Potent Odorants in Black Tea (Dimbula) Infusion.J. Agric. Food Chem. 2006, 54 (13), 4795-4801.

Zh. A. Krasnaya; S. A. Burova; V. S. Bogdanov; Yu. V. Smirnova. Synthesis of δ-hetaryl-α,α-dicarbonylalkadienes and a study of their isomerization.Chemistry of Heterocyclic Compounds. 1997, 33 410-422.

Stable ylide, which undergoes Wittig olefination with aldehydes, but not usually with ketones, to give enals: J. Chem. Soc., 1266 (1961); Angew. Chem. Int. Ed., 14, 486 (1975); Tetrahedron Lett., 3071 (1977). See Appendix 1. Reaction with aldehydes generally gives the thermodynamically more stable (E)-enal. Thus glyoxal gives trans,trans-muconic dialdehyde [(E),(E)-2,4-hexadienal]: Chem. Ber., 107, 710 (1974). The following sequence leads to (Z)-enals: Chem. Ber., 115, 161 (1982):

Wittig reaction followed by reduction with DIBAL-H has been used as a route to allylic alcohols. See, e.g.: J. Org. Chem., 47, 1373 (1982).

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

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

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. 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. 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
523797
Harmonized Tariff Code
2931.39
TSCA
No

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