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5,5'-Bis(trimethylstannyl)-2,2'-bithiophene

  • CAS No. 143367-56-0

  • Cat. No. CS-0375726
  • Molecule weight491.87
  • Purity≥96%
  • MDL No.MFCD21363046

*For research and further manufacturing use only, not for direct human use.

5,5'-Bis(trimethylstannyl)-2,2'-bithiophene|CS-0375726

Structure of 143367-56-0

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General Information

  • CAS No. 143367-56-0
  • Cat. No. CS-0375726
  • Purity ≥96%
  • MDL No. MFCD21363046
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₂₂S₂Sn₂
  • Molecular Weight 491.87
  • Synonym(s) 5,5'‐ bis(triMethylstannyl)‐ 2,2'‐bithiophene
  • SMILES C[Sn](C)(C)C1=CC=C(C2=CC=C([Sn](C)(C)C)S2)S1

Description

5,5'-Bis(trimethylstannyl)-2,2'-bithiophene features two trimethylstannyl groups flanking a bithiophene core, delivering high stability and exceptional reactivity in Stille coupling processes. This stannane moiety integrates readily into conjugated polymer architectures, enabling efficient construction of functional organic semiconductors with tailored electronic properties.

Application

5,5'-Bis(trimethylstannyl)-2,2'-bithiophene serves as a versatile Stannylation building block for the palladium-catalyzed construction of conjugated oligothiophenes and functionalized π-systems. Its stannyl groups enable efficient cross-coupling reactions with aryl halides and triflates under standard Suzuki-Miyaura conditions, offering high regioselectivity and excellent functional group tolerance. The molecule exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis of advanced materials and optoelectronic scaffolds.

Safety Information

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GHS Pictogram :
GHS No : GHS06,GHS09
Signal Word : Danger
UN#: 3146
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H300+H310+H330-H410
Precautionary Statements : P260-P262-P264-P270-P271-P273-P280-P284-P302+P352-P304+P340-P330-P361+P364-P391-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   4.567
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   3

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