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414492

Sigma-Aldrich

2-(Tributylstannyl)thiophene

97%

Synonym(s):

2-(Tributyltin)thiophene, 2-Thienyltributyltin, Tributyl(thiophen-2-yl)stannate, Tributyl-2-thienylstannane, Tributylthiophen-2-ylstannane

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About This Item

Empirical Formula (Hill Notation):
C16H30SSn
CAS Number:
54663-78-4
Molecular Weight:
373.18
MDL number:
MFCD00192513
UNSPSC Code:
12352103
PubChem Substance ID:
24865938
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.518 (lit.)

bp

155 °C/0.1 mmHg (lit.)

density

1.175 g/mL at 25 °C (lit.)

SMILES string

CCCC[Sn](CCCC)(CCCC)c1cccs1

InChI

1S/C4H3S.3C4H9.Sn/c1-2-4-5-3-1;3*1-3-4-2;/h1-3H;3*1,3-4H2,2H3;

InChI key

UKTDFYOZPFNQOQ-UHFFFAOYSA-N

Application

2-(Tributylstannyl)thiophene has been used to synthesize diphenylquinoxaline monomer for the electrochromism polymers. It can also be used as a reactant in Stille coupling reaction.

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)

221.0 °F - closed cup

Flash Point(C)

105 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK6797
MKCH4280
SHBJ7924
SHBJ6519
SHBJ0646

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Sigma-Aldrich

T50202

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Tetrahedron Letters, 49(8), 1328-1330 (2008)
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2,5-Bis(thiophene) and 2,5-bis(ethylenedioxy-thiophene) (EDOT) derivatives of 3,6-diethoxy-1,4-benzoquinone (para isomers) were prepared by Stille coupling between the 2,5-dibromo-3,6-diethoxy-1,4-benzoquinone precursors and (n-Bu)3Sn-R (R = 2-thiophenyl or 3,4-ethylenedioxy-2-thiophenyl) reagents. In a parallel series of experiments 2,6-bis(thiophene) and 2,6-EDOT-3,5-diethoxy-1,4-benzoquinone (meta isomers) were synthesized by
Two-dimensional structural motif in thienoacene semiconductors: Synthesis, structure, and properties of tetrathienoanthracene isomers.
Brusso JL, et al.
Chemistry of Materials, 20(7), 2484-2494 (2008)
John A Roque et al.
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Hypoxia presents a challenge to anticancer therapy, reducing the efficacy of many available treatments. Photodynamic therapy is particularly susceptible to hypoxia, given that its mechanism relies on oxygen. Herein, we introduce two new osmium-based polypyridyl photosensitizers that are active in
Anna Nowakowska-Oleksy et al.
Journal of fluorescence, 21(1), 169-178 (2010-07-14)
A few new phenoxazine-based conjugated monomers were synthesized, characterized, and successfully used as semiconducting materials. The phenoxazine-based oligomers have low ionization potentials or high-lying HOMO levels (~4.7 eV), which were estimated from cyclic voltammetry. Conjugated oligomers offer good film-forming, mechanical and
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