20195-60-2

Basic information

• Product Name: 1,1-dimethyl-2,3,4,5-tetraphenyl-1H-stannole
• CAS NO: 20195-60-2
• Molecular Formula: C₃₀H₂₆Sn
• Molecular Weight: 505.2374
• Mol File: 20195-60-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 580.3°C at 760 mmHg
• Flash Point: 298.1°C
• Vapor Pressure: 7.48E-13mmHg at 25°C
• CAS DataBase Reference: 1,1-dimethyl-2,3,4,5-tetraphenyl-1H-stannole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-dimethyl-2,3,4,5-tetraphenyl-1H-stannole(20195-60-2)
• EPA Substance Registry System: 1,1-dimethyl-2,3,4,5-tetraphenyl-1H-stannole(20195-60-2)

Safety Data

• Hazardous Substances Data: 20195-60-2(Hazardous Substances Data)

Usage

Type of compound

Organotin compound

Contains

Tin atom bonded to a cyclic hydrocarbon ring

Specific type

Stannole

Number of phenyl groups

Four

Number of methyl groups

Two

Reactivity

Highly reactive

Usage

Often used in organic synthesis as a reagent for various chemical reactions

Utility

Useful building block for the development of new organic compounds

Safety

Potentially hazardous properties, requires careful handling and storage according to proper safety protocols

Upstream product

• 21813-34-3 hexaphenylstannol 
• 74-88-4 methyl iodide 
• 917-54-4 methyllithium 
• 55690-98-7 1,1-dibromo-2,3,4,5-tetraphenylstannole 
• 753-73-1 dimethyltin dichloride 
• 21289-08-7 1,4-dilithio-1,2,3,4-tetraphenylbutadiene 
• 21289-08-7 (E,E)-(1,2,3,4-tetramethyl-1,3-butadien-1,4-ylidene)-dilithium 
• 431063-50-2 di(1,2,3,4,5-pentaphenyl-1-stanna-cyclopentadienyl) 
• 77904-06-4 1-bromo-1,2,3,4-tetraphenyl-4-(tribromostannyl)-1,3-butadiene 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 78479-57-9 2,3,4,5-Tetraphenyliodolium Tetraphenylborate 
• 34143-19-6 2,3,4,5-Tetraphenyliodolium Iodide 
• 34143-19-6 2,3,4,5-Tetraphenyliodolium Iodide Hydrate 
• 78479-58-0 2,3,4,5-Tetraphenyliodolium Hexachloroantimonate 
• 27766-75-2 1,4-Dibrom-1,2,3,4-tetraphenyl-cis,cis-butadien-(1,3) 
• 77904-14-4 1,4-Dichlor-cis,cis-1,2,3,4-tetraphenylbutadien-(1,3) 
• 20195-59-9 1,2,3,4,5-pentaphenyl-1H-borole 
• 97923-33-6 (CH₃)2Sn(C₄(C₆H₅)4I)I 
• 96969-75-4 (CH₃)2Sn(Br)C(C₆H₅)C(C₆H₅)C(C₆H₅)C(C₆H₅)Br 
• 96969-76-5 Cl(CH₃)2SnC(C₆H₅)C₂(C₆H₅)2C(C₆H₅)I 
• 13293-57-7 dimethyltin bis(acetate) 
• 62707-08-8 7-methyl-1,2,3,4,5,6-hexaphenyl-7-borabicyclo{2.2.1}heptadiene 
• 1056-77-5 2,3,4,5-tetraphenylfuran 
• 753-73-1 dimethyltin dichloride 

Relevant articles and documents

Formation of the first monoanion and dianion of stannole

The first syntheses of mono- and dianions of stannole were accomplished by transmetallation or reduction of the novel bi(1,1-stannole).

Synthesis and structures of bi(1,1-stannole)s

The synthesis and structures of bi(1,1-stannole)s are described. Treatment of 1-bromo-4-(dibromophenylstannyl)-1,3-butadiene with tert-butyllithium gives the bi(1,1-stannole) having a phenyl group on each tin atom, whereas treatment of 1-bromo-4-(tribromostannyl)-1,3-butadiene with phenyl- or bulky alkyllithiums gives the bi(1,1-stannole) having a phenyl or an alkyl group on each tin atom. The X-ray analysis of the tert-butyl-substituted bi(1,1-stannole) is also described. All bi(1,1-stannole)s display two shoulder absorption bands due to π-π* and σ-π* transitions. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

Electrochemical and photophysical properties of a series of group-14 metalloles

A series of six group-14 dimethyl- or diphenyl-tetraphenylmetallacyclopentadienes were synthesized and characterized by their spectroscopic and electrochemical properties. The group-14 elements investigated were silicon, germanium, and tin. (The compounds are designated according to the heteroatom and the substituent on the heteroatom, i.e., SiMe, SiPh, SnPh.) Five of the six compounds luminesce in both the solid state and in solution. The emission maxima of SiPh, GePh, and SnPh are invariant to a change in the heteroatom, while for SiMe, GeMe, and SnMe there is a strong dependence of the emission maxima on the identity of the heteroatom. SiMe emits at a longer wavelength than GeMe, while SnMe is not luminescent. The dramatic luminescence difference between the two tin compounds was investigated. 13C NMR coupling to 119/117Sn, observed in both SnMe and SnPh, was used to make 13C NMR resonance assignments. Qualitative results of semiempirical molecular orbital calculations support the 13C NMR assignments. The crystal structure data for SnPh was obtained at 20 °C: a = 10.353(2) A?, b = 16.679(2) A?, c = 9.482(1) A?, α = 99.91(1)°, β = 106.33(1)°, γ = 77.80(1)° with Z = 2 in space group P1. It is proposed that the increased electron density at tin in SnMe is responsible for the deactivation of the emissive state. The presence of phenyl substituents in SnPh serves to stabilize the emissive state and luminescence is observed.