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[ CAS No. 80087-71-4 ] {[proInfo.proName]}

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Chemical Structure| 80087-71-4
Chemical Structure| 80087-71-4
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Product Details of [ 80087-71-4 ]

CAS No. :80087-71-4 MDL No. :MFCD00665747
Formula : C7H4FNS2 Boiling Point : -
Linear Structure Formula :- InChI Key :XDZVUKOOUHIRKY-UHFFFAOYSA-N
M.W : 185.24 Pubchem ID :2737353
Synonyms :

Calculated chemistry of [ 80087-71-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.97
TPSA : 76.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 2.51
Log Po/w (WLOGP) : 3.52
Log Po/w (MLOGP) : 1.86
Log Po/w (SILICOS-IT) : 5.17
Consensus Log Po/w : 2.97

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.18
Solubility : 0.124 mg/ml ; 0.000668 mol/l
Class : Soluble
Log S (Ali) : -3.75
Solubility : 0.0326 mg/ml ; 0.000176 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.36
Solubility : 0.0809 mg/ml ; 0.000437 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 80087-71-4 ]

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 [ 80087-71-4 ]

* 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.

  • Upstream synthesis route of [ 80087-71-4 ]
  • Downstream synthetic route of [ 80087-71-4 ]

[ 80087-71-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 80087-71-4 ]
  • [ 399-74-6 ]
YieldReaction ConditionsOperation in experiment
95%
Stage #1: at 20 - 25℃; for 0.25 h; Inert atmosphere
Stage #2: at 20 - 25℃; for 3 h; Inert atmosphere
General procedure: A mixture of the 2-mercaptobenzo[d]thiazole (>1 g, 1 equiv) and sul-furyl chloride (10 equiv) was stirred at 20–25 °C for 15 min. Next, H 2 O(2 equiv) was added and the mixture was stirred at 20–25 °C for anadditional 3 h. A sample was taken, quenched with MeCN/H 2 O (2:1)and analyzed by HPLC. After completion of the reaction, the mixturewas diluted with MeCN (5 volumes) and slowly quenched with H 2 O(20 volumes). The product precipitated from the aqueous solution.The solid was collected and washed with H 2 O. Drying under vacuumafforded the pure product. In the case of the liquid product 2-chloro-benzo[d]thiazole (13), the reaction mixture was extracted withEtOAc. The organic layer was then dried and concentrated to affordthe product as an oil.
Reference: [1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 727 - 730
[2] Organic Letters, 2017, vol. 19, # 21, p. 5836 - 5839
[3] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
[4] Patent: WO2010/57121, 2010, A1, . Location in patent: Page/Page column 97
[5] Patent: WO2006/44775, 2006, A2, . Location in patent: Page/Page column 21
  • 2
  • [ 75-15-0 ]
  • [ 61272-76-2 ]
  • [ 80087-71-4 ]
YieldReaction ConditionsOperation in experiment
72% With sodiumsulfide nonahydrate In N,N-dimethyl-formamide at 110℃; for 12 h; Sealed tube; Inert atmosphere General procedure: A sealed tube (50 mL) was charged with 2-haloaniline 1a (2mmol), CS2 (10 mmol), Na2S (4mmol) and DMF (2 mL) at room temperature under an argon gas atmosphere and the tube was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically at 110 °C for 12 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, 2 mL HCl (3 mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by dichloromethane (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel colum chromatography (eluent: petroleum ether / ethyl acetate) give the corresponding pure product 2a.
43.8% With sodium sulphide nonahydrate In N,N-dimethyl-formamide at 110℃; for 12 h; Inert atmosphere To the reaction tube was added 0.50 mmol (0 • 1185 g) of 4-fluoro-2-iodoaniline, 0 · 25mmol (0 0600g) of the nine Water sodium sulfide, 2 mL of N, N-dimethylformamide and 1.50 mmol (0.1142 g) of carbon disulfide were added under an inert gas atmosphere and the reaction was stirred at 110 ° C for 12 hours, After the reaction was complete, the reaction solution was cooled to room temperature, and 3 mL of 4N hydrochloric acid was added for 15 min. The reaction solution was extracted three times with methylene chloride. The organic phases were combined and dried over anhydrous magnesium sulfate for 2 hours. And finally the crude dichloromethane solvent was distilled off under reduced pressure to give the crude product. The crude product was subjected to column chromatography (200-300 mesh silica gel) eluting with a petroleum ether and ethyl acetate (8: 1-2: 1) to give a white powder having a purity of more than 99percent Thiobenzothiazole 40.6 mg, the isolated yield was 43.8percent.
Reference: [1] Organic Letters, 2011, vol. 13, # 12, p. 3202 - 3205
[2] Synthetic Communications, 2017, vol. 47, # 20, p. 1916 - 1925
[3] Patent: CN104098529, 2016, B, . Location in patent: Paragraph 0040-0041
  • 3
  • [ 61272-76-2 ]
  • [ 140-89-6 ]
  • [ 80087-71-4 ]
YieldReaction ConditionsOperation in experiment
99% With iron(III) trifluoride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In N,N-dimethyl-formamide at 110℃; for 3 h; Inert atmosphere; Sealed tube General procedure: A 25 mL reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium o-ethyldithiocarbonate 2 (1.8 mmol), FeF3 (0.06 mmol), 2,2’-bis(diphenylphosphino)-1,1’-binaphthyl (0.03 mmol) and DMF (4 mL). The reaction vessel was flushed with argon for three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110 for 3 - 21 hours. The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, then 4 mL HCl (3mol/L) was added and stirred for 30 minutes. Then the reaction mixture solution was extracted by ethyl acetate (3*20 mL). Subsequently, the combined organic solution were dried by anhydrous sodium sulfate and the target product was purified by silica gel colum chromatography (eluent: petroleum ether / ethylacetate) to give the corresponding pure product 3.
95.5% With copper(l) chloride In N,N-dimethyl-formamide at 110℃; for 6 h; Inert atmosphere; Sealed tube General procedure: A 25 mL Wattecs reaction tube was charged with 2-haloaniline 1 (0.6 mmol), potassium O-ethyl dithiocarbonate 2 (1.8 mmol),CuCl (0.06 mmol), and DMF (2 mL). The reaction vessel was flushed with argon three times and sealed. Then the mixture was stirred electromagnetically in an oil bath at 110°C for 6 h.The reaction process was monitored by TLC on silica gel. After the reaction was completed, the reaction mixture was cooled to room temperature, and then HCl (3 mL, 3 mol/L) was added and stirred for another 30 min. The reaction mixture solution was extracted by ethyl acetate (3 × 20 mL). Subsequently, the combined organic solutions were dried by anhydrous sodium sulfate and the target product was purified by chromatography on a silica gel column (eluent: petroleum ether/ethyl acetate) togive the corresponding pure product 3. Complete characterization characterizationof the products (all known) is found in the Supplemental Materials (Figures S1–S13).
Reference: [1] Synthetic Communications, 2015, vol. 45, # 20, p. 2378 - 2385
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2016, vol. 191, # 5, p. 699 - 701
  • 4
  • [ 367-25-9 ]
  • [ 140-89-6 ]
  • [ 80087-71-4 ]
YieldReaction ConditionsOperation in experiment
81% at 120 - 130℃; Inert atmosphere General procedure: A round-bottomed flask was charged with 2-bromoaniline or 2-fluoro-aniline (>3 g, 1.0 equiv) and potassium O-ethyl carbonodithioate(1.5–1.7 equiv). The mixture was dissolved in DMF (10 volumes) andheated to 120–130 °C until the aniline was fully consumed (3–14 h).The reaction mixture was cooled to r.t. and filtered. The filtrate wasdiluted with H 2 O (50 volumes) and the pH was adjusted to 1–2 usingaqueous 2 M HCl. The solid precipitate was collected, washed withH 2 O and dried to yield the pure product.
Reference: [1] Organic Letters, 2017, vol. 19, # 21, p. 5836 - 5839
[2] Advanced Synthesis and Catalysis, 2017, vol. 359, # 11, p. 1837 - 1843
[3] Synthesis (Germany), 2018, vol. 50, # 10, p. 2027 - 2032
  • 5
  • [ 75-15-0 ]
  • [ 1003-98-1 ]
  • [ 80087-71-4 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 12, p. 3202 - 3205
  • 6
  • [ 367-31-7 ]
  • [ 140-89-6 ]
  • [ 80087-71-4 ]
Reference: [1] Patent: WO2010/57121, 2010, A1, . Location in patent: Page/Page column 97
  • 7
  • [ 1003-98-1 ]
  • [ 140-89-6 ]
  • [ 80087-71-4 ]
Reference: [1] Archiv der Pharmazie, 2009, vol. 342, # 10, p. 605 - 613
[2] Synthetic Communications, 2007, vol. 37, # 3, p. 369 - 376
  • 8
  • [ 28563-38-4 ]
  • [ 367-25-9 ]
  • [ 80087-71-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 727 - 730
  • 9
  • [ 75-15-0 ]
  • [ 348-40-3 ]
  • [ 80087-71-4 ]
Reference: [1] Patent: US5451594, 1995, A,
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