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[ CAS No. 827-33-8 ]

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2D
Chemical Structure| 827-33-8
Chemical Structure| 827-33-8
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Product Details of [ 827-33-8 ]

CAS No. :827-33-8MDL No. :MFCD11100159
Formula : C6H4BrClN2O2 Boiling Point : 350.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :251.47Pubchem ID :21846999
Synonyms :

Computed Properties of [ 827-33-8 ]

TPSA : 71.8 H-Bond Acceptor Count : 3
XLogP3 : 2.9 H-Bond Donor Count : 1
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 827-33-8 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 827-33-8 ]

  • Upstream synthesis route of [ 827-33-8 ]
  • Downstream synthetic route of [ 827-33-8 ]

[ 827-33-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1635-61-6 ]
  • [ 827-33-8 ]
YieldReaction ConditionsOperation in experiment
96.5% at 30℃; for 1 h; Step 1: A mixture of 5-chloro-2-nitroaniline (6.0 g, 34.88 mmol) and NBS (6.06 g, 34.0 mmol) in HOAc (240mL) was stirred at 130 °C for 1 h. The reaction mixture was poured into water. The precipitate was collected by filtrationand washed with petroleum ether to give 4-bromo-5-chloro-2-nitroaniline as a light brown solid (8.25 g, 96.5percent). 1H NMR(300 MHz, DMSO-d6) δ 8.24 (s, 1H), 7.62 (br s, 2H), 7.29 (s, 1H). LCMS (ESI) m/z 251 (M+H)+.
80% at 25℃; for 16 h; [00669] A mixture of 5-chloro-2-nitrobenzenamine (17g, O. lmol), NBS (17g, O. lmol) and CH3COOH (210 ml) was stirred for 16 h at 25 °C. The reaction was quenched with water (100 mL) and extracted with ethyl acetate (1000 mL). The organic layer was washed with water (500 mL x 2), dried (Na2S04), filtered and concentrated in vacuo, the crude product was purified by chromatography (silica, ethyl acetate/petroleum ether =1/1) to afford 4-bromo-5-chloro-2-nitrobenzenamine (20g, 0.08mmol, 80percent) as a light yellow solid ESI-MS (EI+, m/z): 251 [M+H]+.
75% With N-Bromosuccinimide In acetic acid for 0.75 h; Reflux 6.OO g (34.768 mmol) of 5-chloro-2-nitroaniline and 6.06 g (34.073 mmol) of N-bromosuccinimide were dissolved in 240 ml acetic acid. The mixture was boiled under reflux for 45 min. After cooling, the reaction mixture was added to 1.5 1 water. The resultant precipitate was filtered off and dried under high vacuum. The residue was purified by preparative HPLC (eluent: acetonitrile/water, gradient 10:90 --> 90: 10). We obtained 6.75 g (75percent of theor.) of the target compound. LC-MS (method 4): R, = 1.19 min; MS (Elmin): m/z = 249 [M-H]+.1H-NMR (400 MHz, DMSO-D6): δ [ppm] = 7.29 (s, IH), 7.62 (sbr, 2H), 8.24 (s, IH).
63.5% for 0.5 h; Heating 30 g (0.117 mol) of 5-chloro-2-ntiroaniline (CAS 1635-61-6) was synthesized according to the synthetic method described in the reference WO WO 02-020363,Was dissolved in 200 ml of acetic acid (hereinafter referred to as AcOH, CAS 64-19-7)NBS 30 9g (0.174 mol) was added. The reaction solution was heated and stirred for 30 minutes, and it was confirmed that the reaction was completed. A large amount of water was poured into the reaction mixture to form precipitates, and 6 g (63.5percent) of intermediate 1-E was obtained in the same manner as in the extraction of intermediate 1-A .
44% at 110℃; for 1 h; Example 45N2-((6-chloro- 1 H-benzo[d]imidazol-5-yl)methyl)-N4-(5-cyclopropyl- 1 H-pyrazol-3 -yl)- pyrimidine-2,4- diamine (1-94) step 1 : - A mixture of 5-chloro-2-nitrobenzenamine (6.0 g, 34.9 mmol) and NBS (6.06 g, 34.0 mmol) in HOAc (240 mL) was heated at 110 °C for 1 h. The solution was cooled to RT and the reaction mixture was poured into an ice-water (800 mL). The resulting solid was filtered, washed with water (50 mL x 3), and dry under vacuum to afford 4.0 g (44percent) of 4-bromo-5-chloro-2-nitrobenzenamine (246) as yellow solid: MS (ESI) m/z = 250.9 (M-l).

Reference: [1] Patent: EP2766359, 2016, B1, . Location in patent: Paragraph 1021
[2] Patent: WO2018/191146, 2018, A1, . Location in patent: Paragraph 00669
[3] Patent: WO2010/20363, 2010, A1, . Location in patent: Page/Page column 78-79
[4] Patent: KR2018/65276, 2018, A, . Location in patent: Paragraph 0143-0146
[5] Patent: WO2013/26914, 2013, A1, . Location in patent: Page/Page column 161-162
  • 2
  • [ 956282-97-6 ]
  • [ 827-33-8 ]
Reference: [1] Patent: US2007/259936, 2007, A1, . Location in patent: Page/Page column 176
  • 3
  • [ 716-66-5 ]
  • [ 827-33-8 ]
Reference: [1] Helvetica Chimica Acta, 2003, vol. 86, # 4, p. 1175 - 1192
  • 4
  • [ 22459-81-0 ]
  • [ 827-33-8 ]
Reference: [1] American Chemical Journal, 1899, vol. 22, p. 273
[2] Helvetica Chimica Acta, 2003, vol. 86, # 4, p. 1175 - 1192
  • 5
  • [ 21402-26-6 ]
  • [ 827-33-8 ]
Reference: [1] Helvetica Chimica Acta, 2003, vol. 86, # 4, p. 1175 - 1192
  • 6
  • [ 588-07-8 ]
  • [ 827-33-8 ]
Reference: [1] American Chemical Journal, 1899, vol. 22, p. 273
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