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[ CAS No. 115933-50-1 ] {[proInfo.proName]}

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Chemical Structure| 115933-50-1
Chemical Structure| 115933-50-1
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Product Details of [ 115933-50-1 ]

CAS No. :115933-50-1 MDL No. :MFCD06204091
Formula : C9H7F3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :WIXKYCQCCJXQPN-UHFFFAOYSA-N
M.W : 220.15 Pubchem ID :13962148
Synonyms :

Calculated chemistry of [ 115933-50-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.75
TPSA : 46.53 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) : -6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.3
Log Po/w (WLOGP) : 3.35
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 2.29
Consensus Log Po/w : 2.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.75
Solubility : 0.39 mg/ml ; 0.00177 mol/l
Class : Soluble
Log S (Ali) : -2.92
Solubility : 0.268 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.79
Solubility : 0.355 mg/ml ; 0.00161 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 115933-50-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 115933-50-1 ]

* 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 [ 115933-50-1 ]
  • Downstream synthetic route of [ 115933-50-1 ]

[ 115933-50-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 67-56-1 ]
  • [ 220239-68-9 ]
  • [ 115933-50-1 ]
YieldReaction ConditionsOperation in experiment
93% With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 18 h; [00344j Step 1: Methyl 4-hydroxy-3-(trifluoromethyl)benzoate [00345j 4-hydroxy-3-(trifluoromethyl)benzoic acid (4.9 g, 23.7 mmol)was dissolved in methanol (15 mL) and DMF (18 jiL, 0.24 mmol), thionyl chloride(5.2 mL, 71.0 mmol) was added dropwise (over a period of 10 mm) to the reaction mixture, and it was allowed to stir for 18 h at rt. Volatiles were then removed under reduced pressure. The remaining solid was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (50 mL). The aqueous layer was furtherextracted with ethyl acetate (2 x 50 mL). All organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide methyl 4-hydroxy-3-(trifluoromethyl)benzoate (4.9 g, 93 percent) as an off-white solid. . ‘H NMR (400 MHz, DMSO)ö 11.68 (s, 1H), 8.00-8.10 (m, 2H), 7.20- 7.07(m, 1H), 3.83 (s, 3H). ESI-MS mlz calc. 220.0, found 221.0 (M+1) Retention time: 1.41 mm(3minrun).
91% at 90℃; for 48 h; 4-Hydroxy-3-(trifluoromethyl) benzoic acid (2g, 9.7mmol) was dissolved in methanol (40mL) and 12N HC1 (10 drops) was added thereto. The reaction mixture was stirred at 90°C for 48 hours, cooled to room temperature and concentrated, and then ethyl acetate (lOOmL) was added thereto. The reaction mixture was washed with sat. NaHC03 solution, and the organic layer was dried with Na2S04, filtered and concentrated to obtain the title compound (2.07g, 91percent) without further purification.1H NMR (300MHz, DMSO-d6) δ 11.60 (s, 1H), 8.02 (m, 2H), 7.10 (d, 1H), 4.26 (q,2H), 1.28(t, 3H).
89% Reflux Cone. H2S04 (1.5 mL) was dissolved in MeOH (20 mL) and 4-hydroxy-3- (trifluoromethyl)benzoic acid (2.0 g, 9.7 mmol) was added. After the addition, the reaction mixture was refluxed overnight. The reaction mixture was concentrated to give the residue, which was treated with EA (50 mL) and washed with <7.sat.NaHC03, brine, dried over Na2S04 and concentrated to give the target compound (1.9 g, 89percent) as a white solid. MS: M/e 221 (M+l)+.
87% for 48 h; Heating / reflux A solution of 3-trifluoromethyl-4-hydroxybenzoic acid (5.00 g, 24.3 mmol) in 15percent methanolic sulfuric acid solution (50 mL) was heated at reflux over 48 h, then poured upon ice and extracted with ethyl acetate. The organic layer was washed with 1 M aq. sodium carbonate solution and brine, dried (MgSO4), and evaporated to afford 4-hydroxy-3-trifluoromethyl-benzoic acid methyl ester (4.67 g, 87percent). Off-white solid, MS (ISP)=219.0 (M-H)-.
2.07 g With hydrogenchloride In methanol at 90℃; for 48 h; Step 1:
Methyl 4-hydroxy-3-(trifluoromethyl)benzoate
4-Hydroxy-3-(trifluoromethyl)benzoic acid (2 g, 9.7 mmol) was dissolved in methanol (40 mL) and 12N HCl (10 drops) was added thereto.
The reaction mixture was stirred at 90° C. for 48 hours, cooled to room temperature and concentrated, and then ethyl acetate (100 mL) was added thereto.
The reaction mixture was washed with sat.
NaHCO3 Solution, and the organic layer was dried with Na2SO4, filtered and concentrated to obtain the title compound (2.07 g, 91percent) without further purification.
1H NMR (300 MHz, DMSO-d6) δ 11.60 (s, 1H), 8.02 (m, 2H), 7.10 (d, 1H), 4.26 (q, 2H), 1.28 (t, 3H).

Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 6, p. 618 - 623
[2] Patent: WO2015/6280, 2015, A1, . Location in patent: Paragraph 00344; 00345
[3] Patent: WO2011/93684, 2011, A2, . Location in patent: Page/Page column 40
[4] Patent: WO2014/206344, 2014, A1, . Location in patent: Page/Page column 104; 131
[5] Patent: US2007/191603, 2007, A1, . Location in patent: Page/Page column 34
[6] Patent: EP2202232, 2010, A1, . Location in patent: Page/Page column 57
[7] Patent: US2006/89392, 2006, A1, . Location in patent: Page/Page column 42
[8] Patent: US2013/53370, 2013, A1, . Location in patent: Paragraph 0311-0313
  • 2
  • [ 2926-29-6 ]
  • [ 99-76-3 ]
  • [ 115933-50-1 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 51, p. 7525 - 7528
  • 3
  • [ 444-30-4 ]
  • [ 115933-50-1 ]
Reference: [1] Patent: US2012/184587, 2012, A1,
  • 4
  • [ 149105-11-3 ]
  • [ 115933-50-1 ]
Reference: [1] Patent: US2012/184587, 2012, A1,
  • 5
  • [ 1285575-67-8 ]
  • [ 115933-50-1 ]
Reference: [1] Patent: US2012/184587, 2012, A1,
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