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[ CAS No. 5328-76-7 ]

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Chemical Structure| 5328-76-7
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CAS No. :5328-76-7 MDL No. :MFCD00156397
Formula : C10H6BrNO2 Boiling Point : 363.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :252.06 g/mol Pubchem ID :219988
Synonyms :

Safety of [ 5328-76-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5328-76-7 ]

  • Upstream synthesis route of [ 5328-76-7 ]
  • Downstream synthetic route of [ 5328-76-7 ]

[ 5328-76-7 ] Synthesis Path-Upstream   1~6

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Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
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YieldReaction ConditionsOperation in experiment
41% at 80 - 85℃; for 0.5 h; To a stirred mixture of 86.6 g (0.5 moles) of 1-nitronaphthalene and 0.8 – 1.0 g of reduced iron powder, maintained at a temperature of 80 – 85°C, was added dropwise over a period of 30min 77.5 g (0.485 moles) of bromine. About an hour later when gas evolution had ceased the reaction mixture was crystallized directly, once from ethanol and then once from acetone using Sorit A both times, average yield 52.0 g of fine yellow needles, m.p. 121 – 122°C (41 percent yield); reported m.p. 122.5°C.
Reference: [1] New Journal of Chemistry, 2005, vol. 29, # 4, p. 579 - 586
[2] Chemistry Letters, 2015, vol. 44, # 6, p. 743 - 745
[3] Angewandte Chemie - International Edition, 2008, vol. 47, # 32, p. 6062 - 6064
[4] Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3873 - 3879
[5] Journal of Organic Chemistry, 1949, vol. 14, p. 111,114
[6] Journal of the Chemical Society, 1937, p. 1103,1107
[7] Journal of the Chemical Society, 1937, p. 1619,1621
[8] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 283[9] Gazzetta Chimica Italiana, 1886, vol. 16, p. 151
[10] Justus Liebigs Annalen der Chemie, 1885, vol. 231, p. 187
[11] Journal of the Chemical Society, 1927, p. 3104
[12] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3356 - 3366
[13] Patent: US2007/274922, 2007, A1,
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Reference: [1] Journal of the Chemical Society, 1933, p. 1620
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Reference: [1] Journal of the Chemical Society, 1937, p. 1103,1107
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YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride In 1,4-dioxane; ethanol; water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetic acid 5-Amino-1-bromonaphthalene (B).
To the solution of 5-nitro-1-bromonaphthalene (A) (2.5 g, 10 mmol) in EtOH/AcOH /Dioxane/H2O (2:2:2:1) (30 mL) was added Fe (5.6 g, 100 mmol) and 2 drops of 2 N HCl.
The reaction mixture was stirred at 100° C. for 2 hrs.
After evaporation of solvent, the residue was dissolved in 100 mL DCM and washed with 5percent NaHCO3 (3*30 mL) and dried over Na2SO4.
After evaporation of solvent, the crude mixture was purified on a silica gel column, eluding with DCM/hexanes (1:1), to give compound B as a white powder (3.0 g, 97percent).
mp 65-66° C.; 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 1H), 7.76 (d, J=8.0, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.39 (t, J=7.6 Hz, 1H), 7.28 (t, J=7.2 Hz, 1H), 6.83 (d, J=7.2 Hz, 1 H), 4.18 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 142.5, 133.0, 130.4, 128.0, 125.1, 125.0, 123.9, 121.0, 118.4, 110.9; ESI-MS (m/z) calcd. for C10H9BrN222.0 (M+H)+, found 222.1. Anal. Calcd for C10H8BrN: C, 54.08; H, 3.63; N, 6.31. Found: C, 53.81; H, 3.46; N, 6.11.
84% With iron; ammonium chloride In ethanol; water at 75℃; To a suspension of 1-bromo-5-nitronaphthalene (2 g, 7.94 mmol) in EtOH (50 mL), a solution of NH4Cl (2.2 g, 41.1 mmol) in water (20 mL) was added, followed by iron powder (1.33 g, 23.82 mmol). The resulting mixture was stirred at 75° C. (bath temperature) for 1.5 h. Celite (3 g) was added, and the mixture was allowed to cool down to rt, diluted with CH2Cl2 (100 mL), filtered through a plug of Celite, washing with CH2Cl2 (150 mL). The filtrate was washed with brine and dried over Na2SO4. Upon evaporation of the filtrate, the crude material was redissolved in CH2Cl2 (20 mL), transferred on top of a 80 g SiO2 column, and ran with 20percent to 80percent EtOAc/hexane gradient. The fractions containing the product were evaporated to viscous light brown oil that quickly crystallized. Yield of 5-bromo-1-aminonaphthalene [West, R. W. J. Chem. Soc. 1925, 127, 494] 1.48 g (84percent). 5-Bromo-1-aminonaphthalene (1.37 g, 6.17 mmol) was dissolved in trimethyl phosphate (760 μL, 6.5 mmol) in a 50 mL round-bottom flask, equipped with an air condenser and a CaCl2 drying tube, the apparatus was flushed with nitrogen, and the mixture was heated at 200° C. (bath temperature) for 1.5 h. The flask was then allowed to cool below 100° C., 1 N NaOH (20 mL) was added, the resulting suspension was sonicated briefly and stirred at rt overnight. The mixture was diluted with brine, extracted with CH2Cl2 (3×50 mL), the combined extracts were dried over Na2SO4. The product was isolated by column chromatography (100 g of SiO2, gradient 10percent to 50percent CH2Cl2/hexane) to yield 1-bromo-5-(dimethylamino)naphthalene 28a [West, R. W. J. Chem. Soc. 1925, 127, 494] as a light-orange viscous oil (1.29 g, 84percent). 1H NMR (301 MHz, CDCl3): δ 8.26 (dt, J=8.6, 1.0 Hz, 1H), 7.95 (dt, J=8.6, 0.9 Hz, 1H), 7.78 (dt, J=7.4, 1.0 Hz, 1H), 7.51 (ddd, J=8.5, 7.5, 0.7 Hz, 1H), 7.32 (ddd, J=8.4, 7.3, 0.7 Hz, 1H), 7.14 (dd, J=7.6, 1.0 Hz, 1H), 2.90 (s, 6H) ppm. 13C NMR (76 MHz, CDCl3): δ 151.3, 133.4, 130.4, 130.1, 127.3, 125.4, 124.3, 123.3, 122.0, 115.0, 45.5.
Reference: [1] New Journal of Chemistry, 2005, vol. 29, # 4, p. 579 - 586
[2] Patent: US2007/274922, 2007, A1,
[3] Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3873 - 3879
[4] Organic Letters, 2018, vol. 20, # 4, p. 1261 - 1264
[5] Patent: US2018/223102, 2018, A1, . Location in patent: Paragraph 0260-0262
[6] Organic Letters, 2017, vol. 19, # 23, p. 6380 - 6383
[7] Angewandte Chemie - International Edition, 2008, vol. 47, # 32, p. 6062 - 6064
[8] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 283[9] Gazzetta Chimica Italiana, 1886, vol. 16, p. 151
[10] Chemische Berichte, 1902, vol. 35, p. 2810
[11] Chemische Berichte, 1924, vol. 57, p. 507
[12] Journal of the Chemical Society, 1927, p. 3104
[13] Journal of the American Chemical Society, 1946, vol. 68, p. 1602,1603
[14] Chemische Berichte, 1924, vol. 57, p. 507
[15] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 3356 - 3366
[16] Chemistry Letters, 2015, vol. 44, # 6, p. 743 - 745
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Reference: [1] Journal of the Chemical Society, 1937, p. 1619,1621
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