[ CAS No. 3796-23-4 ] {[proInfo.proName]}

Name: 3796-23-4|3-(Trifluoromethyl)pyridine|98%
Brand: Ambeed
SKU: A270544
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Quality Control of [ 3796-23-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3796-23-4 ]

SDS Specification

Alternatived Products of [ 3796-23-4 ]

Product Details of [ 3796-23-4 ]

CAS No. :	3796-23-4	MDL No. :	MFCD00100032
Formula :	C₆H₄F₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JTZSFNHHVULOGJ-UHFFFAOYSA-N
M.W :	147.10	Pubchem ID :	77417
Synonyms :

Calculated chemistry of [ 3796-23-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	29.24
TPSA :	12.89 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) :	-5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.47
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	3.25
Log Po/w (MLOGP) :	1.58
Log Po/w (SILICOS-IT) :	2.36
Consensus Log Po/w :	2.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.23
Solubility :	0.874 mg/ml ; 0.00594 mol/l
Class :	Soluble
Log S (Ali) :	-1.63
Solubility :	3.47 mg/ml ; 0.0236 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.89
Solubility :	0.189 mg/ml ; 0.00129 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.34

Safety of [ 3796-23-4 ]

Signal Word:	Danger	Class:	3,6.1
Precautionary Statements:	P210-P233-P240-P301+P310-P303+P361+P353-P305+P351+P338	UN#:	1992
Hazard Statements:	H226-H300-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 3796-23-4 ]

* 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 [ 3796-23-4 ]
Downstream synthetic route of [ 3796-23-4 ]

[ 3796-23-4 ] Synthesis Path-Upstream 1~13

1
[ 110-86-1 ]
[ 75-63-8 ]
[ 3796-24-5 ]
[ 3796-23-4 ]
[ 368-48-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 8, p. 2293 - 2299

2
[ 110-86-1 ]
[ 887144-97-0 ]
[ 3796-24-5 ]
[ 3796-23-4 ]
[ 368-48-9 ]

Reference： [1] Journal of Fluorine Chemistry, 2010, vol. 131, # 9, p. 951 - 957

3
[ 110-86-1 ]
[ 2314-97-8 ]
[ 3796-23-4 ]
[ 1744-46-3 ]
[ 368-48-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 661 - 664

4
[ 110-86-1 ]
[ 3796-24-5 ]
[ 3796-23-4 ]
[ 368-48-9 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 12898 - 12902[2] Angew. Chem., 2017, vol. 129, # 42, p. 13078 - 13082,5

5
[ 110-86-1 ]
[ 76-05-1 ]
[ 3796-24-5 ]
[ 3796-23-4 ]
[ 368-48-9 ]

Reference： [1] Dalton Transactions, 2018, vol. 47, # 29, p. 9608 - 9616

6
[ 110-86-1 ]
[ 2314-97-8 ]
[ 3796-24-5 ]
[ 3796-23-4 ]
[ 20857-47-0 ]
[ 455-00-5 ]
[ 368-48-9 ]

Reference： [1] Journal of Fluorine Chemistry, 1985, vol. 30, p. 73

7
[ 3796-23-4 ]
[ 65753-52-8 ]

Reference： [1] Science, 2013, vol. 342, # 6161, p. 956 - 960

8
[ 3796-23-4 ]
[ 65753-47-1 ]

Reference： [1] Patent: US2012/259125, 2012, A1,

9
[ 3796-23-4 ]
[ 124-38-9 ]
[ 87407-12-3 ]

Reference： [1] Tetrahedron, 1994, vol. 50, # 42, p. 12259 - 12266

10
[ 186581-53-3 ]
[ 3796-23-4 ]
[ 124-38-9 ]
[ 588702-69-6 ]

Reference： [1] European Journal of Organic Chemistry, 2003, # 8, p. 1569 - 1575

11
[ 3796-23-4 ]
[ 7677-24-9 ]
[ 95727-86-9 ]
[ 1214383-56-8 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14733 - 14737

12
[ 3796-23-4 ]
[ 573762-62-6 ]

Reference： [1] Patent: JP2016/11315, 2016, A,
[2] Patent: US9388159, 2016, B2,

13
[ 3796-23-4 ]
[ 406933-21-9 ]

Reference： [1] Patent: JP2016/11315, 2016, A,
[2] Patent: US9388159, 2016, B2,

[ 3796-23-4 ] Synthesis Path-Downstream 1~88

1
[ 626-55-1 ]
[ 75-63-8 ]
[ 3796-23-4 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1992,p. 53 - 54

2
[ 59-67-6 ]
[ 3796-23-4 ]

Reference： [1]Journal of general chemistry of the USSR,1983,vol. 53,p. 85 - 86
Zhurnal Obshchei Khimii,1983,vol. 53,p. 103 - 105

3
[ 109-97-7 ]
[ 791-50-4 ]
[ 3796-23-4 ]

Reference： [1]Journal of Fluorine Chemistry,1981,vol. 18,p. 533 - 536

4
[ 3796-23-4 ]
[ 64035-64-9 ]
[ 91043-82-2 ]

Reference： [1]Chemistry Letters,1984,p. 279 - 280

5
[ 3796-23-4 ]
[ 124-38-9 ]
[ 87407-12-3 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 12259 - 12266

6
[ 141-53-7 ]
[ 65753-47-1 ]
[ 3796-23-4 ]
2-((3-(trifluoromethyl)pyridin-2-yl)oxy)ethan-1-ol [ No CAS ]
[ 170502-06-4 ]
3,3'-Bis(trifluoromethyl)-2,2'-bipyridyl [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 1 - 6

7
[ 65753-47-1 ]
[ 3796-23-4 ]
[ 103-29-7 ]
[ 142946-80-3 ]
[ 170502-06-4 ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 1 - 6

8
[ 65753-47-1 ]
[ 3796-23-4 ]
[ 103-29-7 ]
[ 170502-06-4 ]
3,3'-Bis(trifluoromethyl)-2,2'-bipyridyl [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 1 - 6

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 4 3-methylpyridine (0.26) mole was mixed with anhydrous liquid hydrogen fluoride (5 moles) in a pressure vessel and dibenzoyl peroxide (0.01 mole) was added. Gaseous chlorine was introduced until the gauge pressure was 3 bar and the temperature was then raised to 95° C. After 2 hours at this temperature the mixture was cooled, the gases were vented and the contents of the vessel were repressurised to 3 bar with chlorine. The mixture was then heated to 200° C. for 4 hours. At the end of this period the mixture was cooled, neutralised and extracted with methylene chloride. The product was found by analysis (as before) to contain 3-trifluoromethylpyridine.
32%Spectr.		General procedure: In a 10-15 mL vial with a magnetic stirrer, copper (I) chloride (0.3 g, 3.0 mmol, 1 eq) was added and the vial was sealed in the glove box under argon. To this vial, under argon 3 mL of dry DMF was added and the resulting reaction mixture was stirred at room temperature for 5 minutes. To this reaction mixture a solution of t-BuOK in DMF (0.68 g, 6.06 mmol, 2 eq) was added drop wise and the resulting reaction mixture was stirred at room temperature for 5 minutes. After 5 minutes, CF3H was bubbled into this THF solution for 4 min 11 sec (0.636 g, 9.09 mmol was added total at the rate of 52.5 ml/min, 3 eq) and the resulting reaction mixture was stirred at room temperature for 10 minutes. After 10 minutes, a solution of triethylamine trihydrofluoride (TREAT HF) (0.195 g, 1.21 mmol, 198 mum) was added to the reaction mixture neat. To the same reaction mixture iodobenzene (0.927 g, 4.54 mmol, 1.5 eq) was added neat and the resulting reaction mixture was heated at 50° C. for 24 hours. The reaction mixture was cooled to room temperature and then hexafluorobenzene (C6F6) (0.166 eq) was added to the reaction mixture and it was stirred at room temperature for 10 mins. An aliquot of reaction mixture was taken out and its NMR (19F) was recorded. NMR yields were determined by NMR integrations and are reported in Table 5.

10
[ 3796-23-4 ]
[ 627-31-6 ]
bis-1,3-[3-(trifluoromethyl)pyridinio]propane diiodide [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2005,vol. 126,p. 1160 - 1165

11
[ 3796-23-4 ]
[ 74-88-4 ]
3-(trifluoromethyl)pyridine methiodide [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2005,vol. 126,p. 1160 - 1165

12
[ 3796-23-4 ]
[ 34162-79-3 ]
C₈H₁₀F₃NO₆P₂ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5804 - 5814

13
[ 3796-23-4 ]
[ 91043-75-3 ]

Reference： [1]Chemistry Letters,1984,p. 279 - 280

14
[ 3796-23-4 ]
[ 91043-76-4 ]

Reference： [1]Chemistry Letters,1984,p. 279 - 280

15
[ 3796-23-4 ]
[ 36016-40-7 ]
3-trifluoromethyl-pyridin-1-ylideneamine 2,4,6-trimethylphenylsulphonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 20℃; for 20h;	Solid t-butoxycarbonyl-O-mesitylenesulfonylhydroxylamine (13.44g, 42.5mmol)1 was added portionwise with stirring to TFA (40ml) over 10 minutes then stirred for a further 30 minutes. The solution was poured onto ice (~250ml) and left until the ice melted. The resulting white solid was filtered off, washed with water, and dissolved in DME (200ml). The solution was dried over 4 A mol. sieves for 1.5 hours, filtered, then <strong>[3796-23-4]3-trifluoromethylpyridine</strong> (5g, 34mmol) added and the reaction stirred at ambient temperature for 20h. The intermediate salt was isolated by filtration, washed with DME to give the title compound as a white solid (6.63g, 54percent). 1H NMR delta (DMSO) 9.34 (1H, s); 9.0 (1H, d, J 6Hz); 8.8(2H, br s); 8.68 (1H, d, J 8Hz); 8.22 (1H, t, J 7Hz); 6.75 (2H, s); 2.17 (3H, s) Ref 1 Josef G Krause, Synthesis, 1972, 140

Reference： [1]Patent: EP1127058,2004,B1 .Location in patent: Page 11

16
3-methylpyridine x 3 trifluoroacetic acid [ No CAS ]
[ 3796-23-4 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; at 60℃;UV-irradiation;Product distribution / selectivity;	C5H4N-CH3 + 3 Cl2 < C5H4N-CCI3 + 3 HCI Ansatz : 3-Methylpyridin x 3 TFA 1, 5 MOL 671,0 G CL2 Durchfhrung : 3-Picolin x 3 TFA wurde im Photoreaktor mit Doppelmantel vorgelegt und mittels Thermostat auf 60 C erwrmt, anschlieend wurde die 150 Watt UV-Lampe (mit Pressluft-Khlung) gezndet und nach weiteren 10 min Chlor eingeleitet. Der An- satz frbte sich gelb, aus dem Photoreaktor entwich gasfrmige HCI. IM Reaktor war keinerlei Niederschlag (HCI-ADDUKTE) zu erkennen. Die Selektivitt zu 3-Tri- chlormethylpyridin war 98 percent (Reinheitsbestimmung durch NMR).3.2. Wiederholung mit hoher LAMPENLEISTUNg und hherer EINLEITUNgSgESCHWINDIgKEIT des Chlors Der Versuch wurde mit einer TQ 718 von Heraeus mit 500 W Lampenleistung wiederholt. Die Einleitungsgeschwindigkeit des Chlors konnte ohne Selektivitts- verlust erheblich gesteigert werden. Versuch 3 zeigt, da auch bei anderen Isomeren des Methylpyridins die erfin- dungsgeme photochemische Chlorierung durchgefhrt werden kann. Er zeigt auch, da je nach Chlor-Einsatzmenge die Chlorierung beim monochlorierten Addukt angehalten werden kann oder bis zur Trichlormethylverbindung durchchlo- riert werden kann.

Reference： [1]Patent: WO2004/52860,2004,A1 .Location in patent: Page 8

17
[ 3796-23-4 ]
[ 22134-40-3 ]
1-[2-(N,N-dimethylcarbamate)benzyl]-3-(trifluoromethyl)pyridinium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 25 - 120℃; for 24h;Product distribution / selectivity;	Stage A: 1 -[2-(N,N-dimethylcarbamate)benzyl]-3-(trifluoromethyl)pyridinium chloride To a solution of <strong>[3796-23-4]3-(trifluoromethyl)pyridine</strong> (1.47 g, 10 mmol) described in Eur. J. Org. Chem. 2003, 327-330 in a proper solvent (acetonitrile, DMF, EtOH, acetone) is added carbamic acid, dimethyl-, 2-(chloromethyl)phenyl ester (2.13 g, 10 mmol) reported in Chemical Papers 1985, 39, 413-27. The resultant solution is stirred for 24 hours at the correct temperature (25°C-120°C). The solvent is evaporated to furnish the title compound.

Reference： [1]Patent: WO2006/103120,2006,A2 .Location in patent: Page/Page column 75

18
[ 3796-23-4 ]
[ 7646-85-7 ]
[ 497233-05-3 ]

Reference： [1]Inorganic Chemistry,2003,vol. 42,p. 581 - 589

19
[ 3796-23-4 ]
zinc dibromide [ No CAS ]
[ 497233-06-4 ]

Reference： [1]Inorganic Chemistry,2003,vol. 42,p. 581 - 589

20
[ 3796-23-4 ]
zinc(II) iodide [ No CAS ]
[ 497233-07-5 ]

Reference： [1]Inorganic Chemistry,2003,vol. 42,p. 581 - 589

21
[ 64-67-5 ]
[ 3796-23-4 ]
[ 1093871-12-5 ]

Reference： [1]New Journal of Chemistry,2008,vol. 32,p. 1953 - 1967

22
[ 1120-90-7 ]
potassium (trifluoromethyl)trimethoxyborate [ No CAS ]
[ 3796-23-4 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 2689 - 2697

23
[ 1120-90-7 ]
(1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
[ 3796-23-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 3793 - 3798

24
[ 3796-23-4 ]
[ 140-88-5 ]
[ 910654-23-8 ]
[ 1291078-57-3 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 6964 - 6967

25
[ 3796-23-4 ]
[ 36016-40-7 ]
[ 1326216-43-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2011,vol. 47,p. 897 - 903

26
[ 3796-23-4 ]
[ 400654-03-7 ]
[ 1356925-71-7 ]

Reference： [1]Polyhedron,2012,vol. 33,p. 13 - 18

27
[ 626-55-1 ]
[ 81290-20-2 ]
[ 3796-23-4 ]
3-(pentafluoroethyl)pyridine [ No CAS ]
3-(heptafluoropropyl)pyridine [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 133,p. 67 - 71

28
[ 3796-23-4 ]
[ 65753-47-1 ]

Reference： [1]Patent: US2012/259125,2012,A1

29
[ 3796-23-4 ]
[ 22253-72-1 ]

Yield	Reaction Conditions	Operation in experiment
96%		Toa mixture of 3- (trifluoromethyl) pyridine A7 (1.47 g, 10 mmol) andmethyltrioxorhenium (0.0025 g, 0.01 mmol) in dichloromethane (2 ml), 30percenthydrogen peroxide (4 ml) was added. The mixture was stirred at room temperature for 5 hours. A small amount ofMnO2 (3 mg) was added, and medium was stirred for further 1 hour,and dichloromethane (50ml) was added. Washing the medium with brine, dried overMgSO4, and concentrated to give Compound A8 (1.56g, 9.6mmol, 96percent) asa greyish white powder.
96%		Synthesis of <strong>[3796-23-4]3-(trifluoromethyl)pyridine</strong>-N-oxide, A8 (0055) To a mixture of <strong>[3796-23-4]3-(trifluoromethyl)pyridine</strong> A7 (1.47 g, 10 mmol) and methyltrioxorhenium (0.0025 g, 0.01 mmol) in dichloromethane (2 ml) was added 30percent hydrogen peroxide (4 ml). The mixture was stirred at room temperature for 5 hours. A small portion of MnO2 (3 mg) was added and the medium was stirred for an additional 1 hour and then dichloromethane was added (50 ml). The medium was washed with brine, dried over MgSO4 and concentrated to obtain compound A8 as an off-white powder (1.56 g, 9.6 mmol, 96percent). 1H NMR (400 MHz, CDCl3) delta 7.22-7.23 (m, 2H), 8.15 (d, J=3.6, 1H), 8.23 (s, 1H); 13C NMR (100 MHz, CDCl3) delta 120.50 (q, J=3.5 Hz), 121.58 (q, 271.4 Hz), 126.48, 130.10 (q, J=34.5 Hz), 136.52 (q, J=3.7 Hz), 141.89.
		(1)In a four-necked flask equipped with a stirrer, a thermometer, and a condenser, 147.0 g of <strong>[3796-23-4]3-trifluoromethylpyridine</strong> and 367.75 g of acetic acid were charged.141.71 g of a 30percent hydrogen peroxide aqueous solution was added thereto at from 20 to 30° C., and the contents were allowed to react at from 80 to 90° C. for 7 hours.After the reaction mixture was cooled, 31.51 g of sodium sulfite was added at not higher than 30° C.After the addition, the contents were stirred at from 30 to 40° C. for 3 hours, and it was confirmed by a potassium iodide starch paper that the treatment of excessive hydrogen peroxide in the reaction mixture had been completed.The reaction mixture was heated under a reduced pressure (15 mmHg) until the internal temperature reached 50° C., thereby distilling off the acetic acid.441 mL of water was added thereto, and 204.26 g of a 30percent sodium hydroxide aqueous solution was added dropwise at not higher than 20° C., thereby adjusting the pH to 8.0.Thereafter, extraction with 275.6 g of 1,2-dichloroethane was repeated three times while keeping the temperature at 50° C., thereby obtaining 985.0 g of a 1,2-dichloroethane solution containing 158.16 g of <strong>[3796-23-4]3-trifluoromethylpyridine</strong> N-oxide (melting point: 76.0° C.).

14.2 g

With dihydrogen peroxide; methyltrioxorhenium(VII); In dichloromethane; at 20℃; for 6h;

In 20 ml of dichloromethane, 14.7 g of [3796-23-4]3-trifluoromethyl-pyridine was added.0.025 gMethyl trioxohydrazine, stirred. 40 ml of 30percent hydrogen peroxide was added dropwise. After the addition, the mixture was stirred at room temperature for 6 hours. 30 mg of manganese dioxide was added and stirring was continued for 1 hour. After adding 500 ml of methylene chloride, it was placed in a sep. funnel and washed with a saturated aqueous solution of sodium chloride (2×200 ml). The solid was filtered off, and the filtrate was evaporated to dryness under reduced pressure.There was obtained 14.2 g of [3796-23-4]3-trifluoromethyl-pyridine-N-oxide.

Reference： [1]Patent: JP2016/11315,2016,A .Location in patent: Paragraph 0044
[2]Patent: US9388159,2016,B2 .Location in patent: Page/Page column 11
[3]Patent: US2012/259125,2012,A1 .Location in patent: Page/Page column 2-3
[4]Patent: CN109422725,2019,A .Location in patent: Paragraph 0019-0022

30
[ 1120-90-7 ]
[ 135039-77-9 ]
[ 3796-23-4 ]

Reference： [1]Helvetica Chimica Acta,2012,vol. 95,p. 2231 - 2236

31
[ 3796-23-4 ]
[ 16419-60-6 ]
[ 1441122-89-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Pyridine substrates 7 and 8 were prepared according to literatureprocedures. Substrates 1-6 and 9 were synthesized via Suzuki coupling of 2-bromo-3-methylpyridine with the correspondingarylboronic acids. Pyridine substrates 11e13 were alsoprepared Suzuki couplings of 2-bromopyridine derivatives with otolylphenylboronicacid. Substrate 10 was prepared by Suzuki coupling of 2-methoxyphenylboronic acid with 2-chloropyridine.Potassium 2,6-dimethylphenyltrifluoroborate and potassium 3-acetylphenyltrifluoroborate were synthesized from the correspondingboronic acids and KHF2.

Reference： [1]Tetrahedron,2013,vol. 69,p. 5580 - 5587

32
[ 462-08-8 ]
trifluoromethylsilver [ No CAS ]
[ 3796-23-4 ]

Yield	Reaction Conditions	Operation in experiment
10%Spectr.		General procedure: An oven-dried Schlenk tube (A) equipped with a magnetic stir bar was charged with AgF (132.2 mg, 1.05 mmol, 3.5 equiv), sealed with a septum, and degassed by alternating vacuum evacuation and nitrogen backfill (three times) before freshly distilled EtCN (3 mL)was added. To the resulting suspension, which was precooled to ?78 °C (dry ice?acetone bath), was added TMSCF3 (149.3 mg, 1.05 mmol, 3.5 equiv) by microsyringe. The mixture was allowed towarm to r.t. and stirring was continued for an additional 15 min. In due course, AgF solid dissolved and a gray, dark solution of [Ag-CF3] formed. Another Schlenk tube (B) equipped with a magnetic stir bar was charged with the aniline (ArNH2; 0.30 mmol, 1.0 equiv) in freshly distilled EtCN (1.5 mL). To the resulting solution, which was precooled to 0 °C (ice bath), aq HCl (12 M; 50.0 muL, 0.60mmol, 2.0 equiv) was added; precipitate formed immediately. After 5 min stirring, t-BuONO (37.7 mg, 0.33 mmol, 1.1 equiv) was added by microsyringe, and the mixture was allowed to stir at 0 °C for 15 min. The resulting suspension in Schlenk tube (B) was degassed by alternating vacuum evacuation at ?196 °C (liquid nitrogen), then the solution was allowed to warm to r.t. under a nitrogen atmosphere (three times), and finally cooled to ?78 °C (dry ice?acetone bath). The gray, dark solution of [AgCF3] in Schlenk tube (A), which was precooled to ?78 °C (dry ice?acetone bath), was added to Schlenk tube (B) (ArN2+Cl?) by syringe at ?78 °C (dry ice?acetone bath) over a period of 1 h. After the addition was complete, the reaction mixture was stirred for 3 h at ?78 °C (dry ice?acetone bath), allowed to warm to r.t., and stirring was continued for an additional 1 h. An off-white precipitate was observed, and the reaction mixture was diluted with EtOAc (3 mL) and filtered through a short silica gel column. The solvent was removed under reduced pressure with a rotatory evaporator, and the crude residue was purified by silica gel column chromatography to give the desired trifluoromethylation product 3. The yields of products 3a, 3f, 3g, 3l, 3o, 3r, 3x, and 3zb are based on the 19F NMR spectra with 4-F3COC6H4OMe as internal standard. Analytical data for the representative product ethyl 4-(trifluoromethyl)benzoate (3i) are provided below. Data for other products can be found in the literature.

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 10330 - 10333
[2]Synthesis,2014,vol. 46,p. 2143 - 2148

33
[ 3796-23-4 ]
[ 74-88-4 ]
1-methyl-3-trifluoromethylpyridinium hexafluorophosphate [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 6162 - 6165

34
[ 75-30-9 ]
[ 3796-23-4 ]
1-isopropyl-3-trifluoromethylpyridinium hexafluorophosphate [ No CAS ]

Reference： [1]Organometallics,2013,vol. 32,p. 6162 - 6165

35
[ 3796-23-4 ]
[Cr₃O(O₂CCH₂CH₃)₆(H₂O)₃]NO₃·H₂O [ No CAS ]
[Cr₃O(O₂CEt)₆(3-trifluoromethylpyridine)₃]NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; water;Heating;	General procedure: [Cr3O(O2CCH2CH3)6(H2O)3]NO3·H2O (0.25g, 0.35mmol) and ligand, L, (0.25mL) were dissolved in 1ml EtOH. Ligands, L, were pyridine (py), 3-fluoropyridine (3-F-py), <strong>[3796-23-4]3-trifluoromethylpyridine</strong> (3-CF3-py), and 4-trifluoromethylpyridine (4-CF3-py). The solution was heated in a boiling water bath with stirring until the color changed from green to dark brown and allowed to cool. A gray solid was isolated by filtration and dried under vacuum.

Reference： [1]Polyhedron,2013,vol. 64,p. 136 - 141

36
[ 3796-23-4 ]
[ 38202-27-6 ]
methyl 6-(1-oxo-3-phenyl-2-propyn-1-yl)pyridine-2-carboxylate [ No CAS ]
methyl 6-[[2-phenyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]carbonyl]pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
378 mg		Methyl 6-[[2-phenyl-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl)carbonyl]pyridine-2-carboxylate A 70percent perchloric acid aqueous solution (0.6 mL) was added to a 1,4-dioxane solution (1.5 mL) of ethyl O-mesitylsulfonylacetohydroxamate (1.7 g) under an argon atmosphere under ice-cooling, and then the mixture was stirred for 30 minutes under ice-cooling. Ice water (17.5 mL) was added to the reaction mixture, the precipitated solid was filtered off, the solid thus obtained was dissolved in dichloromethane (5 mL), and the solution was divided into layers. The organic layer was dried over anhydrous magnesium sulfate and filtered off. A dichloromethane solution (5 mL) of <strong>[3796-23-4]3-trifluoromethylpyridine</strong> (0.6 mL) was added to the obtained filtrate under ice-cooling, and the mixture was stirred at normal temperature for 1 hour. The residue obtained by evaporating the reaction mixture was dissolved in an N,N-dimethylformamide-tetrahydrofuran mixed solution (5 mL, 1:1), then potassium carbonate (1.4 g) and methyl 6-(1-oxo-3-phenyl-2-propyn-1-yl)pyridine-2-carboxylate (663 mg) were added at normal temperature, and then the mixture was stirred at normal temperature for 1 hour. Water was added to the reaction mixture, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in this order and then dried over anhydrous magnesium sulfate. The solvent was evaporated and then the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 4:1) to obtain a title compound as a colorless powder (378 mg). 1H-NMR (400 MHz, CDCl3) delta 3.85 (3H, s), 7.08 (2H, t, J = 7.3 Hz), 7.16 (1H, tt, J = 7.3, 1.8 Hz), 7.24-7.28 (2H, m), 7.65 (1H, dd, J = 9.1,1.8 Hz), 7.89 (1H, t, J = 7.9 Hz), 7.97 (1H, dd, J = 7.9, 1.2 Hz), 8.05 (1H, dd, J = 7.9,1.2 Hz), 8.45 (1H, d, J = 9.1 Hz), 8.93 (1H, s).

Reference： [1]Patent: EP2669285,2013,A1 .Location in patent: Paragraph 0341; 0342

37
[ 1120-90-7 ]
[ 77152-08-0 ]
[ 3796-23-4 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11126 - 11146
[2]Chemistry - A European Journal,2013,vol. 19,p. 17692 - 17697

38
[ 626-55-1 ]
[ 77152-08-0 ]
[ 3796-23-4 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 11126 - 11146

39
[ 77152-08-0 ]
[ 1692-25-7 ]
[ 3796-23-4 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 17692 - 17697

40
[ 3796-23-4 ]
[ 141-32-2 ]
[ 1465907-19-0 ]

Reference： [1]Organometallics,2013,vol. 32,p. 6565 - 6575

41
[ 626-55-1 ]
(1,10-phenanthroline)(trifluoromethyl)copper(I) [ No CAS ]
[ 3796-23-4 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1744 - 1747

42
[ 462-08-8 ]
[ 77152-08-0 ]
[ 3796-23-4 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 10237 - 10240

43
[ 3796-23-4 ]
[ 65753-52-8 ]

Reference： [1]Science,2013,vol. 342,p. 956 - 960

44
[ 3796-23-4 ]
[ 585-76-2 ]
2-(3-bromophenyl)-3-trifluoromethylpyridine [ No CAS ]
4-(3-bromophenyl)-3-trifluoromethylpyridine [ No CAS ]
5-(3-bromophenyl)-3-trifluoromethylpyridine [ No CAS ]
6-(3-bromophenyl)-3-trifluoromethylpyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2199 - 2203
Angew. Chem.,2014,vol. 54-127,p. 2227 - 2231

45
[ 3796-23-4 ]
C₈H₁₂N₂O₆S [ No CAS ]
C₂₀H₂₀F₆N₂S⁽²⁺⁾*2NO₃^(1-) [ No CAS ]

Reference： [1]Chemistry of Materials,2016,vol. 28,p. 146 - 152

46
[ 273-53-0 ]
[ 3796-23-4 ]
[ 1130431-15-0 ]
2-(3-trifluoromethylpyridin-5-yl)benzo[d]oxazole [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2415 - 2418

47
[ 3796-23-4 ]
[ 908011-92-7 ]
5-(tert-butyl)-2-(3-trifluoromethylpyridin-6-yl)benzo[d]oxazole [ No CAS ]
5-(tert-butyl)-2-(3-trifluoromethylpyridin-5-yl)benzo[d]oxazole [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 2415 - 2418

48
(phenanthroline)CuIII(CF3)3 [ No CAS ]
[ 1692-25-7 ]
[ 3796-23-4 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 70902 - 70906

49
[ 1120-90-7 ]
[(2,2'-bipyridine)₂Cu][O₂CCF₂Cl] [ No CAS ]
[ 3796-23-4 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 75465 - 75469

50
[ 3796-23-4 ]
[ 100-39-0 ]
N-benzyl-3-(trifluoromethyl)pyridinium bromide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 9528 - 9532

51
[ 3796-23-4 ]
[ 542-91-6 ]
C₁₀H₁₆F₃NSi [ No CAS ]
C₁₀H₁₆F₃NSi [ No CAS ]

Reference： [1]Chemical Science,2016,vol. 7,p. 5362 - 5370

52
[ 3796-23-4 ]
[ 956104-40-8 ]

Reference： [1]Patent: JP2016/11315,2016,A
[2]Patent: US9388159,2016,B2

53
[ 3796-23-4 ]
[ 406933-21-9 ]

Reference： [1]Patent: JP2016/11315,2016,A
[2]Patent: US9388159,2016,B2
[3]Patent: CN109422725,2019,A

54
[ 3796-23-4 ]
[ 573762-57-9 ]

Reference： [1]Patent: JP2016/11315,2016,A
[2]Patent: US9388159,2016,B2
[3]Patent: CN109422725,2019,A

55
[ 3796-23-4 ]
[ 951753-87-0 ]

Reference： [1]Patent: JP2016/11315,2016,A
[2]Patent: US9388159,2016,B2
[3]Patent: CN109422725,2019,A

56
[ 3796-23-4 ]
[ 956104-39-5 ]

Reference： [1]Patent: JP2016/11315,2016,A
[2]Patent: US9388159,2016,B2

57
[ 3796-23-4 ]
[ 140-88-5 ]
[ 917761-10-5 ]