Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

332364

Sigma-Aldrich

Allyltriphenylstannane

97%

Synonym(s):

2-Propenyl-triphenylstannane, Allyltriphenyltin

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Looking for similar products? Visit Product Comparison Guide

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.[1]

Application

Allyltriphenylstannane can be used:
  • As a reagent in the C-H phenylation of azoles catalyzed by palladium.[2]
  • As an allylating reagent in the alkylidene Meldrum′s acids allylation catalyzed by Sc(OTf)3.[3]
  • As a reagent in the total synthesis of an antifungal molecule (+)-ambruticin S.[4]

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBN3943V
MKBD7182
MKAA2684
02009CH
02922BW

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Total synthesis of (+)-ambruticin S: probing the pharmacophoric subunit
Hanessian S, et al.
The Journal of Organic Chemistry, 75(16), 5601-5618 (2010)
Allyltriphenylstannane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
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)
Sc (OTf) 3-Catalyzed Conjugate Allylation of Alkylidene Meldrum′s Acids
Dumas AM and Fillion E
Organic Letters, 11(9), 1919-1922 (2009)
Journal of the American Chemical Society, 103, 1969-1969 (1981)

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service