ALLYLTRIPHENYLTIN

Base Information

• Chemical Name: ALLYLTRIPHENYLTIN
• CAS No.: 76-63-1
• Molecular Formula: C21H20 Sn
• Molecular Weight: 391.1
• European Community (EC) Number: 200-975-4
• NSC Number: 99168,227360
• UNII: WZ237DXN26
• DSSTox Substance ID: DTXSID70226896
• Mol file: 76-63-1.mol

Synonyms:Stannane,allyltriphenyl- (8CI); Stannane, triphenyl-2-propenyl- (9CI); Tin,allyltriphenyl- (6CI,7CI); 3-(Triphenylstannyl)-1-propene;Allyltriphenylstannane; Allyltriphenyltin; Dowco 187; ENT 50909; NSC 227360;NSC 99168; Triphenyl(2-propenyl)stannane

Chemical Property of ALLYLTRIPHENYLTIN

Chemical Property:

• Vapor Pressure: 6.42E-07mmHg at 25°C
• Melting Point: 71-74 °C(lit.)
• Boiling Point: 421.4°C at 760 mmHg
• Flash Point: >100
• PSA: 0.00000
• Density: 1,07 g/cm3
• LogP: 3.34280
• Water Solubility.: Insoluble in water
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 392.058703
• Heavy Atom Count: 22
• Complexity: 284

Purity/Quality:

98%,99%, ^*data from raw suppliers

Allyltriphenyltin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison. TWA 0.1 mg(Sn)/m³; STEL 0.2 mg(Sn)/m³ (skin).
• Hazard Codes: T,N
• Statements: 23/24/25-50/53
• Safety Statements: 26-27-28-45-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Tin Compounds, Organic
• Canonical SMILES: C=CC[Sn](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Allyltriphenylstannane can be used:As a reagent in the C-H phenylation of azoles catalyzed by palladium.As an allylating reagent in the alkylidene Meldrum′s acids allylation catalyzed by Sc(OTf)3.As a reagent in the total synthesis of an antifungal molecule (+)-ambruticin S. Allyltriphenyltin is an insect chemosterilants.

Technology Process of ALLYLTRIPHENYLTIN

There total 11 articles about ALLYLTRIPHENYLTIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.5%

triphenyltin chloride (639-58-7) + allylmagnesium bromide (1730-25-2) → allytriphenyltin (76-63-1)

Guidance literature:

In tetrahydrofuran; refluxing;;

DOI:10.1021/jo01124a008

Reference yield: 80.0%

triphenyltin chloride (639-58-7) + allyl bromide (106-95-6) → hexaphenylditin (1064-10-4) + allytriphenyltin (76-63-1)

Guidance literature:

With ammonium chloride; zinc; In tetrahydrofuran; water; byproducts: Ph3SnSnPh3; Ph3SnCl is added to THF/H2O (NH4Cl saturated) mixt. with excess of zinc powder, appropriate allyl bromide is added dropwise under stirring within 5 min, filtn. after 1 h of mixing, THF is removed, residue is treated with chloroform; extn. (chloroform), drying (Na2SO4), solvent is evapd., treated with petroleum ether or n-hexane, solvent is evapd., crystd. (ethanol);

DOI:10.1021/om00015a025

Reference yield: 75.0%

Mo(C5H5)(CO)(NO)(CH2CHCH2Sn(C6H5)3) (89958-47-4) → Mo(C5H5)(CO)(NO)(P(C6H5)3) (32660-56-3) + allytriphenyltin (76-63-1)

Guidance literature:

With triphenylphosphine; In toluene; A soln. of reagents in toluene was refluxed for 3 h (N2 atm.);; solvent was pumped off, ppt. was chromd. on silica gel with hexane-toluene;;

upstream raw materials:

triphenyltin chloride

allyl bromide

allylmagnesium bromide

allyltriethylgermane

Downstream raw materials:

C₁₈H₂₀OS

C₁₈H₂₀OS

(4RS,6RS)-6-(Phenylmethoxy)hept-1-en-4-ol

(4SR,6RS)-6-(Phenylmethoxy)hept-1-en-4-ol

Refernces

• 1、 Von Gyldenfeldt, Friederike,Marton, Daniele,Tagliavini, Giuseppe. "Wurtz-type reductive coupling reaction of allyl bromides and haloorganotins in cosolvent/H2O(NH4Cl)/Zn media as a route to allylstannanes and hexaaryldistannanes". . p. 906 - 913. Retrieved 2008/10/08.
• 2、 Ichinose, Yoshifumi,Oshima, Koichiro,Utimoto, Kiitiro. "Hydrostannation and Hydrogermylation of Allenes". . p. 2693 - 2695. Retrieved 2007/10/02.