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2605-67-6 molecular structure
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methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate

ChemBase ID: 67362
Molecular Formular: C21H19O2P
Molecular Mass: 334.348121
Monoisotopic Mass: 334.11226648
SMILES and InChIs

SMILES:
P(=CC(=O)OC)(c1ccccc1)(c1ccccc1)c1ccccc1
Canonical SMILES:
COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
InChI:
InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3
InChIKey:
NTNUDYROPUKXNA-UHFFFAOYSA-N

Cite this record

CBID:67362 http://www.chembase.cn/molecule-67362.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate
methyl 2-(triphenyl-λ5-phosphanylidene)acetate
IUPAC Traditional name
methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate
methyl 2-(triphenyl-λ5-phosphanylidene)acetate
Synonyms
Carbomethoxymethylene triphenylphosphorane
(Methoxycarbonylmethylene)triphenylphosphorane
Methyl (triphenylphosphoranylidene)acetate 98%
(Carbomethoxymethylene)triphenylphosphorane
Methyl (triphenylphosphoranylidene)acetate
Methyl (triphenylphosphoranylidene)acetate
(Methoxycarbonylmethylene)triphenylphosphorane
Methyl(triphenylphosphoranylidene)acetate
(三苯基膦烯)乙酸甲酯
甲氧羰基亚甲基三苯基正磷
甲氧甲酰基亚甲基三苯基膦
(甲氧基羰基亚甲基)三苯基膦烷
CAS Number
2605-67-6
EC Number
220-018-4
MDL Number
MFCD00008455
Beilstein Number
618430
PubChem SID
24849709
162033097
PubChem CID
17453

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 5.8956  LogD (pH = 7.4) 5.8956 
Log P 5.8956  Molar Refractivity 98.4491 cm3
Polarizability 38.770615 Å3 Polar Surface Area 26.3 Å2
Rotatable Bonds Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
159-162°C expand Show data source
165-169°C expand Show data source
168-172 °C expand Show data source
168-172 °C(lit.) expand Show data source
Storage Condition
Refrigerator expand Show data source
Storage Warning
Air Sensitive expand Show data source
IRRITANT expand Show data source
Irritant expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
false expand Show data source
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥97.0% (CH) expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
(C6H5)3P=CHCO2CH3 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 157929 external link
Application
Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters.1 Also used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.2
Packaging
25, 100 g in poly bottle
5 g in glass bottle

REFERENCES

REFERENCES

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  • • For tandem Wittig reaction and Cope rearrangement, see: J. Chem. Soc., Chem. Commun., 381 (1995):
  • • Review of phosphacumulene ylides: Angew. Chem. Int. Ed.,16, 349 (1977).
  • • 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).
  • • 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):
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PATENTS

PATENTS

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INTERNET

INTERNET

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