[ CAS No. 24821-17-8 ] {[proInfo.proName]}

Name: 24821-17-8|2-Nitro-6-(trifluoromethyl)aniline|99%
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Quality Control of [ 24821-17-8 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 24821-17-8 ]

CAS No. :	24821-17-8	MDL No. :	MFCD08532494
Formula :	C₇H₅F₃N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MFLJFFUIURSSKM-UHFFFAOYSA-N
M.W :	206.12	Pubchem ID :	10703457
Synonyms :

Calculated chemistry of [ 24821-17-8 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.67
TPSA :	71.84 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	2.51
Log Po/w (WLOGP) :	3.36
Log Po/w (MLOGP) :	1.37
Log Po/w (SILICOS-IT) :	0.03
Consensus Log Po/w :	1.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.88
Solubility :	0.269 mg/ml ; 0.0013 mol/l
Class :	Soluble
Log S (Ali) :	-3.66
Solubility :	0.0446 mg/ml ; 0.000217 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.31
Solubility :	1.0 mg/ml ; 0.00488 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 24821-17-8 ]

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 [ 24821-17-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 24821-17-8 ]
Downstream synthetic route of [ 24821-17-8 ]

[ 24821-17-8 ] Synthesis Path-Upstream 1~5

1
[ 98-46-4 ]
[ 121-01-7 ]
[ 24821-17-8 ]
[ 400-98-6 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 442 - 443
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444

2
[ 88-17-5 ]
[ 121-01-7 ]
[ 24821-17-8 ]

Reference： [1] Synthesis, 1989, # 10, p. 761 - 763

3
[ 98-46-4 ]
[ 121-01-7 ]
[ 24821-17-8 ]
[ 400-98-6 ]

Reference： [1] Journal of Organic Chemistry, 1996, vol. 61, # 2, p. 442 - 443
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 11, p. 1437 - 1444

4
[ 24821-17-8 ]
[ 360-60-1 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1969, vol. 39, p. 2007 - 2010[2] Zhurnal Obshchei Khimii, 1969, vol. 39, # 9, p. 2053 - 2056
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 543 - 548

5
[ 24821-17-8 ]
[ 157026-18-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 18 h;	C. 4-Bromo-2-nitro-6-trifluoromethyl-phenylamine2-Nitro-6-trifluoromethyl-phenylamine (10.0 g, 48.5 mmol) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar. Glacial acetic acid (100 mL) and bromine (3.24 mL, 63.1 mmol) were added, and the mixture was stirred at RT for 18 h. The mixture was poured into ice (200 mL), and the excess bromine was quenched with 10 percent aq Na₂S₂O₃ (25 mL). The precipitate was isolated by filtration and washed with water. The solid was air- dried and then dried under vacuum to yield 13.8 g (100 percent) of the title compound. ¹H-NMR (400 MHz, CDCl₃) δ: 8.49 (d, J = 2.3 Hz, IH), 7.83 (d, J = 1.8 Hz, IH).

Reference： [1] Patent: WO2010/45166, 2010, A1, . Location in patent: Page/Page column 50

[ 24821-17-8 ] Synthesis Path-Downstream 1~29

1
[ 88-17-5 ]
[ 121-01-7 ]
[ 24821-17-8 ]

Reference： [1]Synthesis,1989,p. 761 - 763

2
[ 24821-19-0 ]
[ 24821-17-8 ]

Reference： [1]Journal of general chemistry of the USSR,1969,vol. 39,p. 2007 - 2010
Zhurnal Obshchei Khimii,1969,vol. 39,p. 2053 - 2056

3
[ 24821-17-8 ]
[ 360-60-1 ]

Reference： [1]Journal of general chemistry of the USSR,1969,vol. 39,p. 2007 - 2010
Zhurnal Obshchei Khimii,1969,vol. 39,p. 2053 - 2056
[2]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548

4
[ 98-46-4 ]
[ 121-01-7 ]
[ 24821-17-8 ]
[ 400-98-6 ]

Reference： [1]Journal of Organic Chemistry,1996,vol. 61,p. 442 - 443
[2]Journal of the Chemical Society. Perkin transactions I,1999,p. 1437 - 1444

5
[ 603-11-2 ]
[ 24821-17-8 ]

Reference： [1]Journal of general chemistry of the USSR,1969,vol. 39,p. 2007 - 2010
Zhurnal Obshchei Khimii,1969,vol. 39,p. 2053 - 2056

6
[ 39974-35-1 ]
[ 24821-17-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In ethanol;	B. 2-Amino-3-nitrobenzotrifluoride Eleven and two tenths grams (0.05m) of 2-chloro-3-nitrobenzotrifluoride, 200 ml. of liquid ammonia and 200 ml. of 2B ethanol were heated in a sealed autoclave at 100 C. for 4 hours. After cooling and venting, the reaction mixture was diluted with water. The aqueous mixture was extracted with ethyl acetate. The ethyl acetate phase was washed with water, dried, and was evaporated in vacuo to yield crude 2-amino-3-nitrobenzotrifluoride.

Reference： [1]Patent: US4024142,1977,A

7
[ 24821-17-8 ]
[ 157026-18-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bromine; acetic acid; at 20.0℃; for 18h;	C. 4-Bromo-2-nitro-6-trifluoromethyl-phenylamine2-Nitro-6-trifluoromethyl-phenylamine (10.0 g, 48.5 mmol) was placed in a 200 mL round-bottom flask equipped with a magnetic stir bar. Glacial acetic acid (100 mL) and bromine (3.24 mL, 63.1 mmol) were added, and the mixture was stirred at RT for 18 h. The mixture was poured into ice (200 mL), and the excess bromine was quenched with 10 % aq Na2S2O3 (25 mL). The precipitate was isolated by filtration and washed with water. The solid was air- dried and then dried under vacuum to yield 13.8 g (100 %) of the title compound. 1H-NMR (400 MHz, CDCl3) δ: 8.49 (d, J = 2.3 Hz, IH), 7.83 (d, J = 1.8 Hz, IH).

Reference： [1]Patent: WO2010/45166,2010,A1 .Location in patent: Page/Page column 50

8
[ 1445-45-0 ]
[ 24821-17-8 ]
[ 384-32-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With indium; acetic acid; In ethyl acetate; for 4h;Reflux; Inert atmosphere;	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8027 - 8033

9
[ 24821-17-8 ]
[ 707-07-3 ]
[ 7641-27-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With indium; acetic acid; In ethyl acetate; for 2.5h;Reflux; Inert atmosphere;	General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Reference： [1]Tetrahedron,2011,vol. 67,p. 8027 - 8033

10
[ 24821-17-8 ]
[ 431-03-8 ]
5-trifluoromethyl-2,3-dimethylquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With indium; indium(III) chloride; In methanol; for 1.33333h;Reflux; Inert atmosphere;	General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

Reference： [1]Tetrahedron,2015,vol. 71,p. 1215 - 1226

11
[ 24821-17-8 ]
[ 134-81-6 ]
[ 389-61-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	With indium; indium(III) chloride; In methanol; for 0.833333h;Reflux; Inert atmosphere;	General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

Reference： [1]Tetrahedron,2015,vol. 71,p. 1215 - 1226

12
[ 7333-07-5 ]
[ 24821-17-8 ]
5-trifluoromethyl-2,3-di-2-thiophenylquinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With indium; acetic acid; In methanol; for 0.0833333h;Reflux; Inert atmosphere;	General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

Reference： [1]Tetrahedron,2015,vol. 71,p. 1215 - 1226

13
[ 492-73-9 ]
[ 24821-17-8 ]
5-trifluoromethyl-2,3-di(pyridin-2-yl)quinoxaline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With indium; acetic acid; In methanol; at 50.0℃; for 2.83333h;Inert atmosphere;	General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

Reference： [1]Tetrahedron,2015,vol. 71,p. 1215 - 1226

14
[ 24821-17-8 ]
[ 84-11-7 ]
[ 62686-17-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With indium; acetic acid; In methanol; for 0.416667h;Reflux; Inert atmosphere;	General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

Reference： [1]Tetrahedron,2015,vol. 71,p. 1215 - 1226

15
[ 24821-17-8 ]
tert-butyl (2-amino-3-(trifluoromethyl)phenyl)carbamate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548

16
[ 24821-17-8 ]
tert-butyl (2-((5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)amino)-3-(trifluoromethyl)phenyl)carbamate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548

17
[ 24821-17-8 ]
N<SUP>1</SUP>-(5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)-6-(trifluoromethyl)benzene-1,2-diamine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548

18
[ 24821-17-8 ]
N-(2-((5-((2,6-dichloro-3,5-dimethoxybenzyl)oxy)pyrimidin-2-yl)amino)-3-(trifluoromethyl)phenyl)acrylamide [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 543 - 548

19
[ 24821-17-8 ]
C₇H₄F₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		To a solution of <strong>[24821-17-8]2-nitro-6-(trifluoromethyl)aniline</strong> (5 g, 24.26 mmol) in MeOH (100 mL) was added palladium on carbon (10% by weight) (0.52 g, 0.49 mmol), and the reaction was stirred under a 25 psi atmosphere of hydrogen for 2 h. The reaction mixture was then filtered through celite and the filtrate was concentrated. The resulting residue was dissolved in 150 mL of acetic acid and sodium nitrite (1.67 g, 24.3 mmol) was added slowly in small portions. The reaction was stirred at room temperature for 3 h. The reaction mixture was then concentrated. To the resulting residue was added 100 mL of water and the mixture was stirred for 5 minutes. The resulting solid was collected and washed with water (30 mL x 3) followed by hexane (10 mL x 2) and then dried to give Intermediate I-5a (3.96 g, 21.16 mmol, 87 % yield). NMR (499 MHz, (0796) CHLOROFORM-d) δ 12.63 - 12.35 (Bbr. s, IH), 8.44 - 8.15 (m, IH), 7.83 (d, J=7.3 Hz, IH), 7.65 - 7.52 (t, IH).

Reference： [1]Patent: WO2019/46498,2019,A1 .Location in patent: Page/Page column 90; 91

20
[ 24821-17-8 ]
(5-chlorofuro[2,3-c]pyridin-2-yl)-(2,6-difluoro-3,5-dimethoxyphenyl)methanone [ No CAS ]
(2,6-difluoro-3,5-dimethoxyphenyl)(5-(2-nitro-6-(trifluoromethyl)phenylamino)furo[2,3-c]pyridin-2-yl)methanone [ No CAS ]

Reference： [1]Patent: WO2019/80878,2019,A1 .Location in patent: Page/Page column 74

21
2-fluoro-1-nitro-3-(trifluoromethyl)benzene [ No CAS ]
[ 24821-17-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With ammonia; In methanol; at 70.0℃; for 16h;	2-fluoro-l-nitro-3 -(triflu orom ethyl )benzene 7 (1.1 g, 5.26 mmol) in a solution of ammonia in methanol (7N, 10 mL) was stirred at 70 C for 16 hours. The resulting mixture was concentrated in vacuo to afford a residue. The residue was purified by flashchromatography over silica gel eluting with 10: 1 petroleum ether/ethyl acetate to afford 2- nitro-6-(trifluoromethyl)aniline 12 as a yellow oil (1.0 g, 90%). LCMS analysis of 12:97.4%, and [M+H]+= 207.

Reference： [1]Patent: WO2020/163236,2020,A1 .Location in patent: Page/Page column 33

22
[ 24821-17-8 ]
N-(2-amino-3-(trifluoromethyl)phenyl)-2-methoxybenzamide [ No CAS ]

Reference： [1]Patent: WO2020/163236,2020,A1

23
[ 24821-17-8 ]
2-(2-methoxyphenyl)-7-(trifluoromethyl)-1H-benzo[d]imidazole [ No CAS ]

Reference： [1]Patent: WO2020/163236,2020,A1

24
[ 91367-05-4 ]
[ 24821-17-8 ]
C₁₆H₁₃F₃N₂O₄ [ No CAS ]