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Chemistry
Organic Building Blocks
Benzothiazoles
fluorobenzo
GW 610
Chemistry
Organic Building Blocks
Heterocyclic Building Blocks
Benzothiazoles
Aryls Fluorinated Building Blocks Benzene Compounds
fluorobenzo
dimethoxyphenyl

[ CAS No. 872726-44-8 ] {[proInfo.proName]}

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CAS No. :872726-44-8 MDL No. :MFCD12024619
Formula : C15H12FNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :ZRLSVQBGBBYEAZ-UHFFFAOYSA-N
M.W : 289.32 Pubchem ID :6712941
Synonyms :
NSC 721648
Chemical Name :2-(3,4-Dimethoxyphenyl)-5-fluorobenzo[d]thiazole

Safety of [ 872726-44-8 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 872726-44-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 872726-44-8 ]

[ 872726-44-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 120-14-9 ]
  • [ 224791-45-1 ]
  • [ 872726-44-8 ]
YieldReaction ConditionsOperation in experiment
90% With toluene-4-sulfonic acid; triphenylphosphine for 15h; Heating;
88% With toluene-4-sulfonic acid; triphenylphosphine In toluene for 24h; Heating;
88% With toluene-4-sulfonic acid; triphenylphosphine In toluene for 24h; Heating / reflux; B General Method B: For the Synthesis of 2-arylbenzothiazoles Substituted in the Benzothiazole Ring; Disubstituted benzaldehyde (3.5 mmol), p-toluenesulphonic acid (0.35 mmol) and triphenylphosphine (1.75 mmol) were added to a solution of disulfide (1.75 mmol) in toluene (20 mL). The reaction mixture was heated at reflux for 24 hrs then allowed to cool and concentrated in vacuo. The crude product was purified by column chromatography (2% MeOH/CH2Cl2) to give the required substituted 2-phenylbenzothiazole in good yield. 5-Fluoro-2-(3,4-dimethoxyphenyl)benzothiazole (1). From bis(2-amino-4-fluorophenyl)disulfide and 3,4-dimethoxybenzaldehyde (88% yield), mp 110° C.; IR νmax 1597, 1485, 1443, 1269, 1140, 1121, 959, 843 cm-1; 1H NMR (DMSO-d6) δ 8.17 (1H, dd, J=8.8, 5.4 Hz, H-4), 7.89 (1H, dd, J=10.0, 2.5 Hz, H-7), 7.64 (2H, m, H-2',6'), 7.37 (1H, td, J=9.1, 2.5 Hz, H-6), 7.15 (1H, d, J=9.0 Hz, H-5'), 3.91 (3H, s, OCH3), 3.88 (3H, s, OCH3); m/z (CI) 290 (M++1). Anal. (C15H12NO2SF) C, H, N. C: found 62.34%, calc. 62.27%; H: found 4.12%, calc. 4.18%; N: found 4.76%, calc. 4.84%.
87% With sodium metabisulfite In dimethyl sulfoxide at 120℃; 4.2. General procedure for the synthesis of substituted 2-phenylbenzothiazoles General procedure: The appropriate 4- or 5-substituted 2-aminothiophenol disulfide (0.86 mmol), substituted benzaldehyde (0.88 mmol) and sodium metabisulfite (0.88 mmol) were dissolved in anhydrous DMSO (5 mL). The resulting reaction mixture was stirred at 120 °C and the formation of the desired compound monitored by TLC analysis. On completion of reaction (in most cases between 40 and 90 min) the mixture was cooled to room temperature, water was added and the resulting precipitate was collected by vacuum filtration. The precipitate was then washed with excess water, re-dissolved in dichloromethane (25 mL) and the remaining traces of sodium metabisulfite were removed by washing with brine (25 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. In a minority of cases further purification was required, and the product was either recrystallised or washed through a plug of silica (using dichloromethane as eluent) and reduced to dryness.
68% With toluene-4-sulfonic acid; triphenylphosphine In toluene for 24h; Reflux;

Reference： [1]Wang, Min; Gao, Mingzhang; Mock, Bruce H.; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8599 - 8607]
[2]Mortimer, Catriona G.; Wells, Geoffrey; Crochard, Jean-Philippe; Stone, Erica L.; Bradshaw, Tracey D.; Stevens, Malcolm F. G.; Westwell, Andrew D. [Journal of Medicinal Chemistry, 2006, vol. 49, # 1, p. 179 - 185]
[3]Current Patent Assignee: PHARMINXO - US2006/63816, 2006, A1 Location in patent: Page/Page column 8
[4]Weekes, Ashley A.; Bagley, Mark C.; Westwell, Andrew D. [Tetrahedron, 2011, vol. 67, # 40, p. 7743 - 7747]
[5]Wang, Kai; Guengerich, F. Peter [Chemical Research in Toxicology, 2012, vol. 25, # 8, p. 1740 - 1751]
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Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 8599 - 8607
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 179 - 185
[3]Chemical Research in Toxicology,2012,vol. 25,p. 1740 - 1751
  • 3
  • [ 345-17-5 ]
  • [ 5763-61-1 ]
  • [ 872726-44-8 ]
Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 13808 - 13812
    Angew. Chem.,2014,vol. 126,p. 14028 - 14032,5
  • 4
  • [ 345-17-5 ]
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  • [ 872726-44-8 ]
Reference： [1]Green Chemistry,2017,vol. 19,p. 4289 - 4293

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