Description

(3,3′-Difluoro-(2,2′-bithiophene)-5,5′-diyl)bis(trimethylstannane) (CAS No. 1619967-09-7) is a high-purity organotin compound with the molecular formula C₁₄H₂₀F₂S₂Sn₂. This specialized reagent features a bithiophene core functionalized with fluorine atoms at the 3 and 3′ positions and trimethylstannyl groups at the 5 and 5′ positions, making it a valuable building block for advanced organic synthesis and materials science applications. The compound is particularly useful in Stille coupling reactions for the construction of conjugated systems in organic electronics. Supplied as a stable solid with >95% purity (GC), it is rigorously tested for moisture and oxygen sensitivity to ensure optimal performance. Proper handling under inert atmosphere is recommended to maintain integrity.

Properties

• CAS Number: 1619967-09-7
• Complexity: 320
• IUPAC Name: [4-fluoro-5-(3-fluoro-5-trimethylstannyl-2-thienyl)-2-thienyl]-trimethyl-stannane
• InChI: InChI=1S/C8H2F2S2.6CH3.2Sn/c9-5-1-3-11-7(5)8-6(10)2-4-12-8;;;;;;;;/h1-2H;6*1H3;;
• InChI Key: LHSHSFDCEZYLMZ-UHFFFAOYSA-N
• Exact Mass: 527.90126
• Molecular Formula: C14H20F2S2Sn2
• Molecular Weight: 527.9
• SMILES: C[Sn](C)(C)C1=CC(=C(S1)C2=C(C=C(S2)[Sn](C)(C)C)F)F
• Topological: 56.5
• Monoisotopic Mass: 529.90185
• Synonyms: 1619967-09-7, (3,3′-difluoro-[2,2′-bithiophene]-5,5′-diyl)bis(trimethylstannane), (3,3′-Difluoro-(2,2′-bithiophene)-5,5′-diyl)bis(trimethylstannane), 834-552-6, MFCD30543603, [4-fluoro-5-(3-fluoro-5-trimethylstannylthiophen-2-yl)thiophen-2-yl]-trimethylstannane, Stannane, 1,1′-(3,3′-difluoro[2,2′-bithiophene]-5,5′-diyl)bis[1,1,1-trimethyl-, C14H20F2S2Sn2, SCHEMBL19460979, SY100713, CS-0198569, D5436, D78057, (3,3 inverted exclamation mark -Difluoro-[2,2 inverted exclamation mark -bithiophene]-5,5 inverted exclamation mark -diyl)bis(trimethylstannane)

Application

This compound serves as a key precursor in the synthesis of fluorinated conjugated polymers for organic photovoltaic (OPV) devices and field-effect transistors (OFETs). Its dual stannane functionality enables efficient Stille cross-coupling reactions with various aryl halides. The fluorine substitution enhances electronic properties while maintaining processability. Researchers utilize it to develop novel semiconducting materials with tailored HOMO-LUMO levels. Particularly valuable for creating donor-acceptor copolymers in bulk heterojunction solar cells.

Safety and Hazards

GHS Hazard Statements

• H300+H310+H330 (100%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
• H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]
• H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]
• H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
• H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statements

• P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 2 (100%)
• Acute Tox. 1 (100%)
• Acute Tox. 2 (100%)
• Aquatic Acute 1 (100%)
• Aquatic Chronic 1 (100%)

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