[ CAS No. 97914-59-5 ] {[proInfo.proName]}

Name: 97914-59-5|2-(Difluoromethoxy)benzoic acid|98%
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Quality Control of [ 97914-59-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 97914-59-5 ]

CAS No. :	97914-59-5	MDL No. :	MFCD00236223
Formula :	C₈H₆F₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AGDOJFCUKQMLHD-UHFFFAOYSA-N
M.W :	188.13	Pubchem ID :	2063348
Synonyms :

Safety of [ 97914-59-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 97914-59-5 ]

* 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 [ 97914-59-5 ]

[ 97914-59-5 ] Synthesis Path-Downstream 1~35

1
[ 67-56-1 ]
[ 97914-59-5 ]
[ 97914-53-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	sulfuric acid;Heating / reflux;	a) 2-Difluoromethoxy-benzoic acid methyl ester2.0 g of 2-difluoromethoxy-benzoic acid (10.6 mmol, 1.0 eq) were dissolved <n="137"/>in MeOH (15 mL) and a catalytic quantity of sulfuric acid was added; the mixture was heated at reflux overnight. The solvent was then evaporated and the residue was dissolved in DCM and washed with saturated NaHCO3. The organic phase was dried and evaporated to give 1.9 g of title product (yield 87%).C9H8F2O31H-NMR (dmso-d6): 3.82 (3H, s); 6.99-7.40 (2H5 m); 7.31 (IH, d, J=8.4 Hz); 7.63-7.67 (IH5 m); 7.82-7.84 (IH5 m).

Reference： [1]Patent: WO2008/87529,2008,A1 .Location in patent: Page/Page column 135-136
[2]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

2
[ 444287-40-5 ]
[ 97914-59-5 ]
[ 927671-99-6 ]

Yield	Reaction Conditions	Operation in experiment
65%		5.143 2-DIFLUOROMETHOXY-N-[2-(2,6-DIOXO-PIPERIDIN-3-YL)-1,3-DIOXO-2,3-DIHYDRO-1H-ISOINDOL-4-YLMETHYL]-BENZAMIDE To a stirred suspension of 4-aminomethyl-2-(2,6-dioxo-piperidin-3-yl)-isoindole-1,3-dione hydrochloride (0.70 g, 2.2 mmol) in CH3CN (60 ml), was added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.82 g, 5.4 mmol). After stirring for 10 minutes, 1-hydroxybenzenetriazole (0.35 g, 2.6 mmol) and 2-difluoromethoxy benzoic acid (0.45 g, 2.4 mmol) were added, followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.62 g, 3.2 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated in vacuo, and the residue was dissolved in CH2Cl2 (50 mL). The CH2Cl2 solution was then washed with water (2×30 mL) and brine (30 mL), and dried over MgSO4. Solvent was removed in vacuo, and the resulting oil was purified by ISCO silica gel flash chromatography (eluent: 0% MeOH in CH2Cl2 to 5% MeOH in 10 min then stay at this ratio for 15 min) to afford 4-difluoromethoxy-N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-ylmethyl]-benzamide as a solid (0.64 g, 65%): mp, 164-166 C.; HPLC: Waters Symmetry C-18, 3.9×150 mm, 5 micro, 1 mL/min, 240 nm, 40/60 (CH3CN/H2O): tR=3.6 (99%); 1H NMR (DMSO-d6): δ 2.04-2.09 (m, 1H), 2.53-2.64 (m, 2H), 2.85-2.93 (m, 1H), 4.92 (d, J=6.0 Hz, 2H), 5.14-5.20 (dd, J=5, 12 Hz, 1H), 6.97-7.86 (m, 8H), 8.97 (t, J=5.8 Hz, 1H), 11.15 (s, 1H). 13C NMR (DMSO-d6) δ: 21.95, 30.91, 38.29, 48.86, 113.18, 116.60, 119.08, 120.02, 121.91, 125.34, 127.12, 128.74, 129.58, 131.48, 131.54, 132.96, 134.64, 138.89, 147.66, 165.60, 166.94, 167.51, 169.80, 172.73. Anal Calcd for C22H17F2N3O6: C, 57.77; H, 3.75; N, 9.19; F, 8.31. Found: C, 57.62; H, 3.60; N, 8.99; F, 8.32.

Reference： [1]Patent: US2007/49618,2007,A1 .Location in patent: Page/Page column 125

3
[ 1000387-18-7 ]
[ 97914-59-5 ]
[ 1000387-24-5 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediate 17: 5-Amino-λ/-(2-r(((2-r(difluoromethvϖoxylphenyl\|carbonyl)(2-r(1.1- dimethylethvϖoxy1ethyl}amino)methyl1-3,3,3-trifluoro-2-hvdroxypropyl>-1-(4-fluorophenvϖ- 1/-/-pyrazole-4-carboxamide; solution of O-(7-azabenzotriazol-1 -yl)-N,N, N', N'-tetramethyluronium hexafluorophosphate (HATU) (498.1 mg, 1.31 mmol) in dimethylformamide (2.5ml) was added to 2-difluoromethoxybenzoic acid (246.3mg, 1.31 mmol ). After 10 minutes, a solution of 5-amino-λ/-{2-[({2-[(1 ,1-dimethylethyl)oxy]ethyl}amino)methyl]-3,3,3-trifluoro-2- hydroxypropyl}-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxamide (550mg, 1.19mmol) and diisopropylethylamine (461.6mg, 3.57mmol) in dimethylformamide (2.5ml) was added and the solution was stirred under nitrogen at room temperature. After 3.5 hours, the reaction mixture was concentrated in vacuo and the residue was purified by the Flashmaster with 0-100% ethyl acetate in cyclohexane gradient over 60 minutes as eluent. This gave the title product (423mg).1H NMR (400 MHz, CHLOROFORM-cQ δ ppm 7.74 (s, 1 H) 7.47 (s, 2H) 7.42 (s, 3H) 7.25 - 7.31 (m, 1 H) 7.13 - 7.24 (m, 2H) 5.52 (br. s., 2H) 3.15 - 4.24 (m, 9H) 1.13 (s, 9H). LC-MS Retention Time 3.37mins, MH+ 631.

Reference： [1]Patent: WO2008/777,2008,A2 .Location in patent: Page/Page column 64

4
[ 97914-59-5 ]
[ 1608129-74-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

5
[ 97914-59-5 ]
[ 1608129-59-4 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

6
[ 97914-59-5 ]
4-pyrrolidin-1-yl-piperidine-1-carboxylic acid [5-(2-difluoromethoxyphenyl)-2H-pyrazol-3-yl]amide formate salt [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

7
[ 97914-59-5 ]
[ 1016690-71-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

8
[ 97914-59-5 ]
[ 1608129-78-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

9
[ 97914-59-5 ]
[ 1040724-27-3 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

10
[ 97914-59-5 ]
[ 1040721-25-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

11
[ 97914-59-5 ]
[ 1040721-31-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 78,p. 401 - 418

12
[ 97914-59-5 ]
4-(2-amino-3-methylbutanoyl)benzonitrile hydrochloride [ No CAS ]
N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-yl)-2-(difluoromethoxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%		2-(Difluoromethoxy)benzoic acid (CAS 97914-59-5, 33.1 mg, 0.18 mmol) was dissolved in DMF (200 iL). HBTU (83 mg, 0.22 mmol) and TEA (61.1 iL, 0.44 mmcl) were added. The solution was stirred for 6 mm before 4-(2-amino-3-methylbutanoyl)benzonitrile hydrochloride (Example 49b, 35 mg, 0.15 mmol) in DMF (400 iL) and TEA (61.1 iL, 0.44 mmol) was added. The reaction mixture was stirred for 1 h at rt before purified bypreparative HPLC to give N-(1-(4-cyanophenyl)-3-methyl-1-oxobutan-2-yl)-2- (difluoromethoxy)benzamide (46.7 mg, 86%).1H NMR (500 MHz, CDCI3) 5 ppm 0.88 (d, 3 H) 1.09 (d, 3 H) 2.27 (m, 1 H) 5.74 (dd, 1 H) 6.53 -6.92 (m, 1 H) 7.19 (d, 1 H) 7.29 - 7.36 (m, 1 H) 7.47 - 7.55 (m, 1 H) 7.75 (d, 1 H) 7.82 (d, 2 H)8.06 (dd, 1 H) 8.14 (d, 2 H).MS (ESI) m/z 370.8 [M-H]

Reference： [1]Patent: WO2014/184235,2014,A1 .Location in patent: Page/Page column 95

13
[ 97914-59-5 ]
C₁₂H₁₅N₃O [ No CAS ]
C₂₀H₁₉F₂N₃O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2488 - 2492

14
[ 97914-59-5 ]
2-(2-(1,4-diazepan-1-yl)-5-methyloxazol-4-yl)propan-2-ol [ No CAS ]
(2-(difluoromethoxy)phenyl)(4-(4-(2-hydroxypropan-2-yl)-5-methyloxazol-2-yl)-1,4-diazepan-1-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20 mg		Step 6: (2-(difluoromethoxy)phenyl)(4-(4-(2-hydroxypropan-2-yl)-5-methyloxazol-2-yl)-l,4- diazepan-l-yl)methanone (Example 12) To a solution of 2-(difluoromethoxy) benzoic acid (31 mg, 0.15 mmol) in DMF (2 mL) was added HATU (57 mg, 0.15 mmol) and DIPEA (0.088 mL, 0.50 mmol). After stirring at room temperature for 10 min, 12-5 (30 mg, 0.125 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was purified by preparative HPLC to give Example 12 (20 mg) as a white solid. LRMS m/z (M+H) 410.1 found, 410.2 required.

Reference： [1]Patent: WO2015/95111,2015,A1 .Location in patent: Page/Page column 42

15
[ 97914-59-5 ]
N-(((3aS,6R,6aR)-6-(aminomethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-3a(4H)-yl)methyl)benzamide [ No CAS ]
N-(((3aR,4R,6aS)-6a-(benzamidomethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)-2-(difluoromethoxy)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	General procedure: To a solution of the crude amine, obtained via general procedure1, in DMF (25 mL/mmol) were added the appropriate organicacid (1.5 equiv per amine), EDCHCl (2 equiv per amine), diisopropylethylamine(4 equiv per amine) and a catalytic amount of1-hydroxybenzotriazole. The reaction mixture was stirred 16 h atrt. The mixture was concentrated and partitioned between waterand EtOAc. The organic layer was dried over sodium sulphate, filteredand concentrated in vacuo. The products were purified bycolumn chromatography with appropriate eluents.

Reference： [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4563 - 4575

16
[ 97914-59-5 ]
2-(difluoromethoxy)benzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		2- (difluoromethoxy) benzoic acid (400 mg, 2.13 mmol) in methanol (15 ml) solution was added dropwise concentrated sulfuric acid (64 μl). Under an argon atmosphere, and stirred under reflux conditions overnight. After completion of the reaction, concentrated to dryness. Saturated saline, a saturated aqueous solution of sodium hydrogen carbonate was added, and the mixture was extracted with chloroform. Dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure.ResidueIn ethanol (6 ml) solution,Hydrazine monohydrate (827 μl, 17.0 mmol) was added dropwise. Under an argon atmosphere, was stirred for 4 hours at reflux conditions, it was solidified after completion of the reaction concentrated to dryness. The residue was purified by silica gel column chromatography (chloroform / methanol) to give the title compound (180 mg, 42%)

Reference： [1]Patent: JP2016/124812,2016,A .Location in patent: Paragraph 0345
[2]Patent: WO2021/28382,2021,A1

17
[ 97914-59-5 ]
2-(2-(difluoromethoxy)phenyl)-1,3,4-oxadiazole [ No CAS ]

Reference： [1]Patent: JP2016/124812,2016,A

18
1-(difluoromethoxy)-3-methyl-6-nitro-4-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-3-ium trifluoromethanesulfonate [ No CAS ]
[ 65-85-0 ]
[ 97914-59-5 ]
[ 4837-20-1 ]
[ 4837-19-8 ]

Reference： [1]Chemical Science,2019,vol. 10,p. 3217 - 3222

Yield	Reaction Conditions	Operation in experiment
	With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; In acetonitrile; at 23℃; for 12h;Irradiation; Glovebox; Sealed tube; Inert atmosphere;	General procedure: In a glovebox, to an oven-dried 20 mL screw cap vial was added 1- (difluoromethoxy) -3-methyl-6-nitro-4- (trifluoromethyl) -lff- benzo [d] [1, 2, 3] triazol-3-ium trifluoromethanesulfonate (la) (92.4 mg, 0.200 mmol, 1.00 equiv), (hetero) arene (2.00 mmol, 10.0 equiv), Ru (bpy) 3 (PF6) 2, (0.860 mg, 1.00 pmol, 0.500 mol%), and MeCM (1.00 mL, 0.200 M, with respect to la) . To this suspension or solution was added a magnetic stir bar. Next, the reaction vial was capped and taken out of the glovebox. The reaction mixture was stirred at ambient temperature (23 C) and irradiated with blue LEDs (30 W, Xmax = 450 nm) which was placed 20.0 m from the vial for 12 h. To determine the yield of the products, an internal standard, trifluorotoluene (PhCF3) (14.6 mg, 12.3 pL, 0.100 mmol, 0.500 equiv) was added to the vial. Then, a 100 pL of the reaction mixture was taken and then dilute with 500 pL CD3CN followed by 19F NMR (the NMR sample was recombined with the rest of the reaction mixture afterward) . The combined reaction mixture was then purified by HPLC on the Luna PFP(2) preparative column (250 x 21.2 mm) column eluting with MeCN:H20 (v/v) with a flow rate of 10.6 mL/min to provide the purified products. In cases of closely-eluting peaks, products were isolated as a mixture of isomers. Afterwards, the products were extracted with CDC13 (3 x 1 mL) , dried with magnesium sulfate, and filtered. The filtrate was concentrated in vacuo to afford the desired product (s). For very volatile compounds, the products were extracted immediately with CDCI3 (l x l mL) and then directly characterized. 1H and 13C NMR of these Compound (s) contains MeCN residue signal (1H NMR: ? 1.94, 13C NMR: u 118.26, 1.32 in CDCI3 )

20
[ 97914-59-5 ]
[ 64-17-5 ]
ethyl 2-(difluoromethoxy)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%		Thionyl dichloride (160 mL, 2.2 mmol) was added dropwise to <strong>[97914-59-5]2-(difluoromethoxy)benzoic acid</strong> (100 mg, 532 mmol)under argon, DCM (0.5 mL) was added and it was stirred for 30min at rt. The mixture was cooled to 0 C and ethanol (880 mL) was added dropwise. The mixture was stirred for 30min at 0 C, 1h atrefluxand overnight at rt. The mixture was concentrated under reduced pressure to give 95.0 mg (83 % yield) of the target compound, which was used without further purification.LC-MS (Method 1): Rt = 1.17 min; MS (ESIpos): m/z = 217 [M+H]+1H-NMR (400MHz, DMSO-d6): d [ppm]= 1.30 (t, 3H), 4.30 (q, 2H), 7.18 (t, 1 H), 7.32 (dd, 1H), 7.40 (td, 1H), 7.66 (ddd, 1 H), 7.83 (dd, 1H).

Reference： [1]Patent: WO2021/28382,2021,A1 .Location in patent: Page/Page column 243

21
[ 97914-59-5 ]
(5-(2-methoxyphenyl)-1H-1,2,4-triazol-3-yl)methanamine hydrochloride [ No CAS ]
2-(difluoromethoxy)-N-((5-(2-methoxyphenyl)-1H-1,2,4-triazol-3-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃;	To a stirred solution of <strong>[97914-59-5]2-(difluoromethoxy)benzoic acid</strong> (20 g, 104 mmol) in DCM (500 mL) at 0 oC was added EDC.HCl (30 g, 156 mmol), HOBt (21 g, 156 mmol), (5- (2-methoxyphenyl)-1H-1,2,4-triazol-3-yl)methanamine hydrochloride (25 g, 104 mmol) and followed by triethyl amine (44 mL, 312 mmol). Reaction was stirred at room temperature for 12h. After completion of the reaction, solid was filtered through celite bed, the filtrate obtained was washed once with saturated NaHCO3 solution (500 mL), saturated NH4Cl solution (1 Lit) and brine solution. The organic layer was separated, dried over Na2SO4 concentrated under reduced pressure to get the crude. The crude obtained was triturated with acetonitrile (500 mL), stirred for 1h, filtered and washed with diethyl ether (100 mL), and dried under vacuum to afford 2-(difluoromethoxy)-N-((5-(2-methoxyphenyl)-1H-1,2,4- triazol-3-yl)methyl)benzamide (19 g, yield: 56%) as an off white solid.1H NMR (400 MHz, DMSO-d6): δ 13.55 (s, 1H), 8.76 (bs, 1H), 8.07 (d, J = 7.6 Hz, 1H), 7.61 (d, J = 7.6 Hz, 1H), 7.52 (t, J = 7.6 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.36-6.99 (m, 5H),4.53 (d, J = 5.6 Hz, 2H), 3.94 (s, 3H). LC-MS m/z (M+H): 374.9.

Reference： [1]Patent: WO2021/138540,2021,A1 .Location in patent: Paragraph 00112; 00119-00120

22
[ 97914-59-5 ]
5-(2-methoxyphenyl)-1H-pyrazole-3-sulfonamide [ No CAS ]
2-(difluoromethoxy)-N-((5-(2-methoxyphenyl)-1H-pyrazol-3-yl)sulfonyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.87%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	To a stirred solution of 2-(difluoro methoxy)benzoic acid (44 mg, 0.2371 mmol) in DMF (1 mL) at 0oC, was added HATU (72.13 mg, 0.1897 mmol), 5-(2- methoxyphenyl)-1H-pyrazole-3-sulfonamide (40 mg, 0.1581 mmol) and DIPEA and the resultant mixture was stirred at room temperature for 16h. It was then quenched with ice cold water and extracted with ethyl acetate (2X 50 mL). The combined organic layer washed with brine solution (50 mL), dried over sodium sulfate and concentrated to obtain the crude product. The crude product was further purified by preparative HPLC to afford 2-(difluoro methoxy)-N-((5-(2-methoxyphenyl)-1H-pyrazol-3-yl) sulfonyl)benzamide off-white solid (28 mg,41.87 %).1H NMR (400 MHz, DMSO) δ 13.84 (s, 1H), 12.61 (s, 1H), 7.76 (d, J = 7.2 Hz, 1H), 7.58 (t, J = 6.8 Hz, 1H), 7.52 (d, J = 7.2 Hz, 1H), 7.41 (t, J = 7.2 Hz, 1H), 7.31 (t, J = 6.8 Hz, 1H), 7.24 - 6.95 (m, 5H), 3.91 (s, 3H). LC-MS m/z (M-H): 423.39.

Reference： [1]Patent: WO2021/138540,2021,A1 .Location in patent: Paragraph 00220; 00225-00226

23
[ 97914-59-5 ]
2-(difluoromethoxy)-N-((5-(2-methoxyphenyl)-1H-1,2,4-triazol-3-yl)methyl)benzamide [ No CAS ]