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[ CAS No. 1526-17-6 ]

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Chemical Structure| 1526-17-6
Chemical Structure| 1526-17-6
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CAS No. :1526-17-6 MDL No. :MFCD00042446
Formula : C6H4FNO3 Boiling Point : 201.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :157.10 g/mol Pubchem ID :73710
Synonyms :

Safety of [ 1526-17-6 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P333+P313-P391-P501 UN#:3077
Hazard Statements:H302-H315-H317-H318-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1526-17-6 ]

  • Upstream synthesis route of [ 1526-17-6 ]
  • Downstream synthetic route of [ 1526-17-6 ]

[ 1526-17-6 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 1526-17-6 ]
  • [ 56-81-5 ]
  • [ 35048-10-3 ]
Reference: [1] Chemical Communications, 2006, # 18, p. 1941 - 1943
  • 2
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
Reference: [1] Chinese Chemical Letters, 2010, vol. 21, # 11, p. 1283 - 1286
[2] Patent: WO2013/28474, 2013, A1, . Location in patent: Page/Page column 83
[3] Patent: WO2014/126944, 2014, A2, . Location in patent: Page/Page column 54
[4] Patent: EP2744499, 2016, B1, . Location in patent: Paragraph 0192
  • 3
  • [ 367-12-4 ]
  • [ 7440-44-0 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
YieldReaction ConditionsOperation in experiment
30 % With nitric acid In hexane; dichloromethane A.
2-Fluoro-4-nitrophenol
To a stirred solution of 2-fluorophenol (32.3 g, 0.288 mole) in methylene chloride which was cooled to -10° C. (ice-salt bath), was slowly added 90 percent nitric acid (22 g, 0.31 mole HNO3) over a one-hour period.
During the addition, the temperature was maintained at about -5° C.
After the addition was complete, stirring was continued at 0° C. for an additional hour.
At the end of this period, the precipitate which had formed was filtered and washed with several portions of cold methylene chloride. G.C. and thin-layer chromatography (silica gel, 7:3 hexane-acetone) showed that this material was essentially a single compound and was the more polar and less volatile of the two products which formed in the reaction.
This solid was taken up in ether, washed with water, dried (MgSO4) and the solvent evaporated.
The resulting solid was recrystallized from methylcyclohexane to give 13 g of a light yellow solid: m.p.=119°-121° C. NMR (CDCl3) showed this to be the desired 2-fluoro-4-nitrophenol.
The methylene chloride mother liquor was washed with water, dried (MgSO4) and the solvent evaporated.
The solid which resulted was triturated with boiling hexane (3*150 ml).
This effectively removed all of the least polar-more volatile reaction product.
This hexane solution was treated with charcoal, filtered, concentrated to about 300 ml and cooled to give 13.5 g (30 percent) of by-product 2-fluoro-6-nitrophenol as a yellow solid: m.p.=70°-86° C.
30 % With nitric acid In hexane; dichloromethane A.
2-Fluoro-4-nitrophenol
To a stirred solution of 2-fluorophenol (32.3 g, 0.288 mole) in methylenechloride which was cooled to -10°C (ice-salt bath), was slowly added 90 percent nitric acid (22 g, 0.31 mole HNO3) over a one-hour period.
During the addition, the temperature was maintained at about -5°C.
After the addition was complete, stirring was continued at 0°C for an additional hour.
At the end of this period, the precipitate which had formed was filtered and washed with several portions of cold methylene chloride. G.C. and thin-layer chromatography (silica gel, 7:3 hexane-acetone) showed that this material was essentially a single compound and was the more polar and less volatile of the two products which formed in the reaction.
This solid was taken up in ether, washed with water, dried (MgSO4) and the solvent evaporated.
The resulting solid was recrystallized from methylcyclohexane to give 13 g of a light yellow solid: m.p. = 119-121°C. NMR (CDCl3) showed this to be the desired 2-fluoro-4-nitrophenol.
The methylene chloride mother liquor was washed with water, dried (MgSO4) and the solvent evaporated.
The solid which resulted was triturated with boiling hexane (3 x 150 ml).
This effectively removed all of the least polar - more volatile reaction product.
This hexane solution was treated with charcoal, filtered, concentrated to about 300 ml and cooled to give 13.5 g (30 percent) of 2-fluoro-6-nitrophenol as a yellow solid: m.p. = 70-86°C.
Reference: [1] Patent: US4750931, 1988, A,
[2] Patent: EP142328, 1991, B1,
  • 4
  • [ 402-67-5 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 4979 - 4981
  • 5
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
  • [ 123871-61-4 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310
[2] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310
  • 6
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178
  • 7
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
  • [ 681227-38-3 ]
Reference: [1] Journal of the Chemical Society, 1940, p. 810
  • 8
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
  • [ 351-49-5 ]
Reference: [1] Journal of the Chemical Society, 1940, p. 810
  • 9
  • [ 1526-17-6 ]
  • [ 394-50-3 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178
  • 10
  • [ 367-12-4 ]
  • [ 7440-44-0 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
YieldReaction ConditionsOperation in experiment
30 % With nitric acid In hexane; dichloromethane A.
2-Fluoro-4-nitrophenol
To a stirred solution of 2-fluorophenol (32.3 g, 0.288 mole) in methylene chloride which was cooled to -10° C. (ice-salt bath), was slowly added 90 percent nitric acid (22 g, 0.31 mole HNO3) over a one-hour period.
During the addition, the temperature was maintained at about -5° C.
After the addition was complete, stirring was continued at 0° C. for an additional hour.
At the end of this period, the precipitate which had formed was filtered and washed with several portions of cold methylene chloride. G.C. and thin-layer chromatography (silica gel, 7:3 hexane-acetone) showed that this material was essentially a single compound and was the more polar and less volatile of the two products which formed in the reaction.
This solid was taken up in ether, washed with water, dried (MgSO4) and the solvent evaporated.
The resulting solid was recrystallized from methylcyclohexane to give 13 g of a light yellow solid: m.p.=119°-121° C. NMR (CDCl3) showed this to be the desired 2-fluoro-4-nitrophenol.
The methylene chloride mother liquor was washed with water, dried (MgSO4) and the solvent evaporated.
The solid which resulted was triturated with boiling hexane (3*150 ml).
This effectively removed all of the least polar-more volatile reaction product.
This hexane solution was treated with charcoal, filtered, concentrated to about 300 ml and cooled to give 13.5 g (30 percent) of by-product 2-fluoro-6-nitrophenol as a yellow solid: m.p.=70°-86° C.
30 % With nitric acid In hexane; dichloromethane A.
2-Fluoro-4-nitrophenol
To a stirred solution of 2-fluorophenol (32.3 g, 0.288 mole) in methylenechloride which was cooled to -10°C (ice-salt bath), was slowly added 90 percent nitric acid (22 g, 0.31 mole HNO3) over a one-hour period.
During the addition, the temperature was maintained at about -5°C.
After the addition was complete, stirring was continued at 0°C for an additional hour.
At the end of this period, the precipitate which had formed was filtered and washed with several portions of cold methylene chloride. G.C. and thin-layer chromatography (silica gel, 7:3 hexane-acetone) showed that this material was essentially a single compound and was the more polar and less volatile of the two products which formed in the reaction.
This solid was taken up in ether, washed with water, dried (MgSO4) and the solvent evaporated.
The resulting solid was recrystallized from methylcyclohexane to give 13 g of a light yellow solid: m.p. = 119-121°C. NMR (CDCl3) showed this to be the desired 2-fluoro-4-nitrophenol.
The methylene chloride mother liquor was washed with water, dried (MgSO4) and the solvent evaporated.
The solid which resulted was triturated with boiling hexane (3 x 150 ml).
This effectively removed all of the least polar - more volatile reaction product.
This hexane solution was treated with charcoal, filtered, concentrated to about 300 ml and cooled to give 13.5 g (30 percent) of 2-fluoro-6-nitrophenol as a yellow solid: m.p. = 70-86°C.
Reference: [1] Patent: US4750931, 1988, A,
[2] Patent: EP142328, 1991, B1,
  • 11
  • [ 402-67-5 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 17, p. 4979 - 4981
  • 12
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
  • [ 123871-61-4 ]
Reference: [1] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310
[2] Tetrahedron, 1989, vol. 45, # 5, p. 1299 - 1310
  • 13
  • [ 367-12-4 ]
  • [ 1526-17-6 ]
  • [ 403-19-0 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178
  • 14
  • [ 1526-17-6 ]
  • [ 437-83-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 199 - 210
[2] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178
[3] Patent: WO2013/28474, 2013, A1,
[4] Patent: WO2014/126944, 2014, A2,
[5] Patent: EP2744499, 2016, B1,
  • 15
  • [ 1526-17-6 ]
  • [ 77-78-1 ]
  • [ 484-94-6 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 94,95, 97
[2] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 3-4, p. 175 - 178
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 199 - 210
[4] Patent: WO2006/89054, 2006, A1, . Location in patent: Page/Page column 51-53
[5] Patent: WO2005/19228, 2005, A1, . Location in patent: Page/Page column 54-55
  • 16
  • [ 1526-17-6 ]
  • [ 74-88-4 ]
  • [ 484-94-6 ]
Reference: [1] Patent: WO2013/28474, 2013, A1, . Location in patent: Page/Page column 83
[2] Patent: WO2014/126944, 2014, A2, . Location in patent: Page/Page column 54
[3] Patent: EP2744499, 2016, B1, . Location in patent: Paragraph 0192
  • 17
  • [ 1526-17-6 ]
  • [ 53981-25-2 ]
YieldReaction ConditionsOperation in experiment
87% With palladium 10% on activated carbon; hydrogen In methanol for 1 h; To a of solution of 2-fluoro-6-nitrophenol (6.37 mmol, 1.00 g) in methanol (100 mL), 10percent palladium on activated carbon (10 wtpercent of 2-fluoro-6-nitrophenol,0.10 g) was added. The reaction was flushed with argon followed by hydrogen for fifteen minutes each with constant magnetic stirring. The reaction was then maintained under hydrogen atmosphere at ordinary pressure (balloon) for one hour. Argon was again flushed through the reaction vessel for 15 minutes. Then the reaction contents were filtered over a thin pad of celite which was then washed with methanol (50 mL). The filtrate was concentrated in vacuo yielding a red solid. Silica gel column chromatography (1:1 hexanes/chloroform) provided a crystalline white solid in an 87percent yield.
55.3% With tin(ll) chloride In tetrahydrofuran; waterReflux 2-fluoro-6-nitrophenol (322 mg, 2.05 mmol) and THF (6.4 ml),It was dissolved in water (6.4 ml),Thereto tin chloride (1.943 g, 10.25 mmol) was heated at reflux overnight added. After the reaction, the addition of a saturated aqueous sodium bicarbonate solution and ethyl acetate. The precipitate was filtered. The filtrate was extracted with ethyl acetate. It was washed with saturated brine. Dried over magnesium sulfate, the solvent was distilled off to obtain the title compound (144 mg, 55.3percent) as a white solid.
12%
Stage #1: With water; tin(ll) chloride In tetrahydrofuran at 80℃; for 2 h;
Stage #2: With sodium hydrogencarbonate In water
Step 1. 2-amino-6-fluorophenol To 2-fluoro-6-nitrophenol (SynQuest) (2.4 g, 15 mmol) in THF (70 mL), and water (70 mL) was added tin dichloride (14.6 g, 76.4 mmol). The mixture was then heated at 80° C. for 2 h. The THF was removed in vacuo. A solution of sat'd NaHCO3 was added, followed by EtOAc. Insoluble material was removed by filtration. The layers of the filtrate were separated and the aqueous portion was extracted with ethyl acetate three times. The combined extracts were washed with brine, dried over sodium sulfate, filtered through a plug of silica gel and concentrated. The product was purified by silica gel chromatography, eluting with 0-60percent ethyl acetate in hexanes (230 mg, 12percent).1H NMR (300 MHz, CD3OD): δ 6.56 (ddd, 1H), 6.51 (ddd, 1H), 6.41 (ddd, 1H); 19F NMR (300 MHz, CD3OD): δ -141.27 (dd, 1F); LCMS (M+H)+: 128.1.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3521 - 3525
[2] Patent: JP2016/124812, 2016, A, . Location in patent: Paragraph 0115
[3] Patent: US2010/298334, 2010, A1, . Location in patent: Page/Page column 46
[4] Patent: WO2005/118561, 2005, A1, . Location in patent: Page/Page column 25
[5] Patent: US2005/124667, 2005, A1, . Location in patent: Page/Page column 17
  • 18
  • [ 1526-17-6 ]
  • [ 845829-94-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 199 - 210
[2] Patent: WO2013/28474, 2013, A1,
[3] Patent: WO2014/126944, 2014, A2,
[4] Patent: EP2744499, 2016, B1,
  • 19
  • [ 1526-17-6 ]
  • [ 898832-40-1 ]
Reference: [1] Patent: WO2011/144578, 2011, A1,
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