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[ CAS No. 943-08-8 ] {[proInfo.proName]}

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Chemical Structure| 943-08-8
Chemical Structure| 943-08-8
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Product Details of [ 943-08-8 ]

CAS No. :943-08-8 MDL No. :MFCD00518584
Formula : C8H5F2NS2 Boiling Point : -
Linear Structure Formula :- InChI Key :XYUPZERKMMCICQ-UHFFFAOYSA-N
M.W : 217.26 Pubchem ID :1522327
Synonyms :

Calculated chemistry of [ 943-08-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.44
TPSA : 66.43 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.71 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.28
Log Po/w (XLOGP3) : 4.1
Log Po/w (WLOGP) : 4.45
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 4.05
Consensus Log Po/w : 3.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.15
Solubility : 0.0154 mg/ml ; 0.0000707 mol/l
Class : Moderately soluble
Log S (Ali) : -5.2
Solubility : 0.00137 mg/ml ; 0.0000063 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.69
Solubility : 0.0439 mg/ml ; 0.000202 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.22

Safety of [ 943-08-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 943-08-8 ]

* 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 [ 943-08-8 ]

[ 943-08-8 ] Synthesis Path-Downstream   1~26

YieldReaction ConditionsOperation in experiment
61% With tert.-butylhydroperoxide; trifluoroacetic acid; In dichloromethane; water; for 16h; General procedure: Difluoromethylation of Heterocycles Standard Procedures: Procedure B: To a solution of heterocycle (0.25 mmol, 1.0 equiv) and zinc difluoromethanesulfinate (DFMS) (173 mg, 0.50 mmol, 2.0 equiv ‘calculated as anhydrous’) in dichloromethane (1.0 mL) and water (0.4 rnL) at room temperature was added trifluoroacetic acid (20 μL, 0.25 rnmol, 1.0 equiv) followed by slow addition of tert-butyl hydroperoxide (70% solution in water, 0.1 mL, 0.75 mmol, 3.0 equiv) with vigorous stirring. The reaction was monitored by thin layer chromatography until completion. For substrates which do not go to completion in 24 hours, a second addition of DFMS (2.0 equiv) and tert-butyl hydroperoxide (3.0 equiv) may be added to drive the reaction further. Upon consumption of starting material, the reaction was partitioned between dichioromethane (2.0 mL) and saturated sodium bicarbonate (2.0 mL) . The organic layer was separated, and the aqueous layer was extracted with dichioromethane (3 X 2.0 mL) . The organic layers were dried with sodium sulfate, concentrated and purified by column chromatography on silica gel. If substrates are less reactive, α,α,-trifluorotoluene can be substituted for DCM, as it causes improved reactivity for some cases. For water-soluble starting materials, a purely aqueous reaction (1.0 mL of water) can be run and in some cases, it was also found to display improved reactivity. In lieu of a workup, these reactions can be concentrated and the product purified directly. If the addition of tert-butyl hydroperoxide is performed too rapidly, the resulting exotherm can result in reduced yield and selectivity. This is especially important on larger scales (see gram scale procedure: substrate 2), where a syringe pump can be used to meter in tert-butyl hydroperoxide.It is noted that trifluoroacetic acid (TFA) is not required in either of the above procedures. It was also found that TFA showed improved rate and conversion for selected nitrogen heteroarene substrates, but was not essential to achieve the desired reactivity for most cases. When present, TFA is typically used at about 0.25 to about 2 equivalents per equivalent of nitrogen heteroarene, and more preferably at about 0.5 to about 1.5 equivalents relative to the nitrogen heteroarene.
  • 2
  • [ 75-45-6 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
  • 3-(difluoromethyl)benzo[d]thiazole-2(3H-)-thione [ No CAS ]
  • 3
  • [ 1097192-99-8 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
  • 3-(difluoromethyl)benzo[d]thiazole-2(3H-)-thione [ No CAS ]
  • 4
  • [ 943-08-8 ]
  • [ 186204-66-0 ]
YieldReaction ConditionsOperation in experiment
83% With hexaammonium heptamolybdate tetrahydrate; dihydrogen peroxide; In ethanol; at 20℃; for 42h; A mixture of 7.18 g (33.05 mmol) of 2-[(difluoromethyl)sulfanyl]-1,3-benzothiazole, 2.04 g (1.65 mmol) of ammonium molybdate (NH4)6Mo7O24 x 4 H2O, 33.0 mL of ethanol, and 12.8 mL (132 mmol) of 30% H2O2 was stirred for 24 h at room temperature. An additional 3.5 mL of 30% H2O2 was added, the mixture was stirred for 18 h and diluted with 300 mL of water, and the precipitate was filtered off, washed with 500 mL of water, and dried at 120-130C. Yield 6.80 g (83%), white needles, mp 155-158C (from EtOAc); published data: mp 133-135C [11], 149C [12]. 1H NMR spectrum (CDCl3), δ, ppm: 6.60 t (1H, JHF = 53.1 Hz), 7.66 m (1H), 7.72 m (1H), 8.08 m (1H), 8.33 m (1H). 13C NMR spectrum (CDCl3), δC, ppm: 114.50 t (JCF = 288.1 Hz), 122.38, 126.25, 128.26, 129.07, 137.85, 153.01, 158.90. 19F NMR spectrum (CDCl3): δF -121.41 ppm.
With sodium periodate; rhodium(III) chloride hydrate; In tetrachloromethane; water; acetonitrile; at 20℃; for 48h; in a round bottom flask, add B in order.Acetonitrile,Carbon tetrachloride,Water and hydrated barium chloride.Place it on a stirrer and stir it vigorously.Then add 2.5 equivalents of sodium periodate to it,Finally let it continue to react at room temperature for 48 h.After treatment: saturated sodium bicarbonate solution and the reaction solution,filter,The filter residue was washed with ethyl acetate,The filtrate was extracted three times with ethyl acetate.After the organic phases are combined, they are dried over anhydrous magnesium sulfate.Spin-dry the solvent to give the desired product as a white solid.
With sodium periodate; ruthenium(III) chloride trihydrate; In tetrachloromethane; water; acetonitrile; at 25℃; for 0.5h;Inert atmosphere; Step 2: To a solution of 2-((difluoromethyl)thio)benzo[rfjthiazole (11.1 g, 51 mmol) in a mixture of ACN / CC / water (v : v : v :::: 1 : 1 : 2, 222 mL) were added sodium periodate (34.2 g , 160 mmol) and ruthenium(III) chloride trihydrate (33 mg, 0.13 mmol) portion wise. The resulting solution was stirred at room temperature for 3 h. The mixture was diluted with water (800 ml) and extracted with DCM (1500 mL). The organic phase w?as washed with brine (800 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica (0-20% ethyl acetate/DCM) to give 2-((difluoromethyl)suifonyl)benzo[
  • 5
  • [ 75-45-6 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
YieldReaction ConditionsOperation in experiment
59% With potassium hydroxide; In 1,4-dioxane; water; for 1h; Chloro(difluoro)methane was bubbled over a period of 1 h at a rate of 15-18 mL/min through a mixture of 3.34 g (20 mmol) of 1,3-benzothiazole-2-thiol, 20 mL of dioxane, 13.17 g (200 mmol) of 85% KOH, and 40 mL of water under stirring. The mixture was diluted with 40 mL of water and extracted with methylene chloride (3 x 25 mL), the organic phase was dried over MgSO4, and the solvent was removed under reduced pressure. Yield 2.55 g (59%), yellow liquid. 1H NMR spectrum (CDCl3), δ, ppm: 7.42 t.d (1H, J = 7.7, 1.2 Hz), 7.50 t.d (1H, J = 7.7, 1.2 Hz), 7.65 t (1H, CHF2, J = 56.0 Hz), 7.84 d (1H, J = 8.1 Hz), 8.01 d (1H, J = 8.1 Hz). 13C NMR spectrum (CDCl3), δC, ppm: 120.24 t (CH, JCF = 276.6 Hz), 121.16 (CH), 122.84 (CH), 125.64 (CH), 126.60 (CH), 135.96, 152.90, 157.00 t (JCF = 4.2 Hz). 19F NMR spectrum (CDCl3): δF -93.18 ppm [8].
13.25 g Under N2 atmosphere,Add 1.1 equivalents of 3.2g NaH to the pre-dried N2 pumping three timesShould be in the bottle,Then inject 15mL anhydrous DMF into it.Then the DMF solution of A was added dropwise to the reaction flask.Then after stirring for about half an hour at room temperature, the reaction system was bubbled inChlorodifluoromethane gas about 2h,Finally, the reaction flask was placed in a 60-degree oil bath and stirred for 12 h.After treatment: quench with water,Ether extraction,After the organic phase is washed with 5% potassium hydroxide,Dry with anhydrous magnesium sulfateSpin dry and vacuum distillation13.25 g of the target product B was obtained as a pale yellow oily liquid.
With potassium hydroxide; In 1,4-dioxane; water; at 0 - 20℃; for 13h;Sealed tube; Step 1 : To a solution of benzo[i/]thiazole-2-thiol (50 g, 300 mmol) in 1,4-dioxane (125 mL) and water (125 mL) was added potassium hydroxide (30 g, 540 mmol) at 0 C. Excess chlorodifluorometliane vras bubbled through the resulting mixture over 5h. The reactor was sealed, and the mixture was stirred at room temperature for 8 h before being concentrated under reduced pressure. The residue was purified by column chromatography on silica (neutralized with triethylamine) (0-30% ethyl acetate/hexanes) to give 2-((difluoromethyl)thio)benzo[ jthiazole. MS: 218 (M+l). -NM11 (300 MHz, Chloroform-tf) d 8.05 - 8.02 (m, 1H), 7.89 - 7.86 (m, 1H), 7.67 - 7.41 (m, 3H). 1SF-NMR (282 MHz, Chloroform- d) d -93 20 (s, CF2H).
  • 7
  • [ 75-45-6 ]
  • [ 2492-26-4 ]
  • [ 943-08-8 ]
  • 8
  • bis(((difluoromethyl)sulfinyl)oxy)zinc [ No CAS ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
  • 9
  • [ 1895-39-2 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
  • 3-(difluoromethyl)benzo[d]thiazole-2(3H-)-thione [ No CAS ]
  • 10
  • [ 149-30-4 ]
  • 2,2‐difluoro‐2‐(triphenylphosphonio)acetate [ No CAS ]
  • [ 943-08-8 ]
YieldReaction ConditionsOperation in experiment
87% In tetrahydrofuran; at 60℃; for 8h;Sealed tube; In a 5 mL sealed tube,Triphenyl difluoromethylidene phosphonium salt inner salt (0.57 g, 1.6 mmol)And 2-mercaptobenzothiazole (0.13 g, 0.8 mmol) were dissolved in tetrahydrofuran,At 60 , the tube closure reaction 8h.Then the heating was stopped. After the reaction was cooled, the system was directly separated by column chromatography (petroleum ether: dichloromethane = 4: 1) to give the product (0.15 g). Yield: 87%.
  • 12
  • [ 943-08-8 ]
  • 2-((difluoromethyl)sulfinyl)benzo[d]thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 3-chloro-benzenecarboperoxoic acid; In acetone; at -5℃;Inert atmosphere; General procedure: Underthe N2 atmosphere at -15 oC (for Het-SCH3, and-5 oC for Het-SCF2H and Het-SCFH2),the acetone solution of 3-chloroperoxybenzoic acid (mCPBA, 1.05 equiv) wasslowly added (within 1 hour) to the stirring acetone solution of the sulfide ether. The reaction was maintained at thesame temperature and monitored by TLC, 1H NMR, or 19F NMR (forfluorinated sulfoxide) to avoid over oxidation of sulfoxide to sulfone. Aftercompletion, the resulting mixture was quenched with excess NaHCO3(aq)and then extracted with ether (Et2O, 350 mL). The combined organic layer was washed withsaturated NaHCO3(aq) and NaCl(aq), and then dried with Na2SO4.Solvent was evaporated, the sulfoxide was obtained after flash chromatographypurification.
  • 13
  • [ 136-95-8 ]
  • (1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-yl)(difluoromethylthio)silver [ No CAS ]
  • [ 943-08-8 ]
  • 15
  • [ 943-08-8 ]
  • 2-((1,1-difluoroethyl)sulfonyl)benzo[d]thiazole [ No CAS ]
  • 16
  • [ 943-08-8 ]
  • 2-((chlorodifluoromethyl)sulfonyl)benzo[d]thiazole [ No CAS ]
  • 17
  • [ 943-08-8 ]
  • 2-((bromodifluoromethyl)sulfonyl)benzo[d]thiazole [ No CAS ]
  • 18
  • [ 943-08-8 ]
  • 2-((difluoroiodomethyl)sulfonyl)benzo[d]thiazole [ No CAS ]
  • 19
  • [ 275818-95-6 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
YieldReaction ConditionsOperation in experiment
61% With dipotassium peroxodisulfate; silver nitrate; In water; acetonitrile; at 80℃; for 24h;Inert atmosphere; General procedure: A reaction tube was charged with 4-methylbenzenethiol (1b) (24.8 mg, 0.2 mmol) at room temperature, then trifluoromethanesulfinate (62.4 mg, 0.4 mmol), silver nitrate (3.4 mg, 0.02 mmol), potassium persulfate (108 mg, 0.4 mmol) and MeCN/H2O (1:1, 0.8 mL) were added. The resulting mixture was stirred at 80 under argon atmosphere for 24 h. After cooling to room temperature, the reaction mixture was quenched and purified by flash silica gel column chromatography (eluent: petroleum ether/EtOAc) to afford the desired product 3b (23.0 mg, 60%).
  • 20
  • (difluoromethyl)triphenylphosphonium trifluoromethanesulfonate [ No CAS ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
  • 21
  • [ 137-07-5 ]
  • 2,2‐difluoro‐2‐(triphenylphosphonio)acetate [ No CAS ]
  • [ 943-08-8 ]
  • 22
  • S-difluoromethyl-S-phenyl-2,4,6-trimethoxyphenylsulfonium tetrafluoroborate [ No CAS ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
  • 23
  • [ 1885-46-7 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
YieldReaction ConditionsOperation in experiment
87% With potassium hydroxide; In acetonitrile; for 0.0333333h; 2-Mercaptobenzothiazole (1.0 eq, 3.0 mmol, 0.5 g) was added to a solution of 6M KOH (6 mL) and MeCN (6 mL), afterwards <strong>[1885-46-7]difluoromethyl trifluoromethanesulfonate</strong> (3 eq, 9.0 mmol, 1.2 mL) was added to the mixture. The mixture was stirred for 2 min and was diluted with H2O (25 mL) and extracted with diethyl ether (3 x 10 mL). The organic phase was dried over Na2SO4 and concentrated in vacuo. Colourless solid (0.57 g, 2.6 mmol, 87 %). 1H NMR (400 MHz, Chloroform-d): d 8.01 (d, J = 8.2, 1H, HAr), 7.84 (d, J = 8.0, 1H, HAr), 7.65 (t, J = 56.3, 1H, CF2H), 7.49 (t, J = 8.0, 1H, HAr), 7.41 (t, J = 7.6, 1H).19F NMR (376 MHz, Chloroform-d): d -93.08 (d, J = 56). The Analytical data is in agreement to literature (Hu, Org. Lett.2010, 12, 1444-1447).
  • 24
  • [ 943-08-8 ]
  • [ 333-27-7 ]
  • 2-((difluoromethyl)thio)-3-methylbenzo[d]thiazol-3-ium trifluoromethanesulfonate [ No CAS ]
  • 25
  • [ 149-30-4 ]
  • [ 150542-06-6 ]
  • [ 943-08-8 ]
YieldReaction ConditionsOperation in experiment
92% With water; sodium hydroxide; In acetonitrile; at 20℃; for 0.166667h; General procedure: A mixture of 8 or 10 (1 mmol), NaOH (11 mmol, 0.44 g) was dissolved in CH3CN (CH3CN/H2O 10/1, V/V, 11 mL) in an oven dried 50 mL round bottom flask containing a stir bar. Iododifluoroacetophenone (2) (2 mmol, 0.56 g), was added to the reaction mixture and stirred at room temperature for about 10 min. After the reaction was completed as indicated by TLC the reaction mixture was removed under reduced pressure. And then, the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (25 mL x 3), followed by brine (50 mL). The organic extract was dried over NaSO4, filtered and evaporated under reduced pressure. The crude product was further purified by silica gel column chromatography using (pet ether/EtOAc) to furnish the S- and O-CF2H derivatives 9a-9h and 11a-11h.
  • 26
  • [ 65094-22-6 ]
  • [ 149-30-4 ]
  • [ 943-08-8 ]
YieldReaction ConditionsOperation in experiment
89% General procedure: The starting material (2 mmol) was added to a sealed tube holding 20 mL of a 1:1 mixture of acetonitrile/water and KOH (40 mmol), whichwas cooled using an ice bath. The mixture was vigorously mixed for 15min and then phosphonate 1 (4 mmol) was added to the mixture in oneportion, and mixing and cooling was maintained for an additional 15 -60 min, followed by ~30 min - 2.5 h at r.t. The reaction mixture wasthen diluted with ether (10 mL) and the organic phase separated. Thewater phase was further washed with ether (10 mL). The combinedorganic phase was dried over anhydrous Na2SO4 and the solvent evaporatedto provide a crude product which was purified using columnchromatography on silica gel
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