(Formylmethylene)triphenylphosphorane

• Catalog No.: A11709
• CAS Number: 2136-75-6
• M. F.: C20H17OP
• M. W.: 304.322141
• Purity: 97%, may cont. up to ca 3% water

SYNONYMS

• Title: (甲酰基亚甲基)三苯基磷烷
• IUPAC name: 2-(triphenyl-λ^5-phosphanylidene)acetaldehyde
• IUPAC Traditional name: 2-(triphenyl-λ^5-phosphanylidene)acetaldehyde
• Synonyms: (Triphenylphosphoranylidene)acetaldehyde

DATABASE IDS

• EC Number: 218-375-6
• MDL Number: MFCD00006994
• Beilstein Number: 523797
• CAS Number: 2136-75-6

PROPERTIES

• Purity: 97%, may cont. up to ca 3% water
• Melting Point: 183-188°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• Storage Warning: Air Sensitive
• TSCA Listed: 否

REFERENCES

• 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).