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[ CAS No. 529-23-7 ]

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Chemical Structure| 529-23-7
Chemical Structure| 529-23-7
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CAS No. :529-23-7 MDL No. :MFCD00007709
Formula : C7H7NO Boiling Point : 258.7°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :121.14 g/mol Pubchem ID :68255
Synonyms :

Safety of [ 529-23-7 ]

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

Application In Synthesis of [ 529-23-7 ]

  • Upstream synthesis route of [ 529-23-7 ]
  • Downstream synthetic route of [ 529-23-7 ]

[ 529-23-7 ] Synthesis Path-Upstream   1~26

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  • [ 922-67-8 ]
  • [ 53951-84-1 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 23, p. 5212 - 5220
  • 2
  • [ 631-61-8 ]
  • [ 529-23-7 ]
  • [ 253-82-7 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 550,554
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  • [ 578-67-6 ]
  • [ 10470-83-4 ]
  • [ 59-31-4 ]
  • [ 529-37-3 ]
  • [ 529-23-7 ]
Reference: [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658
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  • [ 42508-60-1 ]
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YieldReaction ConditionsOperation in experiment
4.8 g
Stage #1: With pyridine; dmap In ethanol for 48 h; Inert atmosphere; Schlenk technique; Reflux
Stage #2: With pyrrolidine In ethanol at 20℃; for 16 h; Inert atmosphere; Schlenk technique; Reflux
A mixture of 2-aminobenzaldehyde (6.0 g, 49.58 mmol), 1-(2-oxopropyl)pyridinium chloride (8.98 g, 52.06 mmol), pyridine (2.6 ml, 32.72 mmol) and 4-dimethylaminopyridine (60 mg, 0.49 mmol) in ethanol (75 ml) were refluxed for 48 h. The reaction mixture was cooled to room temperature and pyrrolidine (10.3 ml, 123.96 mmol) was added, and mixture was then refluxed for 16 h. The volatiles were removed under reduced pressure and the resultant mixture was diluted with aqueous sodium bicarbonate solution (200 ml). The mixture was extracted with dichloromethane (2 x 200 ml). The combined organic layers were washed with brine (200 ml) and dried over anhydrous sodium sulphate. The organic layer was filtered and concentrated under reduced pressure. The residue obtained was purified by flash silica gel column chromatography to yield 4.8 g of product as a yellow solid.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 9, p. 2073 - 2078
  • 5
  • [ 529-23-7 ]
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Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
  • 6
  • [ 17282-41-6 ]
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  • [ 21352-22-7 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 13, p. 2937 - 2942
  • 7
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  • [ 21352-22-7 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1957, vol. 602, p. 14,18
  • 8
  • [ 506-93-4 ]
  • [ 529-23-7 ]
  • [ 1687-51-0 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 3509,3511
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  • [ 91-22-5 ]
  • [ 148-24-3 ]
  • [ 578-67-6 ]
  • [ 10470-83-4 ]
  • [ 59-31-4 ]
  • [ 529-37-3 ]
  • [ 529-23-7 ]
Reference: [1] Journal of Physical Chemistry B, 1997, vol. 101, # 14, p. 2650 - 2658
  • 10
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  • [ 6480-68-8 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1996,2000
  • 11
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  • [ 20668-20-6 ]
Reference: [1] Chemische Berichte, 1923, vol. 56, p. 1343
  • 12
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  • [ 529-23-7 ]
  • [ 635-79-0 ]
YieldReaction ConditionsOperation in experiment
88% at 110℃; for 24 h; Inert atmosphere To a stirred solution of 2-aminobenzaldehyde (1a, 206 mg, 1.70 mmol) in 15 mL of toluene, was added methyl acetoacetate (2a, 217 mg, 1.87 mmol, 1.1 equiv) and the solution was refluxed for 24 h during which time a light tan precipitate formed. The reaction mixture was cooled to room temperature, evaporated to one-half its volume, and then cooled to 0 °C using an ice bath. The solid was filtered and washed with 1:1 ether:hexane to give acid 3a. The compound obtained was spectroscopically pure and no further purification was necessary. Note: The reaction was also carried out using xylene as the solvent and no change in the yield or purity was observed. Reactions run in benzene, however, gave mixtures of the acid and its corresponding ester.
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 20, p. 3181 - 3183
[2] Green Chemistry, 2017, vol. 19, # 16, p. 3851 - 3855
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Reference: [1] Chemische Berichte, 1883, vol. 16, p. 1836
[2] Chemische Berichte, 1886, vol. 19, p. 37
[3] Justus Liebigs Annalen der Chemie, 1894, vol. 282, p. 117 Anm.
[4] Chemische Berichte, 1919, vol. 52, p. 490
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  • [ 635-79-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1914, vol. <2> 90, p. 24
[2] Chemische Berichte, 1919, vol. 52, p. 490
[3] Chemische Berichte, 1919, vol. 52, p. 490
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  • [ 30160-03-3 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 20, p. 3181 - 3183
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  • [ 541-50-4 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1932, vol. 497, p. 7,12, 19
  • 17
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4708 - 4714
[2] Patent: WO2007/81569, 2007, A2, . Location in patent: Page/Page column 49
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  • [ 62235-59-0 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 13, p. 2937 - 2942
[2] Journal of Natural Products, 2015, vol. 78, # 10, p. 2398 - 2404
  • 19
  • [ 529-23-7 ]
  • [ 6148-18-1 ]
Reference: [1] Patent: US2013/343992, 2013, A1,
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  • [ 529-23-7 ]
  • [ 26709-65-9 ]
  • [ 31739-56-7 ]
Reference: [1] Heterocycles, 1993, vol. 36, # 11, p. 2513 - 2522
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  • [ 26260-02-6 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 15, p. 4516 - 4520
  • 22
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  • [ 29124-57-0 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 6, p. 1119 - 1123
[2] Patent: WO2004/18461, 2004, A2, . Location in patent: Page 26-27
[3] Inorganic Chemistry, 2016, vol. 55, # 22, p. 11908 - 11919
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Reference: [1] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
  • 24
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  • [ 50910-55-9 ]
YieldReaction ConditionsOperation in experiment
91.1% With bromine; potassium bromide In water (1) Stir and mix ethanol, water and o-nitrobenzaldehyde at a molar ratio of 4:1:0.2.The temperature was raised until the solid o-nitrobenzaldehyde was completely dissolved;(2) Add the reduced iron powder, and add 3 to 5 drops of hydrochloric acid dropwise, fully stir and continue to raise the temperature until the reaction system reaches the reflux temperature, keep the stirring reaction, and follow the progress of the reaction with high performance liquid chromatography (HPLC);(3) The reaction solution is suction filtered, and a mixed solution of bromine, potassium bromide and water is added dropwise to the obtained filtrate, and after the completion of the dropwise addition, the temperature is maintained and the reaction is stirred;(4) Add an excess of saturated sodium bicarbonate solution to the reaction mixture, stir it well, accompanied by solid precipitation, and obtain 2-amino-3,5-dibromobenzaldehyde by filtration.In this example, the molar ratio of o-aminobenzaldehyde, bromine, and potassium bromide is 1:1.93:9.5.The yield of 2-amino-3,5-dibromobenzaldehyde was 91.1percent and the purity was 99.4percent.
91.9% With bromine; potassium bromide In ethanol; water at 20℃; for 1 h; 1. Stir and mix ethanol and o-aminobenzaldehyde at a molar ratio of 5:1;2. Add a solution of bromine, potassium bromide and water to the reaction solution with stirring, wherein the molar ratio of o-aminobenzaldehyde, bromine and potassium bromide is 1:1.9:9, and the dripping time is 40 minutes;3. Stir the reaction at 20°C for 1 hour and follow the progress of the reaction with high performance liquid chromatography (HPLC);4. Continue adding excess saturated sodium bicarbonate solution to the reaction mixture and stir until solid precipitates and obtain 2-amino-3,5-dibromobenzaldehyde by filtration. The yield of 2-amino-3,5-dibromobenzaldehyde was 91.9percent.
75.7% With dihydrogen peroxide; bromine; potassium bromide In ethanol at 5℃; for 0.666667 h; (1) Stir and mix ethanol and o-aminobenzaldehyde at a molar ratio of 5:1;(2) Add dropwise bromine and 30percent hydrogen peroxide to the reaction mixture, including o-aminobenzaldehyde, bromine and bromination.The molar ratio of potassium is 1:1.93:9.5, the dropwise addition time is 10 minutes, and the molar ratio of bromine to hydrogen peroxide is 1.2:1;(3) Stir the reaction at a temperature of 5°C for 30 minutes and follow the progress of the reaction with high performance liquid chromatography (HPLC);(4) Continue adding excess saturated sodium bicarbonate solution to the reaction mixture and stir it thoroughly.After the solid precipitated, 2-amino-3,5-dibromobenzaldehyde was obtained by filtration.The yield of 2-amino-3,5-dibromobenzaldehyde was 75.7percent
Reference: [1] Patent: CN107488121, 2017, A, . Location in patent: Paragraph 0017; 0018; 0019; 0020-0023; 0025-0030; 0032-0037
[2] Patent: CN107488124, 2017, A, . Location in patent: Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0038
[3] Australian Journal of Chemistry, 1980, vol. 33, # 1, p. 91 - 99
[4] Patent: CN107488126, 2017, A, . Location in patent: Paragraph 0018-0024; 0027-0031; 0034-0038
[5] Chemische Berichte, 1901, vol. 34, p. 1338
[6] Chemische Berichte, 1909, vol. 42, p. 3697
[7] Chemische Berichte, 1909, vol. 42, p. 3697
[8] Organic Letters, 2010, vol. 12, # 23, p. 5502 - 5505
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Reference: [1] Chemische Berichte, 1909, vol. 42, p. 3697
[2] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
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Reference: [1] Chemische Berichte, 1909, vol. 42, p. 3697
[2] Monatshefte fuer Chemie, 1915, vol. 36, p. 132
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