[ CAS No. 454-89-7 ] {[proInfo.proName]}

Name: 454-89-7|3-(Trifluoromethyl)benzaldehyde|97%
Brand: Ambeed
SKU: A110535
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2D 3D

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Quality Control of [ 454-89-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 454-89-7 ]

SDS Specification

Alternatived Products of [ 454-89-7 ]

Product Details of [ 454-89-7 ]

CAS No. :	454-89-7	MDL No. :	MFCD00003373
Formula :	C₈H₅F₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NMTUHPSKJJYGML-UHFFFAOYSA-N
M.W :	174.12	Pubchem ID :	67990
Synonyms :

Calculated chemistry of [ 454-89-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.83
TPSA :	17.07 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) :	-5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	2.47
Log Po/w (WLOGP) :	3.67
Log Po/w (MLOGP) :	2.52
Log Po/w (SILICOS-IT) :	2.98
Consensus Log Po/w :	2.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.71
Solubility :	0.337 mg/ml ; 0.00193 mol/l
Class :	Soluble
Log S (Ali) :	-2.47
Solubility :	0.586 mg/ml ; 0.00337 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.23
Solubility :	0.103 mg/ml ; 0.000592 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.08

Safety of [ 454-89-7 ]

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

Application In Synthesis of [ 454-89-7 ]

* 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 [ 454-89-7 ]
Downstream synthetic route of [ 454-89-7 ]

[ 454-89-7 ] Synthesis Path-Upstream 1~14

1
[ 454-89-7 ]
[ 2740-83-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 39, p. 9306 - 9311

2
[ 454-89-7 ]
[ 1801-10-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: With hydroxylamine hydrochloride; sodium carbonate In water at 20℃; for 0.5 h; Schlenk technique Stage #2: With [(η(5)-C5Me5)Ir(III)(H2O)3](OTf)2 In water at 110℃; for 12 h;	3-Trifluoromethylbenzaldehyde (87.1 mg, 0.5 mmol),Hydroxylamine hydrochloride (34.7 mg, 0.5 mmol)Sodium carbonate (26.5 mg, 0.25 mmol)And water (1 ml) were sequentially added to a 25 ml Schlenk reaction flask,After half an hour of room temperature reaction,[Cp * Ir (H2O) 3] [OTf] 2 (10.2 mg, 0.0150 mmol, 3 molpercent) was addedThe reaction mixture was reacted at 110 ° CAfter hours,Cooled to room temperature,Rotary evaporation to remove water,Column to give the title compound,Yield: 75percent.

Reference： [1] Patent: CN104418762, 2016, B, . Location in patent: Paragraph 0035; 0036; 0037; 0038
[2] RSC Advances, 2016, vol. 6, # 43, p. 37093 - 37098

3
[ 1117-96-0 ]
[ 454-89-7 ]
[ 1533-03-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1968, vol. 717, p. 80 - 90

4
[ 75-52-5 ]
[ 454-89-7 ]
[ 115665-96-8 ]

Reference： [1] Australian Journal of Chemistry, 1976, vol. 29, p. 2607 - 2614
[2] Catalysis Science and Technology, 2016, vol. 6, # 14, p. 5714 - 5720

5
[ 141-82-2 ]
[ 454-89-7 ]
[ 779-89-5 ]

Reference： [1] Synthetic Communications, 2008, vol. 38, # 10, p. 1512 - 1517
[2] Chemical Biology and Drug Design, 2013, vol. 81, # 2, p. 275 - 283
[3] Chemistry - A European Journal, 2013, vol. 19, # 12, p. 3833 - 3837
[4] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 517 - 525
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5726 - 5732

6
[ 454-89-7 ]
[ 108-24-7 ]
[ 779-89-5 ]

Reference： [1] Patent: WO2008/58235, 2008, A2, . Location in patent: Page/Page column 22

7
[ 454-89-7 ]
[ 779-89-5 ]

Reference： [1] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 870 - 878

8
[ 454-89-7 ]
[ 78573-45-2 ]

Reference： [1] Patent: EP2013209, 2011, B1,
[2] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1366 - 1373

9
[ 454-89-7 ]
[ 585-50-2 ]

Reference： [1] Patent: EP2013209, 2011, B1,
[2] Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 1366 - 1373

10
[ 75-52-5 ]
[ 454-89-7 ]
[ 52516-30-0 ]

Reference： [1] Molecular Pharmacology, 2005, vol. 68, # 1, p. 20 - 33

11
[ 2295-31-0 ]
[ 454-89-7 ]
[ 438190-29-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 4, p. 1077 - 1084
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 74 - 86

12
[ 454-89-7 ]
[ 328-99-4 ]
[ 188815-30-7 ]

Reference： [1] Organic Process Research and Development, 2008, vol. 12, # 2, p. 339 - 344

13
[ 141-82-2 ]
[ 454-89-7 ]
[ 143438-91-9 ]

Yield	Reaction Conditions	Operation in experiment
255 g	With ammonium formate In ethanol for 12 h; Reflux	(0549) (0550) A mixture of malonic acid (298.82 g, 2872 mmol), ammonium formate (362.14 g, 5743 mmol) and 3-(trifluoromethyl)benzaldehyde (500 g, 2873 mmol) in ethanol (1000 mL) was refluxed for 12 h. The reaction mixture was evaporated to remove ethanol and the residue was triturated with acetone (2500 mL). The solid was filtered and dried to afford 3-amino-3-[3-(trifluorome- thyl)phenyl]propanoic acid (255 g) as white solid. (0551) NMR (400 MHz, AcOH-d₄) δ 7.87-7.81 (m, 2H), 7.74 (d, 1H, J = 7.6 Hz), 7.66-7.62 (m, 1H), 4.98 (br. S, 1H), 3.36 (dd, 1H, J = 16.0, 8.0 Hz), 3.13 (dd, 1H, J = 17.6, 5.6 Hz); (0552) MS: m z 234 (M+l).

Reference： [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 4, p. 2440 - 2446
[2] Patent: WO2017/144183, 2017, A1, . Location in patent: Page/Page column 65

14
[ 454-89-7 ]
[ 885268-02-0 ]

Reference： [1] Chemical Communications, 2016, vol. 52, # 56, p. 8757 - 8760

[ 454-89-7 ] Synthesis Path-Downstream 1~87

1
[ 50548-43-1 ]
[ 454-89-7 ]
[ 574-83-4 ]

Reference： [1]Journal of the American Chemical Society,1946,vol. 68,p. 426

2
[ 349-75-7 ]
[ 401-79-6 ]
[ 454-89-7 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4079,4082

3
[ 368-77-4 ]
[ 454-89-7 ]

Reference： [1]Patent: EP1389608,2004,A1 .Location in patent: Page/Page column 6
[2]Patent: EP1389608,2004,A1 .Location in patent: Page/Page column 6
[3]Journal of the Chemical Society,1949,p. Spl. 113

4
[ 274-56-6 ]
[ 454-89-7 ]
[ 143307-85-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 5538 - 5540
[2]Journal of Organic Chemistry,1992,vol. 57,p. 5538 - 5540

5
[ 17407-44-2 ]
[ 454-89-7 ]
[ 123760-87-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1988,vol. 23,p. 523 - 532

6
[ 349-75-7 ]
[ 454-89-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hypochlorite solution; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; isocyanuric acid; In ethyl acetate; at 0 - 10℃; for 5h;pH > 12;	General procedure: To a mixture of the alcohol (3.839 mmol), K2CO3 (2.0 equiv, 7.678 mmol) and cyanuric acid (0.1 equiv, 0.384 mmol) in 20 mL of ethyl acetate were added TEMPO or AZADO (3 mol%, 0.115 mmol) and 12% NaOCl (1.2 equiv, 4.607 mmol, Wako Pure Chemical Industries, Ltd.) at 0-10C. The mixture was then stirred to complete. The reaction mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford the corresponding product.
98%	With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium carbonate; isocyanuric acid; In water; ethyl acetate; at 0 - 10℃; for 5h;Inert atmosphere;	To a mixture of 16 (676 mg, 3.84 mmol), cyanuric acid (50 mg, 0.38mmol, 0.1 equiv), and K2CO3 (1.06 g, 7.68 mmol, 2.0 equiv) in EtOAc(10 mL) were added TEMPO (18 mg, 0.12 mmol, 0.03 equiv) and 12%(w/w) aq NaOCl (2.86 g, 4.61 mmol, 1.2 equiv) at 0-10 C, and themixture was stirred for 5 h at 0-10 C. The mixture was then extractedwith EtOAc (20 mL). The organic layer was washed with 10% aq.NaCl (10 mL) then concentrated under reduced pressure. The residuewas purified by column chromatography (silica gel, EtOAc-hexane) togive a colorless oil; yield: 398 mg (98%).1H NMR (600 MHz, CDCl3): delta = 7.70 (t, J = 7.7 Hz, 1 H), 7.90 (d, J = 7.9Hz, 1 H), 8.09 (d, J = 7.6 Hz, 1 H), 8.15 (s, 1 H), 10.09 (s, 1 H).13C NMR (151 MHz, CDCl3): delta = 123.6 (q, J = 272.5 Hz), 126.5 (q, J = 3.8Hz), 129.8, 130.8 (q, J = 3.3 Hz), 131.9 (q, J = 33.2 Hz), 132.7, 136.9,190.7.
85%	With tert.-butylhydroperoxide; 2,2?-((1E,1?E)-(1,2-phenylenebis(azanylylidene))bis(methanylylidene))diphenolcopper(II); sodium hydroxide; In water; acetonitrile; at 20℃;	General procedure: Alcohol (0.5 mmol), salophen copper (II) complex (2 mol%), NaOH (0.6 equiv), and 70% TBHP in water (1.1 equiv) were dissolved in acetonitrile (5 mL), and the homogeneous solution was stirred at room temperature in air overnight. After completion of the reaction, the solvent was evaporated under reduced pressure. The residue was purified over silica gel by column chromatography (10-25% EtOAc in hexane).

73%

With Nitrogen dioxide; In acetonitrile; at 140℃; under 760.051 Torr; for 5h;Sealed tube;

General procedure: To a dried 45 mL tube equipped with a magnetic stirring, 2 mL acetonitrile, 0.5 mmol substrate and 0.046 mmol NO2 were sequentially added (note: the air in the tube was not removed). Then the reaction tube was sealed and stirred magnetically at a constant-temperature to perform the reaction for 5 h. Once the reaction time was reached, GCanalysis of the mixture provided the GC yields of the products. Then the crude product from another parallel experiment was purified by silicagel chromatography to give the desired product.

Reference： [1]Chemical Communications,1999,p. 1907 - 1908
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 448 - 452
[3]Tetrahedron Letters,2015,vol. 56,p. 3905 - 3908
[4]Synthesis,2015,vol. 47,p. 3467 - 3472
[5]Synlett,1999,p. 1489 - 1490
[6]Chemistry - A European Journal,2016,vol. 22,p. 4008 - 4014
[7]Synthetic Communications,2015,vol. 45,p. 1334 - 1341
[8]Chemistry - A European Journal,2016,vol. 22,p. 8814 - 8822
[9]Catalysis Communications,2017,vol. 101,p. 98 - 101
[10]Journal of Organic Chemistry,1988,vol. 53,p. 2154 - 2159
[11]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1995,vol. 34,p. 968 - 974
[12]International Journal of Chemical Kinetics,1997,vol. 29,p. 9 - 16
[13]Tetrahedron,1993,vol. 49,p. 7267 - 7276
[14]Journal of Chemical Research, Miniprint,1998,p. 2251 - 2272
[15]Journal of Chemical Research - Part S,1998,p. 644 - 645
[16]Journal of Chemical Research, Miniprint,1999,p. 2118 - 2135
[17]Journal of Chemical Research, Miniprint,2001,p. 562 - 585
[18]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2000,vol. 39,p. 1258 - 1263
[19]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2002,vol. 41,p. 493 - 499
[20]Journal of Physical Organic Chemistry,2002,vol. 15,p. 721 - 727
[21]Journal of the Indian Chemical Society,2004,vol. 81,p. 467 - 473
[22]Journal of Chemical Research,2004,p. 581 - 584
[23]Advanced Synthesis and Catalysis,2003,vol. 345,p. 497 - 505
[24]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2008,vol. 47,p. 669 - 676
[25]Journal of the Indian Chemical Society,2008,vol. 85,p. 496 - 501
[26]European Journal of Organic Chemistry,2010,p. 3445 - 3448
[27]Journal of Catalysis,2010,vol. 274,p. 76 - 83
[28]Journal of Organic Chemistry,2017,vol. 82,p. 11440 - 11446
[29]ACS Catalysis,2018,vol. 8,p. 6939 - 6947
[30]ChemBioChem,2019,vol. 20,p. 276 - 281
[31]Advanced Synthesis and Catalysis,2019,vol. 361,p. 2262 - 2267
[32]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194

7
[ 454-89-7 ]
[ 349-75-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	With [Ir(2,2':6',2'?-terpyridine)(1,10-phenanthroline)Cl](PF6)2; sodium formate; In ethanol; water; at 100℃; for 0.5h;Microwave irradiation;	General procedure: An aldehyde (1 mmol),sodium formate (4.5 eq), and catalyst (0.2 mol%) were taken in70% ethanol in water (4 mL) in a microwave vial and vortexed togenerate a homogenous solution. The mixture was heated in MWat 100 C using 150W of irradiation. Reaction progress was monitored by TLC. If complete conversion took place, the reaction colorturns to emerald green (color disappears after sometime) from paleyellow, and byproduct Na2CO3 precipitates. The Na2CO3 solid wasremoved by decanting the supernatant. The solid was washed withethyl acetate (20 mL). The combined decanted solution waswashed with water (5.0 mL), followed by brine solution (5.0 mL),dried over Na2SO4, filtered, and evaporated to dryness to affordthe desired alcohol as a pale-yellow liquid or off-white solid.

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 9080 - 9083
Angew. Chem.,2016,vol. 128,p. 9226 - 9229,4
[2]Journal of Catalysis,2019,vol. 378,p. 283 - 288
[3]Tetrahedron Letters,1988,vol. 29,p. 4057 - 4060
[4]Bioorganic and Medicinal Chemistry Letters,1996,vol. 6,p. 311 - 314
[5]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017
[6]Journal of the American Chemical Society,2007,vol. 129,p. 2772 - 2773
[7]Tetrahedron Letters,2009,vol. 50,p. 4624 - 4628
[8]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1768 - 1777
[9]Inorganic Chemistry,2017,vol. 56,p. 11282 - 11298

8
[ 454-89-7 ]
[ 10495-09-7 ]
(E,Z)-ethyl 4,4-diethoxy-2-<3-(trifluoromethyl)benzylidene>acetoacetate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 3033 - 3040

9
[ 454-89-7 ]
[ 274-85-1 ]
[ 143307-80-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 5538 - 5540

10
[ 454-89-7 ]
[ 74-89-5 ]
[ 90390-07-1 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 140 - 145

11
[ 454-89-7 ]
[ 17396-35-9 ]
[ 61448-83-7 ]

Reference： [1]Journal of Medicinal Chemistry,1982,vol. 25,p. 1482 - 1488

12
[ 75-52-5 ]
[ 454-89-7 ]
[ 115665-96-8 ]

Reference： [1]Australian Journal of Chemistry,1976,vol. 29,p. 2607 - 2614
[2]Catalysis science and technology,2016,vol. 6,p. 5714 - 5720

13
[ 22908-28-7 ]
[ 454-89-7 ]
(E)-2-(5-Chloro-2-nitro-phenyl)-3-(3-trifluoromethyl-phenyl)-acrylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 775 - 780

14
[ 454-89-7 ]
[ 1735-91-7 ]
[ 38635-49-3 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 775 - 780

15
[ 50681-25-9 ]
[ 454-89-7 ]
[ 174812-94-3 ]

Reference： [1]Heterocycles,1996,vol. 43,p. 151 - 172

16
[ 349-75-7 ]
hydrogen [ No CAS ]
CO [ No CAS ]
CoCO₃ [ No CAS ]
octacarbonyl dicobalt [ No CAS ]
[ 401-79-6 ]
[ 454-89-7 ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4079,4082

17
[ 380633-51-2 ]
[ 2557-13-3 ]
[ 454-89-7 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 1802 - 1807

18
[ 454-89-7 ]
[ 870-63-3 ]
[ 349-75-7 ]
2,2-dimethyl-1-(3-trifluoromethyl-phenyl)-but-3-en-1-one [ No CAS ]
2,2-dimethyl-1-(3-trifluoromethyl-phenyl)-but-3-en-1-ol [ No CAS ]
3-trifluoromethyl-benzoic acid 2,2-dimethyl-1-(3-trifluoromethyl-phenyl)-but-3-enyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 1975 - 1981

19
[ 454-89-7 ]
[ 2136-75-6 ]
[ 262268-58-6 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; for 40h;Reflux;	(2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enal 3-(Trifluoromethyl)benzaldehyde (0.70 g) was dissolved in toluene (16 mL), and (triphenylphosphoranylidene)acetoaldehyde (1.22 g) was added. The reaction mixture was heated under reflux for 40 hr and concentrated, and the residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.41g) as an oil. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 6.78 (1 H, dd, J=16.1, 7.4 Hz), 7.41 - 7.87 (5 H, m), 9.75 (1 H, d, J=7.5 Hz)
	In acetonitrile; at 20℃; for 18h;	Preparation of 8-nitro-2-(3-(trifluoromethyl)phenyl)quinoline: 3-Trifluoromethylbenzaldehyde (20.0 g, 0.115 mol) was taken up in 500 mL of CH3CN along with (triphenylphosphoranylidene)acetaldehyde (35 g, 0.115 mol). The reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in 800 mL of 1:1 pentane/EtOAc and filtered. The filtrate was concentrated under reduced pressure to afford crude (E)-3-(3-(trifluoromethyl)phenyl)acrylaldehyde as a dark red oil. This material was taken up in 30 mL of CH2Cl2. The resulting mixture was slowly added to a suspension of 2-nitroaniline (4 g, 0. 029 mol) in concentrated HCl (50 mL) at 90 C over a period of 30 min. The resulting reaction mixture was stirred at 90 C for an additional 1 h. The reaction mixture was cooled to room temperature and washed with CH2Cl2 (2 x 100 mL). The aqueous layer was neutralized with 5% aqueous NaOH and extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (pentane/EtOAc) to afford 800 mg of 8-nitro-2-(3-(trifluoromethyl)phenyl)quinoline. MS (ESI) calcd for C16H9F3N2O2 (m/z): 318.06, found: 319 [M+1].

Reference： [1]Chemical Communications,2005,p. 340 - 341
[2]Patent: EP2264017,2010,A1 .Location in patent: Page/Page column 80
[3]Patent: EP2273992,2016,B1 .Location in patent: Paragraph 0208; 0209

20
[ 75-52-5 ]
[ 454-89-7 ]
[ 52516-30-0 ]

Reference： [1]Molecular Pharmacology,2005,vol. 68,p. 20 - 33

21
[ 67-56-1 ]
[ 454-89-7 ]
[ 2557-13-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With diphenyl diselenide; dihydrogen peroxide; at 50℃; for 2h;Green chemistry;	General procedure: Diphenyl diselenide (3, 0.006 g; 0.02 mmol) was treated with H2O2 (30%·w/w, 0.15 mL, 1.5 mmol)and stirred at room temperature until the discoloration of the reaction mixture. Then, the aldehyde 1(1 mmol) and the appropriate alcohol (2.5 mmol) were added. The reaction mixture was stirred at50 C for 2 h and extracted three times with EtOAc (3 × 20 mL). The collected organic layers were driedover Na2SO4 and the solvent evaporated under reduced pressure.

Reference： [1]Molecules,2015,vol. 20,p. 10496 - 10510
[2]Tetrahedron Letters,2005,vol. 46,p. 8303 - 8306

22
[ 13623-11-5 ]
[ 454-89-7 ]
2-[2-hydroxy-2-(3-trifluoromethylphenyl)ethyl]-4,5-dimethyl-1,3-thiazole [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2005,vol. 41,p. 877 - 882

23
[ 931-53-3 ]
[ 454-89-7 ]
[ 104-86-9 ]
[ 6622-92-0 ]
2-(N-(4-chlorobenzyl)-N-(2,6-dimethylpyrimidin-4-yl)amino)-N-cyclohexyl-2-(3-(trifluoromethyl)phenyl)acetamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4169 - 4180

24
[ 454-89-7 ]
[ 368-77-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With ammonium hydroxide; sodium persulfate; sodium iodide; iron(II) chloride; In 1,2-dichloro-ethane; at 20 - 50℃; for 16h;	General procedure: To a solution of aldehydes 1 (3 mmol) in 1,2-dichloroethane (10 mL) was added FeCl2(0.3 mmol), Na2S2O8 (4.5 mmol), NaI (0.15 mmol), and NH3.H2O (9 mL) at room temperature. After the mixture was stirred at 50 C for 16 hours, it was poured into water (30 mL) and extracted with DCM (3 × 30 mL). The combined organic extracts were washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The crude product was purified by column chromatography on silica gel to afford the product 2.
87%	With hydroxylamine hydrochloride; In methanol; water; at 20℃; for 18h;Irradiation;	General procedure: A round bottom flask was charged with a mixture of benzaldehyde 1(1.0 mmol), NH2OH.HCl 2 (1.5 mmol), Cog-C3N4 (20 mg) in H2O/MeOH (1:1, 5 mL) and stirred under the visible light condition at roomtemperature for 14-20 h. After completion of the reaction (monitored by TLC), the catalyst was filtered and added EtOAc (10 mL). Remaining organic layer was washed with brine (2×5 mL) and distilled water(1×10 mL) and dried over anhydrous sodium sulfate. Solvent was evaporated under reduced pressure to afford the crude residue, which was further purified by flash chromatography, EtOAc/n-hexane: 10:90 to obtain the analytically pure product 3

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1434 - 1436
[2]Catalysis Communications,2019,vol. 119,p. 76 - 81
[3]Journal of Organic Chemistry,2006,vol. 71,p. 7785 - 7792
[4]European Journal of Organic Chemistry,2019,vol. 2019,p. 3190 - 3194
[5]RSC Advances,2020,vol. 10,p. 17288 - 17292

25
[ 454-89-7 ]
[ 262268-58-6 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 694 - 707
[2]Chemistry - A European Journal,2013,vol. 19,p. 3833 - 3837
[3]Synthetic Communications,2014,vol. 44,p. 1924 - 1929

26
[ 454-89-7 ]
[ 14355-04-5 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1111 - 1118

27
[ 454-89-7 ]
[ 90390-07-1 ]

Reference： [1]Journal of Medicinal Chemistry,1984,vol. 27,p. 1111 - 1118

28
[ 454-89-7 ]
[ 21906-39-8 ]

Reference： [1]Synthesis,1977,p. 474 - 476
[2]Chimica Therapeutica,1968,vol. 3,p. 313 - 320

29
[ 2380-84-9 ]
[ 454-89-7 ]
[ 475576-93-3 ]

Yield	Reaction Conditions	Operation in experiment
26%		EXAMPLE 54 2-Amino-3-cyano-4-(3-trifluromethyl-phenyl)-4H-indolo[7,6-b]pyran The title compound was prepared from <strong>[2380-84-9]7-hydroxyindole</strong> and 3-trifluromethyl- benzaldehyde by a procedure similar to that described in Example 46 in 26% yield. 1H NMR (CDCl3): 8.41 (brs, 1H), 7.51-7.42 (m, 4H), 7.31 (d, J=8.4 Hz, 1H), 7.27-7.25 (m, 1H), 6.62 (dd, J=0.6, 8.4 Hz, 1H), 6.56-6.54 (m, 1H), 4.95 (s, 1H), 4.71 (brs, 2H).

Reference： [1]Patent: US2003/65018,2003,A1

30
[ 75-34-3 ]
[ 454-89-7 ]
[ 393-36-2 ]
3-[(3-(trifluoromethyl)-4-bromophenyl)[[3-(1,1,1-trifluoromethyl)phenyl]methyl]-amino]-1,1,1-trifluoro-2-propanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid;	3-[4-bromo-3-(trifluoromethyl)phenyl[[3-(trifluoromethyl)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol EX-625A) The alpha,alpha,alpha-trifluoro-m-tolualdehyde (3.63 g, 0.021 mol) was added neat to 4-bromo-3-trifluoromethylaniline (5.0 g, 0.021 mol). Dichloroethane (50 mL) was added followed by sodium triacetoxyborohydride (4.85 g, 0.023 mol) and acetic acid (1.42 g, 0.024 mol). The resulting mixture was stirred at room temperature for 18 h, then diluted with methylene chloride, quenched with sodium bicarbonate and extracted with methylene chloride. The organic layers were combined and dried over MgSO4 and concentrated to give 6.97 g of the desired 3-[4-bromo-3-(trifluoromethyl)-phenyl[[3-(trifluoromethyl)phenyl]methyl]amine product as a yellow oil, which was carried forward without purification. ESMS m/z=397 [M+H]+.

Reference： [1]Patent: US2002/120011,2002,A1

31
[ 454-89-7 ]
[ 7048-04-6 ]
[4R]-2-(m-trifluoromethylphenyl)-4-thiazolidinecarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium acetate; In ethanol; water;	EXAMPLE 14 [4R]-3-(3-Acetylthio-3-benzoyl-2-methylpropionyl)-2-(m-trifluoromethylphenyl)-4-thiazolidinecarboxylic acid To a solution of 10.0 g. (0.057 mole) of <strong>[7048-04-6]L-cysteine hydrochloride hydrate</strong> and 6.0 g. (0.061 mole) of potassium acetate in 280 ml. of ethanol:water (3:2) is added 13.06 g. (0.075 mole) of m-trifluoromethylbenzaldehyde dropwise over a 10 minute period. The mixture is stirred for 24 hours at room temperature and filtered. The solid (17.0 g.) is recrystallized from methanol to give 13.2 g. of [4R]-2-(m-trifluoromethylphenyl)-4-thiazolidinecarboxylic acid as white crystals, m.p. 152-154 C.

Reference： [1]Patent: US4374249,1983,A

32
[ 454-89-7 ]
[ 120-35-4 ]
4-Methoxy-3-(3-trifluoromethyl-benzylamino)-N-phenyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 269 4-Methoxy-3-(3-trifluoromethyl-benzylamino)-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 3-trifluoromethylbenzaldehyde as starting materials, which can be purchased from Aldrich; m.p. 167-171 C.

Reference： [1]Patent: US6268387,2001,B1

33
[ 454-89-7 ]
[ 136-64-1 ]
C₂₄H₁₆F₆N₄O₂ [ No CAS ]

Reference： [1]Bioorganic Chemistry,2007,vol. 35,p. 50 - 58

34
[ 141-82-2 ]
[ 454-89-7 ]
[ 779-89-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With piperidine; pyridine; at 110℃;	General procedure: To a solution of pyridine (3 vol), was added aldehyde (1 mmol) malonic acid (2 mmol)followed by catalytic amount of piperidine (0.1 mmol). The reaction mass was slowly heatedto 110 0C and maintained for 10 - 12 hr at 110 0C. Reaction was monitored by TLC. Reactionmass was cooled to room temperature and quenched into 10 vol of water of pyridine. To thequenched mass was added, NaOH (2 mmol). Reaction mixture was stirred to obtain clearsolution. Then reaction mixture was washed with ethyl acetate (20 vol X 2). Aqueous layerwas then acidified with 50 percent sulfuric acid till pH 2.The precipitated solid was filtered andwashed with water (5 vol X 2) followed by pet ether wash 2 vol. The product was suck driedon buchner funnel for 15 min to 60 min. The solid product was dried in oven at 50 to 60 °Covernight. Cinnamic acids were obtained in 80 - 90 percent yield.
	With piperidine; pyridine; for 3h;	General procedure: To a mixture of the corresponding aldehyde (10 mmol), pyridine (6 mL) and piperidine (0.6 mL) was added malonic acid (1.25 g, 12 mmol). The mixture was stirred for 3 h at 90-100 °C, then cooling to room temperature. The reaction mixture was neutralized with hydrochloric acid solution (10 mol/L, 80 mL) at 0 °C. The white solid was filtered, washed with cold water, and dried to afford the corresponding acid.
	With piperidine; pyridine; at 90℃;Inert atmosphere;	General procedure: To a stirred solution of malonic acid (10 mmol) in pyridine(5 mL) and piperidine (3?5 drops) the corresponding aldehydes1a-p (8 mmol) were added. The resulting mixture was stirred at 90°C for 8?12 h. The progress of the reaction was monitored byTLC analyses which indicated the disappearance of the starting material. After the completion of the reactions the reaction mixture were cooled to ambient temperature and the reaction mixture was neutralized with 1N HCl in ice bath resulting a white solid.This soled was filtered and washed three times with cold water.The recrystallization were done from aqueous ethanol (1:1)afforded the product 2a-p.

Reference： [1]Bioorganic Chemistry,2019,vol. 86,p. 507 - 512
[2]Synthetic Communications,2008,vol. 38,p. 1512 - 1517
[3]Chemical Biology and Drug Design,2013,vol. 81,p. 275 - 283
[4]Chemistry - A European Journal,2013,vol. 19,p. 3833 - 3837
[5]European Journal of Medicinal Chemistry,2017,vol. 126,p. 517 - 525
[6]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5726 - 5732

35
[ 109-97-7 ]
[ 454-89-7 ]
[ 3264-82-2 ]
(C₆H₄CF₃)4C₂₀H₈N₄Ni [ No CAS ]
[F₃CC₆H₄CC₄H₂NC(O)(C₆H₄CF₃)(C₄H₂N)]3Ni₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 2306 - 2309

36
[ 454-89-7 ]
[ 108-24-7 ]
[ 779-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 175℃; for 5.25h;	EXAMPLE 1 : PREPRATION OF 3-TRI FLU ROM ETHYL CINNAMIC ACID:Trifluromethyl benzaldehyde (10 g) was taken into a round bottom flask containing acetic anhydride (3.8 g) and stirred for 15 minutes. The reaction mass was heated to about 175 0C and stirred for about 5 hours. After completion of the reaction, the reaction mass was cooled to about 80 0C followed by addition of water (40 ml) and again stirring for 15 minutes. pH of the reaction solution was adjusted to about 10 by addition of 100 ml of 10percent sodium carbonate solution and stirring for about 15 minutes. The water was distilled at about 110 0C under vacuum and the separated solid was filtered.The obtained filtrate was charged into a fresh round bottom flask and cooled to about 0 0C. pH of the solution was adjusted to about 2 by the addition of concentrated HCI (25 ml) and stirred for solid separation. The separated solid was filtered and washed with water (40 ml). The resultant solid was dried under vaccum at about 50 0C to afford 2.4 g of the title compound.Mass (m/z) : 215 a.m.u.

Reference： [1]Patent: WO2008/58235,2008,A2 .Location in patent: Page/Page column 22

37
[ 70-49-5 ]
[ 454-89-7 ]
[ 101-79-1 ]
[ 1059199-13-1 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene; at 110℃; for 48h;	[3-[4-(4-Chloro-phenoxy)-phenyl]-4-oxo-2-(3-trifluoromethyl-phenyl)- thiazolidin-5-yl] -acetic acid: A solution of 4-(4-chlorophenoxy)aniline (1.1 g, 5.0 mmol) in toluene is added mercaptosuccinic acid (0.75 g, 10.0 mmol), followed by alpha,alpha,alpha- trifluoro-m-tolualdehyde (0.67 mL, 5.0 mmol). The solution is heated at 110 0C for 2 <n="34"/>days before cooling down to room temperature. After diluting with ethyl acetate, the solution is washed with IN HCl, saturated NaHCpsi3, and water and dried over MgSO4. Filtration and concentration followed by purification with HPLC (eluent: 20-90 percent acetonitrile/water) gives the desired product as a yellow syrup. 1H NMR (CDCI3) delta (ppm) 7.54 (m, 3H), 7.42 (m, IH), 7.27 (m, 2H), 7.05 (m, 2H), 6.86 (m, 4H), 6.12 (s, IH), 4.50 (m, IH), 3.15 (m, 2H); HPLC-MS calculated for C24H17ClF3NO4S (M+H+): 508.1, found 508.1.

Reference： [1]Patent: WO2008/112674,2008,A1 .Location in patent: Page/Page column 32-33

38
[ 454-89-7 ]
[ 107-96-0 ]
[ 101-79-1 ]
[ 1059197-34-0 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 4-(4-chlorophenoxy)aniline (50 mg, 0.228 mmol) and a,a,a- trifluoro-m-tolualdehyde (61 muL, 0.457 mmol) in THF is stirred at ice cooled temperatures for 5 min, followed by addition of 3-mercaptopropionic acid (60 muL, 0.684 mmol). After stirring for another 5 min, dicyclohexylcarbodiimide (71 mg, 0.342 mmol) is added. The resulting reaction mixture is then warmed to room temperature and stirred overnight. Filtration and concentration followed by purification with HPLC (20-100 percent water/acetonitrile) gives 3-[4-(4-chloro-phenoxy)-phenyl]-2-(3-trifluoromethyl-phenyl)- [l,3]thiazinan-4-one as the product. 1H NMR (CDCl3) delta (ppm) 7.56 (m, 4H), 7.27 (d, <n="32"/>2H), 7.11 (d, 2H), 6.88 (m, 4H), 5.92 (d, IH), 2.96 (m, 4H); HPLC-MS calculated for C23H17ClF3NO2S (M+H+): 464.1, found 464.1.

Reference： [1]Patent: WO2008/112674,2008,A1 .Location in patent: Page/Page column 30-31

39
[ 56341-39-0 ]
[ 454-89-7 ]
[ 1148119-16-7 ]
(Z)-6-fluoro-3-(3-(trifluoromethyl)benzylidene)indolin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 2077 - 2090

40
[ 454-89-7 ]
[ 75416-50-1 ]
[ 1207968-95-3 ]

Yield	Reaction Conditions	Operation in experiment
74%		A mixture of <strong>[75416-50-1]8-chloro-1,2,3,4-tetrahydroisoquinoline</strong> (4.5 g, 22.0 mmol), 3-trifluoromethylbenzaldehyde (3.25 mL, 24.3 mmol), sodium acetate (1.81 g, 22.0 mmol), and acetic acid (0.63 mL, 11.0 mmol) in ethanol was stirred for 1 hour. Sodium triacetoxyborohydride (5.60 g, 26.5 mmol) was added a little at a time over a period of 30 min, and the mixture was then stirred for 15 hours. The reaction solution was diluted with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was then distilled off at reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=10:1), the resulting oily substance was dissolved in isopropyl alcohol (30 mL), and 4 N hydrogen chloride/ethyl acetate (5 mL) was added. The precipitated crystals were filtered off to give 5.89 g of the titled compound (yield 74%). Melting point: 217-218 C.1H-NMR (DMSO-d6) delta: 3.00-3.40 (4H, m), 4.20-4.40 (2H, m), 4.50-4.80 (2H, m), 7.25 (1H, d, J=7.5 Hz), 7.32 (1H, d, J=7.2 Hz), 7.38 (1H, t, J=7.2 Hz), 7.74 (1H, t, J=7.5 Hz), 7.80-7.90 (1H, m), 7.90-8.00 (1H, m), 8.10 (1H, s), 11.24 (1H, br s).

Reference： [1]Patent: US2010/41891,2010,A1 .Location in patent: Page/Page column 42

41
[ 454-89-7 ]
[ 81237-69-6 ]
[ 1207968-97-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium tris(acetoxy)borohydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 15h;	Sodium triacetoxyborohydride (5.81 g, 27.4 mmol) was added to a THF (100 mL)-DMF (10 mL) mixed solution of <strong>[81237-69-6]5-bromo-1,2,3,4-tetrahydroisoquinoline</strong> (2.90 g, 13.7 mmol) and 3-(trifluoromethyl)benzaldehyde (2.74 mL, 20.6 mmol), and the mixture was stirred for 15 hours at room temperature. The reaction solution was treated with the addition of water and 1 N sodium hydroxide aqueous solution, and was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and then concentrated at reduced pressure. The residue was purified by silica gel column chromatography to give 4.77 g of the titled compound (yield 94%) in the form of an oily substance.1H-NMR (CDCl3) delta: 2.72-2.80 (2H, m), 2.82-2.92 (2H, m), 3.62 (2H, s), 3.72 (2H, s), 6.91-6.96 (1H, m), 6.96-7.03 (1H, m), 7.40 (1H, dd, J=7.5, 1.3 Hz), 7.46 (1H, d, J=7.5 Hz), 7.51-7.56 (1H, m), 7.58 (1H, d, J=7.5 Hz), 7.65 (1H, s)

Reference： [1]Patent: US2010/41891,2010,A1 .Location in patent: Page/Page column 43

42
[ 454-89-7 ]
[ 405939-39-1 ]
[ 1081314-08-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4159 - 4166

43
[ 454-89-7 ]
[ 91188-13-5 ]
[ 1219626-10-4 ]

Yield	Reaction Conditions	Operation in experiment
		Example 180; 2-(2-oxo-3,3-diphenylpiperidin-l-yl)-7V-{l-[3-(trifluoromethyl)benzyl]azetidin-3- yl}acetamide; Example 180A; tert-buty l-[3-(trifluoromethyl)benzyl]azetidin-3-ylcarbamate; To a solution of tert-butyi azetidin-3-ylcarbamate (0.34 g, 2 mmol) in dichloroethane was added 3-(trifluoromethyl)benzaldehyde (0.45 g, 2.6 mmol) and sodium triacetoxyborohydride (0.64 g, 3 mmol). The resultant mixture was stirred at room temperature for 16 hours, and then the mixture was diluted with dichloromethane and washed with aqueous NaHCO3 solution. The organic layer was separated, dried over MgSO4, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 30-70% ethyl acetate/hexane to yield the title compound.

Reference： [1]Patent: WO2010/39947,2010,A1 .Location in patent: Page/Page column 148

44
[ 454-89-7 ]
[ 78573-45-2 ]

Reference： [1]Patent: EP2013209,2011,B1
[2]Beilstein Journal of Organic Chemistry,2012,vol. 8,p. 1366 - 1373

45
[ 454-89-7 ]
[ 585-50-2 ]

Reference： [1]Patent: EP2013209,2011,B1
[2]Beilstein Journal of Organic Chemistry,2012,vol. 8,p. 1366 - 1373

46
[ 931-53-3 ]
[ 454-89-7 ]
[ 18212-21-0 ]
[ 95-74-9 ]
[ 1203472-33-6 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 2755 - 2762

47
[ 13909-73-4 ]
[ 454-89-7 ]
[ 1309371-16-1 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4147 - 4159

48
[ 600-18-0 ]
[ 454-89-7 ]
[ 64465-53-8 ]
[ 1335116-53-4 ]

Yield	Reaction Conditions	Operation in experiment
53%		EXAMPLE 33-(1 ,4'-bipiperidin-1 '-ylmethyl)-6-(ethylsulfonyl)-7-(methyloxy)-2-r3-(trifluoromethyl)phenyll-A/- r(1 f?)-2,2,2-trifluoro-1-phenylethyll-4-quinolinecarboxamide; 6-fluoro-3-methyl-7-(methyloxy)-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxylic acidA solution of the 4-fluoro-3-(methyloxy)aniline (1 1.29 g, 80 mmol) and 3- (trifluoromethyl)benzaldehyde (13.93 g, 80 mmol) in ethanol (200 mL) was heated to reflux for 1 h. 2-Oxobutanoic acid (8.17 g, 80 mmol) was added portionwise. The reaction mixture was stirred at reflux for additional 3 h, cooled to room temperature, and stirred at room temperature overnight. The solid was collected by filtration, washed with ethanol, and air dried to give 6- fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (16.05 g, 53% yield). 1H NMR (400 MHz, DMSO-d6) delta 14.35 (br. s., 1 H), 7.93 - 8.00 (m, 2H), 7.85 - 7.91 (m, J = 7.78 Hz, 1 H), 7.74 - 7.81 (m, 1 H), 7.68 - 7.73 (m, J = 8.53 Hz, 1 H), 7.54 (d, J = 12.05 Hz, 1 H), 4.03 (s, 3H), 2.38 (s, 3H); MS (m/z) 380.1 (M+H+).
49%		EXAMPLE 1323-( 1 ,4'-bipiperidin-1 '-ylmethyl)-6-r( 1 -methylethyl)sulfonyll-7-(methyloxy)-A/-( 1 - phenylcvclopropyl)-2-[3-(trifluoromethyl)phenyll-4-quinolinecarboxamide6-fluoro-3-methyl-7-(methyloxy)-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxy acidTo a solution of 4-fluoro-3-(methyloxy)aniline (13.6 g, 96 mmol) in ethanol (200 mL) was added 3-(trifluoromethyl)benzaldehyde (16.78 g, 96 mmol) dropwise. The mixture was stirred at reflux for 1 h, and 2-oxobutanoic acid (9.84 g, 96 mmol) was added portionwise. The reaction mixture was stirred at reflux for an additional 3 h, cooled to room temperature, and stirred overnight. The mixture was filtered to collect the precipitate, and the solid was washed with ethanol and air dried to give 6-fluoro-3-methyl-7-(methyloxy)-2-[3- (trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (17.9 g, 49% yield). MS (m/z) 380.1 (M+H+).

Reference： [1]Patent: WO2011/119701,2011,A1 .Location in patent: Page/Page column 48
[2]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 62-63

49
[ 600-18-0 ]
[ 454-89-7 ]
[ 7664-66-6 ]
[ 1336966-72-3 ]

Yield	Reaction Conditions	Operation in experiment
10.62%		EXAMPLE 913-(1 ,4'-bipiperidin-1 '-ylmethyl)-6-[(1-^(trifluorometh l)phenyll-4-quinolinecarboxamide3- methyl-6-r(1-methylethyl)oxyl-2-r3-(trifluoromethyl)phenyll-4-quinolin acidTo a solution of {{4-[(1 -methylethyl)oxy]phenyl}amine4- [(1-methylethyl)oxy]aniline (15 g, 99 mmol) in ethanol (165 ml.) was added 3- (trifluoromethyl)benzaldehyde (17.27 g, 99 mmol) dropwise. The mixture was stirred at reflux for l h. 2-Oxobutanoic acid (10.13 g, 99 mmol) was added portionwise. The mixture was stirred at reflux for an additional 3 h, warmed to room temperature and stirred overnight. The suspension was filtered and the filter cake was washed with ethanol to afford a white solid. The filter cake was collected and set aside. The filtrate was concentrated and purified via (Biotage, 3 column volumes of water, 0-50% CH3CN/Water over 10 column volumes, basic conditions- pH 10). The impure fractions were combined and repurified via reverse phase HPLC (Waters, Basic conditions, 10-50% CH3CN/Water over 14 min). The product collected from both HPLC purifications were dissolved in methanol and purified via SCX column (MeOH, NH3/MeOH).The filter cake was dissolved in ethyl acetate, filtered, concentrated and purified via column chromatography (ISCO, 330 g column, ethyl acetate/methylene chloride 100% methanol). The appropriate fractions were concentrated, dissolved in methanol, and passed through an SCX column (eluting with MeOH, NH3/MeOH).The fractions collected from both SCX columns were combined and concentrated to afford 3-methyl-6-[(1 -methylethyl)oxy]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (38.6 g, 10.62% yield) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.80 - 7.91 (m, 4H), 7.70 - 7.77 (m, 1 H), 7.30 - 7.34 (m, 2H), 7.16 (d, J = 2.76 Hz, 1 H), 4.70 (dt, J = 6.02, 12.05 Hz, 1 H), 2.28 (s, 3H), 1 .34 (d, J = 6.02 Hz, 6H); MS (m/z) 390.1 (M+H+)

Reference： [1]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 62-63

50
[ 600-18-0 ]
[ 6358-06-1 ]
[ 454-89-7 ]
[ 1336904-56-3 ]

Yield	Reaction Conditions	Operation in experiment
73%		+). EXAMPLE 713-(1 ,4'-bipiperidin-1 '-ylmethyl)-6-chloro-7-(ethyloxy)-/\\/-(1 -phenylcvclopropyl)-2-[3- (trifluorometh l)phenyll-4-quinolinecarboxamide6-chloro-7-hvdroxy-3-methyl-2-[3-(trifluoromethyl)phenyll-4-quinolinecarbox acidTo a solution of <strong>[6358-06-1]5-amino-2-chlorophenol</strong> (5.74 g, 40 mmol) in ethanol (100 mL) was added 3-(trifluoromethyl)benzaldehyde (6.96 g, 40.0 mmol) dropwise. The mixture was stirred at reflux for 1 h. 2-Oxobutanoic acid (4.08 g, 40.0 mmol) was added portionwise. The reaction mixture was stirred at reflux for additional 3 h, cooled to room temperature and stirred overnight. The mixture was filtered, and the filter cake was washed with ethanol and air dried to give 6-chloro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4- quinolinecarboxylic acid (1 1 .2 g, 73percent yield). MS (m/z) 382.0 (M+H+).

Reference： [1]Patent: WO2011/119704,2011,A1 .Location in patent: Page/Page column 127

51
[ 454-89-7 ]
[ 226256-56-0 ]

Reference： [1]Patent: US2012/309842,2012,A1
[2]Patent: US2012/309842,2012,A1
[3]Patent: CN104592037,2016,B

52
[ 454-89-7 ]
[ 90536-66-6 ]
[ 1430809-28-1 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium acetate; acetic anhydride; at 120℃; for 18.5h;	General procedure: Potassium acetate (982 mg, 10 mmol) or triethylamine (1.5 mL, 10.75 mmol; for the synthesis of 13, 14, 15, 18, 20, 22, 23, and 25) was added to a stirred mixture of the appropriate arylacetic acid (7.5 mmol), aromatic aldehyde (7.5 mmol) and acetic anhydride (3 mL, 32 mmol). The reaction mixture was stirred at 100-140 C for 3.5-70 h. Then it was cooled to rt, water was added (40 mL) and the mixture was treated with a solution of 10 M NaOH until pH 12 was reached, followed by conc. HCl (to pH 1). The resulting mixture was extracted with CH2Cl2 (3 × 80 mL). Organic phases were extracted with 2 M NaOH (3 × 80 mL) and water (80 mL). The combined aqueous solutions were washed with CH2Cl2 (100 mL) to remove the impurities and traces of starting materials, then acidified with conc. HCl (until pH was 1), and finally extracted with CH2Cl2 (4 × 50 mL). The methylene chloride phase was washed with brine (100 mL), dried over anhydrous sodium sulfate, evaporated to dryness and the residue was crystallized from a suitable solvent.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 62,p. 89 - 97

53
[ 1193-79-9 ]
[ 454-89-7 ]
[ 1449846-76-7 ]

Yield	Reaction Conditions	Operation in experiment
23%	With sodium hydroxide; In ethanol; at 20℃; for 3h;	General procedure: General procedure for the synthesis of chalcones (5a - 5r) Ketone (8.57 mmol, 1 equiv) and benzaldehyde (8.57 mmol, 1 equiv) was dissolved in a minimum amount of ethanol, and stirred at room temperature. To this mixture, a solution of 40% (w/v) sodium hydroxide (0.5 equiv) was added dropwise. After the reaction mixture was stirred at room temperature for 2-3 hours, the residue that formed was filtered and washed with cold ethanol. The resulting solid was recrystallised from ethanol (Cocconcelli et al., 2008).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4985 - 4989

54
[ 454-89-7 ]
[ 328-99-4 ]
[ 188815-30-7 ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 339 - 344

55
[ 454-89-7 ]
[ 170961-15-6 ]
[ 1081314-08-0 ]

Yield	Reaction Conditions	Operation in experiment
31%	With n-butyllithium; In tetrahydrofuran; at -78℃; for 2h;Inert atmosphere;	General procedure: n-BuLi (2.5M in THF, 1.4equiv) was added drop wise to a mixture of compound 1a or 1b (1equiv) and aldehyde (1.2equiv) in THF (?20mL) at -78C for 2h. The reaction was quenched by adding a saturated aqueous solution of NH4Cl, extracted with EtOAc, washed with water and then brine. The organic phase was dried over anhydrous Na2SO4, evaporated, and the residue was purified by silica gel column chromatography

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 532 - 547

56
[ 454-89-7 ]
malonic [ No CAS ]
[ 779-89-5 ]

Reference： [1]Letters in drug design and discovery,2015,vol. 12,p. 20 - 28

57
[ 454-89-7 ]
[ 39549-79-6 ]
7-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium hydrogensulfite; In N,N-dimethyl acetamide; at 150℃;	General procedure: Sodium hydrogen sulfite (4 mmol) was added to a solution of anthranilamide 1 (2 mmol) and benzaldehyde 2 (2 mmol) in N,N- dimethylacetamide (5 mL). The mixture was heated under continuous stirring at 150 o C for 2-3 h and poured into ice water. The precipitate was then filtered, washed with water followed byethanol, and dried to yield the 2-arylquinazolinones 3-31.#10;#10;

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 69 - 79

58
[ 454-89-7 ]
[ 40545-33-3 ]
6-methyl-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With sodium hydrogensulfite; In N,N-dimethyl acetamide; at 150℃;	General procedure: Sodium hydrogen sulfite (4 mmol) was added to a solution of anthranilamide 1 (2 mmol) and benzaldehyde 2 (2 mmol) in N,N- dimethylacetamide (5 mL). The mixture was heated under continuous stirring at 150 o C for 2-3 h and poured into ice water. The precipitate was then filtered, washed with water followed byethanol, and dried to yield the 2-arylquinazolinones 3-31.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 103,p. 69 - 79

59
[ 56341-39-0 ]
[ 454-89-7 ]
[ 1148119-16-7 ]

Reference： [1]ChemMedChem,2015,vol. 10,p. 1548 - 1558

60
[ 454-89-7 ]
[ 4336-70-3 ]
[ 95728-83-9 ]

Yield	Reaction Conditions	Operation in experiment
4 g		To a stirred mixture of sodium hydride (1.0 g, 43.1 mmol) in tetrahydrofuran (60 mL) at 0 C was added <strong>[4336-70-3](cyanomethyl)triphenylphosphonium chloride</strong> (11.6 g, 34.4 mmol) in portions and the resulting mixture stirred for 15 min. A solution of 3-(trifluoromethyl) benzaldehyde (5.0 g, 28.7 mmol) in tetrahydrofuran was added dropwise and the resulting reaction mixture stirred for 2 h at room temperature. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined organic extracts were dried (Na2S04) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with 7% ethyl acetate/petroleum ether to give the title compound (4.0 g).H NMR delta 7.8-7.5 (m, 4H), 7.4 (d, 1H), 6.0 (d, 1H).

Reference： [1]Patent: WO2016/3997,2016,A1 .Location in patent: Page/Page column 42

61
[ 454-89-7 ]
[ 1801-10-1 ]

Yield	Reaction Conditions	Operation in experiment
75%		3-Trifluoromethylbenzaldehyde (87.1 mg, 0.5 mmol),Hydroxylamine hydrochloride (34.7 mg, 0.5 mmol)Sodium carbonate (26.5 mg, 0.25 mmol)And water (1 ml) were sequentially added to a 25 ml Schlenk reaction flask,After half an hour of room temperature reaction,[Cp * Ir (H2O) 3] [OTf] 2 (10.2 mg, 0.0150 mmol, 3 mol%) was addedThe reaction mixture was reacted at 110 CAfter hours,Cooled to room temperature,Rotary evaporation to remove water,Column to give the title compound,Yield: 75%.

Reference： [1]Patent: CN104418762,2016,B .Location in patent: Paragraph 0035; 0036; 0037; 0038
[2]RSC Advances,2019,vol. 10,p. 724 - 728
[3]RSC Advances,2016,vol. 6,p. 37093 - 37098

62
[ 5307-14-2 ]
[ 454-89-7 ]
(4-amino-3-nitrophenyl)[(3-trifluoromethylphenyl)methyl]amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; for 5h;Reflux; Dean-Stark;	(4-Amino-3-nitrophenyl)[3-(trifluoromethyl)phenyl]methyl}amine (1-19). A solution of 2- nitro-/?-phenylenediamine (0.753 g, 4.67 mmol) and PTSA (0.050 g, 0.26 mmol) in toluene (25 mL) was treated via syringe with 3-(trifluoromethyl)benzaldehyde (0.620 mL, 4.64 mmol). The resulting solution was heated to reflux with a Dean-Stark trap for 5 h, filtered through a Buchner funnel packed with a thin pad of S1O2, and allowed to cool to rt. The solvent was removed under reduced pressure to give the crude imine (1.203 g) as bright orange solid, that was suspended in a mixture of 1,4-dioxane (3.7 mL) and MeOH (0.90 mL) and NaBH4 (0.117 g, 0.655 mmol) was added in 3 portions at 15 minute intervals. The resulting solution was allowed to stir at rt for 3 h, quenched with H2O (25 mL), and extracted with CH2CI2 (3 x 100 mL). The combined organic extracts were washed with brine, dried (Na2S04), filtered, and the solvent evaporated under reduced pressure to give crude 1-19 (1.141 g). Purification by chromatography on S1O2 (70% CTLCk in hexanes) gave 1-19 (1.10 g, 3.35 mmol, 72%) as a dark purple powder: Mp 95-96 C (CH2CI2); IR (ATR) 3456.00, 3396.67, 3330.69, 1515.08, 1323.54 cm 1; NMR (CDCb, 400 MHz) delta 7.64 (s, 1 H), 7.55 (m, 2 H), 7.47 (m, 1 H), 7.29 (d, 1 H, / = 2.8 Hz), 6.86 (dd, 1 H, / = 8.8, 2.8 Hz), 6.71 (d, 1 H, / = 8.8 Hz), 5.74 (br s, 2 H), 4.36 (s, 2 H), 3.89 (br s, 1 H); 13C NMR (CDCI3, 100 MHz) delta 140.0, 139.16, 138.5, 132.6, 131.2 (q, 7 = 32 Hz), 131.0, 129.3, 125.4, 124.5 (q, / = 3.7 Hz), 124.4 (q, J = 3.8 Hz), 124.2 (q, J = 271 Hz), 120.3, 106.2, 48.6; HRMS (ESI) m/z calcd for C14H13N2O3F3 (M+H) 312.0954, found 312.0947.
	With toluene-4-sulfonic acid; In toluene; for 5h;Reflux; Dean-Stark; Inert atmosphere;	A solution of 2-nitro-pphenylenediamine (0.753 g, 4.67 mmol) and PTSA (0.050 g, 0.26 mmol) in toluene (25 mL) was treated via syringe with 3-(trifluoromethyl)benzaldehyde (0.620 mL, 4.64 mmol). The resulting solution was heated to reflux with a Dean-Stark trap for 5 h, filtered through a Buchner funnel packed with a thin pad of SiO2, and allowed to cool to rt. The solvent was removed under reduced pressure to give the crude imine (1.203 g) as bright orange solid, that was suspended in amixture of 1,4-dioxane (3.7 mL) and MeOH (0.90 mL) and NaBH4 (0.117 g, 0.655 mmol) was added in 3 portions at 15 minute intervals. The resulting solution was allowed to stir at rt for 3 h,quenched with H2O (25 mL), and extracted with CH2Cl2 (3 x 100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and the solvent evaporated under reduced pressure to give crude product (1.141 g). Purification by chromatography on SiO2 (70% CH2Cl2 in hexanes) gave (4-amino-3-nitro)phenyl[3-(trifluoromethyl)phenyl]methyl}amine (1.10 g, 3.35 mmol, 72%) as a dark purple powder.

Reference： [1]Patent: WO2016/77724,2016,A1 .Location in patent: Page/Page column 44
[2]Molecular Pharmacology,2016,vol. 89,p. 667 - 677

63
[ 454-89-7 ]
[ 885268-02-0 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 8757 - 8760

64
[ 454-89-7 ]
[ 51114-94-4 ]
C₁₁H₉F₃O₂ [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 8757 - 8760

65
[ 1906-82-7 ]
[ 454-89-7 ]
[ 564441-49-2 ]

Reference： [1]Organic Letters,2016,vol. 18,p. 3586 - 3589

66
[ 13388-75-5 ]
[ 454-89-7 ]
(Z)-2-(3,5-dimethoxyphenyl)-3-(3-(trifluoromethyl)phenyl)acrylonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.5%		General procedure: A 50 mL round-bottomed flask was charged with 3 (0.177 g, 1 mmol), aromatic aldehyde or substituted aromatic aldehyde (1 mmol) and 10 mL methanol with stirring, and the mixture was heated to 60 C. After 30 min, sodium methoxide (0.027 g, 0.5 mmol) was added to the mixture and keep the temperature for 4-6 h. After completion of the reaction as indicated by TLC, the reaction mixture was cooled to RT, and the precipitate was separated by filter and recrystallized from methanol to give 4a-4z and 5a-5d.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 81 - 85

67
[ 454-89-7 ]
[ 779-89-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 126,p. 870 - 878

68
[ 14804-38-7 ]
[ 454-89-7 ]
3,5-dimethyl-4-methoxyphenyl-3'-trifluoromethylphenylmethanol [ No CAS ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2017,vol. 55,p. 1048 - 1058

69
[ 3470-49-3 ]
[ 454-89-7 ]
(E)-5-hydroxy-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide; In ethanol; water; at 25℃; for 2h;	General procedure: To a stirred solution of hydroxylated indanone (1.0 eq.) and arylaldehyde (R1=b-m) in ethanol (3 mL), 50% aqueous KOH (9.0 eq.,1.0 mL) solution was added dropwise and the reaction was stirredfor 15 min to 3 h till orange precipitation was obtained. The progressof the reactionwas checked by using TLC. Upon completion, icewas added to the reaction mixture and then neutralized by 6 Maqueous HCl solution (pH adjusted to 2) to get white precipitation.The resulted precipitatewas filtered,washed with excess water anddried. The solid residue was further purified by recrystallizationusing ethyl acetate and n-hexane to afford compound 14-61 in48%-99% yield.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 121 - 138

70
[ 6968-35-0 ]
[ 454-89-7 ]
(E)-7-hydroxy-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium hydroxide; In ethanol; water; at 25℃; for 3h;	General procedure: To a stirred solution of hydroxylated indanone (1.0 eq.) and arylaldehyde (R1=b-m) in ethanol (3 mL), 50% aqueous KOH (9.0 eq.,1.0 mL) solution was added dropwise and the reaction was stirredfor 15 min to 3 h till orange precipitation was obtained. The progressof the reactionwas checked by using TLC. Upon completion, icewas added to the reaction mixture and then neutralized by 6 Maqueous HCl solution (pH adjusted to 2) to get white precipitation.The resulted precipitatewas filtered,washed with excess water anddried. The solid residue was further purified by recrystallizationusing ethyl acetate and n-hexane to afford compound 14-61 in48%-99% yield.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 133,p. 121 - 138

71
[ 454-89-7 ]
[ 75-07-0 ]
[ 262268-58-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 - 25℃; for 48h;	In a four-necked flask, 17.41 g of m-trifluoromethylbenzaldehyde (0.1 mol), 68.0 mL of tetrahydrofuran and 3.04 g of DBU (0.02 mol), freshly distilled 11.01 g of acetaldehyde (0.25 mol) was added with stirring, and the mixture was stirred at room temperature (20 to 25C)Stirring 48h, sampling, HPLC control, to the raw material disappeared, the end of the reaction.Maintain the material temperature below 30 under reduced pressure distillation, remove excess acetaldehyde and solvent, and then add 1mol / L dilutionHydrochloric acid to pH 3 to 5, extracted with dichloromethane, and the organic phase was concentrated under reduced pressure to remove the solvent and distilled under reduced pressure to give a colorless oilWas obtained in a yield of 15.0g, 75.0% and a purity of 98.5% (HPLC).

Reference： [1]Patent: CN106748695,2017,A .Location in patent: Paragraph 0020; 0021

72
[ 141-82-2 ]
[ 454-89-7 ]
[ 143438-91-9 ]

Yield	Reaction Conditions	Operation in experiment
255 g	With ammonium formate; In ethanol; for 12h;Reflux;	(0549) (0550) A mixture of malonic acid (298.82 g, 2872 mmol), ammonium formate (362.14 g, 5743 mmol) and 3-(trifluoromethyl)benzaldehyde (500 g, 2873 mmol) in ethanol (1000 mL) was refluxed for 12 h. The reaction mixture was evaporated to remove ethanol and the residue was triturated with acetone (2500 mL). The solid was filtered and dried to afford 3-amino-3-[3-(trifluorome- thyl)phenyl]propanoic acid (255 g) as white solid. (0551) NMR (400 MHz, AcOH-d4) delta 7.87-7.81 (m, 2H), 7.74 (d, 1H, J = 7.6 Hz), 7.66-7.62 (m, 1H), 4.98 (br. S, 1H), 3.36 (dd, 1H, J = 16.0, 8.0 Hz), 3.13 (dd, 1H, J = 17.6, 5.6 Hz); (0552) MS: m z 234 (M+l).
255 g	With ammonium formate; In ethanol; for 12h;Reflux;	A mixture of malonic acid (298.82 g, 2872 mmol), ammonium formate (362.14 g, 5743 mmol) and 3-(trifluoromethyl)benzaldehyde (commercially available) (500 g, 2873 mmol) in ethanol (1000 mL) was refluxed for 12 h. The reaction mixture was evaporated to remove ethanol and the residue was triturated with acetone (2500 mL). The solid was filtered and dried to afford 3-amino-3-[3- (trifluoromethyl)phenyl]propanoic acid (255 g) as a white solid. NMR (400 MHz, AcOH-d4) delta 7.87-7.81 (m, 2H), 7.74 (d, 1H, J = 7.6 Hz), 7.66- 7.62 (m, 1H), 4.98 (br. S, 1H), 3.36 (dd, 1H, J = 16.0, 8.0 Hz), 3.13 (dd, 1H, J = 17.6, 5.6 Hz); MS: m/z 234 (M+l).
255 g	With ammonium formate; In ethanol; for 12h;Reflux;	A mixture of malonic acid (298.82 g, 2872 mmol), ammonium formate (362.14 g, 5743 mmol) and 3-(trifluoromethyl)benzaldehyde (commercially available) (500 g, 2873 mmol) in ethanol (1000 mL) was refluxed for 12 h. The reaction mixture was evaporated to remove ethanol and the residue was triturated with acetone (2500 mL) The solid was filtered and dried to afford 3-amino-3-[3- (trifluoromethyl)phenyl]propanoic acid (255 g) as a white solid. NMR (400 MHz, AcOH-d4) delta 7.87-7.81 (m, 2H), 7.74 (d, 1H, J = 7.6 Hz), 7.66- 7.62 (m, 1H), 4.98 (br. S, 1H), 3.36 (dd, 1H, J = 16.0, 8.0 Hz), 3.13 (dd, 1H, J = 17.6, 5.6 Hz);MS: m/z 234 (M+l).

Reference： [1]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 2440 - 2446
[2]Patent: WO2017/144183,2017,A1 .Location in patent: Page/Page column 65
[3]Patent: WO2019/34603,2019,A1 .Location in patent: Page/Page column 65; 66
[4]Patent: WO2019/38315,2019,A1 .Location in patent: Page/Page column 61

73
[ 2516-97-4 ]
[ 454-89-7 ]
1-(3-trifluoromethylphenyl)-2-(methylsulfonyl) ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With thionyl chloride; ammonium acetate; In methanol; for 17h;Reflux;	Add 500 ml of methanol to a 500 ml three-necked flask, 13.0 g of <strong>[2516-97-4]2-<strong>[2516-97-4](methylsulfonyl)acetic acid</strong></strong> and 10.9 g of ammonium acetate, heated to 50C, dropping 10.0 g of 3-trifluoromethylbenzaldehyde, dropping, heating and refluxing reaction. Cooled to 0~5 , dropping 55 g of thionyl chloride, heating reflux 17 h, the methanol was distilled off. To the residue was added 50 ml of dichloromethane and the pH was adjusted to 6-7 with 5N NaOH solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined and concentrated to give 9.8 g of a colorless oil, 98% HPLC purity, 58% yield,

Reference： [1]Patent: CN106588718,2017,A .Location in patent: Paragraph 0012

74
[ 6154-04-7 ]
[ 454-89-7 ]
C₁₀H₁₀F₃N₅ [ No CAS ]

Reference： [1]Molecules,2017,vol. 22

75
[ 454-89-7 ]
[ 62942-43-2 ]
[ 262268-58-6 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 8439 - 8443

76
[ 454-89-7 ]
[ 137686-07-8 ]
ethyl 2-[(tert-Butoxycarbonyl)amino]-3-hydroxy-3-[3-(trifluoromethyl)phenyl]propanoate [ No CAS ]
C₁₆H₂₀F₃NO₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 8081 - 8091

77
[ 16313-65-8 ]
[ 454-89-7 ]
6-nitro-2-(3-(trifluoromethyl)phenyl)quinazolin-4(3H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 7952 - 7976

78
[ 454-89-7 ]
[ 101-79-1 ]
[ 1059197-84-0 ]
[ 1059197-86-2 ]

Reference： [1]Patent: WO2008/112674,2008,A1

79
[ 444343-55-9 ]
[ 454-89-7 ]
C₁₂H₁₃F₃O [ No CAS ]

Reference： [1]Chemical Science,2018,vol. 9,p. 8951 - 8956

80
[ 53137-27-2 ]
[ 931-53-3 ]
[ 454-89-7 ]
[ 106-49-0 ]
N-(2-(cyclohexylamino)-2-oxo-1-(3-(trifluoromethyl)phenyl)ethyl)-2,4-dimethyl-N-(p-tolyl)thiazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		General procedure: The aldehyde (0.8 equivalent) and amine (0.7 equivalent) were dissolved in methanol (2.0 mL) and stirred for two to 3 h depending upon the starting material. The acid (100 mg, 1 equivalent) and isocyanide (0.7 equivalent) were added in the reaction mixture and further stirred. The reaction mixture was monitored using TLC analysis.Water (4 mL) was added upon completion of the reaction.The resulted solid was filtered off and dissolved in ethyl acetate(10 mL), washed with water (2 3 mL) and dried over sodium sulphate. The crude product was purified using silica gel column chromatography. The ethyl acetate:hexane (6:4) solvent system was used for the purification of these compounds.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 164,p. 665 - 677

81
[ 53137-27-2 ]
[ 931-53-3 ]
[ 454-89-7 ]
[ 62-53-3 ]
N-(2-(cyclohexylamino)-2-oxo-1-(3-(trifluoromethyl)phenyl)ethyl)-2,4-dimethyl-N-phenylthiazole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.5%		General procedure: The aldehyde (0.8 equivalent) and amine (0.7 equivalent) were dissolved in methanol (2.0 mL) and stirred for two to 3 h depending upon the starting material. The acid (100 mg, 1 equivalent) and isocyanide (0.7 equivalent) were added in the reaction mixture and further stirred. The reaction mixture was monitored using TLC analysis.Water (4 mL) was added upon completion of the reaction.The resulted solid was filtered off and dissolved in ethyl acetate(10 mL), washed with water (2 3 mL) and dried over sodium sulphate. The crude product was purified using silica gel column chromatography. The ethyl acetate:hexane (6:4) solvent system was used for the purification of these compounds.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 164,p. 665 - 677

82
[ 454-89-7 ]
[ 51114-94-4 ]
(E)-4-((m-trifluoromethyl)phenyl)but-3-enoic acid [ No CAS ]

Reference： [1]Organic Letters,2019

83
[ 454-89-7 ]
[ 87189-16-0 ]
[ 90605-29-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 100℃;Sealed tube; Inert atmosphere;	General procedure: An oven-dried 3-neck round-bottomed ask equipped with amagnetic stir bar was charged with aryl aldehyde (1.0 equiv.) andtriphenylphosphine (1.2 or 1.5 equiv.). The system was sealed withthree PFTE septa, and subsequently evacuated and backlled withN2 three times. Dry NMP was added via syringe transfer (PTFE sy-ringe with oven-dried stainless-steel needle), and the system wasimmersed in a preheated 100C oil bath. Once no solid reagentsremained (approximately 2 min of heating), potassium bromodi-uoroacetate (1.5 or 1.8 equiv.) was added portionwise over 0.5 h,with the rate of addition controlling the evolution of CO2 gas. Onceall of the potassium bromodiuoroacetate was added, the solutionwas allowed to stir for 0.5e1 h. Upon completion, the reaction wascooled to room temperature and then quenched with H2O. Subse-quently, Et2O was added to the reaction, and the mixture waswashed with H2O (ve times), and the aqueous layer was back-extracted with Et2O (two times). The combined organic layerswere dried over Na2SO4 and concentrated. The crude material wasdry-packed onto silica gel and then eluted through a plug of silicagel with EtOAc:hexanes (1:1) to remove triphenylphosphine oxide.Subsequently, H2O2 (30% in H2O) was added to the mother liquorand allowed to react for 30 min to oxidize the residual triphenyl-phosphine. The organic layer was washed with H2O (three times),dried over Na2SO4, concentrated, and subjected to normal phaseash chromatography using EtOAc and hexanes.

Reference： [1]Tetrahedron,2019,vol. 75,p. 4325 - 4336

84
[ 1994-13-4 ]
[ 454-89-7 ]
3,3′-((3′′-(trifluoromethyl)phenyl)methylene)bis(6-fluoro-4-hydroxy-2H-chromen-2-one) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetraethylammonium bromide; In water; for 2h;Reflux;	General procedure: 6-Fluoro-4-hydroxy /6-chloro-4-hydroxy /4-hydroxy coumarin(1 mmol), and a variety of aromatic aldehydes (0.5 mmol), as well as 10 mol% of tetraethylammonium bromide (TEAB) were dissolved indistilled water (15 mL) in a 100 mL round-bottommed flask. The reactionmixture was refluxed for 2 h. Periodic TLC was taken to check theprogress of reaction. Resulting precipitates were filtered, and washedwith distilled water. This afforded products 1-44 in high yields.

Reference： [1]Bioorganic Chemistry,2019,vol. 91

85
[ 2033-24-1 ]
[ 17721-06-1 ]
[ 454-89-7 ]
7-[3-(trifluoromethyl)phenyl]-6,7-dihydrothieno[3,2-b]pyridin-5(4H)-one [ No CAS ]

Reference： [1]Archiv der Pharmazie,2019,vol. 352

86
[ 454-89-7 ]
[ 73183-34-3 ]
[ 325142-82-3 ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 423 - 427

87
[ 454-89-7 ]
[ 204255-11-8 ]
(3R,4R,5S)-4-acetamido-5-((3-trifluoromethylbenzyl)amino)-3-((pentan-3-yl)-oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium cyanoborohydride; In methanol; ethanol; at 20℃; for 6h;	General procedure: The solution of <strong>[204255-11-8]oseltamivir phosphate</strong> (0.82 g, 2.0 mmol) and akind of aldehyde (2.4 mmol, 1.2 equiv) in 30 mL methanol andethanol (V : V 2 : 1) was stirred at room temperature for half anhour. And then, NaBH3CN (0.31 g, 5.0 mmol, 2.5 equiv) was addedslowly to the solution. After that, the mixture was stirred for 6 h atroom temperature. The solvent was removed under reduced pressure,water (30 mL) was added to the residue and extracted withethyl acetate (3 30 mL). The combined organic phasewas washedwith saturated sodium chloride (2 30 mL) and dried with anhydrousMgSO4 and concentrated under reduced pressure. Theconcentrated crude was purified by flash column chromatographyto obtain the corresponding pure intermediates 1a-1g. Ethyl(3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-((3-(trifluoromethyl)benzyl)amino)cyclohex-1-ene-1-carboxylate (1a).72% yield. 1H NMR (400 MHz, DMSO-d6): d 7.81 (d, J 8.9 Hz, 1H),7.69 (s, 1H), 7.64e7.49 (m, 3H), 6.64 (s, 1H), 4.13 (q, J 6.6 Hz, 2H),4.02 (d, J 6.4 Hz, 1H), 3.86 (d, J 14.0 Hz, 1H), 3.74 (dd, J 20.3,11.4 Hz, 2H), 2.80e2.69 (m, 1H), 2.64 (d, J 17.5 Hz, 1H), 2.11 (s, 2H),1.85 (s, 3H), 1.50e1.34 (m, 4H), 1.21 (t, J 6.9 Hz, 3H), 0.82 (dt,J 14.0, 7.1 Hz, 6H). 13C NMR (100 MHz, DMSO-d6) d 169.99, 166.28,143.53, 138.42, 132.32, 129.47, 129.36 (q, 2JCF 33.0), 129.17, 124.87(q, 1JCF 270.4), 124.67 (q, 3JCF 3.5), 123.63 (q, 3JCF 3.5), 81.34, 75.72, 60.79, 55.21, 54.51, 49.44, 30.92, 26.09, 25.66, 23.39, 14.52,9.89, 9.41.

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 191

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3'-(Trifluoromethyl)acetophenone

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 454-89-7 ] {[proInfo.proName]}

Quality Control of [ 454-89-7 ]

Related Doc. of [ 454-89-7 ]

Product Details of [ 454-89-7 ]

Calculated chemistry of [ 454-89-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 454-89-7 ]

Application In Synthesis of [ 454-89-7 ]

[ 454-89-7 ] Synthesis Path-Upstream 1~14

[ 454-89-7 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 454-89-7 ]

Fluorinated Building Blocks

Aryls

Aldehydes

Trifluoromethyls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 454-89-7 ]