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[ CAS No. 114435-86-8 ] {[proInfo.proName]}

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Chemical Structure| 114435-86-8
Chemical Structure| 114435-86-8
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Product Details of [ 114435-86-8 ]

CAS No. :114435-86-8 MDL No. :MFCD20482732
Formula : C8H9FO3S Boiling Point : -
Linear Structure Formula :- InChI Key :RFCGZPLGJZELOK-UHFFFAOYSA-N
M.W : 204.22 Pubchem ID :13862289
Synonyms :

Calculated chemistry of [ 114435-86-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.64
TPSA : 51.75 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) : -6.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.04
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 3.13
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 1.42
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.741 mg/ml ; 0.00363 mol/l
Class : Soluble
Log S (Ali) : -2.6
Solubility : 0.514 mg/ml ; 0.00252 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.14
Solubility : 0.148 mg/ml ; 0.000724 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.17

Safety of [ 114435-86-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P210-P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H227-H302-H314-H317 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 114435-86-8 ]

* 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.

  • Upstream synthesis route of [ 114435-86-8 ]
  • Downstream synthetic route of [ 114435-86-8 ]

[ 114435-86-8 ] Synthesis Path-Upstream   1~7

  • 1
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  • [ 114435-86-8 ]
YieldReaction ConditionsOperation in experiment
88% With cesium fluoride In tert-Amyl alcohol at 90℃; for 0.25 h; Microwave irradiation; Sealed tube Methylene ditosylate (100 mg, 0.28 mmol) and caesium fluoride (213 mg, 1.4 mmol) were dissolved in tert-amyl alcohol (5 mL) and irradiated in a microwave for 15 minutes at 90 °C. The reaction was allowed to cool and the tert-amyl alcohol was removed under reduced pressure, ice-cold diethyl ether was added and the suspension filtered, then washed with plenty of ice-cold diethyl ether. The filtrate was concentrated under reduced pressure to yield Fluoromethyl 4-methylbenzenesulfonate as a colourless oil (49 mg, 88percent yield). 1H NMR (500 MHz, CDCl3) δ: 2.43 (s, 3H, ArCH3), 5.72 (d, 2H, CH2, J = 51.0 Hz), 7.35 (d, 2H, ArH, J = 8.0 Hz), 7.81 (d, 2H, ArH, J = 8.0 Hz); 13C (125 MHz, CDCl3) δ: 21.67, 98.16 (d, J = 221 Hz), 127.87, 129.96, 133.77, 145.63; 19F (471 MHz, CDCl3) δ: -153.24 (t, J = 50.7 Hz).
41.3% With pentaethylene glycol; cesium fluoride In acetonitrile for 2.5 h; Reflux A stirred solution of methylene bis(tosylate) (2.0 g, 5.61 mmol), hexaethylene glycol(2.11 mL, 8.42 mmol) and cesium fluoride (1.279 g, 8.42 mmol) in acetonitrile(17 mL) was refluxed for 2.5 h. The reaction mixture was diluted with ether, and extracted three times with water to remove hexaethylene glycol. The ether layer was dried over anhydrous sodium sulfate, filtered, and evaporated. The residue was subjected to flash chromatography (4 g silica-gel column, flow rate of 24 ml/min) eluting with100percent hexane for 3 min and increased ethyl acetate from 0percent to 10percent in 20 min togive the product as colorless oil (473 mg, 2.32 mmol, 41.3percent yield).1H NMR (500MHz, CDCl3) δ ppm 7.84 (d, J= 8.0 Hz, 2H), 7.36 (d, J = 8.0 Hz,2H), 5.74 (d, J = 51.0 Hz, 2H), 2.46(s, 3H); 13C NMR (125 MHz, CDCl3) δ ppm 145.92, 134.14, 130.27, 128.22, 98.45 (d, J = -229.5 Hz), 22.01; 19FNMR (470 MHz, CDCl3) δppm 153.2 (t, J = 50.5 Hz).
11% With potassium fluoride; [2.2.2]cryptande In acetonitrile at 110℃; for 1 h; Inert atmosphere Example 3. Preparation of Fluoromethyltosylate (8)C H2OTos2 ^ FCH2OTos7 8 Methylene ditosylate (7) was prepared according to an established literature procedure and analytical data was consistent with reported values (Emmons, W.D., et al. , Journal of the American Chemical Society, 1953; 75:2257; and Neal, T.R., et al. , Journal of Labelled Compounds and Radiopharmaceuticals 2005; 48:557-68).To a solution of methylene ditosylate (7) (0.67 g, 1.89 mmol) in dry acetonitrile (10 mL) was added Kryptofix K222 [4,7,13,16,21,24-hexaoxa-l,10- diazabicyclo[8.8.8]hexacosane] (1.00 g, 2.65 mmol) followed by potassium fluoride (0.16 g, 2.83 mmol). The suspension was then heated to 110°C under nitrogen. After 1 h TLC (7:3 hexane/ethyl acetate/silica/UV254) indicated complete conversion of (7). The reaction mixture was diluted with ethyl acetate (25 mL), washed with water (2 x 15 mL) and dried over MgS04. Chromatography (5--> 10percent ethyl acetate/hexane) gave the desired product (8) as a colorless oil (40 mg, 11percent). ]H NMR (CDC13, 400 MHz) δ 7.86 (d, 2H, / = 8 Hz, aryl CH), 7.39 (d, 2 H, / = 8 Hz, aryl CH), 5.77 (d, 1 H, / = 52 Hz, CH2F), 2.49 (s, 3H, tolyl CH3). 13C NMR (CDC13) δ 145.6 (aryl), 133.8 (aryl), 129.9 (aryl), 127.9 (aryl), 98.1 (d, / = 229 Hz, CH2F), 21.7 (tolyl CH3). HRMS (CI) = 222.0604 (M + NH4)+. Calcd. for C8H13FN03S 222.0600.
11% With potassium fluoride; [2.2.2]cryptande In acetonitrile at 110℃; for 1 h; Inert atmosphere Example 3. Preparation of Fluoromethyltosylate (8)C H2OTos2 ^ FCH2OTos7 8 Methylene ditosylate (7) was prepared according to an established literature procedure and analytical data was consistent with reported values (Emmons, W.D., et al. , Journal of the American Chemical Society, 1953; 75:2257; and Neal, T.R., et al. , Journal of Labelled Compounds and Radiopharmaceuticals 2005; 48:557-68).To a solution of methylene ditosylate (7) (0.67 g, 1.89 mmol) in dry acetonitrile (10 mL) was added Kryptofix K222 [4,7,13,16,21,24-hexaoxa-l,10- diazabicyclo[8.8.8]hexacosane] (1.00 g, 2.65 mmol) followed by potassium fluoride (0.16 g, 2.83 mmol). The suspension was then heated to 110°C under nitrogen. After 1 h TLC (7:3 hexane/ethyl acetate/silica/UV254) indicated complete conversion of (7). The reaction mixture was diluted with ethyl acetate (25 mL), washed with water (2 x 15 mL) and dried over MgS04. Chromatography (5--> 10percent ethyl acetate/hexane) gave the desired product (8) as a colorless oil (40 mg, 11percent). ]H NMR (CDC13, 400 MHz) δ 7.86 (d, 2H, / = 8 Hz, aryl CH), 7.39 (d, 2 H, / = 8 Hz, aryl CH), 5.77 (d, 1 H, / = 52 Hz, CH2F), 2.49 (s, 3H, tolyl CH3). 13C NMR (CDC13) δ 145.6 (aryl), 133.8 (aryl), 129.9 (aryl), 127.9 (aryl), 98.1 (d, J = 229 Hz, CH2F), 21.7 (tolyl CH3). HRMS (CI) = 222.0604 (M + NH4)+. Calcd. for C8H13FN03S 222.0600.
11% With potassium fluoride; [2.2.2]cryptande In acetonitrile at 110℃; for 1 h; Inert atmosphere Example 3. Preparation of Fluoromethyltosylate (8)C H2OTos2 FCH2OTos7 8Methylene ditosylate (7) was prepared according to an established literature procedure and analytical data was consistent with reported values (Emmons, W.D., et al. , Journal of the American Chemical Society, 1953; 75:2257; and Neal, T.R., et al. , Journal of Labelled Compounds and Radiopharmaceuticals 2005; 48:557-68).To a solution of methylene ditosylate (7) (0.67 g, 1.89 mmol) in dry acetonitrile (10 mL) was added Kryptofix K222 [4,7,13,16,21,24-hexaoxa-l,10- diazabicyclo[8.8.8]hexacosane] (1.00 g, 2.65 mmol) followed by potassium fluoride (0.16 g, 2.83 mmol). The suspension was then heated to 110°C under nitrogen. After 1 h TLC (7:3 hexane/ethyl acetate/silica/UV254) indicated complete conversion of (7). The reaction mixture was diluted with ethyl acetate (25 mL), washed with water (2 x 15 mL) and dried over MgS04. Chromatography (5--> 10percent ethyl acetate/hexane) gave the desired product (8) as a colorless oil (40 mg, 11percent). ]H NMR (CDC13, 400 MHz) δ 7.86 (d, 2H, / = 8 Hz, aryl CH), 7.39 (d, 2 H, / = 8 Hz, aryl CH), 5.77 (d, 1 H, / = 52 Hz, CH2F), 2.49 (s, 3H, tolyl CH3). 13C NMR (CDC13) δ 145.6 (aryl), 133.8 (aryl), 129.9 (aryl), 127.9 (aryl), 98.1 (d, / = 229 Hz, CH2F), 21.7 (tolyl CH3). HRMS (CI) = 222.0604 (M + NH4)+. Calcd. for C8H13FN03S 222.0600.

Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1635 - 1637
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 18, p. 3956 - 3960
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2003, vol. 46, # 6, p. 555 - 566
[4] ChemMedChem, 2016, vol. 11, # 1, p. 108 - 118
[5] Patent: WO2012/40133, 2012, A2, . Location in patent: Page/Page column 36-37
[6] Patent: WO2012/40138, 2012, A2, . Location in patent: Page/Page column 36
[7] Patent: WO2012/40151, 2012, A2, . Location in patent: Page/Page column 39
[8] ChemMedChem, 2014, vol. 9, # 7, p. 1476 - 1487
[9] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 8, p. 557 - 568
[10] Journal of Labelled Compounds and Radiopharmaceuticals, 2013, vol. 56, # 7, p. 360 - 363
[11] Patent: WO2014/137883, 2014, A1, . Location in patent: Page/Page column 62
[12] Patent: WO2015/120320, 2015, A1, . Location in patent: Page/Page column 89
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Reference: [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 8, p. 1885 - 1889
  • 3
  • [ 75-11-6 ]
  • [ 16836-95-6 ]
  • [ 114435-86-8 ]
YieldReaction ConditionsOperation in experiment
28% for 20 h; Reflux Example 8. Synthesis of cold Fluoromethyltosylate (15)i iiCH2I2 CH2OTos2 FCH2OTos13 14 15 Scheme 3 i: Silver p-toluenesulfonate, MeCN, reflux, 20 h;ii: KF, MeCN, reflux, 1 h.According to Scheme 3 above:(a) Synthesis of methylene ditosylate (14)Commercially available diiodomethane (13) (2.67 g, 10 mmol) was reacted with silver tosylate (6.14 g, 22 mmol), using the method of Emmons and Ferris, to give methylene ditosylate (10) (0.99g) in 28percent yield (Emmons, W.D., et ah, "Metathetical Reactions of Silver Salts in Solution. II. The Synthesis of Alkyl Sulfonates", Journal of the American Chemical Society, 1953; 75:225).
Reference: [1] Patent: WO2012/40151, 2012, A2, . Location in patent: Page/Page column 43
  • 4
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 33, p. 9930 - 9934[2] Angew. Chem., 2017, vol. 129, p. 10062 - 10066,5
  • 5
  • [ 16836-95-6 ]
  • [ 114435-86-8 ]
Reference: [1] Patent: WO2012/40133, 2012, A2,
[2] ChemMedChem, 2014, vol. 9, # 7, p. 1476 - 1487
[3] Patent: WO2014/137883, 2014, A1,
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 18, p. 3956 - 3960
[5] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1635 - 1637
[6] Patent: WO2012/40138, 2012, A2,
  • 6
  • [ 24124-59-2 ]
  • [ 455-16-3 ]
  • [ 114435-86-8 ]
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 17, p. 1635 - 1637
  • 7
  • [ 104-15-4 ]
  • [ 114435-86-8 ]
Reference: [1] ChemMedChem, 2014, vol. 9, # 7, p. 1476 - 1487
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