Structure of 287966-64-7
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 287966-64-7 |
| Formula : | C18H10Br2N2S |
| M.W : | 446.16 |
| SMILES Code : | BrC1=CC=C(C2=CC=C(C3=CC=C(Br)C=C3)C4=NSN=C42)C=C1 |
| English Name : | 4,7-Bis(4-bromophenyl)benzo[c][1,2,5]thiadiazole |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 87% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 3 - 20℃; for 10h; Inert atmosphere; | 3 Under nitrogen atmosphere, the intermediate product 2,1,3-benzothiadiazole-4,7-diphenyl (1.7 g, 5.9 mmol) was added to a three-necked flask with magnetron,N,N-dimethylformamide 3 mL,After benzothiadiazole-4,7-diphenyl is completely dissolved,Prepare solution A with a concentration of 1.96 mol/L, and lower the reaction system to 3 °C with an ice-water bath; N-bromosuccinimide (2.31 g, 12.97 mmol)Dissolved in 20 mL of N,N-dimethylformamide,Prepare solution B with a concentration of 0.65 mol/L,The ratio of the amount of N,N-dimethylformamide in solution B to the amount of N,N-dimethylformamide in solution A is 20:3. The reaction temperature was controlled at 3 °C,Slowly add solution B dropwise to solution A using a constant pressure funnel. After dripping,React for 10 hours at room temperature. Pour into 200 mL of distilled water, white precipitate appeared immediately, filter the white precipitate, wash with water three times, and dry at 100 °C to obtain the crude product.The crude product was purified by recrystallization from dichloromethane,2.3 g of high-purity 4,7-bis(4-bromophenyl)benzo[1,2,5]thiadiazole was obtained with a yield of 87%. |
| 78% | With bromine; iodine In chloroform at 20℃; for 12h; | |
| 78% | With bromine; iodine In chloroform at 20℃; for 12h; |
| 77% | With bromine; iodine In chloroform at 20℃; for 12h; | 2.2.4. 4,7-Bis(4-bromophenyl)benzo[c][1,2,5]thiadiazole (5) A solution of bromine (1.2 mL, 23.3 mmol) in chloroform(1.5 mL) was added dropwise to a mixture of 4 (288 mg, 1.0 mmol),iodine (15 mg, 0.06 mmol) and chloroform (4 mL). The resultingmixture was stirred at room temperature for 12 h. After workup,the solid was filtered off and washed sequentially with aqueousNaHSO3, water and methanol to afford the crude product. Recrystallizationin toluene gave the title compound as yellow needles 5.Yield: 350 mg (77%). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.86 (d,J 8.5 Hz, 4H), 7.77 (s, 2H), 7.68 (d, J 8.5 Hz, 4H). HRMS-EI (m/z):[M + H]+ calcd for C18H11Br2N2S: 444.9010; found: 444.9016. |
| With bromine; iodine In chloroform at 20℃; for 12h; | ||
| With bromine; iodine In dichloromethane Inert atmosphere; | ||
| With bromine; iodine In dichloromethane | ||
| With bromine; iodine In chloroform |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate In toluene at 90℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate In toluene at 90℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With potassium carbonate In toluene at 90℃; for 48h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 1: hydrogen bromide; bromine / water / 6 h / Reflux 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 3: bromine; iodine / chloroform / 12 h / 20 °C |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 27% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In toluene for 12h; Inert atmosphere; Reflux; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / tetrahydrofuran; water / 24 h / Inert atmosphere; Reflux 2: bromine; iodine / chloroform / 12 h / 20 °C | ||
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene 2: iodine; bromine / dichloromethane | ||
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate 2: bromine; iodine / chloroform |
| Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / 48 h / 110 °C / Inert atmosphere 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 10 h / 3 - 20 °C / Inert atmosphere |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 71% | With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 40 - 110℃; for 26h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 78% | With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate In toluene at 40 - 110℃; for 26h; Inert atmosphere; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; water / 5 h / 90 °C / Inert atmosphere 2: bromine; iodine / chloroform / 12 h / 20 °C | ||
| Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene 2: iodine; bromine / dichloromethane | ||
| Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / toluene / 48 h / 110 °C / Inert atmosphere 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 10 h / 3 - 20 °C / Inert atmosphere |