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731625

Sigma-Aldrich

trans-1,2-Bis(tributylstannyl)ethene

97%

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Synonym(s):
(E)-1,2-Bis(tributylstannyl)ethane, (E)-1,2-Bis(tributylstannyl)ethylene, (E)-1,2-Bis(tributyltin)ethylene, (E)-1,2-Ethenediylbis[tributylstannane], (E)-Bis(tributylstannyl)ethene, 1,2-Ethenediylbis[tributylstannane], trans-1,2-Bis(tributylstannyl)ethylene, trans-Bis(tributylstannyl)ethene, trans-Bis(tributylstannyl)ethylene
Empirical Formula (Hill Notation):
C26H56Sn2
CAS Number:
14275-61-7
Molecular Weight:
606.14
MDL number:
MFCD01631299
UNSPSC Code:
12352103
PubChem Substance ID:
329764672
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.502

density

1.132 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

CCCC[Sn](CCCC)(CCCC)\C=C\[Sn](CCCC)(CCCC)CCCC

InChI

1S/6C4H9.C2H2.2Sn/c6*1-3-4-2;1-2;;/h6*1,3-4H2,2H3;1-2H;;

InChI key

VNKOWRBFAJTPLS-UHFFFAOYSA-N

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Application

trans-1,2-Bis(tributylstannyl)ethene can be used to prepare:
  • Polyarylenevinylene polymers having triphenylamine core moieties.
  • Two (E)-2-(2-(thiophen-2-yl)vinyl)thiophen based copolymers through Pd-catalyzed Stille coupling reaction.
  • Vinylstannanes by reacting with aryl halides, which in turn can be used in the synthesis of substituted pyridines.

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Tuning optical and electronic properties of poly (4, 4′-triphenylamine vinylene) s by post-modification reactions
Grigoras M, et al.
Dyes and Pigments, 113, 227-238 (2015)
A novel strategy for the synthesis of 2-arylpyridines using one-pot 6π-azaelectrocyclization
Kobayashi T, et al.
Tetrahedron Letters, 49(28), 4349-4351 (2008)
Synthesis, characterization, and field-effect properties of (E)-2-(2-(thiophen-2-yl) vinyl) thiophen-based donor-acceptor copolymers
Wang L, et al.
Polymer, 68, 302-307 (2015)
Brigitte Holzer et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(13), 2869-2882 (2019-11-16)
A reliable synthetic protocol toward a series of fused chalcogenopheno[1]benzochalcogenophene (CBC) building blocks was developed based on a Fiesselmann reaction. The obtained CBC units were applied in McMurry and Stille coupling reactions toward symmetric regioisomeric ene-linked dimers. These π-conjugated compounds

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