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[ CAS No. 1077-01-6 ]

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3d Animation Molecule Structure of 1077-01-6

Chemical Structure| 1077-01-6

Chemical Structure| 1077-01-6

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Quality Control of [ 1077-01-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 1077-01-6 ]

CAS No. :	1077-01-6	MDL No. :	MFCD00236323
Formula :	C₇H₄F₄O	Boiling Point :	105°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	180.10 g/mol	Pubchem ID :	2777286
Synonyms :

Calculated chemistry of of [ 1077-01-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	33.08
TPSA :	9.23 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) :	-4.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	3.57
Log Po/w (WLOGP) :	4.41
Log Po/w (MLOGP) :	2.72
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	3.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.44
Solubility :	0.0648 mg/ml ; 0.00036 mol/l
Class :	Soluble
Log S (Ali) :	-3.45
Solubility :	0.064 mg/ml ; 0.000355 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.3
Solubility :	0.0898 mg/ml ; 0.000499 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.63

Safety of [ 1077-01-6 ]

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

Application In Synthesis of [ 1077-01-6 ]

* 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 [ 1077-01-6 ]
Downstream synthetic route of [ 1077-01-6 ]

[ 1077-01-6 ] Synthesis Path-Upstream 1~10

1
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9645 - 9649[2] Angew. Chem., 2018, vol. 130, p. 9793 - 9797,5

2
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13784 - 13789[2] Angew. Chem., 2018, vol. 130, p. 13980 - 13985,6

3
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13795 - 13799[2] Angew. Chem., 2018, vol. 130, # 42, p. 13991 - 13995,5

4
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9645 - 9649[2] Angew. Chem., 2018, vol. 130, p. 9793 - 9797,5

5
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13784 - 13789[2] Angew. Chem., 2018, vol. 130, p. 13980 - 13985,6

6
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13795 - 13799[2] Angew. Chem., 2018, vol. 130, # 42, p. 13991 - 13995,5

7
[ 372-20-3 ]
[ 1077-01-6 ]

Reference： [1] Journal of Fluorine Chemistry, 2017, vol. 203, p. 130 - 135

8
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9645 - 9649[2] Angew. Chem., 2018, vol. 130, p. 9793 - 9797,5

9
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13784 - 13789[2] Angew. Chem., 2018, vol. 130, p. 13980 - 13985,6

10
[ 462-06-6 ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 42, p. 13795 - 13799[2] Angew. Chem., 2018, vol. 130, # 42, p. 13991 - 13995,5

[ 1077-01-6 ] Synthesis Path-Downstream 1~23

Yield	Reaction Conditions	Operation in experiment
		...presented by the following formula (4) which can respectively correspond to the formula (1) can be obtained. (D) Fluorine substituted aromatic compound represented by the formula (4) corresponding to the hydroxy compound wherein X1 is a substituent of the group (a) in the formula(1): ... 2-fluorobenzophenone, 3-fluorobenzophenone, 4-fluorobenzophenone, 2-trifluoromethylfluorobenzene, 3-trifluoromethylfluorobenzene, 4-trifluoromethylfluorobenzene, 2-trichloromethylfluorobenzene, 3-trichloromethylfluorobenzene, 4-trichloromethylfluorobenzene, 2-trifluoromethoxyfluorobenzene, 3-trifluoromethoxyfluorobenzene, 4-trifluoromethoxyfluorobenzene, 2-trichloromethoxyfluorobenzene, 3-trichloromethoxyfluorobenzene, 4-trichloromethoxyfluorobenzene, 2-fluorophenylmethylsulfone, 3-fluorophenylmethylsulfone, ...

2
[ 1077-01-6 ]
[ 866632-57-7 ]

Yield	Reaction Conditions	Operation in experiment
		To the solution of 3- (trifluoromethoxy)fluorobenzen(1g, 5.5 mmol) in lOmL THF at -78C, n-BuLi (1.6M, 3.75mL) was added dropwise. The resulting solution was stirred at -78C for 30 min. 12 (2.1g, 8.25 mmol) in THF (5mL) was added. The mixture was warmed to room temperature and then quenched with Na2C03 in saturated Na2S203 (1: 10) (30mL). The crude product was extracted with ether. The ether layer was dried over Na2S04 and filtered through a short silica gel column to give the desired iodide as an oil. ¹H NMR (CDC13): 7.39 (m, 1H), 7.12 (d, J=9.0 Hz, 1H), 7.05 (t, J=6.0 Hz, 1H) MS (ESI): m/e 307 (M+1)+

Reference： [1]Patent: WO2005/97136,2005,A1 .Location in patent: Page/Page column 40-41

3
[ 1077-01-6 ]
[ 68-12-2 ]
[ 1105060-20-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of l-fluoro-3-trifluoromethoxy-benzene (1.73g, 9.6 mmol) inTHF (20 mL) at -78 0C was added nBuLi (1.2eq, 4.6 mL of 2.5M in hexanes). The mixture was stirred for 180 minutes and quenched with DMF (2 mL) and allowed to warm to room temperature. Solvents were removed, the reaction was washed with H2O (10 mL) and the organics concentrated giving the crude product.
		4-Fluoro-2-trifluoromethoxy-benzaldehyde To a solution of <strong>[1077-01-6]1-fluoro-3-trifluoromethoxy-benzene</strong> (1.73g, 9.6 mmol) in THF (20 mL) at -78 C. was added nBuLi (1.2 eq, 4.6 mL of 2.5M in hexanes). The mixture was stirred for 180 minutes and quenched with DMF (2 mL) and allowed to warm to room temperature. Solvents were removed, the reaction was washed with H2O (10 mL) and the organics concentrated giving the crude product.

Reference： [1]Patent: WO2009/11787,2009,A1 .Location in patent: Page/Page column 81-82
[2]Patent: US2010/29655,2010,A1 .Location in patent: Page/Page column 75-76

4
[ 1077-01-6 ]
[ 123572-65-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With sulfuric acid; potassium nitrate; at 0 - 5℃; for 2h;Inert atmosphere;	<strong>[1077-01-6]1-fluoro-3-(trifluoromethoxy)benzene</strong> (7.5 g, 41.6 mmol) was dissolved in concentrated sulfuric acid (30 mL),and the mixuture was cooled to 0 C. KNO3 (1.04 g, 10.25 mmol) was added slowly in batches. The internal temperatureis keeped below 5 C. Upon completion of the addition, the mixture was stirred for 2 hours. An eice-water mixture (about50 mL) was added. The reaction solution was extracted with methyl tert-butyl ether (2033 mL), and the organic phaseswere combined, dried and filtered. The filtrate was concentrated and purified by flash silica gel column chromatographyto obtain 4-fluoro-1-nitro-2-(trifluoromethoxy)benzene (4.0 g, 42%).
16%	With sulfuric acid; nitric acid; at -10℃;	(Comparative Example 6); 4-Fluoro-l-nitro-2- (trifluoromethoxy) benzeneFuming nitric acid (20 mL) was added dropwise to concentrated sulfuric acid (40 ml) under cooling (-100C), and subsequently, 1- fluoro-3- (trifluoromethoxy) benzene (15 g, 83 mmol) was added to the mixture at -100C, and the mixture was stirred for 0.5 hours. After the mixture was added into ice-water to stop the reaction, it was extracted with dichloromethane . After the obtained organic layer was washed with a IN aqueous sodium hydroxide solution and water, it was dried with anhydrous sodium sulfate. After filtration, the solution was concentrated and the residue was purified by silica gel column chromatography (100:0-97:3, hexane : ethyl acetate) to give the title compound (3.1 g, 16%) as an oil.1H-NMR (400 MHz, CDCl3) delta: 8.10 (IH, dd, J = 5.5, 9.4 Hz) , 7.23-7.15 (2H, m) .
12 g	With sulfuric acid; potassium nitrate; at 0℃; for 3h;Cooling with ice;	Under ice cooling mixture of 3-fluoro - trifluoromethoxyphenyl (20g) was dissolved in 40 ml of concentrated sulfuric acid, with rapid stirringWas added portionwise potassium nitrate (28g), was stirred at 0oC 3 hours and stirred at room temperature overnight, the reaction solution was carefullyGo on into 1 kg ice, stirred for 30 minutes, extracted with ethyl acetate, dried over sodium sulfate, filtered, and the filtrate was evaporated, the residue was purified by column chromatography to give 12 g pale yellow liquid.

0.5 g	With sulfuric acid; nitric acid; at -10 - 20℃; for 0.5h;	To a 100 mL round-bottomed flask were added concentrated H2SO4 (25 mL), fuming HNO3 (25 mL), and <strong>[1077-01-6]1-fluoro-3-(trifluoromethoxy)benzene</strong> (9.0 g, 50 mmol) at -10 C. in sequence. The mixture was stirred at rt for 30 min then poured onto ice and extracted with EtOAc (3*20 mL). The combined organic layers were washed with saturated aqueous NaHCO3 solution (30 mL), brine (30 mL), dried over anhydrous Na2SO4, concentrated to dryness, and purified by FCC to give the title compound as a pale-yellow oil (0.50 g). 1H NMR (300 MHz, CDCl3): delta 8.21-8.14 (m, 1H), 7.21-7.12 (m, 2H).
8.5 g	With sulfuric acid; potassium nitrate; at -5 - 0℃; for 1h;	Add 20 mL of concentrated sulfuric acid to a 250 mL three-necked flask.The ice salt bath is cooled to -5-0 C,Adding m-fluorotrifluoromethoxybenzene(10 g, 60 mmol), then potassium nitrate (5.9 g, 60 mmol) was added portionwise.The reaction was stirred at 0 C for 1 h.Slowly pour the reaction into the iceIn water, extracted with ethyl acetate (40 mL×3) three times, and the organic phases were combined.Wash 3 times with saturated saline (20mL × 3),Dry over anhydrous sodium sulfate for 0.5 h, suction filtration under reduced pressure.The filtrate was concentrated under reduced pressure at 45 C to give 8.5 g of pale yellow oil.

Reference： [1]Patent: EP3205650,2017,A1 .Location in patent: Paragraph 0106; 0111; 0112; 0213; 0214
[2]Patent: WO2010/42626,2010,A1 .Location in patent: Page/Page column 37-38
[3]Patent: CN105503827,2016,A .Location in patent: Paragraph 0082; 0083; 0084
[4]Patent: US2018/289706,2018,A1 .Location in patent: Paragraph 0632
[5]Patent: CN108707139,2018,A .Location in patent: Paragraph 0724; 0727; 0728; 0729

5
[ 1077-01-6 ]
[ 123572-65-6 ]
[ 123572-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid; at 0 - 20℃;	11A) 4-Fluoro-1-nitro-2-trifluoromethoxy-benzene To 1-fluoro-3-trifluoromethoxybenzene (1 mL) was added concentrated sulfuric acid (1 mL) at 0 C. To the cold solution was added dropwise (0.7 mL) of a solution made from concentrated nitric acid (1 mL) and concentrated sulfuric acid (1 mL). The reaction was slowly allowed to warm to room temperature then poured onto ice and extracted with ether. The organic layer was separated and washed with sodium hydroxide 1N, then brined and dried over magnesium sulfate. The solvent was removed under reduce pressure at room temperature. A pale yellow oil (1 g) was recovered and used without further purification.

Reference： [1]Patent: US2009/143367,2009,A1 .Location in patent: Page/Page column 36

6
[ 4472-41-7 ]
[ 1077-01-6 ]
[ 1620158-84-0 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: To reactant 1 or 3 (1 g, 8.76 mmol) in THF (50 ml), was added LDA (condition A) or n-BuLi (condition B) (4.82 ml, 9.64 mmol) at -78 C slowly, after 30 min, added EtO-13CHO/DMF-13CHO (0.736 ml, 9.64 mmol) and left for stirring at -78 C for 30 min. Quenched with a few drops of dil H2SO4 (aq) and satd NH4Cl (aq 50 mL), extracted with Et2O (3 × 50 mL), dried, purified by column chromatography on silica gel eluting with a solution of EtOAc/hexane(1:9) to give products 2 or 4 (0.860 g, 69% yield).

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 4442 - 4444

7
[ 1077-01-6 ]
[ 123572-66-7 ]

Reference： [1]Patent: CN105503827,2016,A
[2]Patent: EP3205650,2017,A1

8
[ 1077-01-6 ]
4-fluoro-5-nitro-2-(trifluoromethoxy)aniline [ No CAS ]

Reference： [1]Patent: CN105503827,2016,A
[2]Patent: EP3205650,2017,A1

9
[ 1077-01-6 ]
N-(4-fluoro-5-nitro-2-(trifluoromethoxy)phenyl)-4-(1-methyl-1H-indol-3-yl)pyrimidin-2-amine [ No CAS ]

Reference： [1]Patent: EP3205650,2017,A1

10
[ 1077-01-6 ]
N₁-(2-(dimethylamino)ethyl)-N₁-methyl-N₄-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-2-nitro-5-(trifluoromethoxy)benzene-1,4-diamine [ No CAS ]

Reference： [1]Patent: EP3205650,2017,A1

11
[ 1077-01-6 ]
N₁-(2-(dimethylamino)ethyl)-N₁-methyl-N₄-(4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)-5-(trifluoromethoxy)benzene-1,2,4-triamine [ No CAS ]

Reference： [1]Patent: EP3205650,2017,A1

12
[ 1077-01-6 ]
N-(2-((2-(dimethylamino)ethyl)(methyl)amino)-5-((4-(1-methyl-1H-indol-3-yl)pyrimidin-2-yl)amino)-4-(trifluoromethoxy)phenyl)acrylamide [ No CAS ]

Reference： [1]Patent: EP3205650,2017,A1

13
[ 372-20-3 ]
[ 1077-01-6 ]

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 203,p. 130 - 135

14
2,2-difluoro-2-(3-fluorophenoxy)acetic acid [ No CAS ]
[ 1077-01-6 ]

Yield	Reaction Conditions	Operation in experiment
54%Spectr.	With phosphoric acid; silver trifluoromethanesulfonate; Selectfluor; In dichloromethane; water; at 55℃; for 1h;Inert atmosphere; Glovebox;	General procedure: A microwave vial (5 mL) was sealed under an inert atmosphere (Argon glovebox) with a stir bar, Selectfluor (177.1 mg, 0.5 mmol, 2 equiv), silver trifluoromethanesulfonate (12.8 mg, 0.05 mmol, 20 mol%) and aryloxydifluoroacetic acids (0.25 mmol, 1.0 equiv). To this vial DCM (1.8 mL), trifluoroacetic acid (76.5 muL, 1.0 mmol, 4.0 equiv) and water (0.2 mL) were injected. This mixture was heated for an hour at 55 C. The resulting mixture was cooled down to room temperature, diluted with dichloromethane (4 mL), washed with water (3×5 mL), brine (5 mL), dried over anhydrous MgSO4 and filtered. The dried extract was concentrated on a rotary evaporator. The resulting crude product was dissolved in a small quantity of dichloromethane and loaded on to a silica cartridge (10 g, Biotage), airdried and eluted with pentane. The pure fractions were combined and the solvent was evaporated to obtain the pure products.

Reference： [1]Journal of Fluorine Chemistry,2017,vol. 203,p. 130 - 135

15
[ 1077-01-6 ]
2-nitro-5-(trifluoromethoxy)phenol [ No CAS ]

Reference： [1]Patent: WO2018/37223,2018,A1

16
[ 1077-01-6 ]
[ 123572-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; potassium nitrate; at 0℃; for 1h;	To a solution of <strong>[1077-01-6]1-fluoro-3-(trifluoromethoxy)benzene</strong> (2.Og, 11.lmmol) in H2504 (5.OmL) was added KNO3 (1.34g, 13.3mmol) at 0C. The reaction mixture was stirred at 0 O for 1 h. TLC showed the reaction to be complete. The reaction mixture was diluted with H20 (5OmL) and extracted with EtOAc (3x50m1). The organic layer was dried over Na2504 and concentrated under reduced pressure. The residue was triturated with 10% EtOAc in hexane to afford 2-fluoro-1-nitro-4- (trifluoromethoxy)benzene as a yellow liquid. Yield: 1.8g (crude). The crude data showed product and it was used in the next step without further purification.

Reference： [1]Patent: WO2018/37223,2018,A1 .Location in patent: Page/Page column 204

17
[ 462-06-6 ]
2-(3,5-bis(trifluoromethyl)phenyl)-4-nitro-1-(trifluoromethoxy)-6-(trifluoromethyl)-1H-benzo[d]imidazole [ No CAS ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 20℃; for 16h;Glovebox; Irradiation; Sealed tube; Inert atmosphere;	General procedure: In a glovebox, to an oven-dried 20 mL screw cap vial was added 2- (3, 5-bis (trifluoromethyl) phenyl) -4-nitro-l- (trifluoromethoxy) -6- (trifluoromethyl) -lii-benzo [d] imidazole (1) (105 mg, 0.200 mmol, 1.00 equiv) , arene (2.00 mmol, 10.0 equiv) and Ru (bpy) 3 ( REe) 2, (0.0516 mg, 0.0600 pmol, 0.0300 moll) . Then MeCN (1.00 mL, 0.200 M) and a magnetic stir bar were added. The vial was capped and taken out of the glovebox. The reaction mixture was then stirred and irradiated with a 10 W LED (402 nm) at room temperature. After 16 h, an internal standard PhCF3 (5.84 mg, 4.95 pL, 0.04 mmol, 0.200 equiv) was added to the reaction vial, 0.200 mL of the resulting mixture was transferred to a 2 mL vial containing 0.500 mL of CDCI3. After the yield was determined using 19F NMR, the NMR sample was combined with the rest of the reaction mixture and the solvent was removed in vacuo. The crude material was purified by HPLC under noted conditions. The fractions containing the desired product were combined and extracted with CDCI3 (3 1 mL) , dried with magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to furnish the desired product of trifluoromethoxylation . For volatile compounds, after purification by HPLC, the desired product was extracted with 1 mL CDC13 and then directly characterized. The NMR peaks are referring to CH3CN residue signal ^H-NMR: d 1.94, 13C~NMR: 5 118.26, 1.32).2

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 9645 - 9649
Angew. Chem.,2018,vol. 130,p. 9793 - 9797,5
[2]Patent: WO2019/168874,2019,A1 .Location in patent: Page/Page column 43; 46; 56; 57

18
[ 462-06-6 ]
4-cyano-1- (trifluoromethoxy)pyridin-1-ium bis((trifluoromethyl)sulfonyl)amide [ No CAS ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 13784 - 13789
Angew. Chem.,2018,vol. 130,p. 13980 - 13985,6

19
[ 462-06-6 ]
3-methyl-4-nitro-1-(trifluoromethoxy)-6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate [ No CAS ]
[ 2106-18-5 ]
[ 1077-01-6 ]
[ 352-67-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 20℃; for 16h;Glovebox; Irradiation; Sealed tube; Inert atmosphere;	General procedure: In a glovebox, to an oven-dried 20 mL screw cap vial was added 3- methyl-4-nitro-l- ( trifluoromethoxy) -6- (trifluoromethyl ) -1H- benzo[d] [1, 2, 3] triazol-3-ium trifluoromethanesulfonate (lb) (98.0 mg, 0.200 mmol, 1.00 equiv), arene (2.00 mmol, 10.0 equiv) and Ru (bpy) 3 (PFe) 2, (1.72 mg, 2.00 pmol, 1.00 mol%). Then MeCN (1.00 mL, 0.200 M) and a magnetic stir bar were added. The vial was capped and taken out of the glovebox. The reaction mixture was then stirred and irradiated with 2 of 10 W LED (Xmax = 447 nm) at room temperature. After 16 h, an internal standard PhCF3 (24.6 pL, 0.200 mmol, 1.00 equiv) was added to the reaction vial, 0.200 mL of the resulting mixture was transferred to a 2 mL vial containing 0.500 mL of CDC13. After the yield was determined using 19F NMR, the NMR sample was combined with the rest of the reaction mixture and the solvent was removed in vacuo. The crude material was purified by HPLC under noted conditions. The fractions containing the desired product were combined and extracted with CDC13 (3 x 10.0 mL) , dried with magnesium sulfate, and filtered unless otherwise noted. The filtrate was concentrated in vacuo to furnish the desired product of trifluoromethoxylation . For volatile compounds, after purification by HPLC, the desired product was extracted with 1 mL CDCI3 and then directly characterized. The NMR peaks are referring to CCN residue signal (1H-NMR : d 1.94, 13C-NMR: d 118.26, 1.32).2

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 13795 - 13799
Angew. Chem.,2018,vol. 130,p. 13991 - 13995,5
[2]Patent: WO2019/168874,2019,A1 .Location in patent: Page/Page column 75; 79; 118-119; 120

20
[ 372-19-0 ]
trifluoromethyl 4-fluorobenzene-1-sulfonate [ No CAS ]
[ 1077-01-6 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 7840 - 7844
Angew. Chem.,2019,vol. 131,p. 7922 - 7926,5

21
[ 372-19-0 ]
[ 1006904-72-8 ]
[ 1077-01-6 ]

Reference： [1]Organic Letters,2019,vol. 21,p. 8003 - 8007

22
[ 1077-01-6 ]
N-{4-[3,5-bis(trifluoromethyl)phenoxy]phenyl}-2-fluoro-6-(trifluoromethoxy)benzamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 10221 - 10244

23
[ 124-38-9 ]
[ 1077-01-6 ]
2-fluoro-6-(trifluoromethoxy)benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 10221 - 10244

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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