1-(Triphenylphosphoranyliden)aceton

1-(Triphenylphosphoranylidene)acetone

HCID 15038CAS 1439-36-7

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Grundinformationen

Standard-SMILES: CC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
InChIKey: KAANTNXREIRLCT-UHFFFAOYSA-N
Summenformel: C21H19OP
Durchschnittliche Molmasse: 318,3 g/mol
Monoisotopische Masse: 318,11735186

Namen und Bezeichner

Bevorzugter Name: 1-(Triphenylphosphoranylidene)acetone
IUPAC: 1-(triphenyl-λ5-phosphanylidene)propan-2-one
Lokaler Name: 1-(Triphenylphosphoranyliden)aceton
Englischer Name: (Acetylmethylene)triphenylphosphorane
Summenformel: C21H19OP
Molmasse: 318.35

Namen und Synonyme

2-Propanone, 1-(triphenylphosphoranylidene)-1-(Triphenylphosphoranylidene)acetoneAcetylmethylenetriphenylphosphoraneRefChem:428861215-878-21439-36-7(Acetylmethylene)triphenylphosphorane1-(Triphenylphosphoranylidene)propan-2-one1-(Triphenylphosphoranylidene)-2-propanoneMFCD00008774(Acetonylidenetriphenyl)phosphorane(Acetylmethylene)triphenylphosphine

Weitere Namen anzeigen

triphenylphosphoranylidene-2-propanon(2-Oxopropylidene)triphenylphosphoraneNSC 4073941-(TriphenyLphosphoranyLAURORA KA-1177idene)-2-propanoneTriphenyl(acetylMethylene)phospho

(Triphenylacetylmethylene)phosphorane2-Propanone, (triphenylphosphoranylidene)-C21H19OP1-(triphenyl-lambda5-phosphanylidene)propan-2-oneAcetylmethylene-triphenylphosphoraneAI3-63066EINECS 215-878-2Triphenylphosphoranylidene-2-propanone

Datenbank-Bezeichner

CAS: 1439-36-7
PubChem CID: 15038
DTXSID: DTXSID60162572
EC Number: 215-878-2
Nikkaji: J40.756I

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3,6
Polarare Oberfläche (TPSA): 17,1 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 1
Frei drehbare Bindungen: 4
Schwere Atome: 23
Formalladung: 0
Komplexität: 382

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesChemical shift

Physikochemische Eigenschaften

Schmelzpunkt: 203 · 203-205 °C (lit.)
Siedepunkt: 478.5 · 478.5±28.0 °C(Predicted)
Dichte: 1.14 · 1.14
storage temp.: Inert atmosphere,Room Temperature
Löslichkeit: Soluble in chloroform. Slightly soluble in methanol.
Aggregatzustand: Powder
Farbe: White to off-white
BRN: 750077 · 750077
Stabilität: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: InChI=1S/C21H19OP/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-17H,1H3
InChIKey: KAANTNXREIRLCT-UHFFFAOYSA-N
SMILES: C(=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1)C(=O)C
CAS Datenbank: 1439 · 1439-36-7(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Chemical: 2-Propanone, 1-(triphenylphosphoranylidene)-

Acetylmethylenetriphenylphosphorane: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29319090
RTECS-Nr.: UC3900000
risk_code: 22-36/37/38
safety_code: 22-24/25
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 1 Eintrag

Verwenden(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.