103731-96-0

Basic information

• Product Name: [β-11C]Styrene
• Synonyms: [β-11C]Styrene
• CAS NO: 103731-96-0
• Molecular Weight: 103.141
• Mol File: 103731-96-0.mol

Chemical Properties

• CAS DataBase Reference: [β-11C]Styrene(CAS DataBase Reference)
• NIST Chemistry Reference: [β-11C]Styrene(103731-96-0)
• EPA Substance Registry System: [β-11C]Styrene(103731-96-0)

Safety Data

• Hazardous Substances Data: 103731-96-0(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 108-88-3 toluene 

Relevant articles and documents

Functionalisation of11C-labelled olefins via a Heck coupling reaction

A method for incorporation of 11C (β+, t1/2 = 20.3 min) in internal alkenes has been developed. [β-11C]Styrene and [1-11C]pent-l-ene were synthesized from benzaldehyde and butyraldehyde respectively, using [11C]methylenetri-o-tolylphosphorane in a Wittig reaction. The radiochemical yield based on analytical liquid chromatography was 85-90%. The 11C-labelled olefins were further coupled with several aromatic halides in a palladium mediated cross-coupling reaction forming the compounds (E)-[β-11C]stilbene) (4′-amino[β-11C]stilbene, (E)-[β-11C]stilbene-2′-methanol, (E)-3′-ethoxycarbonyl[β-11C]stilbene, (E)-4′-methyl[β-11C]stilbene, (E)-1-phenyl[1-11C]pent-1-ene and (E)-1-(4-aminophenyl)[1-11C]pent-l-ene. The reaction sequence was performed without purification of the intermediate 11C-labelled olefin. Radiochemical yields of the coupling products were 47-55% according to analytical liquid chromatography. The decay-corrected isolated radiochemical yield of (E)-[β-11C]stilbene was approximately 38% and the total synthesis time was 40 min, counted from the end of radionuclide production to the isolated product. In a typical experiment starting from 4.7 GBq [11C]methyl iodide, 450 MBq of (E)[β-11C]stilbene was obtained in a radiochemical purity higher than 95%. This method was also used for the synthesis of (E)-(β-13C)stilbene, which was used to verify the labelling position by 13C NMR. The Royal Society of Chemistry 2000.

Reactions of Recoiling 11C Atoms with Toluene

Formation of benzocyclobutene, a characteristic rearrangement product of tolylmethylenes, strongly suggest that these species are formed as intermediates in the reactions of recoiling carbon-11 atoms and toluene.Degradation and additive studies indicated that both singlet and triplet carbon atoms can lead to benzocyclobutene formation through insertion into ring C-H bonds.Styrene is also formed, predominantly by insertion of singlet C-11 atoms into a methyl C-H bond, followed by rearrangement of the resulting benzylmethylene.