240800-45-7|5-Fluoro-2-(trifluoromethyl)benzonitrile| Ambeed

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Quality Control of [ 240800-45-7 ] Purity: 98% SDS Specification

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Product Details of [ 240800-45-7 ]

CAS No. :	240800-45-7
Formula :	C₈H₃F₄N
M.W :	189.11
SMILES Code :	N#CC1=CC(F)=CC=C1C(F)(F)F
MDL No. :	MFCD00236281
InChI Key :	SQAZPEKSXOYPDX-UHFFFAOYSA-N
Pubchem ID :	2737551

Safety of [ 240800-45-7 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301+H331-H315-H319-H335
Precautionary Statements:	P261-P301+P310-P305+P351+P338-P311
Class:	6.1
UN#:	3439
Packing Group:	Ⅲ

Application In Synthesis of [ 240800-45-7 ]

* 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.

Downstream synthetic route of [ 240800-45-7 ]

[ 240800-45-7 ] Synthesis Path-Downstream 1~27

1
[ 240800-45-7 ]
[ 354814-19-0 ]

Yield	Reaction Conditions	Operation in experiment
61.0%	With ammonium hydroxide; In 1,4-dioxane; at 120.0℃; under 7600.51 Torr;	mixture of 63 (15.0 g, 79.4 mmol, 1.0 eq) in NH4OH (150 mL) and 1,4-dioxane (40 mL) was heated to 120 C in a Parr bomb under 10 atm overnight. The reaction mixture was extracted with DCM (100 mL x 3). The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by SGC (eluting with Petroleum ether / ethyl acetate, 4 / 1) to give the desired product 64 (9.00 g,48.4 mmols, 61.0%) as a white solid.[00453] LCMS: ESI-MS: m/z: 187.1 [M+H1 RT = 1.46 mm. (Method A)
52%	With ammonia; In 1,4-dioxane; water; at 120.0℃; under 10343.2 Torr; for 18.0h;	Preparation of intermediate 39; <n="40"/>Intermediate 36; 5-amino-2-(trifluoromethyl)benzonitrile; A solution of 5-fluoro-2-(trifluoromethyI)benzonitrile (7.Og, 37.0 mmol, 1 equiv) and 1 ,4-dioxane (10 mL) in ammonia hydroxide (100 mL) 1 ,4-dioxane (10 mL) was heated to 120 0C in Parr bomb under 200 psi for 18 h. The reaction mixture was concentrated down and the residue partitioned between dichloromethane and water. The organics were dried over Na2SO4, filtered and concentrated and the residue purified by silica gel flash column chromatography (0 → 40% ethyl acetate : hexanes) to give intermediate 36 (3.5 g, 52% yield) as a white solid. 1H NMR (400 MHz, DMSOd6) δ ppm 7.49 (d, J=8.79 Hz, 1 H), 7.02 (d, J=2.20 Hz, 1 H), 6.77 - 6.91 (m, 1 H), 6.32 (s, 2 H). ES-LCMS: m/z 187.2 (M+H).
	With ammonium hydroxide; In 1,4-dioxane; at 130.0℃; under 10343.2 Torr; for 20.0h;	Intermediate 37: 5-Amino-2-(trifluoromethyl)benzonitrile; Ammonium hydroxide solution (50 mL) was added to a stirred solution of 5-fluoro-2- (trifluoromethyl)benzonitrile (commercially available, for example from Alfa Aesar, Ward Hill, MA, USA, 2.0 g, 10.6 mmol) in 1 ,4-dioxane (10 mL) and the reaction mixture was heated to 130C for 20 h under 200 psi pressure in a steel bomb. The reaction mixture was evaporated to dryness, and the residue was diluted with DCM and washed with water. The organic layer was dried over anhydrous Na2S04 and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40%EtOAc/petroleum ether, to give the title compound (1.2 g).MS ES+ve m/z 185 (M-H).1H NMR (400 MHz, Chloroform-d) δ ppm 4.02-4.30 (br s, 2 H), 6.85 (dd, 1 H), 7.00 (d, 1 H), 7.50 (d, 1 H).

References: [1]Patent: WO2016/144792,2016,A1 .Location in patent: Paragraph 00451; 00452; 00453.
[2]Patent: WO2009/58919,2009,A1 .Location in patent: Page/Page column 39.
[3]Journal of Medicinal Chemistry,2019,vol. 62,p. 10362 - 10375.
[4]Patent: WO2012/4604,2012,A1 .Location in patent: Page/Page column 64.

2
[ 240800-45-7 ]
[ 1354947-86-6 ]

References: [1]Patent: WO2012/4604,2012,A1 .

3
[ 240800-45-7 ]
[ 1354947-88-8 ]

References: [1]Patent: WO2012/4604,2012,A1 .

4
[ 240800-45-7 ]
[ 1354947-90-2 ]

References: [1]Patent: WO2012/4604,2012,A1 .

5
[ 240800-45-7 ]
[ 1354947-92-4 ]

References: [1]Patent: WO2012/4604,2012,A1 .

6
[ 240800-45-7 ]
[ 269409-70-3 ]
[ 1367127-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃;	Compound 5d: A mixture of compound 6 (2.1 g, 10.9 mmol), compound 7 (2.4g, 10.9 mmol) and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the plug was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was purified by column chromatography (40 g silica gel, 0-30% EtOAc/Hexane) to obtain compound 5d (2.3 g, 6.9 mmol). 1H NMR (400MHz, CD3OD): 7.81 (d, 2H, J=8.8Hz), 7.63 (d, 1H, J=8.8Hz), 7.26 (d, 1H, J=2.4Hz), 7.17 (dd, 1H, Jl=2.4, J2=8.8Hz), 6.98 (d, 2H, J=8.8Hz), 1.28 (s, 12H).
2.3 g	With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 4.0h;	[0323] (c) Compound 12 was prepared as follows:[0324] A mixture of compound 16 (2.1 g, 10.9 mmol), compound 17 (2.4g, 10.9 mmol) and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the plug was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was purified by column chromatography (40 g silica gel, 0-30% EtOAc/Hexane) to obtain compound 12 (2.3 g, 6.9 mmol). ? NMR (400MHz, CD3OD): ? 7.81 (d, 2H, J=8.8Hz), 7.63 (d, 1H, J=8.8Hz), 7.26 (d, 1H, J=2.4Hz), 7.17 (dd, 1H, Jl=2.4, J2=8.8Hz), 6.98 (d, 2H, J=8.8Hz), 1.28 (s, 12H).

References: [1]Patent: WO2012/35421,2012,A2 .Location in patent: Page/Page column 246-247.
[2]Patent: WO2013/64883,2013,A1 .Location in patent: Paragraph 0323; 0324.

7
[ 240800-45-7 ]
[ 269409-70-3 ]
[ 1433051-89-8 ]

References: [1]Patent: WO2013/64883,2013,A1 .

8
[ 240800-45-7 ]
[ 71597-85-8 ]
[ 1437035-07-8 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium carbonate; In water; N,N-dimethyl-formamide; at 100.0℃; for 3.0h;	A mixture of 3-cyano-4-trifluoromethyl- l -fluorobenzene (70 g, 0.37 mol, Oakwood), 4-hydroxyphenylboronic acid (50 g, 0.36 mol, Boron Molecular), K2C03 (70 g) and DMF/water (400 mL/40 mL) was heated to 100C for 3h. After cooling to RT, the mixture was diluted with water (1 L) and extracted with EtOAc (1.5 L). The organic layer was washed with water (0.5 L) and brine, concentrated and purified by chromatographed over silica gel with 4% MeOH in chloroform to give (4-(3-cyano-4-(trifluoromethyl)phenoxy)phenyl)boronic acid as pink solid (50 g, 45%).
42%	With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 4.0h;	A mixture of compound 27 (2.1 g, 10.9 mmol), compound 28 (2.4 g), and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was diluted with water (l OOmL) and extracted with EtOAc (3x100 mL). The combined organic layer was washed with brine, concentrated and purified by column chromatography (silica gel,EtOAc/hexanes 1/1 ) to give (4-(3-cyano-4-trifluoromethyl)phenoxy)phenyl)boronic acid (29) (pink solid, 42%). ? NMR (400MHz, CD3OD): 7.59 - 7.86 (3H, m), 7.31 - 7.37 ( 1 H, m), 7.19 - 7.26 (1 H, m), 6.9 - 7.10 (2H, m).

References: [1]Patent: WO2013/136170,2013,A1 .Location in patent: Page/Page column 88; 89.
[2]Patent: WO2013/72758,2013,A1 .Location in patent: Page/Page column 97-98.

9
[ 240800-45-7 ]
[ 71597-85-8 ]
[ 1454918-08-1 ]

References: [1]Patent: WO2013/136170,2013,A1 .

10
[ 106-41-2 ]
[ 240800-45-7 ]
5-(4-bromophenoxy)-2-(trifluoromethyl)benzonitrile [ No CAS ]