2-(triphenyl-λ5-phosphanylidene)acetaldehyde

• ChemBase ID: 69431
• Molecular Formular: C20H17OP
• Molecular Mass: 304.322141
• Monoisotopic Mass: 304.10170179
• SMILES: P(=CC=O)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: O=CC=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C20H17OP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H
• InChIKey: CQCAYWAIRTVXIY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(triphenyl-λ^5-phosphanylidene)acetaldehyde; 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde
• IUPAC Traditional name: 2-(triphenyl-λ^5-phosphanylidene)acetaldehyde; 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde
• Synonyms: (Triphenylphosphoranylidene)acetaldehyde; (Formylmethylene)triphenylphosphorane; (Formylmethylene)triphenylphosphorane; (Formylmethylene)triphenylphosphorane; (Triphenylphosphoranylidene)acetaldehyde; Formylmethylenetriphenylphosphorane; 2-(Triphenylphosphoranylidene)-acetaldehyde; (2-Oxoethylidene)triphenylphosphorane; (Triphenylphosphoranylidene)acetaldehyde; (甲酰基亚甲基)三苯基磷烷; (甲酰亚甲基)三苯基正膦; 甲酰甲撑基三苯基磷

Database IDs

• CAS Number: 2136-75-6
• EC Number: 218-375-6
• MDL Number: MFCD00006994
• Beilstein Number: 523797
• PubChem SID: 162035157; 24856960
• PubChem CID: 75051

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.1108
• LogD (pH = 7.4): 5.1108
• Log P: 5.1108
• Molar Refractivity: 92.7414 cm^3
• Polarizability: 36.27359 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 183-188°C; 184-187 °C; 185-188 °C(lit.); 185-188°C; 185-188°C

Safety Information

• Storage Warning: Air Sensitive; IRRITANT; Irritant/Air Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95% (NT/PNMR); 95%; 95+%; 97%; 97%, may cont. up to ca 3% water; 98%
• Grade: technical
• Loss on Drying: ≤2% loss on drying, 110°C
• Linear Formula: HCOCH=P(C6H5)3

DETAILS

Sigma Aldrich - 280933

Application
Wittig reagent for the conversion of aldehydes and ketones to two-carbon homologated, α,β-unsaturated carbonyl compounds.1,2
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 47720

Other Notes
Wittig reagent for the stereoselective synthesis of Z-α,β-unsaturated aldehydes1

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).