[ CAS No. 124236-37-9 ] {[proInfo.proName]}

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Quality Control of [ 124236-37-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 124236-37-9 ]

SDS Specification

Alternatived Products of [ 124236-37-9 ]

Product Details of [ 124236-37-9 ]

CAS No. :	124236-37-9	MDL No. :	MFCD08741523
Formula :	C₈H₆F₃NO₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	CHRQADSGOKVKER-UHFFFAOYSA-N
M.W :	205.13	Pubchem ID :	18996919
Synonyms :

Calculated chemistry of [ 124236-37-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.52
TPSA :	39.19 ?2

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) :	-5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	2.37
Log Po/w (WLOGP) :	3.04
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	2.24
Consensus Log Po/w :	2.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.72
Solubility :	0.387 mg/ml ; 0.00189 mol/l
Class :	Soluble
Log S (Ali) :	-2.83
Solubility :	0.301 mg/ml ; 0.00147 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.99
Solubility :	0.208 mg/ml ; 0.00101 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 124236-37-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P305+P351+P338	UN#:
Hazard Statements:	H302-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 124236-37-9 ]

* 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 [ 124236-37-9 ]
Downstream synthetic route of [ 124236-37-9 ]

[ 124236-37-9 ] Synthesis Path-Upstream 1~1

1
[ 124236-37-9 ]
[ 31181-84-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 0 - 20℃;	IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of methyl 5-trifluoromethyl-pyridine-2-carboxylate (2 g, 9.75 mmol) in MeOH (30 mL) at 0°C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93percent yield): 1H NMR (400 MHz, CDC1₃) δ ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)⁺.
82.2%	at 0 - 20℃; for 1 h;	Compound SM (1.0 g, 4.87 mmol) was dissolved in MeOH (15 mL). At 0 ° C, NaBH4 (368.9 mg, 9.75 mmol) was added portionwise with stirring. Reaction at room temperature for 1 hour. TLC showed the reaction was completed. The pH was adjusted to 5-6 with 1 M HCl solution and the EA extracted (20 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (710.0 mg, 82.2percent).
72%	Stage #1: With sodium tetrahydroborate In ethanolHeating / reflux Stage #2: With water; ammonium chloride In ethanol at 20℃;	NaBH₄ (0.369 g, 9.75 mmol) was added to Example 34A (1 g, 5 mmol) in EtOH (40 mL). The suspension was heated at reflux overnight. The reaction was cooled to ambient temperature and quenched with saturated NH₄Cl solution. The mixture was diluted with water and extracted with EtOAc. The separated organic layer was washed with water and brine, dried (Na₂SO₄), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix.(R). 25*40 column, 30percent-50percent EtOAc/hexanes eluant) to afford 0.62 g (72percent) of the title compound as a colorless oil. ¹H NMR (300 MHz, CDCl₃) δ 8.84 (s, 1H), 7.94 (dd, J=8.3, 2.1 1H), 7.43 (dd, J=8.2, 0.6 1H), 4.85 (d, J=5.2, 2H), 3.46 (t, J=5.3, 1H).

Reference： [1] Patent: WO2013/166621, 2013, A1, . Location in patent: Page/Page column 48
[2] Patent: CN106831840, 2017, A, . Location in patent: Paragraph 0102; 0103; 0104
[3] Patent: US2009/124666, 2009, A1, . Location in patent: Page/Page column 25-26

[ 124236-37-9 ] Synthesis Path-Downstream 1~12

1
[ 67-56-1 ]
[ 201230-82-2 ]
[ 50488-42-1 ]
[ 124236-37-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; at 80℃; under 3102.97 Torr; for 3h;	A solution of 2-bromo-5-(trifluoromethyl)pyridine (9 g, 40 mmol) in MeOH (130 mL) was added to Pd-dppf (0.813 g, 0.996 mmol) and Et3N (11 mL, 80 mmol) in a 250 mL pressure bottle. The mixture was pressurized with carbon monoxide (60 psi), and stirred 3 hr at 80 C. The reaction was cooled to ambient temperature, filtered, and the solvents evaporated at reduced pressure. The residue was partitioned between water and ethyl acetate. The separated organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix 40*240 column, 10%-40% EtOAc/hexanes eluant) to afford 8.52 g (104%) of the title compound as a white solid. 1H NMR (300 MHz, CDCl3) delta 9.01 (m, 1H), 8.28 (d, J=8.1, 1H), 8.12 (dd, J=2.1, 8.2, 1H), 4.06 (s, 3H). MS (ESI+) m/z 206 (M+H).

Reference： [1]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 25

2
[ 124236-37-9 ]
[ 31181-84-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With methanol; sodium tetrahydroborate; at 0 - 20℃;	IV. (5-trifluoromethyl-2-pyridinyl)methanol To a solution of <strong>[124236-37-9]methyl 5-trifluoromethyl-pyridine-2-carboxylate</strong> (2 g, 9.75 mmol) in MeOH (30 mL) at 0C was added NaB (738 mg, 19.5 mmol) portionwise. The mixture was stirred at room temperature for 2 h and concentrated. The residue was diluted with water (30 mL), acidified to pH~5 (IN HC1), extracted with EA (3 X 50 mL), dried, concentrated and purified by column chromatography on silica gel to give the title compound as a colorless oil (1.6 g, 93% yield): 1H NMR (400 MHz, CDC13) delta ppm 8.82 (s, 1H), 7.90-7.92 (m, 1H), 7.40-7.42 (m, 1H), 4.82-4.83 (m, 2H), 3.44-3.46 (m, 1H); ES-LCMS m/z 178 ( +H)+.
82.2%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1h;	Compound SM (1.0 g, 4.87 mmol) was dissolved in MeOH (15 mL). At 0 C, NaBH4 (368.9 mg, 9.75 mmol) was added portionwise with stirring. Reaction at room temperature for 1 hour. TLC showed the reaction was completed. The pH was adjusted to 5-6 with 1 M HCl solution and the EA extracted (20 mL x 3). The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated to give the title compound (710.0 mg, 82.2%).
72%		NaBH4 (0.369 g, 9.75 mmol) was added to Example 34A (1 g, 5 mmol) in EtOH (40 mL). The suspension was heated at reflux overnight. The reaction was cooled to ambient temperature and quenched with saturated NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The separated organic layer was washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix 25*40 column, 30%-50% EtOAc/hexanes eluant) to afford 0.62 g (72%) of the title compound as a colorless oil. 1H NMR (300 MHz, CDCl3) delta 8.84 (s, 1H), 7.94 (dd, J=8.3, 2.1 1H), 7.43 (dd, J=8.2, 0.6 1H), 4.85 (d, J=5.2, 2H), 3.46 (t, J=5.3, 1H).

Reference： [1]Patent: WO2013/166621,2013,A1 .Location in patent: Page/Page column 48
[2]Patent: CN106831840,2017,A .Location in patent: Paragraph 0102; 0103; 0104
[3]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 25-26

3
[ 124236-37-9 ]
C₁₂H₁₀F₃NO₃ [ No CAS ]