1526-17-6

Basic information

• Product Name: 2-Fluoro-6-nitrophenol
• Synonyms: 6-FLUORO-2-NITROPHENOL;2-NITRO-6-FLUORO PHENOL;2-FLUORO-6-NITROPHENOL;2-Fluoro-6-nitrophenol 98%;2-Fluoro-6-nitrophenol98%;Fluoro-6-nitrophenol, 2-;2-Fluoro-6-nitrophen;3-Fluoro-2-hydroxynitrobenzene
• CAS NO: 1526-17-6
• Molecular Formula: C₆H₄FNO₃
• Molecular Weight: 157.1
• EINECS: 216-199-4
• Product Categories: Fluorobenzene
• Mol File: 1526-17-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 92-94°C
• Boiling Point: 201.5 ºC at 760 mmHg
• Flash Point: 75.6 ºC
• Appearance: /
• Density: 1.511 g/cm³
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 5.67±0.24(Predicted)
• BRN: 1870307
• CAS DataBase Reference: 2-Fluoro-6-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-6-nitrophenol(1526-17-6)
• EPA Substance Registry System: 2-Fluoro-6-nitrophenol(1526-17-6)

Safety Data

• Hazard Codes: Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39-36/37
• RIDADR: 2811
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 1526-17-6(Hazardous Substances Data)

Usage

Uses

2-Fluoro-6-nitrophenol has antifungal- and high plant-growth-regulating activity.

InChI:InChI=1/C6H4FNO3/c7-4-2-1-3-5(6(4)9)8(10)11/h1-3,9H

Synthetic route

2-fluorophenol (367-12-4) → 2-fluoro-6-nitrophenol (1526-17-6)

Conditions	Yield
With trichloroisocyanuric acid; bismuth subnitrate/charcoal In dichloromethane at 20℃; for 1h; regioselective reaction;	85%
With nitric acid In dichloromethane at 0℃; for 1h;
With nitric acid In dichloromethane at 0 - 5℃; for 1h;
With nitric acid In dichloromethane at 0℃; for 1h;

3-fluoro-1-nitrobenzene (402-67-5) → 2-fluoro-6-nitrophenol (1526-17-6) + 2-fluoro-4-nitrophenol (403-19-0)

Conditions	Yield
With tert.-butylhydroperoxide; potassium tert-butylate; ammonia In tetrahydrofuran for 0.25h;	A 7% B 76%

2-fluorophenol (367-12-4) → 2-fluoro-6-nitrophenol (1526-17-6) + 2-fluoro-4-nitrophenol (403-19-0)

Conditions	Yield
With Nitrogen dioxide In pentane 35 min, 0 deg C then 20 min, room temperature;	A 47% B 49%

2-fluorophenol (367-12-4) → 2-fluoro-6-nitrophenol (1526-17-6) + fluoro-[1,4]benzoquinone-4-oxime (681227-38-3)

Conditions	Yield
With hydrogenchloride; sodium nitrite at 0℃;

2-fluorophenol (367-12-4) → 2-fluoro-6-nitrophenol (1526-17-6) + 2-fluoro-4-nitroso-phenol (351-49-5)

Conditions	Yield
With hydrogenchloride; sodium nitrite at 0℃;

2-fluorophenol (367-12-4) → 2-fluoro-6-nitrophenol (1526-17-6) + 2-fluoro-4-nitrophenol (403-19-0) + 6-fluoro-6-nitrocyclohexa-2,4-dienone (123871-61-4)

Conditions	Yield
With nitric acid In acetic anhydride at -60℃; Title compound not separated from byproducts;
With nitric acid In acetic anhydride Title compound not separated from byproducts;

5-fluoro-3-nitro-4-methoxy-benzene-sulfonic acid-(1) → 2-fluoro-6-nitrophenol (1526-17-6)

Conditions	Yield
With steam at 170 - 190℃;

2-fluorophenol (367-12-4) + pyrographite (7440-44-0) → 2-fluoro-6-nitrophenol (1526-17-6) + 2-fluoro-4-nitrophenol (403-19-0)

Conditions	Yield
With nitric acid In hexane; dichloromethane	A 13.5 g (30 %) B n/a
With nitric acid In hexane; dichloromethane	A 13.5 g (30 %) B n/a

2-fluoro-6-nitrophenol (1526-17-6) + ethyl bromoacetate (105-36-2) → ethyl2-(2-fluoro-6-nitrophenoxy)acetate

Conditions	Yield
Stage #1: 2-fluoro-6-nitrophenol With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide for 24h; Further stages.;	99%
With potassium carbonate In acetonitrile at 90℃; for 2h;	74.7%

trifluoromethylsulfonic anhydride (358-23-6) + 2-fluoro-6-nitrophenol (1526-17-6) → 2-fluoro-6-nitrophenyl trifluoromethanesulfonate (122455-35-0)

Conditions	Yield
With potassium carbonate	98%
With potassium carbonate In acetone at 20℃; for 4h;	40%
Stage #1: 2-fluoro-6-nitrophenol With potassium carbonate In acetone at 20℃; for 0.333333h; Stage #2: trifluoromethylsulfonic anhydride In acetone at 20℃; for 4h;	40%
With pyridine In dichloromethane at 0℃; for 2h;

2-fluoro-6-nitrophenol (1526-17-6) + bromoacetic acid methyl ester (96-32-2) → (2-fluoro-6-nitrophenoxy)acetic acid, methyl ester (698984-51-9)

Conditions	Yield
With potassium carbonate In acetone at 65℃; for 3h;	98%
With potassium carbonate In acetone for 5h; Reflux;	93%

2-fluoro-6-nitrophenol (1526-17-6) + 2-Bromopropionic acid (598-72-1) → (2-fluoro-6-nitrophenoxy)acetic acid, methyl ester (698984-51-9)

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating / reflux;	93%

2-fluoro-6-nitrophenol (1526-17-6) → 2-amino-6-fluoro phenol (53981-25-2)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol for 1h;	87%
With tin(ll) chloride In tetrahydrofuran; water Reflux;	55.3%
Stage #1: 2-fluoro-6-nitrophenol With water; tin(ll) chloride In tetrahydrofuran at 80℃; for 2h; Stage #2: With sodium hydrogencarbonate In water	12%
With ammonium formate; palladium 10% on activated carbon In methanol at 20℃; for 0.5h;
With hydrogen; nickel In methanol under 760.051 Torr;

(S)-Ethyl lactate (687-47-8) + 2-fluoro-6-nitrophenol (1526-17-6) → ethyl (2R)-2-(2-fluoro-6-nitrophenoxy)propanoate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 1.5h;	83%

2-fluoro-6-nitrophenol (1526-17-6) + allyl bromide (106-95-6) → 2-fluoro-6-nitrophenyl prop-2-en-1-yl ether

Conditions	Yield
With potassium carbonate; calcium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;	83%
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 6h;	83%

3-Hydroxytetrahydrofuran (453-20-3) + 2-fluoro-6-nitrophenol (1526-17-6) → 3-(2-fluoro-6-nitrophenoxy)-tetrahydrofuran (917909-41-2)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 20h;	68%

2-fluoro-6-nitrophenol (1526-17-6) + C10H9NO2 → C16H11FN2O4 + C16H11FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A 58% B n/a

2-fluoro-6-nitrophenol (1526-17-6) + C13H17NO2 → C19H19FN2O4 + C19H19FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A 54% B n/a

2-fluoro-6-nitrophenol (1526-17-6) + C9H6BrNO2 → C15H8BrFN2O4 + C15H8BrFN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A 50% B n/a

2-fluoro-6-nitrophenol (1526-17-6) + C13H9NO2 → C19H11FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	49%

2-fluoro-6-nitrophenol (1526-17-6) + C9H7NO2 → C15H9FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	46%

2-fluoro-6-nitrophenol (1526-17-6) + C9H6ClNO2 → C15H8ClFN2O4 + C15H8ClFN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A n/a B 46%

2-fluoro-6-nitrophenol (1526-17-6) + C15H11NO2 → C21H13FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	43%

2-fluoro-6-nitrophenol (1526-17-6) + C7H5NO3 → C13H7FN2O5 + C13H7FN2O5

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A 43% B n/a

2-fluoro-6-nitrophenol (1526-17-6) + C7H5NO2S → C13H7FN2O4S + C13H7FN2O4S

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A 42% B n/a

2-fluoro-6-nitrophenol (1526-17-6) + C11H7NO2S → C17H9FN2O4S

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	41%

2-fluoro-6-nitrophenol (1526-17-6) + C10H6F3NO2 → C16H8F4N2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	39%

2-fluoro-6-nitrophenol (1526-17-6) + C9H6ClNO2 → C15H8ClFN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	39%

2-fluoro-6-nitrophenol (1526-17-6) + C9H6(2)HNO2 → C15H8(2)HFN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	39%

2-fluoro-6-nitrophenol (1526-17-6) + C9H6BrNO2 → C15H8BrFN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	38%

2-fluoro-6-nitrophenol (1526-17-6) + C11H9NO2 → C17H11FN2O4 + C17H11FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	A 37% B n/a

2-fluoro-6-nitrophenol (1526-17-6) + C11H7NO3 → C17H9FN2O5

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	35%

2-fluoro-6-nitrophenol (1526-17-6) + N-tert-butoxycarbonyl-L-serine benzyl ester (59524-02-6) → (S)-2-(tert-butoxycarbonylamino)-3-(2-fluoro-6-nitrophenoxy)propanoic acid

Conditions	Yield
Stage #1: 2-fluoro-6-nitrophenol With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -3℃; for 0.166667h; Stage #2: N-tert-butoxycarbonyl-L-serine benzyl ester at 20℃; for 16h;	30%

2-fluoro-6-nitrophenol (1526-17-6) + C7H11NO2 → C13H13FN2O4

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In ethyl acetate at 25℃; for 0.12h; Schlenk technique;	18%

Upstream product

• 367-12-4 2-fluorophenol 
• 7440-44-0 pyrographite 
• 402-67-5 3-fluoro-1-nitrobenzene 

Downstream Products

• 484-94-6 1-fluoro-2-methoxy-3-nitrobenzene 

Relevant articles and documents

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula Ia and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and conditions associated with excessive salt and water retention.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula Ia and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and conditions associated with excessive salt and water retention.

Fluorophenoxy compounds, herbicidal compositions and methods

-