3-ethoxy-2-nitropyridine
3-hydroxy-2-nitropyridine
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; water at 90℃; for 12h; | 69% |
3-HYDROXYPYRIDINE
3-hydroxy-2-nitropyridine
Conditions | Yield |
---|---|
With aluminium trinitrate In acetonitrile at 50℃; regioselective reaction; | 60% |
With sulfuric acid; nitric acid at 20 - 30℃; | |
With sulfuric acid; nitric acid at 35 - 50℃; |
3-hydroxy-2-nitropyridine
Conditions | Yield |
---|---|
With sulfuric acid at 50℃; | |
With sulfuric acid at 50℃; |
3-HYDROXYPYRIDINE
3-hydroxy-2-nitropyridine
3-hydroxy-2-nitropyridine
1-(2,6-dichloro-3-fluorophenyl)ethanol
(±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere; | 100% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4h; | 98% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4h; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h; Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h; Stage #2: Ethyl 2-bromopropionate In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h; Stage #2: 2-bromo-pentanoic acid ethyl ester In N,N-dimethyl-formamide | 100% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h; Stage #2: Ethyl 2-bromohexanoate In N,N-dimethyl-formamide | 100% |
3-hydroxy-2-nitropyridine
Diethyl 2-bromomalonate
diethyl 2-[(2-nitro-3-pyridyl)oxy]malonate
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium fluoride In N,N-dimethyl-formamide at 0℃; for 0.5h; Kikelj reaction; Stage #2: Diethyl 2-bromomalonate In N,N-dimethyl-formamide at 20℃; for 24h; | 99% |
3-hydroxy-2-nitropyridine
4,4,4-trifluorobutanol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2.5h; Mitsunobu Displacement; | 99% |
3-hydroxy-2-nitropyridine
1-(2,6-dichloro-3-fluorophenyl)ethanol
3-[(2,6-dichloro-3-fluorophenyl)methoxy]-2-nitropyridine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4h; | 98% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4h; Inert atmosphere; | 98% |
3-hydroxy-2-nitropyridine
6-bromo-2-nitropyridin-3-ol
Conditions | Yield |
---|---|
With bromine; sodium methylate In methanol at 0 - 20℃; for 1h; | 96% |
Stage #1: 3-hydroxy-2-nitropyridine With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: With bromine In methanol at 0℃; for 0.5h; Stage #3: With acetic acid In methanol | 96% |
Stage #1: 3-hydroxy-2-nitropyridine With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: With bromine In methanol at 0℃; for 0.5h; Stage #3: With acetic acid In methanol | 96% |
3-hydroxy-2-nitropyridine
trifluoromethylsulfonic anhydride
2-nitro-3-(trifluoromethylsulfonyloxy)pyridine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 2h; | 95% |
With triethylamine In dichloromethane for 2h; Cooling with ice; | 95% |
With triethylamine In dichloromethane for 2h; Cooling with ice; | 95% |
3-hydroxy-2-nitropyridine
4-methoxy-phenyl-sulphonyl chloride
4-methoxy-benzenesulfonic acid 2-nitro-pyridin-3-yl ester
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane | 95% |
3-hydroxy-2-nitropyridine
(R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; | 95% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere; | 95% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20 - 30℃; Cooling with ice; | 80% |
Stage #1: 3-hydroxy-2-nitropyridine; (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol With triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 30℃; | 80% |
Stage #1: 3-hydroxy-2-nitropyridine; (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol With triphenylphosphine In toluene at 10℃; for 0.166667h; Stage #2: With di-isopropyl azodicarboxylate In toluene at 8 - 25℃; for 5h; | 68.8 g |
3-hydroxy-2-nitropyridine
N,N-Dimethylthiocarbamoyl chloride
N,N-dimethyl-1-[(2-nitropyridin-3-yl)oxy]methanethioamide
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide for 24h; | 93% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h; | 69% |
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 24h; | |
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 24h; |
3-hydroxy-2-nitropyridine
C9H9Cl2FO3S
(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran for 4h; Reagent/catalyst; Solvent; Temperature; Reflux; | 92.1% |
3-hydroxy-2-nitropyridine
(S)-Ethyl lactate
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine; (S)-Ethyl lactate With triphenylphosphine In dichloromethane at 20℃; for 0.3h; Stage #2: With di-isopropyl azodicarboxylate In dichloromethane at 20℃; for 16h; | 92% |
3-hydroxy-2-nitropyridine
8-azido-3,6-dioxaoctyl tosylate
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 8-azido-3,6-dioxaoctyl tosylate In N,N-dimethyl-formamide at 90℃; for 48h; | 92% |
ethyl 2-bromoisobutyrate
3-hydroxy-2-nitropyridine
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h; Reagent/catalyst; Solvent; Temperature; | 91.57% |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide for 0.333333h; | 90.9% |
3-hydroxy-2-nitropyridine
(2,6-dichloro-3-fluorophenyl)methanol
3-[(2,6-dichloro-3-fluorophenyl)methoxy]-2-nitropyridine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 16h; Mitsunobu Displacement; Inert atmosphere; | 90% |
3-hydroxy-2-nitropyridine
(S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol
(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 13h; | 88.3% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 13h; | 88.3% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 88% |
3-hydroxy-2-nitropyridine
(R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol
(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine; (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol With triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 0℃; for 12h; | 88.3% |
3-hydroxy-2-nitropyridine
2,4-Dichlorobenzyl chloride
3-((2,4-dichlorobenzyl)oxy)-2-nitropyridine
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 90℃; for 2h; Inert atmosphere; | 88% |
With caesium carbonate In acetonitrile at 90℃; for 2h; | 88% |
2-bromo-2-methylpropionic acid methyl ester
3-hydroxy-2-nitropyridine
methyl 2-methyl-2-[(2-nitropyridin-3-yl)oxy]propanoate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide | 87% |
3-hydroxy-2-nitropyridine
B
3-[(R)-1-(5-fluoro-2-methoxyphenyl)ethoxy]-2-nitropyridine
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃; | A n/a B 86% |
1-(pyridine-2-yl)ethanol
3-hydroxy-2-nitropyridine
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-2-nitropyridine; C12H16FNO2 With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 20℃; Inert atmosphere; Stage #2: With zinc(II) chloride In ethanol at 20℃; for 5h; Solvent; | 85% |
3-hydroxy-2-nitropyridine
methyl (3,4,5-tri-O-acetyl-β-D-arabino-hex-2-ulopyranosyl)onate bromide
Conditions | Yield |
---|---|
With potassium carbonate In acetone Heating; | 82% |
3-hydroxy-2-nitropyridine
epichlorohydrin
2-nitro-3-oxiranylmethoxypyridine
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 72h; | 81% |
With potassium carbonate In acetonitrile |
The 3-Hydroxy-2-nitropyridine, with the CAS registry number 15128-82-2 and EINECS registry number 239-191-2, has the systematic name of 2-nitropyridin-3-ol. It is a kind of yellow crystalline powder, and belongs to the following product categories: Nitro; Blocks; Nitro Compounds; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivates; Chiral chemicals. And the molecular formula of this chemical is C5H4N2O3.
The physical properties of 3-Hydroxy-2-nitropyridine are as followings: (1)ACD/LogP: 0.93; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.16; (4)ACD/LogD (pH 7.4): -1.82; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 6.14; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 67.94 Å2; (13)Index of Refraction: 1.623; (14)Molar Refractivity: 32.77 cm3; (15)Molar Volume: 92.9 cm3; (16)Polarizability: 12.99×10-24cm3; (17)Surface Tension: 73.3 dyne/cm; (18)Density: 1.507 g/cm3; (19)Flash Point: 185.6 °C; (20)Enthalpy of Vaporization: 65.65 kJ/mol; (21)Boiling Point: 383.2 °C at 760 mmHg; (22)Vapour Pressure: 2.02E-06 mmHg at 25°C.
Uses of 3-Hydroxy-2-nitropyridine: It can react with sulfuric acid dimethyl ester to produce 3-methoxy-2-nitro-pyridine. This reaction will need reagent K2CO3, and the solvent acetone. The reaction time is 2 hours with heating, and the yield is about 61%.
You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(nc1)[N+](=O)[O-])O
(2)InChI: InChI=1/C5H4N2O3/c8-4-2-1-3-6-5(4)7(9)10/h1-3,8H
(3)InChIKey: QBPDSKPWYWIHGA-UHFFFAOYAW
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 180mg/kg (180mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04089, |
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