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[ CAS No. 533-58-4 ]

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Chemical Structure| 533-58-4
Chemical Structure| 533-58-4
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CAS No. :533-58-4 MDL No. :MFCD00013963
Formula : C6H5IO Boiling Point : 187.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :220.01 g/mol Pubchem ID :10784
Synonyms :

Safety of [ 533-58-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 533-58-4 ]

  • Upstream synthesis route of [ 533-58-4 ]
  • Downstream synthetic route of [ 533-58-4 ]

[ 533-58-4 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 533-58-4 ]
  • [ 4265-16-1 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2865 - 2868
  • 2
  • [ 533-58-4 ]
  • [ 33421-36-2 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 50, p. 6985 - 6988
[2] Tetrahedron, 2010, vol. 66, # 17, p. 3135 - 3146
  • 3
  • [ 110-86-1 ]
  • [ 533-58-4 ]
  • [ 33421-36-2 ]
  • [ 54168-07-9 ]
  • [ 86610-20-0 ]
Reference: [1] Heterocycles, 2004, vol. 64, p. 499 - 504
[2] Tetrahedron, 2006, vol. 62, # 33, p. 7824 - 7837
  • 4
  • [ 533-58-4 ]
  • [ 3663-80-7 ]
Reference: [1] Patent: CN105985328, 2016, A,
  • 5
  • [ 533-58-4 ]
  • [ 67713-99-9 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 33, p. 10249 - 10254
  • 6
  • [ 138769-92-3 ]
  • [ 533-58-4 ]
  • [ 626-02-8 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 34, p. 14056 - 14069,14
[2] Journal of the American Chemical Society, 2012, vol. 134, # 34, p. 14056 - 14069
  • 7
  • [ 533-58-4 ]
  • [ 70201-81-9 ]
  • [ 67191-35-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 10, p. 2712 - 2715[2] Angew. Chem., 2018, vol. 130, p. 2742 - 2745,4
  • 8
  • [ 533-58-4 ]
  • [ 5399-03-1 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1902, vol. 134, p. 358[2] Bulletin de la Societe Chimique de France, 1902, vol. <3> 27, p. 400
  • 9
  • [ 533-58-4 ]
  • [ 28177-52-8 ]
Reference: [1] ACS Catalysis, 2018, vol. 8, # 5, p. 4033 - 4043
[2] Canadian Journal of Chemistry, 1965, vol. 43, p. 650 - 658
[3] Patent: WO2009/158467, 2009, A2, . Location in patent: Page/Page column 79-80
  • 10
  • [ 533-58-4 ]
  • [ 28177-52-8 ]
  • [ 71643-66-8 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
[2] Organic Letters, 2016, vol. 18, # 21, p. 5476 - 5479
  • 11
  • [ 67-66-3 ]
  • [ 533-58-4 ]
  • [ 60032-63-5 ]
  • [ 23602-64-4 ]
Reference: [1] Journal of the American Chemical Society, 1950, vol. 72, p. 4324
  • 12
  • [ 50-00-0 ]
  • [ 533-58-4 ]
  • [ 60032-63-5 ]
Reference: [1] Patent: DE105798, , ,
  • 13
  • [ 50-00-0 ]
  • [ 533-58-4 ]
  • [ 38170-02-4 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine; magnesium chloride In acetonitrile at 10 - 72℃; for 2 h; 4-(nitrooxy)butyl (2R)-7-benzyl-6-chloro-2-(trifluoromethyl)-2H-chromene-3- carboxylate; Step 1; Preparation of 2-hydroxy-4-iodobenzaldehyde; [0168] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl2 (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 0C, followed by paraformaldehyde (28.6 g, 954 mmole) and TEA (76 mL, 545 mmole) producing a 15 °C exotherm. The solution was heated to 72 0C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 mL). The combined organic phases were washed with aqueous NaHCO3 solution (2 X 150 mL), aqueous IN HCl solution (2 X 150 mL), and brine (2 X 150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5percent Ethyl acetate/ Hexane). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79percent) as a yellow solid. This salicylaldehyde was of suitable purity to use without further purification.
79% With triethylamine; magnesium chloride In acetonitrile at 10 - 72℃; for 2 h; [0232] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl2 (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 °C, followed by PARAFORMALDEHYDE (28.6 g, 954 mmole) and TEA (76 mL, 545 mmole) producing a 15 °C exotherm. The solution was heated to 72 °C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 mL). The combined organic phases were washed with aqueous NAHC03 solution (2 X 150 mL), aqueous 1N HCL solution (2 X 150 mL), and brine (2 X 150 mL), dried OVER NA2S04, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5percent Ethyl ACETATE/HEXANE). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79percent) as a yellow solid. This salicylaldehyde was of suitable purity to use without FURTHER PURIFICATION. HNMR (DMSO-D6/400 MHz) 10.95 (s, 1H), 10.19 (s, 1H), 7.33 (m, 3H), 4.31 (m, 1H).
79% With triethylamine; magnesium chloride In acetonitrile at 10 - 72℃; for 2 h; EXAMPLE 14; (2R)-6-chIoro-5-(3,3-dimethylbutyl)-2-(trifluoromethyl)-l,7b- dihydrocyclopropa[c]chromene-la(2H)-carboxylic acid; Step 1. Preparation of 2-hydroxy-4-iodobenzaldehyde.; [0185] To a chilled solution of commercially available 2-iodophenol (30 g, 136 mmole) in ACN was added MgCl2 (19.5 g, 204 mmole) portion-wise while maintaining the temperature below 10 0C, followed by paraformaldehyde (28.6 g, 954 mmole) and TEA (76 niL, 545 mmole) producing a 15 °C exotherm. The solution was heated to 72 0C for 2 h. The reaction was cooled to room temperature and poured into Saturated aqueous Ammonium Chloride (500 mL), extracted with ethyl acetate (2 X 150 niL). The combined organic phases were washed with aqueous NaHCO3 solution (2 X 150 mL), aqueous IN HCl solution (2 X 150 mL), and brine (2 X 150 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude material was subjected to flash chromatography (Silica, 5percent Ethyl acetate/ Hexane). Desired fractions were collected and combined, removed solvent in vacuo producing the ethyl ester (27 g, 79percent) as a yellow solid. This salicylaldehyde was of suitable purity to use without further purification. 1HNMR (DMSO-J6/400 MHz) 10.95 (s, IH), 10.19 (s, IH), 7.33 (m, 3H), 4.31 (m, IH).
Reference: [1] Patent: WO2006/40676, 2006, A1, . Location in patent: Page/Page column 51
[2] Patent: WO2004/87686, 2004, A2, . Location in patent: Page 12-130
[3] Patent: WO2004/87687, 2004, A1, . Location in patent: Page 12-130
[4] Patent: WO2006/40672, 2006, A1, . Location in patent: Page/Page column 59
  • 14
  • [ 533-58-4 ]
  • [ 207115-22-8 ]
YieldReaction ConditionsOperation in experiment
68% With tetra-N-butylammonium tribromide In methanol; dichloromethane at 20℃; for 2 h; 4-Bromo-2-iodophenol (4). 2-Iodophenol (11 g, 50 mmol) was dissolved in DCM (200 mL) and MeOH (100 mL). Tetrabutylammonium tribromide (TBATB) (25.31 g, 52.5 mmol) was then added portionwise over 10 min. The solution was stirred at room temperature for 2 h and then quenched with 1 N HCl (200 mL). The DCM layer was extracted and the aqueous layer was extracted another two times with DCM. The organic layers were then combined, washed with brine, dried, and concentrated. Purification of the residue with flash chromatography (silica, 50percent-100percent DCM/Hexanes) yielded 4-bromo-2-iodophenol (10.2 g, 68percent).
Reference: [1] Tetrahedron, 2015, vol. 71, # 35, p. 5946 - 5951
[2] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8680 - 8688
[3] Organic Letters, 2015, vol. 17, # 22, p. 5666 - 5669
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1931, vol. 192, p. 1037
[5] Canadian Journal of Chemistry, 1965, vol. 43, p. 650 - 658
  • 15
  • [ 533-58-4 ]
  • [ 5467-74-3 ]
  • [ 21849-89-8 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 15, p. 3962 - 3965
  • 16
  • [ 533-58-4 ]
  • [ 66003-76-7 ]
  • [ 34883-46-0 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 6, p. 1552 - 1555
[2] Chemistry--A European Journal, 2012, vol. 18, # 44, p. 14140 - 14149,10
  • 17
  • [ 533-58-4 ]
  • [ 88284-48-4 ]
  • [ 34883-46-0 ]
Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3198 - 3209
[2] Tetrahedron, 2007, vol. 63, # 2, p. 347 - 355
  • 18
  • [ 533-58-4 ]
  • [ 34883-46-0 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 53, p. 13249 - 13258
  • 19
  • [ 533-58-4 ]
  • [ 1483-73-4 ]
  • [ 34883-46-0 ]
Reference: [1] Journal of Organic Chemistry, 1964, vol. 29, p. 3396 - 3398
  • 20
  • [ 533-58-4 ]
  • [ 15459-51-5 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1931, vol. 192, p. 1037
  • 21
  • [ 533-58-4 ]
  • [ 25015-63-8 ]
  • [ 269409-97-4 ]
Reference: [1] Patent: US6680401, 2004, B1, . Location in patent: Page column 47
[2] Patent: US6680401, 2004, B1, . Location in patent: Page column 67
  • 22
  • [ 533-58-4 ]
  • [ 269409-97-4 ]
Reference: [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851
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