3-Nitro-5-(trifluoromethyl)pyridin-2-ol supplier

Name
2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE
EINECS 692-913-1
CAS No. 33252-64-1
Article Data9
CAS DataBase
Density 1.646 g/cm³
Solubility
Melting Point 189 °C
Formula C₆H₃F₃N₂O₃
Boiling Point 292.891 °C at 760 mmHg
Molecular Weight 208.097
Flash Point 130.936 °C
Transport Information
Appearance
Safety 22-26-36/37/39
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 3-Nitro-5-(trifluoromethyl)-2-pyridinol;3-Nitro-5-(trifluoromethyl)-2-pyridone;2-Hydroxy-3-nitro-5-(trifluoromethyl)pyridine;2(1H)-Pyridone,3-nitro-5-(trifluoromethyl)- (8CI);
PSA 78.94000
LogP 2.23740

Synthetic route

: 53359-69-6
5-(Trifluoromethyl)-3-nitro-2-aminopyridine

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

Conditions

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 0 - 20℃; Inert atmosphere;	73%

: 33252-63-0
2-hydroxy-5-(trifluoromethyl)pyridine

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

Conditions

Conditions	Yield
Stage #1: 2-hydroxy-5-(trifluoromethyl)pyridine With sulfuric acid; nitric acid at 0 - 65℃; for 25h; Stage #2: With sodium hydroxide In water at 20℃;	58%
With sulfuric acid; nitric acid at 80 - 85℃;	28%
With sulfuric acid; potassium nitrate at 0 - 65℃; for 4h;
With sulfuric acid; nitric acid In water at 80℃; for 1h;
With sulfuric acid; nitric acid In water at 60℃; for 18h;

: 74784-70-6
2-amino-5-trifluoromethylpyridine

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid / 0 - 20 °C / Inert atmosphere 2: sulfuric acid; sodium nitrite / water / 0 - 20 °C / Inert atmosphere View Scheme

: 56-93-9
benzyltrimethylammonium chloride

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 72587-15-6
2-chloro-3-nitro-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With trichlorophosphate In acetonitrile for 3h; Heating;	92%

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 72587-15-6
2-chloro-3-nitro-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With quinoline; trichlorophosphate at 50 - 120℃; for 1.5h; Inert atmosphere;	88%
With quinoline; trichlorophosphate for 18h; Heating / reflux;	87%
With trichlorophosphate In DMF (N,N-dimethyl-formamide) at 110℃; for 0.5h;	86%

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 74-88-4
methyl iodide

: 1573056-08-2
1-methyl-3-nitro-5-(trifluoromethyl)pyridin-2(1H)-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 3h;	70%
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;

: 10026-13-8, 874483-75-7
phosphorus pentachloride

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 72587-15-6
2-chloro-3-nitro-5-(trifluoromethyl)pyridine

Conditions

Conditions	Yield
With trichlorophosphate	52%
With trichlorophosphate	52%

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 6-Trifluoromethyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 66 percent / PCl5, POCl3 / 80 °C 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, RT, 18 h 3: 73 percent / Fe, glacial AcOH / 2 h / Heating 4: 43 percent / H2 / 10percent Pd/C / acetic acid / 3 h / 2280 Torr View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 136888-31-8
3-benzyloxycarbonyl-6-trifluoromethyl-4-azaoxindole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 66 percent / PCl5, POCl3 / 80 °C 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, RT, 18 h 3: 73 percent / Fe, glacial AcOH / 2 h / Heating View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 136888-30-7
2-bis(benzyloxycarbonyl)methyl-3-nitro-5-trifluoromethylpyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / PCl5, POCl3 / 80 °C 2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, RT, 18 h View Scheme

: 34040-64-7
p-methyloxycarbonylbenzyl chloride

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 209687-69-4
methyl 4-(3-nitro-5-trifluoromethylpyridine-2-yloxymethyl)benzoate

Conditions

Conditions	Yield
In argon; toluene

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 90778-25-9
2-hydroxy-3-amino-5-trifluoromethylpyridine

Conditions

Conditions	Yield
With hydrogen; 5% Pd(II)/C(eggshell) In methanol at 20℃; under 760.051 Torr; for 2h;
With hydrogen; 5% Pd(II)/C(eggshell) In methanol at 20℃; under 760.051 Torr; for 2h;
With hydrogen; 5%-palladium/activated carbon In methanol at 20℃; under 760.051 Torr; for 2h;

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1192021-84-3
N-[2-hydroxy-5-(trifluoromethyl)pyridin-3-yl]isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 2 h / 20 °C / 760.05 Torr 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 2 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / pyridine / 2 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 2 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 2 h / 80 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / 2 h / 80 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1192021-85-4
3-chloro-N-[2-hydroxy-5-(trifluoromethyl)pyridin-3-yl]isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 2 h / 20 °C / 760.05 Torr 2: triethylamine / N,N-dimethyl-formamide / 1.5 h / 50 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C 2: triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 - 50 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 - 50 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr 2: triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 - 50 °C / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: triethylamine / N,N-dimethyl-formamide / 50 °C / Cooling with ice View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1192021-96-7
N-[2-hydroxy-5-(trifluoromethyl)pyridin-3-yl]-3-(methoxymethyl)isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / 5% Pd(II)/C(eggshell) / methanol / 2 h / 20 °C / 760.05 Torr 2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 50 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C 2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 50 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr 2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 50 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / N,N-dimethyl-formamide / 3 h / 20 - 50 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 89571-66-4
3-amino-5-trifluoromethyl-2-mercaptopyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1286196-41-5
2-(3-fluoropyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C 4.1: dimethyl sulfoxide / 2 h / 170 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1286196-43-7
2-(3-ethoxypyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C 4.1: dimethyl sulfoxide / 2 h / 170 °C 5.1: potassium carbonate / 8 h / Reflux View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1286196-45-9
2-[3-(2,2-difluoroethoxy)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C 4.1: dimethyl sulfoxide / 2 h / 170 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C 5.2: 1 h / 20 °C / Cooling with ice View Scheme

Yield

Multi-step reaction with 5 steps
1.1: trichlorophosphate; quinoline / 5.5 h / Reflux
1.2: Cooling with ice
2.1: thiourea / ethanol / 5.5 h / 50 °C
2.2: 1.5 h / 20 °C
2.3: Cooling with ice
3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C
4.1: dimethyl sulfoxide / 2 h / 170 °C
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 20 °C
5.2: 1 h / 20 °C / Cooling with ice
View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1286196-46-0
2-[3-(methylthio)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C 4.1: dimethyl sulfoxide / 2 h / 170 °C 5.1: N,N-dimethyl-formamide / 2 h / Cooling with ice View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1286196-47-1
2-[3-(ethylthio)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C 4.1: dimethyl sulfoxide / 2 h / 170 °C 5.1: N,N-dimethyl-formamide / 1 h / Cooling with ice View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

A: 1286196-49-3
2-[3-(ethanesulfinyl)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

B: 1286196-48-2
2-[3-(ethanesulfonyl)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice 3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C 4.1: dimethyl sulfoxide / 2 h / 170 °C 5.1: N,N-dimethyl-formamide / 1 h / Cooling with ice 6.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: trichlorophosphate; quinoline / 5.5 h / Reflux
1.2: Cooling with ice
2.1: thiourea / ethanol / 5.5 h / 50 °C
2.2: 1.5 h / 20 °C
2.3: Cooling with ice
3.1: acetic acid; iron / ethyl acetate; water / 0.17 h / 70 °C
4.1: dimethyl sulfoxide / 2 h / 170 °C
5.1: N,N-dimethyl-formamide / 1 h / Cooling with ice
6.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 1 h / 0 °C
View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 89571-67-5
5-trifluoromethyl-2-mercapto-3-nitropyridine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate; quinoline / 5.5 h / Reflux 1.2: Cooling with ice 2.1: thiourea / ethanol / 5.5 h / 50 °C 2.2: 1.5 h / 20 °C 2.3: Cooling with ice View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1282532-89-1
2-[2-(2,2,2-trifluoroethoxy)-phenyl]-6-trifluoromethyl-oxazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h 3.1: trichlorophosphate / 4 h / 120 °C 3.2: pH 7 / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h / 20 °C 3.1: trichlorophosphate / 4 h / 120 °C 3.2: pH 7 / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h 3.1: trichlorophosphate / 4 h / 120 °C 3.2: pH ~ 7 / Cooling with ice View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h 3.1: trichlorophosphate / 4 h / 120 °C 3.2: pH ~ 7 / Cooling with ice View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1282541-13-2
N-(2-hydroxy-5-trifluoromethylpyridin-3-yl)-3-(2,2,2-trifluoroethoxy)-isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr 2.1: tetrahydrofuran / 22.5 h / 20 °C / Cooling with ice 2.2: 4.5 h View Scheme
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: tetrahydrofuran / 20 °C / Cooling with ice View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1192021-97-8
N-[2-hydroxy-6-(trifluoromethyl)pyridin-3-yl]-isonicotinamide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / 5%-palladium/activated carbon / ethyl acetate / 2 h / 20 °C / 760.05 Torr 2: triethylamine / N,N-dimethyl-formamide / 3.5 h / 20 - 50 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 2-[2-(2,2,2-trifluoroethoxy)phenyl]-6-trifluoromethyloxazolo[5,4-b]pyridine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen / 5%-palladium/activated carbon / methanol / 2 h / 20 °C / 760.05 Torr 2: tetrahydrofuran / 20 °C / Cooling with ice 3: trichlorophosphate / 4 h / 120 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 866775-16-8
3-nitro-5-trifluoromethyl-pyridine-2-carbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2: tetrabutylammomium bromide / toluene / 10 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2: tetrabutylammomium bromide / toluene / 9 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: phosphorus(V) oxybromide / 20 °C / Reflux 2: tetrabutylammomium bromide / toluene / 9 h / Reflux View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 866775-17-9
3-amino-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 10 h / Reflux 3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 18 h / Inert atmosphere 4.1: hydrogenchloride; water / 24 h / Reflux 5.1: sulfuric acid / 48 h / Reflux 5.2: 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 9 h / Reflux 3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h 3.2: 24 h / Reflux 3.3: 84 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: phosphorus(V) oxybromide / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 9 h / Reflux 3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h 3.2: 24 h / Reflux 3.3: 84 h / Reflux View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 866775-18-0
3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 10 h / Reflux 3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 18 h / Inert atmosphere 4.1: hydrogenchloride; water / 24 h / Reflux 5.1: sulfuric acid / 48 h / Reflux 5.2: 20 °C 6.1: bromine; sulfuric acid; acetic acid / water / 20 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 9 h / Reflux 3.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h 3.2: 24 h / Reflux 3.3: 84 h / Reflux 4.1: bromine; acetic acid; sulfuric acid / water / 19.5 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: phosphorus(V) oxybromide / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 9 h / Reflux 3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h 3.2: 24 h / Reflux 3.3: 84 h / Reflux 4.1: bromine; acetic acid; sulfuric acid / water / 19.5 h / 20 °C View Scheme

: 33252-64-1
3-nitro-5-trifluoromethylpyridin-2-ol

: 1334546-75-6
3-amino-6-methoxy-5-trifluoromethylpyridine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-2-methylpropyl)amide

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux 2.1: tetrabutylammomium bromide / toluene / 10 h / Reflux 3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 18 h / Inert atmosphere 4.1: hydrogenchloride; water / 24 h / Reflux 5.1: sulfuric acid / 48 h / Reflux 5.2: 20 °C 6.1: bromine; sulfuric acid; acetic acid / water / 20 h / 20 °C 7.1: toluene-4-sulfonic acid / toluene / 2 h / Reflux 8.1: sodium hydroxide; water / 1 h / 20 °C 8.2: pH 1 9.1: hydroxylamine hydrochloride; triethylamine; ethanol / 5 h / Reflux 10.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 2 h View Scheme
Multi-step reaction with 8 steps 1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C 2.1: tetrabutylammomium bromide; copper(l) cyanide / toluene / 10 h / Reflux 3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h 3.2: 24 h / Reflux 3.3: 48 h / Reflux 4.1: sulfuric acid / water / 0.5 h 4.2: 18 h / 20 °C 5.1: toluene-4-sulfonic acid / toluene / 20 °C / Reflux; Dean-Stark 6.1: sodium hydroxide; methanol / 1 h / 20 °C 7.1: triethylamine; hydroxylamine hydrochloride / water; ethanol / 5 h / Reflux 8.1: HATU; N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h View Scheme

Yield

Multi-step reaction with 10 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C / Reflux
2.1: tetrabutylammomium bromide / toluene / 10 h / Reflux
3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 18 h / Inert atmosphere
4.1: hydrogenchloride; water / 24 h / Reflux
5.1: sulfuric acid / 48 h / Reflux
5.2: 20 °C
6.1: bromine; sulfuric acid; acetic acid / water / 20 h / 20 °C
7.1: toluene-4-sulfonic acid / toluene / 2 h / Reflux
8.1: sodium hydroxide; water / 1 h / 20 °C
8.2: pH 1
9.1: hydroxylamine hydrochloride; triethylamine; ethanol / 5 h / Reflux
10.1: N-ethyl-N,N-diisopropylamine; HATU / 1-methyl-pyrrolidin-2-one / 2 h
View Scheme

Multi-step reaction with 8 steps
1.1: phosphorus(V) oxybromide / acetonitrile / 20 °C
2.1: tetrabutylammomium bromide; copper(l) cyanide / toluene / 10 h / Reflux
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h
3.2: 24 h / Reflux
3.3: 48 h / Reflux
4.1: sulfuric acid / water / 0.5 h
4.2: 18 h / 20 °C
5.1: toluene-4-sulfonic acid / toluene / 20 °C / Reflux; Dean-Stark
6.1: sodium hydroxide; methanol / 1 h / 20 °C
7.1: triethylamine; hydroxylamine hydrochloride / water; ethanol / 5 h / Reflux
8.1: HATU; N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h
View Scheme

3-Nitro-5-(trifluoromethyl)pyridin-2-ol Specification

The 3-Nitro-5-(trifluoromethyl)pyridin-2-ol is an organic compound with the formula C₆H₃F₃N₂O₃. The IUPAC name of this chemical is 3-nitro-5-(trifluoromethyl)-1H-pyridin-2-one. With the CAS registry number 33252-64-1, it is also named as 2-pyridinol, 5-nitro-3-(trifluoromethyl)-. The product's category is Pyridines. Additionally, this chemical should be stored at room temperature.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.62; (4)ACD/LogD (pH 7.4): -1.69; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 10.14; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 66.13 Å²; (13)Index of Refraction: 1.489; (14)Molar Refractivity: 37.31 cm³; (15)Molar Volume: 129.1 cm³; (16)Surface Tension: 39.8 dyne/cm; (17)Enthalpy of Vaporization: 49.27 kJ/mol; (18)Vapour Pressure: 0.0165 mmHg at 25°C; (19)Tautomer Count: 2; (20)Exact Mass: 208.009577; (21)MonoIsotopic Mass: 208.009577; (22)Topological Polar Surface Area: 74.9; (23)Heavy Atom Count: 14; (24)Complexity: 350.

Uses of 3-Nitro-5-(trifluoromethyl)pyridin-2-ol: It is used to produce 2-chloro-3-nitro-5-trifluoromethylpyridine. This reaction needs reagents PCl₅ and POCl₃ at temperature of 80 °C. The yield is 66%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:FC(F)(F)C\1=C\C(=C/NC/1=O)[N+]([O-])=O
2. InChI:InChI=1/C6H3F3N2O3/c7-6(8,9)4-1-3(11(13)14)2-10-5(4)12/h1-2H,(H,10,12)
3. InChIKey:BHUILUYFGJBXHQ-UHFFFAOYAP

Product Name

2-HYDROXY-5-NITRO-3-(TRIFLUOROMETHYL)PYRIDINE

Synthetic route

3-Nitro-5-(trifluoromethyl)pyridin-2-ol Specification

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