76-63-1

Basic information

• Product Name: ALLYLTRIPHENYLTIN
• Synonyms: TINALLYLTRIPHENYL;TRIPHENYLALLYLTIN;allyltriphenyl-stannan;allyltriphenylstannane;dowco187;ent50909;triphenyl-2-propenyl-stannan;ALLYLTRIPHENYLTIN
• CAS NO: 76-63-1
• Molecular Formula: C21H20Sn
• Molecular Weight: 391.09
• EINECS: 200-975-4
• Product Categories: Classes of Metal Compounds;Sn (Tin) Compounds;Typical Metal Compounds;Chemical Synthesis;Organometallic Reagents;Organotin;Organotins
• Mol File: 76-63-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 71-74 °C(lit.)
• Boiling Point: 421.4°C at 760 mmHg
• Flash Point: >100
• Appearance: /solid
• Density: 1,07 g/cm3
• Vapor Pressure: 6.42E-07mmHg at 25°C
• Water Solubility: Insoluble in water
• BRN: 3612762
• CAS DataBase Reference: ALLYLTRIPHENYLTIN(CAS DataBase Reference)
• NIST Chemistry Reference: ALLYLTRIPHENYLTIN(76-63-1)
• EPA Substance Registry System: ALLYLTRIPHENYLTIN(76-63-1)

Safety Data

• Hazard Codes: T,N
• Statements: 23/24/25-50/53
• Safety Statements: 26-27-28-45-60-61
• RIDADR: UN 3146 6.1/PG 3
• WGK Germany: 3
• RTECS: WH6705000
• TSCA: No
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 76-63-1(Hazardous Substances Data)

Usage

Description

Allyltriphenylstannane, also known as allyltriphenyltin, is an organotin compound characterized by its needle-like crystalline structure. It is soluble in most organic solvents and is widely recognized for its utility as an allylating and radical chain transfer reagent. This versatile compound also serves as a source of allyl radicals, making it a valuable asset in various chemical reactions and applications.

Uses

Used in Chemical Synthesis:
Allyltriphenyltin is used as an allylating reagent for the C-H phenylation of azoles, which is catalyzed by palladium. This application is crucial in the synthesis of complex organic molecules and contributes to the development of novel chemical compounds with potential applications in various industries.
Used in Alkylidene Meldrum's Acids Allylation:
In the alkylidene Meldrum's acids allylation, catalyzed by Sc(OTf)3, allyltriphenyltin plays a vital role as an allylating reagent. This process is essential for the synthesis of various organic compounds, including those with potential pharmaceutical or industrial applications.
Used in Total Synthesis of Antifungal Molecules:
Allyltriphenyltin is employed as a reagent in the total synthesis of (+)-ambruticin S, an antifungal molecule. This application highlights the compound's importance in the development of new antifungal agents, which are crucial for treating various fungal infections.
Used in Insect Chemosterilants:
Allyltriphenyltin is also utilized as an insect chemosterilant, playing a significant role in pest control and management. By disrupting the reproductive capabilities of insects, this compound contributes to the development of environmentally friendly and sustainable pest control strategies.

Hazard

A poison.

InChI:InChI=1/3C6H5.C3H5.Sn/c3*1-2-4-6-5-3-1;1-3-2;/h3*1-5H;3H,1-2H2;/rC21H20Sn/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h2-17H,1,18H2

Upstream product

• 639-58-7 triphenyltin chloride 
• 106-95-6 allyl bromide 
• 1730-25-2 allylmagnesium bromide 
• 4167-90-2 lithium triphenylstannide 
• 463-49-0 1,2-propanediene 
• 892-20-6 triphenylstannane 
• 89958-47-4 Mo(C₅H₅)(CO)(NO)(CH₂CHCH₂Sn(C₆H₅)3) 
• 107-05-1 3-chloroprop-1-ene 
• 1793-90-4 allyltriethylgermane 
• 7646-78-8 tin(IV) chloride 

Downstream Products

• 2114-42-3 allylcyclohexane 
• 64198-20-5 3-cyclohexylbutyronitrile 
• 102776-07-8 (1S,2R)-1-Methylsulfanyl-1-phenyl-pent-4-en-2-ol 
• 102776-07-8 (1S,2S)-1-Methylsulfanyl-1-phenyl-pent-4-en-2-ol 
• 17180-49-3 2-methyl-1-phenylpent-4-en-1-one 
• 3112-87-6 1-methyl-4-(prop-2-ene-1-sulfonyl)benzene 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 389887-83-6 allyltridurylsilane 
• 144026-89-1 allylperoxytriphenyltin 
• 144026-91-5 4-triphenylstannyl-1,2-dioxolane 
• 144026-90-4 3-(triphenylstannyl)allyl hydroperoxide 
• 79634-85-8 allyl triphenylstannanedithiocarboxylate 
• 135039-69-9 ClCF₃(C₆H₅)3SnCH₂C₃H₃ 

Relevant articles and documents

Nucleophilicity vs basicity in the reaction of sodium tert-butoxide with β-stannyl ketones

The reaction of 3-stannyl-1,2,3-triphenyl- and 3-stannyl-1,3-diphenyl-2-methylpropanones with sodium tert-butoxide in either t-BuOH or dimethyl sulfoxide (DMSO) as solvent leads to elimination and/or substitution products. The composition of the product m

The effect of ligands, solvent and temperature on the reactions of allyltin(IV) compounds with singlet oxygen

The reaction of singlet oxygen with a variety of allyltin compounds CH2=CHCH2SnR3 (R3 = Me3, Bu3, allyl3, (cyclo-C6H11)3, Ph3, allylBu2, Bu2Cl, Bu2OAc, allylCl2, allylCl2bipy) has been investigated, and the allylperoxytin compounds, 3-stannylallyl hydroperoxides, and 4-stannyl-1,2-dioxolanes which result from M-ene, H-ene and cycloaddition processes, respectively, have been identified by NMR spectroscopy.As the tin centre becomes more electropositive, as indicated by the 13C NMR shift of the allylic CH2 group, the proportion of the M-ene reaction increases, and when δCH2 is above about 23.7, the allylperoxytin compound is the only product.An exception to this rule is tetraallyltin, δCH2 16.13, which similarly shows only the M-ene reaction.This is tentatively ascribed to the special effect of hyperconjugation between the C-Sn ?-bond and the remaining ?-systems.A polar solvent favours the M-ene reaction.The cycloaddition reaction is favoured by low temperature, and at -70 deg C in a non-polar solvent it may become the major route.Diallylmercury and allylmercury chloride react with singlet oxygen to show only the M-ene reaction, but also undergo extensive photosensitized decomposition.With 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD), allylmercury chloride shows only the M-ene reaction.

Transition-metal complexes corresponding to the insertion into a group 4B element-carbon bond. 3. Reactivity of complexes with unsaturated carbon-carbon bonds. Crystal structure of (η5-cyclopentadienyl)(triphenylgermyl) (η3-hexenyl) nitrosylmolybdenum

Anions of the type [(η5-C5H5)(CO)(L)(M4BPh 3)MT]- (L = CO, NO; M4B - Si, Ge, Sn; MT = Mn, Mo, W) react with allyl halides, affording neutral σ-bonded alkenyl derivatives. These new complexes can rearrange to η3-allyl complexes and also lose (allyl)M4B to give η2-allyl complexes. According to the nature of both the transition metal and the group 4B metal η1, η3, or η2 complexes are obtained. A mechanism for these successive reactions is proposed. Butenyl and hexenyl iodides also react with the anions, affording η1 complexes that can eliminate CO and rearrange to a η3 ligand as shown by X-ray structure determination.