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[ CAS No. 532-11-6 ]

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Chemical Structure| 532-11-6
Chemical Structure| 532-11-6
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Product Details of [ 532-11-6 ]

CAS No. :532-11-6 MDL No. :MFCD00129751
Formula : C10H8OS3 Boiling Point : 398.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :240.36 g/mol Pubchem ID :2194
Synonyms :

1. Anethole trithione

Safety of [ 532-11-6 ]

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

Application In Synthesis of [ 532-11-6 ]

  • Upstream synthesis route of [ 532-11-6 ]
  • Downstream synthetic route of [ 532-11-6 ]

[ 532-11-6 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 532-11-6 ]
  • [ 18274-81-2 ]
YieldReaction ConditionsOperation in experiment
85% at 220℃; for 0.416667 h; Inert atmosphere ADT-OMe (2.00 g, 8.32 mmol),and anhydrous pyridine hydrochloride (5.77 g, 49.9 mmol) were added to an oven-dried pressurevessel under N2. The apparatus was submerged into an oil bath and stirred at 220 °C. Afterstirring for 25 minutes, the reaction flask was cooled to room temperature, and the contents weredissolved in methanol and transferred to a round bottom flask. The methanol was removed, andthe contents of the round bottom were dissolved in a 50:50 mixture of 0.5 M HCl and EtOAc inorder to solubilize the crude product. This mixture was then further diluted with water andextracted into EtOAc. The organic layer was dried with Na2SO4 and purified by columnchromatography (3:2 Hex:EtOAc) to afford ADT-OH as a lovely golden orange solid (1.60 g,85percent).
84.5% at 220℃; for 0.333333 h; Inert atmosphere A mixture of ATT 1 (10.05 g, 40 mmol) and anhydrous pyridine hydrochloride (34.07 g, 290 mmol) was heated to 220 °C for 20 min under argon atmosphere. The system was cooled to room temperature, and then 100 ml water was poured in and stirred for 5 min. The suspension was filtered,and the filter cake was collected. The solid was dissolved in 100 ml of 10percent NaOH aqueous solution and stirred for 10 min, then filtered, the filtrate was acidified to pH 1 by conc HCl to form massive solid, then filtered and the filtter cake was dried in vacuo to afford 2 as orange solid (7.65g, 84.5percent).
79% With pyridine hydrochloride In neat (no solvent) at 200℃; for 0.116667 h; Microwave irradiation Compound 1 (200 mg, 1.0 eq.) and pyridine hydrochloride (577 mg, 6.0 eq) were added to a 10 mL microwave reaction vessel. The reaction conditions were as follows: temperature: 200°C, power: 200 Watt, ramp time: 1 min, hold time: 6 min. After cooling, the reaction mixture was dissolved in a mixture of CH2Cl2 (8 mL) and CH3OH (0.5 mL). H2O (30 mL) was added and the aqueous phase was extracted with CH2Cl2 (3x30 mL). The combined organic layers were washed with saturated aqueous sodium chloride, dried (Na2SO4), filtered and concentrated in vacuo. Flash column chromatography (CH2Cl2/CH3OH 99:1) afforded 2 (148 mg, 79percent) as a dark orange solid.
49% at 220℃; for 1 h; Dry anethol sulfur (6.0185 g)With anhydrous pyridine hydrochloride (30.1553 g)In a dry crystallized 250 ml three-necked round bottom flask,The oil bath was heated to 220 ° C, the solid melted and the reaction started.The reaction is terminated in 60 min.Cool to room temperature, add 1M / L dilute HCl to dissolve and filter. The filtrate was discarded, washed with distilled water until neutral and filtered.Finally, the product was recrystallized from absolute ethanol (2.9444g).Yield: 49percent

Reference: [1] Synlett, 2016, vol. 27, # 9, p. 1349 - 1353
[2] Chinese Chemical Letters, 2010, vol. 21, # 12, p. 1427 - 1429
[3] Letters in Drug Design and Discovery, 2010, vol. 7, # 10, p. 747 - 753
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 9, p. 2355 - 2359
[5] Tetrahedron Letters, 2017, vol. 58, # 24, p. 2378 - 2380
[6] European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 3005 - 3010
[7] Organic and Biomolecular Chemistry, 2014, vol. 12, # 31, p. 5995 - 6004
[8] Patent: CN106928208, 2017, A, . Location in patent: Paragraph 0048; 0049
[9] Chemische Berichte, 1951, vol. 84, p. 458,460
[10] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1950, vol. 230, p. 1774
[11] Patent: WO2006/66894, 2006, A1, . Location in patent: Page/Page column 16-19
[12] Patent: WO2006/134489, 2006, A1, . Location in patent: Page/Page column 13-14
[13] Patent: EP1645288, 2006, A1, . Location in patent: Page/Page column 5
[14] Patent: EP1980559, 2008, A1, . Location in patent: Page/Page column 9
[15] Patent: WO2009/65926, 2009, A2, . Location in patent: Page/Page column 18
[16] Patent: US2010/168216, 2010, A1, . Location in patent: Page/Page column 4
[17] Molecules, 2015, vol. 20, # 8, p. 14595 - 14610
[18] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1776 - 1790
[19] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5368 - 5373
[20] Drug Metabolism and Disposition, 2018, vol. 46, # 10, p. 1390 - 1395
[21] Patent: WO2006/111791, 2006, A1, . Location in patent: Page/Page column 9-10
[22] Patent: EP1939186, 2008, A1, . Location in patent: Page/Page column 6
[23] Patent: WO2008/146105, 2008, A1, . Location in patent: Page/Page column 17-18
[24] Patent: WO2009/37556, 2009, A1, . Location in patent: Page/Page column 20
[25] Bioorganic Chemistry, 2019, vol. 82, p. 192 - 203
  • 2
  • [ 104-46-1 ]
  • [ 532-11-6 ]
YieldReaction ConditionsOperation in experiment
34% With sulfur In N,N-dimethyl-formamide at 170℃; for 8 h; Inert atmosphere Anethole (4.15 g, 28.0 mmol)and sulfur (6.00 g, 187 mmol) were dissolved in DMF (25 mL) and refluxed at 170 °C under N2 for 8 hours. After the reaction flask was cooled to room temperature, the reaction mixture wasdiluted into water and extracted into toluene. The toluene fractions were dried with Na2SO4 andconcentrated, and the remaining solid was recrystallized from 5percent methanol/DCM. These crystalswere then further purified by column chromatography (4:1 Hex:EtOAc) to give pure product as a brownish-red crystalline solid (2.27 g, 34percent yield).
Reference: [1] Synlett, 2016, vol. 27, # 9, p. 1349 - 1353
[2] Patent: EP1980559, 2008, A1, . Location in patent: Page/Page column 9
[3] Patent: WO2009/65926, 2009, A2, . Location in patent: Page/Page column 17-18
[4] Patent: US2010/168216, 2010, A1, . Location in patent: Page/Page column 4
[5] Molecules, 2015, vol. 20, # 8, p. 14595 - 14610
[6] Patent: WO2009/37556, 2009, A1, . Location in patent: Page/Page column 20
  • 3
  • [ 4180-23-8 ]
  • [ 532-11-6 ]
YieldReaction ConditionsOperation in experiment
32% With sulfur In neat (no solvent) at 200℃; for 0.166667 h; Microwave irradiation Entry 10: Anethole (500 mg, 1.0 eq.) and elemental sulfur (433 mg, 4.0 eq.) were added with a magnetic stir bar to a 10 mL microwave reaction vessel and a condenser was attached. The reaction conditions were regulated through the CEM-software as follows: temperature: 200°C, power: 200 Watt, ramp time: 1 min, hold time: 9 min. After reaction completion, the vessel was removed from the reactor and cooled immediately in an ice bath and the 1H ΝΜR spectrum of the crude soluble reaction mixture was recorded. The crude material was purified by flash column chromatography (Hex/EtOAc 95:5) to afford 1 (256 mg, 32percent) as a dark red solid.
Reference: [1] Tetrahedron Letters, 2017, vol. 58, # 24, p. 2378 - 2380
[2] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 479
[4] Patent: WO2006/66894, 2006, A1, . Location in patent: Page/Page column 16-19
[5] Patent: WO2006/134489, 2006, A1, . Location in patent: Page/Page column 13-14
[6] Patent: WO2006/111791, 2006, A1, . Location in patent: Page/Page column 8-10
[7] Patent: EP1939186, 2008, A1, . Location in patent: Page/Page column 6
[8] Patent: WO2008/146105, 2008, A1, . Location in patent: Page/Page column 17-18
  • 4
  • [ 25679-28-1 ]
  • [ 532-11-6 ]
Reference: [1] Patent: EP1645288, 2006, A1, . Location in patent: Page/Page column 5
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 5, p. 1776 - 1790
  • 5
  • [ 75-15-0 ]
  • [ 100-06-1 ]
  • [ 532-11-6 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 36, p. 6977 - 6980
  • 6
  • [ 20365-71-3 ]
  • [ 532-11-6 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 23, p. 11594 - 11602
  • 7
  • [ 82203-83-6 ]
  • [ 532-11-6 ]
Reference: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 20, p. 3911 - 3915
  • 8
  • [ 140-67-0 ]
  • [ 532-11-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 577
  • 9
  • [ 4180-23-8 ]
  • [ 532-11-6 ]
  • [ 77150-78-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 479
[3] Justus Liebigs Annalen der Chemie, 1947, vol. 557, p. 89,105
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1947, vol. 224, p. 479
  • 10
  • [ 831-30-1 ]
  • [ 532-11-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1950, vol. 568, p. 227,237
  • 11
  • [ 50849-98-4 ]
  • [ 532-11-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 1398,1400
  • 12
  • [ 100-06-1 ]
  • [ 532-11-6 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1959, p. 1398,1400
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