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Sigma-Aldrich

Tributyl(phenylethynyl)tin

95%

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About This Item

Linear Formula:
C6H5C≡CSn[(CH2)3CH3]3
CAS Number:
3757-88-8
Molecular Weight:
391.18
MDL number:
MFCD00075186
UNSPSC Code:
12352103
PubChem Substance ID:
24860802

assay

95%

form

liquid

refractive index

n20/D 1.532 (lit.)

density

1.116 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)C#Cc1ccccc1

InChI

1S/C8H5.3C4H9.Sn/c1-2-8-6-4-3-5-7-8;3*1-3-4-2;/h3-7H;3*1,3-4H2,2H3;

InChI key

PYMPTRMDPJYTDF-UHFFFAOYSA-N

Application

Tributyl(phenylethynyl)tin can be used:
  • As a substrate in the palladium-catalyzed homocoupling of organostannanes to yield biaryl compounds.
  • To prepare various enynals, which are employed in the synthesis of substituted benzene derivatives catalyzed by nickel.
  • In one of the key synthetic steps for the preparation of β-alkynylcorroles.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT RE 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

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Efficient Synthesis of beta-Alkynylcorroles
Stefanelli M, et al.
European Journal of Organic Chemistry, 2015(31), 6811-6816 (2015)
Palladium-iminophosphine-catalyzed homocoupling of alkynylstannanes and other organostannanes using allyl acetate or air as an oxidant
Shirakawa E, et al.
Journal of Organometallic Chemistry, 670(1-2), 132-136 (2003)
A multicomponent approach to substituted benzenes involving sequential nickel-catalyzed reactions
ElDouhaibi AS, et al.
Tetrahedron, 62(49), 11460-11469 (2006)

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