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[ CAS No. 103935-47-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 103935-47-3
Chemical Structure| 103935-47-3
Chemical Structure| 103935-47-3
Structure of 103935-47-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 103935-47-3 ]

CAS No. :103935-47-3 MDL No. :MFCD11656439
Formula : C3H4BrF3O3S Boiling Point : -
Linear Structure Formula :- InChI Key :KENPFZUYYWVXNW-UHFFFAOYSA-N
M.W : 257.03 Pubchem ID :10923169
Synonyms :

Calculated chemistry of [ 103935-47-3 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 34.65
TPSA : 51.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.47
Log Po/w (XLOGP3) : 1.62
Log Po/w (WLOGP) : 3.59
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 1.5
Consensus Log Po/w : 1.86

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.19
Solubility : 1.66 mg/ml ; 0.00645 mol/l
Class : Soluble
Log S (Ali) : -2.32
Solubility : 1.23 mg/ml ; 0.0048 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.1
Solubility : 2.05 mg/ml ; 0.00798 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.72

Safety of [ 103935-47-3 ]

Signal Word:Danger Class:6.1,8
Precautionary Statements:P261-P280-P305+P351+P338-P310 UN#:2927
Hazard Statements:H301+H311+H331-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 103935-47-3 ]

* 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 [ 103935-47-3 ]
  • Downstream synthetic route of [ 103935-47-3 ]

[ 103935-47-3 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 103935-47-3 ]
  • [ 762-49-2 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 4, p. 658 - 664
  • 2
  • [ 358-23-6 ]
  • [ 540-51-2 ]
  • [ 103935-47-3 ]
YieldReaction ConditionsOperation in experiment
93.33%
Stage #1: With pyridine In dichloromethane at -20℃; for 0.5 h; Inert atmosphere; Large scale
Stage #2: at 0℃; for 1 h; Inert atmosphere; Large scale
Under N2 protection, a solution of pyridine (1.74 Kg, 22.01 mol, 1.10 equiv) in dichloromethane (20 L) was cooled to -20 °C, trifluoromethanesulfonic anhydride (5.87 Kg, 20.81 mol, 1.04 eq.) was slowly added dropwise.The reaction system was stirred at -20°C for 0.5 hour and 2-bromoethanol (2.50 Kg, 20.01 mol, 1.0 equiv) was slowly added dropwise.The reaction temperature was maintained below 0° C. and stirred for 1.0 hour. TLC (petroleum ether:ethyl acetate=5:1) showed that the reaction was complete. After the reaction was completed, the reaction system was filtered, the filtrate was concentrated, petroleum ether (15 L) was added, the precipitated solid was filtered, and the filtrate was concentrated to give compound b. (4.80 Kg, yield 93.33percent) was a dark yellow oil
87%
Stage #1: With pyridine In dichloromethane at -20℃; for 0.0833333 h; Inert atmosphere
Stage #2: at -20 - 20℃;
INTERMEDIATE 732-Bromoethyl trifluoromethanesulfonateAnhydrous pyridine (8.5 mL, 105 mmol) and dry DCM (100 mL) were added to a 3-necked round-bottomed flask under a nitrogen atmosphere. The reaction flask was then cooled to about -2O0C with a dry ice/ethylene glycol bath. Trifluoromethanesulfonic anhydride (17 mL, 100 mmol) was added, whereupon a white/pink precipitate formed immediately. 2-Bromoethanol (7.1 mL, 100 mmol) was added after 5 minutes. The precipitate disappeared and then after a few minutes a new white precipitate formed. The reaction mixture was stirred for 20 minutes during which time it gradually warmed to r.t. The reaction mixture was then filtered through a phase separator and the residue was washed with 1:1 DCM/hexane (2 x 10 mL). The filtrate was run through a 4 cm silica plug with 1 :1 DCM/hexane solution (300 mL). The solvent was removed in vacuo to give the title compounds a brown oil (21.2 g, 87percent). δH (CDCl3) 4.76 (2H, t, J 6.4 Hz), 3.62 (2H, t, J6.4 Hz).
78%
Stage #1: at -20℃; for 0.166667 h;
Stage #2: at 20℃; for 0.166667 h;
To a stirred solution of pyridine (0.712 mL, 8.80 mrnoi) in 80 mL at -20°C in an ethylene glycol-dry ice bath was added trifluorornethanesulfonicanhydride (1344 mU 8.00 mmoi) dropwise. The reaction was stirred for 10 mm, followed by slow addition 2-bromoethanol (0567 ml, 800 rnrnoi), and the reaction was again left to stir, warming to RT for 10 minutes. The resulting suspension was filtered, concentrated (using a rotary evaporator, keeping the water bath temp he/ow 20 °C) and petroleum ether (3 mL) was added Themixture was filtered and concentrated again under reduced pressure to give the title product 2-brornoethyl trifluoromethanesulfonate (1.6 g, 6.23 mrnol, 78percent) as a clear colorless oil, which was stored cold in a freezer to prevent decomposition.
49.6% With pyridine In dichloromethane at -78 - 20℃; for 0.5 h; Synthesis of 2-bromoethyl triflate: To a solution of 2-bromoethanol (0.878, 7.026 mmol) in dry DCM (dichloromethane) (10 mL) was added pyridine (0.625 mL, 1.1 eq.) at RT. The solution was cooled to −78° C. and Tf2O (Trifluoromethanesulfonic anhydride) (1.18 mL, 1.1 eq.) was added dropwise. After the addition, the reaction was stirred at RT for 30 min. The mixture was washed with 1M HCl, sated. NaHCO3, dried over anhydrous MgSO4 and evaporated on a rotary evaporator. The residue was distilled using a Kugelrohr apparatus to give 0.892 g (49.6percent). 1H NMR (300 MHz, CDCl3): δ 4.78 (t, J=6.3 Hz, 2H), 3.64 (t, J=6.3 Hz, 2H).
2.38 g
Stage #1: With pyridine In dichloromethane at -20℃; for 0.166667 h;
Stage #2: at -20℃; for 0.25 h;
A solution of triflic anhydride (1.81 mL, 11 mmol) in CH2Cl2(5 mL) was added to a solution of pyridine (0.88 mL, 11 mmol) in CH2Cl2(5 mL) at −20°C. After stirring for 10 min, 2-bromoethanol (15) (0.71 mL, 10 mmol) was added to the mixture and the reaction mixture was stirred at −20°C for 15 min. The precipitate was removed by filtration and washed with Et2O (10 mL). The combined filtrates were concentrated in vacuo, and the residue was diluted with hexane (30 mL). The precipitate was removed by filtration and washed with Et2O (5 mL). The combined filtrates were concentrated in vacuoto provide crude product 16(2.38 g), which was used in the next step without further purification.Diphenyl sulfide (6.90 g, 18.5 mmol) was added to a solution of crude product 16in toluene (9 mL) at r.t. The reaction mixture was then heated at 100°C and stirred for 7 h. The solution was allowed to cool to r.t. and Et2O (20 mL) was added, resulting in the formation of a white precipitate. The mixture was stirred at r.t. overnight and the precipitate was collected by suction, washed with Et2O (3 mL) and dried in vacuoto provide 13(3.10 g, 70percent) as a white solid: mp 85.0–86.0°C (lit.,17)mp 86.5–88.0°C); IR (KBr, cm−1) ν3065, 2986, 1448, 1274, 1149, 1032, 755, 638; 1H-NMR (400 MHz, CDCl3) δ: 8.13–8.09 (m, 4H), 7.81–7.70 (m, 6H), 4.93–4.87 (m, 2H), 3.71–3.67 (m, 2H); 13C-NMR (100 MHz, CDCl3) δ: 135.3, 131.9, 131.1, 122.7, 48.5, 24.0.

Reference: [1] Patent: CN107955019, 2018, A, . Location in patent: Paragraph 0098; 0099; 0100
[2] Tetrahedron, 1999, vol. 55, # 35, p. 10659 - 10672
[3] Patent: WO2009/153554, 2009, A1, . Location in patent: Page/Page column 62
[4] Angewandte Chemie - International Edition, 2008, vol. 47, # 20, p. 3784 - 3786
[5] Patent: WO2017/147410, 2017, A1, . Location in patent: Page/Page column 180
[6] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 21, p. 7441 - 7448
[7] Journal of Organic Chemistry, 1987, vol. 52, # 4, p. 658 - 664
[8] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 20, p. 9121 - 9126
[9] Patent: US2017/152222, 2017, A1, . Location in patent: Paragraph 0107; 0108; 0126; 0127
[10] Organic and Biomolecular Chemistry, 2018, vol. 16, # 15, p. 2634 - 2638
[11] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 20, p. 5779 - 5786
[12] Journal of medicinal chemistry, 1990, vol. 33, # 5, p. 1482 - 1490
[13] Journal of Medicinal Chemistry, 1991, vol. 34, # 4, p. 1363 - 1368
[14] Heterocycles, 2004, vol. 63, # 12, p. 2813 - 2826
[15] Chemistry - An Asian Journal, 2011, vol. 6, # 2, p. 372 - 375
[16] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2342 - 2352
[17] Organic and Biomolecular Chemistry, 2014, vol. 12, # 47, p. 9621 - 9630
[18] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 12, p. 1763 - 1768
[19] Patent: EP3290419, 2018, A1, . Location in patent: Paragraph 0286; 0287; 0288
  • 3
  • [ 108-48-5 ]
  • [ 141072-57-3 ]
  • [ 103935-47-3 ]
YieldReaction ConditionsOperation in experiment
72% With trifluoromethanesulfonic acid anhydride In dichloromethane C
Trifluoromethanesulfonic acid 2-bromoethyl ester
240 g of trifluoromethanesulfonic anhydride (0.805 mol) are added in 1.5 h, under inert atmosphere, to a solution of bromoethanol (57 mL; 0.80 mol) and 2,6-lutidine (104 mL; 0.89 mol) in CH2Cl2 cooled at -5° C.
After 10 min the mixture is concentrated to one fourth the volume, then eluted through a small layer of silica gel (eluent n-hexane/EtOAc=9:1).
By evaporation and drying, the desired product is obtained (147.2 g; 0.57 mol).
Yield: 72percent
Reference: [1] Patent: US2003/13859, 2003, A1,
  • 4
  • [ 74-85-1 ]
  • [ 103935-47-3 ]
  • [ 106-93-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1546 - 1547[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 8, p. 1768 - 1769
  • 5
  • [ 74-85-1 ]
  • [ 35895-70-6 ]
  • [ 103935-47-3 ]
  • [ 106-93-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1546 - 1547[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 8, p. 1768 - 1769
  • 6
  • [ 74-85-1 ]
  • [ 33454-82-9 ]
  • [ 103935-47-3 ]
  • [ 106-93-4 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 1546 - 1547[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 8, p. 1768 - 1769
  • 7
  • [ 2923-28-6 ]
  • [ 106-93-4 ]
  • [ 18928-34-2 ]
  • [ 103935-47-3 ]
Reference: [1] Journal of Fluorine Chemistry, 1985, vol. 29, p. 123
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