[ CAS No. 209991-62-8 ] {[proInfo.proName]}

Name: 209991-62-8|3,4,5-Trifluorophenylacetic acid|97%
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Quality Control of [ 209991-62-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 209991-62-8 ]

CAS No. :	209991-62-8	MDL No. :	MFCD00083532
Formula :	C₈H₅F₃O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PQGPUBAARWWOOP-UHFFFAOYSA-N
M.W :	190.12	Pubchem ID :	2777952
Synonyms :

Calculated chemistry of [ 209991-62-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.86
TPSA :	37.3 Å²

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) :	-6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.42
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	2.99
Log Po/w (MLOGP) :	2.94
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	2.37

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.29
Solubility :	0.968 mg/ml ; 0.00509 mol/l
Class :	Soluble
Log S (Ali) :	-2.09
Solubility :	1.55 mg/ml ; 0.00816 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.02
Solubility :	0.183 mg/ml ; 0.000964 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 209991-62-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 209991-62-8 ]

* 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 [ 209991-62-8 ]
Downstream synthetic route of [ 209991-62-8 ]

[ 209991-62-8 ] Synthesis Path-Upstream 1~1

1
[ 238743-47-0 ]
[ 209991-62-8 ]

Reference： [1] Patent: EP1484304, 2004, A1, . Location in patent: Page 9

[ 209991-62-8 ] Synthesis Path-Downstream 1~37

1
[ 209991-62-8 ]
[ 953-91-3 ]
C₁₄H₁₅F₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3262 - 3265

2
[ 209991-62-8 ]
C₂₇H₃₂F₃N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3262 - 3265

3
[ 209991-62-8 ]
C₈H₄ClF₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane; for 4h;Reflux;	General procedure: SOCl2 (1.65 mL) was added to a solution of benzoic or phenylaceticacid derivatives (2 mmol) in dry CH2Cl2 (1.65 mL), and thesuspension was refluxed for 4 h. The resulting solution was evaporated,the residue was dissolved in dry acetone (10 mL) and 3-(4-aminophenyl)-7-hydroxy-coumarin 4 (0.51 g, 2 mmol) was added.The mixture was refluxed with anhydrous K2CO3 (1.104 g, 8 mmol)for 4 h. Acetone was removed under reduced pressure and coldwater (20 mL) was added. 3 N HCl was added until the solutionbecame acidic. The resulting precipitate was filtered, washed withwater and recrystallized from methanol or ethanol to give thedesired products 5a-k.

Reference： [1]Patent: EP1191008,2002,A1 .Location in patent: Page 68
[2]Chemical Biology and Drug Design,2016,vol. 87,p. 233 - 238
[3]European Journal of Medicinal Chemistry,2017,vol. 128,p. 79 - 87
[4]Chemical Biology and Drug Design,2017,vol. 90,p. 156 - 161
[5]Biomolecules,2020,vol. 10

4
[ 238743-47-0 ]
[ 209991-62-8 ]

Yield	Reaction Conditions	Operation in experiment
		An emulsion of 0.06mol, 13.1g ethyl 3,4,5-trifluorophenylacetate and 100ml 1.35M aqueous NaOH solution (5.4g, 0.135mol, 2eq) is refluxed for 3h. 4 equivalents HCl (diluted aqueous solution) are added after cooling to room temperature. The white precipitate of 3,4,5-trifluorophenylacetic acid (8.7g) is filtered off and recrystallized from hexane (7.7g) (melting point: 100C).

Reference： [1]Patent: EP1484304,2004,A1 .Location in patent: Page 9

5
[ 209991-62-8 ]
[ 106-95-6 ]
[ 1123192-11-9 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLES 107, 108, 109 AND 110; Synthesis of (6R,8S)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-6-ol, (6S,8R)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-6-ol, (6S,8S)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-6-ol and (6R,8R)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-6-ol Synthesis of 2-(3,4,5-trifluorophenyl)-4-pentenoic acidn-Butyl lithium (7.89 mL; 2.66 M solution in hexane) was added to a solution of <strong>[209991-62-8]3,4,5-trifluorophenylacetic acid</strong> (2 g) in THF (50 mL) at -78 C. The reaction solution was stirred at -78 C. for 20 minutes. Then, the reaction solution was heated to 0 C. and further stirred for 30 minutes. Allyl bromide (0.999 mL) was added dropwise to the reaction solution, and the reaction solution was stirred at room temperature for three hours. A 1 N sodium hydroxide solution and diethyl ether were added to the reaction solution, and the aqueous layer was separated. 5 N hydrochloric acid and ethyl acetate were added to the resulting aqueous layer, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.45 g of the title compound. The property values of the compound are as follows.1H-NMR (CDCl3) δ (ppm): 2.44-2.52 (m, 1H), 2.72-2.81 (m, 1H), 3.58 (t, J=7.6 Hz, 1H), 5.03-5.10 (m, 2H), 5.60-5.71 (m, 1H), 6.90 (dd, J=8.4, 6.4 Hz, 2H).

Reference： [1]Patent: US2009/62529,2009,A1 .Location in patent: Page/Page column 92

6
[ 209991-62-8 ]
[ 501-53-1 ]
[ 1123191-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 0℃; for 0.583333h;	EXAMPLES 103 AND 104; Synthesis of (7S,8S)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-ol and (7R,8R)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-8-(3,4,5-trifluorophenyl)-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-7-ol Synthesis of benzyl (3,4,5-trifluorophenyl)acetateTriethylamine (0.808 mL) and benzyl chloroformate (0.752 mL) were sequentially added dropwise to a solution of <strong>[209991-62-8]3,4,5-trifluorophenylacetic acid</strong> (1 g) in methylene chloride (15 mL) at 0 C., and the reaction solution was stirred at 0 C. for five minutes. DMAP (64.4 mg) was added to the reaction solution which was then stirred at 0 C. for 30 minutes. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 1.43 g of the title compound. The property values of the compound are as follows.1H-NMR (CDCl3) δ (ppm): 3.59 (s, 2H), 5.14 (s, 2H), 6.90 (dd, J=8.0, 6.4 Hz, 2H), 7.29-7.38 (m, 5H), 3.83 (s, 3H), 3.89 (s, 3H), 6.44 (s, 1H), 6.95 (brs, 1H), 7.04 (d, J=1.6 Hz, 1H), 7.07 (dd, J=8.0, 1.6 Hz, 1H), 7.20 (t, J=8.8 Hz, 2H), 7.28 (d, J=8.0 Hz, 1H), 7.78 (d, J=1.2 Hz, 1H), 7.83 (s, 1H), 8.09 (dd, J=8.8, 5.2 Hz, 2H).

Reference： [1]Patent: US2009/62529,2009,A1 .Location in patent: Page/Page column 89-90

7
[ 209991-62-8 ]
[ 944915-75-7 ]
[ 1191255-40-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5114 - 5118

8
[ 209991-62-8 ]
[ 949560-37-6 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 1-amino-3-(3,4,5-trifluorophenyl)piperidin-2-one 6.6 g of the title compound was obtained from <strong>[209991-62-8]3,4,5-trifluorophenylacetic acid</strong> (11 g) according to the method in Examples 20 and 21. The property value of the compound is as follows. ESI-MS; m/z 245 [M++H].

Reference： [1]Patent: EP2181992,2010,A1

9
[ 209991-62-8 ]
[ 107-04-0 ]
[ 949167-77-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; ethyl acetate;	Synthesis of 4-chloro-2-(3,4,5-trifluorophenyl)butyric acid A 2.66 M solution of butyl lithium in hexane (20 mL) was added to a solution of <strong>[209991-62-8]3,4,5-trifluorophenylacetic acid</strong> (5.00 g) in THF (150 mL) in a nitrogen atmosphere at -78C, and the reaction solution was stirred at -78C for 20 minutes. The reaction solution was further stirred at 0C for one hour. Then, 1-bromo-2-chloroethane (2.2 mL) was added at 0C, and the reaction solution was stirred at room temperature for 14 hours. Ethyl acetate and 1 N hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 4.54 g of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) δ (ppm): 2.13-2.22 (m, 1H), 2.45-2.54 (m, 1H), 3.36 (ddd, J=11.6, 8.4, 4.8Hz, 1H), 3.58 (ddd, J=11.6, 6.4, 5.2Hz, 1H), 3.89 (dd, J=7.6, 7.6Hz, 1H), 6.94-7.02 (m, 2H).
		A 2.66 M solution of butyl lithium in hexane (20 mL) was added to a solution of <strong>[209991-62-8]3,4,5-trifluorophenylacetic acid</strong> (5.00 g) in THF (150 mL) in a nitrogen atmosphere at -78 C., and the reaction solution was stirred at -78 C. for 20 minutes. The reaction solution was further stirred at 0 C. for one hour. Then, 1-bromo-2-chloroethane (2.2 mL) was added at 0 C., and the reaction solution was stirred at room temperature for 14 hours. Ethyl acetate and 1 N hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 4.54 g of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) δ (ppm): 2.13-2.22 (m, 1H), 2.45-2.54 (m, 1H), 3.36 (ddd, J=11.6, 8.4, 4.8 Hz, 1H), 3.58 (ddd, J=11.6, 6.4, 5.2 Hz, 1H), 3.89 (dd, J=7.6, 7.6 Hz, 1H), 6.94-7.02 (m, 2H).

Reference： [1]Patent: EP2181992,2010,A1
[2]Patent: US2007/219181,2007,A1 .Location in patent: Page/Page column 114-115

10
[ 209991-62-8 ]
[ 109-70-6 ]
[ 949166-97-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		To a solution of (3,4,5-trifluorophenyl)acetic acid (561 mg, 2.95 mmol) in THF (12 mL) was added dropwise n-butyllithium 1.6 M hexane solution (3.69 mL, 5.90 mmol) at - 78C, and the mixture was stirred under ice-cooling for 1 hr. 1-Bromo-3-chloropropane (0.305 mL, 3.10 mmol) was added, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was extracted with 1 M aqueous sodium hydroxide solution. The extract was acidified with 3 M hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80 - 50/50) to give the title compound as a colorless oil (0.535 g, 68%). 1H NMR (CDCl3) δ: 1.60 - 2.01 (3 H, m), 2.11 - 2.27 (1 H, m), 3.41 - 3.62 (3 H, m), 6.86 - 7.06 (2 H, m).

Reference： [1]Patent: EP2455380,2012,A1 .Location in patent: Page/Page column 74

11
[ 209991-62-8 ]
[ 1262106-25-1 ]

Reference： [1]Patent: EP2455380,2012,A1

12
[ 209991-62-8 ]
[ 1262106-94-4 ]

Reference： [1]Patent: EP2455380,2012,A1

13
[ 209991-62-8 ]
[ 1262106-34-2 ]

Reference： [1]Patent: EP2455380,2012,A1

14
[ 209991-62-8 ]
C₅₂H₆₅Cl₂N₄O₁₈P₂Pol [ No CAS ]
C₆₀H₆₈Cl₂F₃N₄O₁₉P₂Pol [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 8014 - 8016

15
[ 209991-62-8 ]
7-hydroxy-3-(3,4,5-trifluorophenyl)coumarin [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2016,vol. 87,p. 233 - 238

16
[ 209991-62-8 ]
3-(3,4,5-trifluorophenyl)coumarin-7-O-sulfamate [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2016,vol. 87,p. 233 - 238

17
[ 209991-62-8 ]
3-{4-[2-(3,4,5-trifluorophenyl)acetylamino]phenyl}coumarin-7-O-sulfamate [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 128,p. 79 - 87

18
[ 209991-62-8 ]
7-hydroxy-3-{4-[2-(3,4,5-trifluorophenyl)acetylamino]phenyl}coumarin [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 128,p. 79 - 87

19
[ 209991-62-8 ]
C₁₆H₁₄F₃NO₂ [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2017,vol. 90,p. 156 - 161

20
[ 209991-62-8 ]
C₁₆H₁₅F₃N₂O₄S [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2017,vol. 90,p. 156 - 161

21
1-(2,2,2-trichloroethyl)-3,4,5-trifluorobenzene [ No CAS ]
[ 209991-62-8 ]

Yield	Reaction Conditions	Operation in experiment
187 g	With sulfuric acid; In water; toluene; at 90 - 100℃; for 8h;Inert atmosphere;	2L three bottles, Under nitrogen protection, Add 600 g of 17% aqueous sulfuric acid solution. Heated to 90-100 C. A solution of 300 g of intermediate 1- (2,2,2-trichloroethyl) -3,4,5-trifluorobenzene and 200 g of toluene was added dropwise. After dripping, the incubation reaction was carried out for 8 hours. The reaction is complete. The system will drop into the ice water quenching. Filtered, washed with water and dried to obtain crude product (332 g). Toluene was recrystallized to give pure 3,4,5-trifluorobenzoic acid (187.0 g) HPLC purity greater than 99 wt%.

Reference： [1]Patent: CN106928044,2017,A .Location in patent: Paragraph 0094; 0095; 0097

22
[ 27757-85-3 ]
[ 209991-62-8 ]
[ 7188-38-7 ]
[ 28809-07-6 ]
C₃₀H₃₁F₃N₂O₅S [ No CAS ]