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[ CAS No. 53218-26-1 ]

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Chemical Structure| 53218-26-1
Chemical Structure| 53218-26-1
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Product Details of [ 53218-26-1 ]

CAS No. :53218-26-1 MDL No. :MFCD04115372
Formula : C7H4BrNS Boiling Point : 291.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :214.08 g/mol Pubchem ID :2795171
Synonyms :

Safety of [ 53218-26-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 53218-26-1 ]

  • Upstream synthesis route of [ 53218-26-1 ]
  • Downstream synthetic route of [ 53218-26-1 ]

[ 53218-26-1 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 124-38-9 ]
  • [ 23451-95-8 ]
  • [ 53218-26-1 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1-methyl-pyrrolidin-2-one at 70℃; for 0.5 h; Schlenk technique
Stage #2: With phenylsilane In 1-methyl-pyrrolidin-2-one at 70℃; for 24 h; Schlenk technique
General procedure: A tube-type Schlenk flask was charged with 0.045 mmol of catalyst D, 0.045 mmol of 1,8-diazabicyclo[5.4.0]undec-7-ene (7μL), and 1mL of N-methylpyrrolidone. The solution was stirred under nitrogen atmosphere at 60–70°C for 30 min. And, 2mL of N-methylpyrrolidone was added, followed by addition of a balloon charged with carbon dioxide gas. The solution was stirred at 60–70°C for 30 min. Then, 2-aminobenzenethiol derivatives (0.5 mmol), phenylsilane (1.5 mmol) dissolved in 0.5mL of N-methylpyrrolidone was added to the mixture. Reaction was carried out at 60–70°C for 18–30h. After the solution was cooled to room temperature, purification by flash chromatography on silica gel with n-hexane and ethyl acetate afforded benzothiazole derivatives.
Reference: [1] RSC Advances, 2014, vol. 4, # 100, p. 56957 - 56960
[2] Tetrahedron, 2017, vol. 73, # 25, p. 3438 - 3442
[3] ACS Catalysis, 2015, vol. 5, # 11, p. 6648 - 6652
  • 2
  • [ 15864-32-1 ]
  • [ 53218-26-1 ]
YieldReaction ConditionsOperation in experiment
79% With silver(I) nitrite In 1,2-dichloro-ethane at 80℃; for 72 h; Sealed tube It was added in a closed reaction vessel 0.3mmol2-amino-6-bromo thiazole, 0.9mmol silver nitrite, 3mL1,2-dichloroethane, the reaction mixture was stirred at the reaction condition of80 72 hours. After the reaction was stopped, cooled to room temperature, thereaction mixture was added 10mL diluted with dichloromethane, filtration andstripped of solvent under reduced pressure, the residue was purified by columnchromatography, eluent V (petroleum ether) / V (ethyl ester) = 6/1, to give6-chlorobenzothiazole, yield 79percent.
Reference: [1] Patent: CN105367442, 2016, A, . Location in patent: Paragraph 0019
[2] Organic Letters, 2013, vol. 15, # 17, p. 4600 - 4603
[3] Tetrahedron, 2014, vol. 70, # 2, p. 245 - 250
  • 3
  • [ 533-30-2 ]
  • [ 53218-26-1 ]
YieldReaction ConditionsOperation in experiment
29%
Stage #1: With tert.-butylnitrite; copper(ll) bromide In acetonitrile at 65℃; for 0.166667 h;
Stage #2: at 65℃; for 0.583333 h;
Add anhydrous copper (II) bromide (1.79 g, 7.99 mmol), tert-butyl nitrite (1.2 mL, 9.98 mmol) and anhydrous acetonitrile (20 mL) to a round bottom flask fitted with a reflux condenser and an addition funnel. Heat at 65 C for 10 min. Add a solution of benzothiazol-6-ylamine (Lancaster; 1 g, 6.66 mmol) in acetonitrile (10 mL) over a period of 5 min via addition funnel. Stir at 65 C for 30 min. Cool to room temperature, pour into 20percent aqueous hydrochloric acid (100 mL), and extract with ether (2 x 100 mL). Wash the organic layer with 20percent aqueous hydrochloric acid. Dry the organic phase with sodium sulfate, filter, evaporate and chromatograph (10percent ethyl acetate/90percent hexanes) to give the title product (0.4 g, 29percent) as a pale yellow solid. MS (ESI) M/E 215 (M+1).
0.26 g
Stage #1: With hydrogen bromide; sodium nitrite In water at 0 - 20℃; for 0.5 h;
Stage #2: With hydrogenchloride; copper(I) bromide In water at 0 - 60℃; for 1.5 h;
[0408] A solution of sodium nitrite (0.147 g, 2.1 mmol) in water (1.0 mL) was slowly added to a suspension of 6-aminobenzothiazole (0.30 g, 2.0 mmol) in HBr (48percent in water, 3 mL) at 0 °C and then the mixture was stirred at roomtemperature for 30 min. The formed solution was then slowly added to a solution of copper (I) bromide (0.435 g, 3.0mmol) in HCl (conc., 5 mL) at 0 °C. After the addition, the mixture was stirred at 60 °C for 1.5 h. Cooled down, and thereaction mixture was basified with excess ammonia and extracted with diethyl ether. The combined extract was washedwith water, brine, dried and concentrated. The 6-bromobenzothiazole (0.26 g) was obtained by Combiflash and thenconverted to the final compound using procedures analogous to those for example 1, MS(ESI): (M+H)+ = 413.1
Reference: [1] Organic Letters, 2007, vol. 9, # 18, p. 3623 - 3625
[2] Patent: WO2004/50659, 2004, A1, . Location in patent: Page 49-50
[3] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00154
[4] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0498
[5] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 126
[6] Patent: EP1622569, 2015, B1, . Location in patent: Paragraph 0408
[7] Patent: WO2018/160878, 2018, A1, . Location in patent: Page/Page column 298
  • 4
  • [ 68-12-2 ]
  • [ 23451-95-8 ]
  • [ 53218-26-1 ]
Reference: [1] New Journal of Chemistry, 2016, vol. 40, # 10, p. 8282 - 8287
  • 5
  • [ 2942-06-5 ]
  • [ 53218-26-1 ]
Reference: [1] Journal of the Chemical Society, 1949, p. 355,361
[2] Patent: WO2014/151147, 2014, A1,
[3] Patent: US2014/357651, 2014, A1,
[4] Patent: US9174994, 2015, B2,
  • 6
  • [ 95-16-9 ]
  • [ 53218-26-1 ]
Reference: [1] Patent: WO2014/151147, 2014, A1,
[2] Patent: US2014/357651, 2014, A1,
[3] Patent: US9174994, 2015, B2,
  • 7
  • [ 557-21-1 ]
  • [ 53218-26-1 ]
  • [ 58249-61-9 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 202 - 205
  • 8
  • [ 53218-26-1 ]
  • [ 5419-55-6 ]
  • [ 499769-91-4 ]
Reference: [1] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00154
[2] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 126
  • 9
  • [ 53218-26-1 ]
  • [ 499769-91-4 ]
Reference: [1] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0498
  • 10
  • [ 53218-26-1 ]
  • [ 124-38-9 ]
  • [ 74-88-4 ]
  • [ 1187928-41-1 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 5, p. 989 - 996
  • 11
  • [ 53218-26-1 ]
  • [ 1187928-41-1 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 15, p. 3986 - 3989
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