1-(Triphenylphosphoranylidene)acetone

HCID 15038CAS 1439-36-7
Substructure searchFind similar structures

Basic information

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
318.11735186

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-propanoneMFCD00008774(Acetonylidenetriphenyl)phosphorane(Acetylmethylene)triphenylphosphine
Show more names
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

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

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

Safety & regulation

GHS classification

GHS Classification · 4 items

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 · 2 items

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

Chemistry & industry

Applications · 1 item

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

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

113 records
New reaction record

Linked notes

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