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734055

Sigma-Aldrich

Tributyl(4,5-dihydrofuran-2-yl)stannane

97%

Synonym(s):

Tributyl(4,5-dihydrofuran-2-yl)tin

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About This Item

Empirical Formula (Hill Notation):
C16H32OSn
CAS Number:
125769-77-9
Molecular Weight:
359.13
MDL number:
MFCD18785742
UNSPSC Code:
12352103
PubChem Substance ID:
329764868
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.493

density

1.128 g/mL at 25 °C

SMILES string

CCCC[Sn](CCCC)(CCCC)C1=CCCO1

InChI

1S/C4H5O.3C4H9.Sn/c1-2-4-5-3-1;3*1-3-4-2;/h1H,2,4H2;3*1,3-4H2,2H3;

InChI key

QTYBKWIPVOTUQI-UHFFFAOYSA-N

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Application

Tributyl(4,5-dihydrofuran-2-yl)stannane is an organotin compound (or organostannane), which can be used as a reactant:
  • In the palladium-catalyzed Stille coupling reaction to prepare furan-containing aryl derivatives by reacting with various aryl halides.
  • To synthesize 2,3-dihydro-5-(2-methylphenyl)furan by coupling with 2-iodotoluene in the presence of a palladium catalyst.
  • In the chemoselective preparation of hexatrienes by the tandem palladium-catalyzed Heck and Stille coupling of bromohexenyl triflates and acrylates.

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBD4354V
MKBG3443

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The Pd (0)-catalysed coupling reactions of 2-(tri-n-butylstannyl)-3, 4-dihydrofuran and-5, 6-dihydropyran.
MacLeod D, et al.
Tetrahedron Letters, 31(42), 6077-6080 (1990)
Preparation of 1-(tri-n-butylstannyl) furanoid glycals and their use in palladium-mediated coupling reactions
Zhang H-C, et al.
Tetrahedron Letters, 34(10), 1571-1574 (1993)
A One-Pot Sequence of Stille and Heck Couplings: Synthesis of Various 1, 3, 5-Hexatrienes and Their Subsequent 6π-Electrocyclizations
von Zezschwitz P, et al.
Chemistry?A European Journal , 7(18), 4035-4046 (2001)

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