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Sigma-Aldrich

Allyltriphenylstannane

97%

Synonym(s):

2-Propenyl-triphenylstannane, Allyltriphenyltin

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About This Item

Linear Formula:
CH2=CHCH2Sn(C6H5)3
CAS Number:
76-63-1
Molecular Weight:
391.09
Beilstein/REAXYS Number:
3612762
EC Number:
200-975-4
MDL number:
MFCD00048162
UNSPSC Code:
12352103
PubChem Substance ID:
24859890
NACRES:
NA.22

assay

97%

form

solid

mp

71-74 °C (lit.)

SMILES string

C=CC[Sn](c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/3C6H5.C3H5.Sn/c3*1-2-4-6-5-3-1;1-3-2;/h3*1-5H;3H,1-2H2;

InChI key

NDUYAGLANMHJHF-UHFFFAOYSA-N

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General description

Allyltriphenylstannane is an organotin compound, which is generally used as allylating and radical chain transfer reagent. It is also used as a source of allyl radicals.

Application

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.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Palladium-Catalyzed Direct Arylations of Azoles with Aryl Silicon and Tin Reagents
Han W, et al.
Chemistry?A European Journal , 17(25), 6904-6908 (2011)
Allyltriphenylstannane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Total synthesis of (+)-ambruticin S: probing the pharmacophoric subunit
Hanessian S, et al.
The Journal of Organic Chemistry, 75(16), 5601-5618 (2010)
Journal of the American Chemical Society, 103, 1969-1969 (1981)
Sc (OTf) 3-Catalyzed Conjugate Allylation of Alkylidene Meldrum′s Acids
Dumas AM and Fillion E
Organic Letters, 11(9), 1919-1922 (2009)

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