1-(Triphenylphosphoranylidene)acetone
Basic information
- CAS
1439-36-7- Standard SMILES
CC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1- InChIKey
KAANTNXREIRLCT-UHFFFAOYSA-N- Molecular formula
- C21H19OP
- Average molar mass
- 318.3 g/mol
- Monoisotopic mass
- 318.11735222
Names & identifiers
- Preferred name
- 1-(Triphenylphosphoranylidene)acetone
- IUPAC
- 1-(triphenyl-λ5-phosphanylidene)propan-2-one
- English name
- (Acetylmethylene)triphenylphosphorane
- Molecular formula
- C21H19OP
- Molecular weight
- 318.35
Names & synonyms
2-Propanone, 1-(triphenylphosphoranylidene)-1-(Triphenylphosphoranylidene)acetoneAcetylmethylenetriphenylphosphoraneRefChem:428861215-878-21439-36-7(Acetylmethylene)triphenylphosphorane1-(Triphenylphosphoranylidene)propan-2-one1-(Triphenylphosphoranylidene)-2-propanone1-TRIPHENYLPHOSPHORANYLIDENE-2-PROPANONEMFCD00008774(Acetonylidenetriphenyl)phosphorane
Show more names
triphenylphosphoranylidene-2-propanon(2-Oxopropylidene)triphenylphosphoraneNSC 4073941-(TriphenyLphosphoranyLAURORA KA-1177idene)-2-propanoneTriphenyl(acetylMethylene)phospho
(Acetylmethylene)triphenylphosphine(Triphenylacetylmethylene)phosphorane2-Propanone, (triphenylphosphoranylidene)-1-(triphenyl-lambda5-phosphanylidene)propan-2-oneAcetylmethylene-triphenylphosphoraneAI3-63066EINECS 215-878-2Triphenylphosphoranylidene-2-propanone
Database identifiers
- CAS
1439-36-7- PubChem CID
- 15038
- DTXSID
DTXSID60162572- EC Number
- 215-878-2
- Nikkaji
- J40.756I
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 382
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Physicochemical properties
- Melting point
- 203 · 203-205 °C (lit.)
- Boiling point
- 478.5 · 478.5±28.0 °C(Predicted)
- Density
- 1.14 · 1.14
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Soluble in chloroform. Slightly soluble in methanol.
- form
- Powder
- color
- White to off-white
- Sensitive
- Air Sensitive
- BRN
- 750077 · 750077
- Stability
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- UC3900000
- hs_code
- 29319090
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Uses(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.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
113 records
Compound notes
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