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[ CAS No. 16588-24-2 ]

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2D
Chemical Structure| 16588-24-2
Chemical Structure| 16588-24-2
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Product Details of [ 16588-24-2 ]

CAS No. :16588-24-2MDL No. :MFCD05863216
Formula : C6H3BrClNO2 Boiling Point : 279.2°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :236.45Pubchem ID :817974
Synonyms :

Computed Properties of [ 16588-24-2 ]

TPSA : 45.8 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.00 Rotatable Bond Count : 0

Safety of [ 16588-24-2 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16588-24-2 ]

  • Upstream synthesis route of [ 16588-24-2 ]
  • Downstream synthetic route of [ 16588-24-2 ]

[ 16588-24-2 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 106-39-8 ]
  • [ 41513-04-6 ]
  • [ 16588-24-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1915, vol. 34, p. 220
  • 2
  • [ 635-22-3 ]
  • [ 16588-24-2 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃;
Stage #2: With copper(I) bromide In water for 1 h;
To a solution of 4-chloro-3-nitro-phenylamine (17.2 g, 0.1 mol) in 260 mL HBr (48percent) at 0°C was added dropwise NaN02 (13.8 g, 0.2 mol) in water. The reaction mixture was stirred for 1 h at 0°C then CuBr (24 g, 0.17 mol) was added in portions to the mixture and stirred for an additional 1 h. Water was added, the mixture allowed to warm to room temperature and was then extracted with EtOAc. The crude product was purified by silica gel column chromatography to give the title compound (13 g, 55percent). 1H NMR CDCI3400 MHz δ 8.03-8.02 (m, 1 H), 7.66-7.63 (m, 1 H), 7.45-7.42 (m, 1 H).
55%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃; for 1 h;
Stage #2: With copper(I) bromide In water at 0℃; for 1 h;
To a solution of 4-chloro-3-nitro-phenylamine (17.2 g, 0.1 mol) in 260 mL HBr (48percent) at 0° C. was added dropwise NaNO2 (13.8 g, 0.2 mol) in water. The reaction mixture was stirred for 1 h at 0° C. then CuBr (24 g, 0.17 mol) was added in portions to the mixture and stirred for an additional 1 h. Water was added, the mixture allowed to warm to room temperature and was then extracted with EtOAc. The crude product was purified by silica gel column chromatography to give the title compound (13 g, 55percent). 1H NMR CDCl3400 MHz δ 8.03-8.02 (m, 1H), 7.66-7.63 (m, 1H), 7.45-7.42 (m, 1H).
Reference: [1] Patent: WO2013/117522, 2013, A1, . Location in patent: Page/Page column 40
[2] Patent: US2015/18367, 2015, A1, . Location in patent: Paragraph 0177; 0178
[3] Journal of the American Chemical Society, 1962, vol. 84, p. 1026 - 1032
[4] Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1795 - 1799[5] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843
  • 3
  • [ 88-73-3 ]
  • [ 16588-24-2 ]
Reference: [1] Chemical Research in Toxicology, 1997, vol. 10, # 4, p. 439 - 449
[2] Journal of the American Chemical Society, 1953, vol. 75, p. 1385
[3] Recueil des Travaux Chimiques des Pays-Bas, 1915, vol. 34, p. 205
[4] Patent: WO2006/81343, 2006, A1, . Location in patent: Page/Page column 72-73
[5] Patent: WO2008/14186, 2008, A1, . Location in patent: Page/Page column 28
[6] Journal of Heterocyclic Chemistry, 2009, vol. 46, # 5, p. 936 - 948
  • 4
  • [ 99277-71-1 ]
  • [ 16588-24-2 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6646 - 6648
  • 5
  • [ 38818-50-7 ]
  • [ 66832-24-4 ]
  • [ 16588-24-2 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 19, p. 4321 - 4328
  • 6
  • [ 96-99-1 ]
  • [ 16588-24-2 ]
Reference: [1] Tetrahedron Letters, 1985, vol. 26, # 48, p. 5939 - 5942
  • 7
  • [ 106-39-8 ]
  • [ 16588-24-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 8
  • [ 875-51-4 ]
  • [ 16588-24-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1915, vol. 34, p. 205
  • 9
  • [ 108-90-7 ]
  • [ 16588-24-2 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 10
  • [ 106-39-8 ]
  • [ 41513-04-6 ]
  • [ 16588-24-2 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1915, vol. 34, p. 220
  • 11
  • [ 16588-24-2 ]
  • [ 60811-17-8 ]
Reference: [1] American Chemical Journal, 1892, vol. 14, p. 571
[2] American Chemical Journal, 1891, vol. 13, p. 425
[3] , 1967, vol. 3, p. 1795 - 1799[4] Zhurnal Organicheskoi Khimii, 1967, vol. 3, # 10, p. 1839 - 1843
[5] Patent: US4061761, 1977, A,
  • 12
  • [ 16588-24-2 ]
  • [ 7439-89-6 ]
  • [ 60811-17-8 ]
Reference: [1] Patent: US2004/162282, 2004, A1,
  • 13
  • [ 16588-24-2 ]
  • [ 823-57-4 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 1 h; To a solution of 4-bromo-1-chloro-2-nitrobenzene (2.94 g, 12.43 minol) in AcOH (50 mL) was added Fe powder (5.67 g, 100.52 minol) at room temperature. The resultingminxture was stirred for 1 h at 80 °C. When the reaction was done, the solids in the reactionminxture were filtered out and the filtrate was concentrated under reduced pressure. The pH value of the residue was adJusted to 7-8 with sodium hydroxide solution (2N). The resultingminxture was extracted with ethyl acetate (100 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to yield 5-bromo-2-chloroaniline as yellow solid (2.06 g, 80percent). MS: m/z = 207.9 [M+Hj.
Reference: [1] Patent: WO2017/106607, 2017, A1, . Location in patent: Paragraph 00512
  • 14
  • [ 16588-24-2 ]
  • [ 112671-42-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1874, vol. 4, p. 341[2] Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1875, p. 317
  • 15
  • [ 16588-24-2 ]
  • [ 1826-67-1 ]
  • [ 126811-30-1 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: at -40℃; for 2 h;
Stage #2: With ammonium chloride In tetrahydrofuran; dihydrogen peroxide
To a solution of 4-bromo-1-chloro-2-nitro-benzene (14 g, 0.059 mol) in 400 mL THF at - 40 °C was added dropwise vinylmagnesium bromide (177 mL of 1.0M solution in THF, 0.177 mol). The reaction mixture was stirred for 2 hrs at -40 °C. Aqueous NH4CI was added and the mixture extracted with ether. The organic phase was dried over Na2S04> concentrated and the residue purified by silica gel column chromatography to give the title compound (6 g, 44 percent). 1H NMR CDCI3400 MHz δ 8.5 (s, 1 H), 7.31-7.29 (m, 1 H), 7.26-7.22 (m, 1 H),7.07-7.05 (m, 1 H), 6.65-6.63 (m,1 H).
44% at -40 - 40℃; for 2 h; To a solution of 4-bromo-1-chloro-2-nitro-benzene (14 g, 0.059 mol) in 400 mL THF at -40° C. was added dropwise vinylmagnesium bromide (177 mL of 1.0M solution in THF, 0.177 mol). The reaction mixture was stirred for 2 hrs at 40° C. Aqueous NH4Cl was added and the mixture extracted with ether. The organic phase was dried over Na2SO4, concentrated and the residue purified by silica gel column chromatography to give the title compound (6 g, 44percent). 1H NMR CDCl3400 MHz δ 8.5 (s, 1H), 7.31-7.29 (m, 1H), 7.26-7.22 (m, 1H), 7.07-7.05 (m, 1H), 6.65-6.63 (m, 1H).
32% at -40℃; for 1 h; Inert atmosphere Under a nitrogen gas, 4-bromo-1-chloro-2-nitrobenzene (25g, 0.107mol) dissolved inTHF (250mL) and then - 40 degree celcius added vinylmagnesium bromide (1M in THF, 321mL, 0.321mol) slowly dropwise, and then stirred at -40 degree celcius for 1 hour. Since, NH4After completion of the reaction with Cl aqueous solution was raised to room temperature.Then, the organic layer was extracted with ethyl acetate, MgSO4to remove moisture in the organic layer, filtered and concentrated and purified by column chromatography to give 4-bromo-7-chloro-1H-indole (7.89g,Yield: 32percent) It was obtained.
Reference: [1] Patent: WO2013/117522, 2013, A1, . Location in patent: Page/Page column 40
[2] Patent: US2015/18367, 2015, A1, . Location in patent: Paragraph 0179; 0180
[3] Patent: KR101601357, 2016, B1, . Location in patent: Paragraph 0392-0394
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