ChemicalBook CAS DataBase List 2,6-Bis(trimethyltin)-4,8-dioctyloxybenzo[1,2-b:3,4-b]dithiophene

2,6-Bis(trimethyltin)-4,8-dioctyloxybenzo[1,2-b:3,4-b]dithiophene synthesis

5synthesis methods

Product Name:2,6-Bis(trimethyltin)-4,8-dioctyloxybenzo[1,2-b:3,4-b]dithiophene
CAS Number:1098102-95-4
Molecular formula:C32H54O2S2Sn2
Molecular Weight:772.32

2,6-DibroMo-4,8-bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene

1294515-75-5
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$45.00/2.5mg

1066-45-1
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$24.10/2g

2,6-Bis(trimethyltin)-4,8-dioctyloxybenzo[1,2-b:3,4-b]dithiophene

1098102-95-4
47 suppliers
$55.00/5mg

Yield: 72%

Reaction Conditions:

Stage #1:2,6-dibromo-4,8-bis(octyloxy)benzo[1,2-b:4,5-b']dithiophene with n-butyllithium in tetrahydrofuran;hexane at -78; for 0.75 h;Inert atmosphere;
Stage #2:trimethyltin(IV)chloride in tetrahydrofuran;hexane at -78 - 20; for 2 h;Inert atmosphere;

Steps:

2.4.5. 2,6-Bis(trimethyltin)-4,8-dioctyloxybenzo[1,2-b; 3,4-b]dithiophene (7)
Compound 6 (5.0 g, 8.3 mmol) was dissolved in tetrahydrofuran(THF) (100 mL) which was cooled down to 78 C under nitrogen.n-Butyllithium (n-BuLi) (7.3 mL, 2.5 M in n-hexane) was addedslowly over a period for 15 min, and then the reaction mixture wasstirred for 30 min. Then, trimethyltin chloride (18 mL, 1 M in nhexane)was added in one portion, and the reactant turned to clearrapidly. The resulting mixture was allowed to warm to room temperatureand stirred for 2 h. The reaction was quenched with coolwater (200 mL) and extracted with diethyl ether. The combinedorganic layer was washed with water, and dried over anhydrousMgSO4. After removing solvent under vacuum, the residue wasrecrystallized by ethyl alcohol twice. The compound 7 was obtained as a colorless solid with a yield of 72%. 1H NMR (500 MHz, CDCl3)d (ppm): 7.50 (s, 2H), 4.28 (t, J 6.4 Hz, 4H), 1.90e1.83 (quin,J 6.4 Hz, 4H), 1.60e1.53 (m, 4H), 1.36e1.29 (m, 16H), 0.88 (t,J 6.0 Hz, 6H), 0.44 (s, 18H). 13C NMR (500 MHz, CDCl3) d (ppm):143.40, 140.78, 134.32, 133.28, 128.31, 73.89, 32.15, 30.83, 29.73,29.64, 26.41, 22.99, 14.42. Anal. calcd (%) for C32H54O2S2Sn2: C,49.76; H, 7.05; found: C, 50.01; H, 7.12.

References:

Pola, Murali Krishna;Boopathi, Karunakara Moorthy;Padhy, Harihara;Raghunath, Putikam;Singh, Ashutosh;Lin, Ming-Chang;Chu, Chih-Wei;Lin, Hong-Cheu [Dyes and Pigments,2017,vol. 139,p. 349 - 360]