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[ CAS No. 37900-81-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 37900-81-5
Chemical Structure| 37900-81-5
Chemical Structure| 37900-81-5
Structure of 37900-81-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 37900-81-5 ]

CAS No. :37900-81-5 MDL No. :MFCD11849933
Formula : C7H4ClF3O Boiling Point : -
Linear Structure Formula :- InChI Key :KQFQPAJCFHNHKB-UHFFFAOYSA-N
M.W : 196.55 Pubchem ID :13609147
Synonyms :

Calculated chemistry of [ 37900-81-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.48
TPSA : 20.23 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) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 3.08
Log Po/w (WLOGP) : 4.22
Log Po/w (MLOGP) : 3.15
Log Po/w (SILICOS-IT) : 3.01
Consensus Log Po/w : 3.02

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.3
Solubility : 0.0978 mg/ml ; 0.000498 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.132 mg/ml ; 0.000673 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.33
Solubility : 0.0921 mg/ml ; 0.000469 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 37900-81-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 37900-81-5 ]

* 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 [ 37900-81-5 ]
  • Downstream synthetic route of [ 37900-81-5 ]

[ 37900-81-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 94444-58-3 ]
  • [ 37900-81-5 ]
YieldReaction ConditionsOperation in experiment
72% With 2-(Trimethylsilyl)ethanol; sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 20 h; Preparation 53-Chloro-4-(trifluoromethyl)phenolTo a stirred sol ution of 2-chloro-4-fluorobenzotrifluoride (500 mg, 2.52 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added 2-(trimethylsilyl)ethanol (0.40 mL, 2.77 mmol) and the reaction mixture was cooled to 0°C. Sodium hydride (302 mg, 60percent w/w dispersion in oil, 7.55 mmol) was then added portionwise. After 5 minutes a thick white suspension had formed . The reaction mixture was warmed to room temperature slowly and then stirred for a further 16 hours. The reaction mixture was then quenched with ice water (50 mL) and washed with diethyl ether (50 mL). The aqueous extracts were acidified with aqueous 2 M hydrogen chloride solution and extracted with diethyl ether (2 x 50 mL). The organic extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo for 16 hours to afford the title compound as a yellow oil (356 mg, 72percent).1H NMR (400 MHz, CDCI3): δ 6.75 (dd, 1 H), 6.95 (d, 1 H), 7.51 (d, 1 H).LCMS Rt = 1 .23 minutes MS m/z 195 [M-H]-
Reference: [1] Patent: WO2012/7868, 2012, A2, . Location in patent: Page/Page column 73-74
[2] Patent: US2012/10207, 2012, A1,
  • 2
  • [ 1354960-72-7 ]
  • [ 37900-81-5 ]
YieldReaction ConditionsOperation in experiment
31% With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane at 20℃; for 18 h; Inert atmosphere To a solution of (2-(3-chloro-4-(trifluoromethyl)phenoxy)ethyl)trimethylsilane (Preparation 15, 3.1 g, 10 mmol) in 1,4-dioxane (5 mL) was added tetrabutylammonium fluoride (10 mL, 1M in THF) and the resulting mixture was stirred at room temperature for 18 hours under nitrogen. The mixture was poured onto water and neutralised with aq. ammonium chloride and extracted with ethyl acetate (3.x.30 mL). The organic layer was separated and washed with 1M sodium hydroxide (3.x.30 mL). The aqueous layers were separated, combined, acidified with aqueous 2M HCl and re-extracted with ethyl acetate (3.x.30 mL), dried (MgSO4), filtered and concentrated in vacuo to afford 2.46 g of a pale yellow oil. The crude oil was purified by silica gel column chromatography eluting with a gradient of 0-50percent ethyl acetate in heptane to afford 619 mg (31percent) of the title compound as a colourless oil.LCMS Rt=2.97 minutes MS m/z 195 [M-H]+1HNMR (400 MHz, CDCl3): δ 6.64 (br s, 1H), 6.76 (m, 1H), 6.96 (m, 1H), 7.50 (m, 1H),
Reference: [1] Patent: US2012/10207, 2012, A1, . Location in patent: Page/Page column 37-38
  • 3
  • [ 445-13-6 ]
  • [ 37900-81-5 ]
YieldReaction ConditionsOperation in experiment
48% at 0 - 110℃; for 3 h; Heating / reflux To a sulfuric acid (14 ml) -H2O (14 ml) solution of 3-chloro-4-(trifluoromethyl)aniline (1.96 g, 10 mmol) was added a H2O (10 mL) solution of sodium nitrite (828 mg,12 mmol) at 0 ° C. The reaction mixture was stirred at ambient temperature for 1 hour. The mixture was poured into 10 M sulfuric acid (50 mL). The stirred mixture was refluxed at 110 ° C. for 2 hours. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with ethyl acetate The organic layer was then washed with brine, dried over sodium sulfate. After the filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give the residue, which was applied to a silica gel chromatography column and eluted with a ethyl acetate/hexane= to furnish 945 mg (48percent yield) of the title compound as a brown oil. 1H NMR (CDCl3, 270 MHz) δ ppm 5.99 (1H, brs), 6.80 (1H, dd, J=2.6, 8.6 Hz), 7.00 (1H, d, J=2.6 Hz), 7.56 (1H, d, J=8.6 Hz). MS (ESI) m/z: 195[M-H-.
Reference: [1] Patent: US2006/100460, 2006, A1, . Location in patent: Page/Page column 22
  • 4
  • [ 108-43-0 ]
  • [ 75-63-8 ]
  • [ 37900-81-5 ]
  • [ 106877-35-4 ]
  • [ 106877-34-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 8, p. 2293 - 2299
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