Category: 2255-80-3

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2255-80-3 as follows. name: 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole

A mixture of compound (1) 4-Bromo-7-methyl-benzo[1,2,5]thiadiazole (4.582 g, 20.00 mmol), tributyl-thiophen-2-yl-stannane (8.956 g, 24.00 mmol) and 3.0 mol % of tetrakis(triphenylphosphine) palladium [Pd(PPh3)4] (0.693 g, 0.600mmol) in N,N-dimethylformamide (DMF) was stirred for 24 hours at 90 C under N2 atmosphere. A portion of 100mLof water was added the mixture and allowed to cool to room temperature. The mixture was extracted with ethyl acetate (EA) and the extracted organic layer was dried over anhydrous MgSO4. The organic solvent was removed by using a rotary evaporator. The crude product was purified by column chromatography on silica gel using EA/n-hexane. The yield of dark brown liquid was 4.820 g (77.95%). 1H-NMR (400 MHz, CDCl3, ppm): delta 8.05?8.04 (dd, J1 = 3.2 Hz, J2 =2.1 Hz, 1H), 7.76?7.74 (d, J = 6.9 Hz, 1H), 7.42?7.37 (m,1H), 7.19?7.16 (dd, J1 = 5.1 Hz,J2 = 3.6 Hz, 1H), 2.75 (s, 3H). 13C NMR (100 MHz, CDCl3, ppm): delta 156.75, 152.82, 139.59,130.35, 128.31, 127.84, 126.93, 126.64, 125.86, 125.08, 17.92. Anal. Calcd. for C11H8N2S2: C,56.87; H, 3.47; N, 12.06; S, 27.60. Found: C, 56.77; H, 3.39; N, 12.02; S, 27.53.

According to the analysis of related databases, 2255-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Sylvianti, Nadhila; Marsya, Mutia Anissa; Kim, Youn Hwan; Park, Chan-Young; Chang, Dong Wook; Moon, Doo Kyung; Kim, Joo Hyun; Molecular Crystals and Liquid Crystals; vol. 653; 1; (2017); p. 78 – 83;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2255-80-3, name is 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2255-80-3, name: 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole

Synthesis of Compound A-4-Bromo-7-dibromomethyl-2,1,3-benzothiadiazole A mixture of 4-bromo-7-methyl-2,1,3-benzothiadiazole (45.82 g, 200 mmol), AlBN (6.57 g, 40 mmol), and NBS (106.2 g, 600 mmol) in chlorobenzene (400 mL) was stirred and heated at 80 C. for 4 hours. After cooling to room temperature, the reaction mixture was filtered to remove the solid succinimide, and then the filtrate was washed with water and brine, dried over anhydrous MgSO4, and filtered. The solvent of the filtrate was removed by rotary evaporation, and the crude product was purified by column chromatography on silica gel with CH2Cl2/hexane (v/v, 1:3) as eluent to afford Compound A as a white solid (56.1 g, 83%). The analytical data obtained from Compound A are listed below. M.p. 119-120 C.; IR (KBr) v 3001, 2922, 1524, 1481, 1315, 1274, 1185, 1097, 937, 880 cm-1; 1H NMR (CDCl3, 400 MHz) delta 7.97-7.90 (m, 2H), 7.40 (s, 1H); 13C NMR (CDCl3, 100 MHz) delta 152.8, 149.6, 133.4, 131.8, 129.4, 115.8, 33.9; HRMS (m/z, FAB+) Calcd. for C7H379Br3N2S 383.7567. found 383.7542, Calcd. for C7H379Br281Br1N2S 385.7547. found 385.7553, Calcd. for C7H379Br181Br2N2S 387.7526. found 387.7524, Calcd. for C7H381Br3N2S 389.7506. found 389.7536.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole, and friends who are interested can also refer to it.

Reference:
Patent; Wong, Ken-Tsung; Lin, Hao-Wu; Lin, Li-Yen; Lin, Francis; Chen, Yi-Hong; Chiu, Shi-Wen; US8802975; (2014); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2255-80-3 as follows. Product Details of 2255-80-3

4-Bromo-7-methylbenzo[c][l,2,5]thiadiazole (0.5 g, 2.2 mmol) was suspended in methanol (7 ml) and warmed to 45 0C (internal temperature). The suspension was then treated with magnesium turnings (0.42 g, 17.6 mmol) and stirred for 30 mins. The reaction was then cooled and the methanol removed in vacuo. The residue was then mixed with aq. NH4Cl and extracted with EtOAc (3 x 30 ml). The organic layers were dried over MgSO4, filtered, concentrated and dried in vacuo to afford 3-bromo- 6-methylbenzene-l,2-diamine (0.39 g, 94%); deltaH(400 MHz, CDCl3) 6.88 (IH, d, J 8, Ar-H), 6.47 (1H, d, J 8, Ar-H), 3.60 (4H, bs, Ar-NH2), 2.16 (3H, s, ArCH3); m/z (EI) 202 ([81Br]M+, 95%), 200 ([79Br]M+, 100%), 120 (M+ -Br, 75%); the resultant solid was used directly in the next stage.46.

According to the analysis of related databases, 2255-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF DURHAM; WO2009/34396; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2255-80-3,Some common heterocyclic compound, 2255-80-3, name is 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole, molecular formula is C7H5BrN2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

4-Bromo-7-methylbenzo[c][l,2,5]thiadiazole (0.25 g, 1.1 mmol) was dissolved in AcOH (12 ml) and H2SO4 (1.7 ml). [CAUTION: Exothermic]. The solution was then treated with chromium (VI) oxide (1.5 g) portionwise and stirred for 30 mins. The reaction was then poured onto ice and allowed to warm to room temperature. The aqueous layer was then extracted with DCM (3 x 30 ml). The aqueous layer was left overnight and the precipitate filtered and washed with water (3 x 2 ml) to afford the title compound as a white solid (0.085 g, 30 %); vmax(thin film) 3100 – 3300 (broad – OH), 1682 (C=O), 1680, 1525, 1312, 1289, 1193 cm-1; deltaH(500 MHz, (CD3)2CO) 8.31 (IH, d, / 8, Ar-H), 8.15 (1eta, d, / 8, Ar-H), 2.09 (1eta, s, CO2H); deltaC (126 MHz, (CDs)2CO) 165.1 (C=O), 154.8 (C=N), 152.6 (C=N), 134.7 (Ar-C), 132.6 (Ar-Q, 124.2 (ipso-Ar-Q, 120.1 (ipso-Ai-Q; m/z (ES”) 259 ([81Br]M”), 257 ([79Br]M”); HRMS (ES”) Found M”, 256.90248 (C7H279BrN2O2S requires 256.90258).

The synthetic route of 2255-80-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF DURHAM; WO2009/34396; (2009); A2;,
Bromide – Wikipedia,
bromide – Wiktionary