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CAS No. : | 75711-00-1 | MDL No. : | MFCD06658397 |
Formula : | C6H5ClN2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XXGPBLSIXOYNEM-UHFFFAOYSA-N |
M.W : | 188.57 | Pubchem ID : | 23456152 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 44.56 |
TPSA : | 67.94 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.31 cm/s |
Log Po/w (iLOGP) : | 1.24 |
Log Po/w (XLOGP3) : | 1.61 |
Log Po/w (WLOGP) : | 1.65 |
Log Po/w (MLOGP) : | 0.47 |
Log Po/w (SILICOS-IT) : | -0.13 |
Consensus Log Po/w : | 0.97 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.26 |
Solubility : | 1.03 mg/ml ; 0.00548 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.423 mg/ml ; 0.00225 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.15 |
Solubility : | 1.33 mg/ml ; 0.00705 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 3.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.33 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: With water; tin(ll) chloride In ethyl acetate at 20℃; for 1 h; Stage #2: With sodium hydroxide In water; ethyl acetate |
To a stirred solution of 2-chloro-3-(methyloxy)-5-nitropyridine (3.00 g, 15.90 mmol) in EtOAc (75 ml) was added SnCl2 dihydrate (21.54 g, 95.00 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH and extracted with EtOAc (5.x.75 ml). The collected organic layers were washed with water (3.x.75 ml), dried (Na2SO4), filtered and evaporated under reduced pressure to give the title compound D46 (2.34 g, 14.80 mmol, 93percent yield) as a brown solid.UPLC: rt=0.43 min, peaks observed: 159 (M+1, 100percent) and 161 (M+1, 33percent). C6H7ClN2O requires 158.1H NMR (400 MHz, DMSO-d6) δ (ppm): 7.29 (d, 1H), 6.71 (d, 1H), 5.50 (bs, 2H), 3.77 (s, 3H). |
78% | Stage #1: With hydrogenchloride; tin(ll) chloride In water at 5 - 80℃; for 1.25 h; Stage #2: With sodium hydroxide In water |
2-chloro-3-methoxy-5-nitropyridine (2.8 g, 14.9 mmol) was dissolved in concentrated HCl (30 mL) at 5 0C, tin chloride (10.0 g) was added and stirred at 5 0C for 15 min and then heated at 80 0C for 1 h. The reaction mixture was cooled and neutralized with 20 percent NaOH until pH 8, extracted with EtOAc, washed with water and dried with sodium sulfate and evaporated to obtain a brown solid (1.83 g, 78 percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 100℃; for 2h; | To a solution of <strong>[75711-00-1]2-chloro-3-methoxy-5-nitro-pyridine</strong> (0.10 g, 0.53 mmol, 1.0 equiv) and {4-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (0.2 g, 0.56 mmol, 1.05 equiv) in 5 Ml DME was added 0.5 Ml saturated potassium carbonate solution and 10 mg Pd(PPh3)4 catalyst. The reaction was heated to 100 C for 2 h. The crude reaction mixture was then concentrated in vacuo and then loaded directly onto a silica gel column. Elution with 30% EtOAc/hexanes afforded the title compound: 1 H NMR (400 MHz, DMSO-d6) delta ppm 1.12 - 1.19 (m, 2 H) 1.15 (d, J=13.14 Hz, 1 H) 1.46 - 1.59 (m, 1 H) 1.51 (dd, J=12.38, 2.78 Hz, 2 H) 1.81 (d, J=5.56 Hz, 4 H) 2.26 (d, J=6.82 Hz, 2 H) 3.61 (s, 3 H) 4.00 (s, 3 H) <n="109"/>501337.36 (d, J=8.34 Hz, 2 H) 7.90 (d, J=8.34 Hz1 2 H) 8.20 (d, J=2.02 Hz, 1 H) 9.05 (s, 1 H); (M+H)+385.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With ammonia; In ethanol; water; at 80℃; | Intermediate 60; Preparation of (7-amino-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol; 2-amino-3-methoxy-5-nitropyridine Into a 250 mL sealed tube were combined <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> (0.50 g, 0.00265 mol), concentrated ammonium hydroxide (5 mL, 0.1 mol) and ethanol (20 mL). The mixture was heated to 80 C. and stirred overnight. After allowing to cool to room temperature, the mixture was reduced in vacuo and the residue was taken up in ethyl acetate (50 mL), then washed with equal amounts of brine and water (1×50 mL each). The organic layer was dried (Na2SO4), filtered and concentrated under vacuum to leave a solid (0.312 g, 69%) which was used directly in the next step without further purification. LC-MS 1.94 min. M/Z=171.0 (M+1). |
69% | With ammonia; In ethanol; water; at 80℃; | Intermediate 23 Preparation of (7-amino-3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-3-yl)methanol 2-amino-3-methoxy-5-nitropyridine; Into a 250 mL sealed tube were combined <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> (0.50 g, 0.00265 mol), concentrated ammonium hydroxide (5 mL, 0.1 mol) and ethanol (20 mL). The mixture was heated to 80 C. and stirred overnight. After allowing to cool to room temperature, the mixture was reduced in vacuo and the residue was taken up in ethyl acetate (50 mL), then washed with equal amounts of brine and water (1×50 mL each). The organic layer was dried (Na2SO4), filtered and concentrated under vacuum to leave a solid (0.312 g, 69%) which was used directly in the next step without further purification. LC-MS 1.94 min. M/Z=171.0 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With phosphorus pentachloride; trichlorophosphate; for 4h;Reflux; | 3-Methoxy-5-nitropyridin-2-ol (1.043 g, 6.13 mmol) and phosphorus pentachloride (0.638 g, 3.07 mmol) was dissolved in phosphoryl chloride (1.71 ml_). The reaction mixture was refluxed for 4 h. After cooling to room temperature, the reaction mixture was poured to crushed ice and stirred for 30 min. Then the mixture was basified by using Na2C03 to pH 7. The solution was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to afford the crude which was purified by column chromatography to give 2-chloro-3-methoxy-5-nitropyridine (920 mg, 80 %). |
80% | With phosphorus pentachloride; trichlorophosphate; In trichlorophosphate; for 4h;Reflux; | Step 2 3-Methoxy-5-nitropyridin-2-ol (1.043 g, 6.13 mmol) and phosphorus pentachloride (0.638 g, 3.07 mmol) was dissolved in phosphoryl chloride (1.71 mL). The reaction mixture was refluxed for 4 h. After cooling to room temperature, the reaction mixture was poured to crushed ice and stirred for 30 min. Then the mixture was basified by using Na2CO3 to pH 7. The solution was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to afford the crude which was purified by column chromatography to give 2-chloro-3-methoxy-5-nitropyridine (920 mg, 80%). |
With phosphorus pentachloride; trichlorophosphate; at 100℃; for 2.5h;Heating / reflux; | The above compound from Step A (3.3 g, 0.019 mol) was mixed with PCl5 (3.0 g) and POCl3 (23 mL) and refluxed for 2.5 h at 100 0C. A dark green solution resulted which was cooled and the POCl3 evaporated off. The mix was then poured into ice-water and the precipitate formed was filtered and washed with water and dried to provide 2.83 g of product as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | To an ice water cooled suspension of sodium hydride (60% in oil) (0.919 g, 22.98 mmol) in DMA (20 mL) was added a solution of (ls,4s)-4-hydroxycyclohexanecarboxylic acid (1.506 g, 10.45 mmol) in DMA (20 mL) over a period of 4 minutes under nitrogen. The resulting suspension was stirred at 0 0C for 1 hour. A solution of 2-chloro-3-methoxy-5- nitropyridine (1.97 g, 10.45 mmol) in DMA (10 mL) was added and the resulting mixture was stirred at ambient temperature over the weekend. The reaction mixture was concentrated, water (50 mL) was added and the mixture was was acidified with 2M HCl. The precipitate was collected by filtration and dried under vacuum to afford (lr,4r)-4-(3- methoxy-5-nitropyridin-2-yloxy)cyclohexanecarboxylic acid (2.91 g, 94 %) as a brown solid, which was used without further purification. 1H NMR (400 MHz, DMSO) delta 1.66 - 1.88 (8H, m), 2.36 - 2.43 (IH, m), 3.92 (3H, s), 5.30 - 5.35 (IH, m), 7.91 (IH, s), 8.65 (IH, s). m/z 295 (M-H)". |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 18-crown-6 ether; potassium carbonate; In acetonitrile;Reflux; | 2-Chloro-3-methoxy-5-nitropyridine (400 mg, 2.12 mmol), pyrrolidine (0.21 ml_, 2.55 mmol), potassium carbonate (880 mg, 6.38 mmol) and 1 ,4,7,10,13,16- hexaoxacyclooctadecane (80 mg) was dissolved in acetonitrile. The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and then was concentrated under reduced pressure. Then the mixture was extracted with ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give 3-methoxy-5-nitro-2-(pyrrolidin-1-yl)pyridine (458 mg, 97 %). |
97% | With 18-crown-6 ether; potassium carbonate; In acetonitrile;Reflux; | Step 3 2-Chloro-3-methoxy-5-nitropyridine (400 mg, 2.12 mmol), pyrrolidine (0.21 mL, 2.55 mmol), potassium carbonate (880 mg, 6.38 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (80 mg) was dissolved in acetonitrile. The reaction mixture was refluxed overnight. The reaction mixture was cooled to room temperature and then was concentrated under reduced pressure. Then the mixture was extracted with ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give 3-methoxy-5-nitro-2-(pyrrolidin-1-yl)pyridine (458 mg, 97%). |
In N,N-dimethyl-formamide; at 100℃; for 4h; | 5.1 3-Methoxy-5-nitro-2-(pyrrolidin-1-yl)pyridine A solution of 3 g (15.91 mmol) of <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> and 2 ml (23.86 mmol) of pyrrolidine in 30 ml of dimethylformamide is heated at 100 C. for 4 hours. The reaction mixture is subsequently concentrated under reduced pressure and then taken up in 100 ml of water and extracted three times with 100 ml of ethyl acetate. The organic phases are combined, then washed twice with 50 ml of water then once with 50 ml of a saturated sodium chloride solution, dried over sodium sulfate and then concentrated under reduced pressure. 3.47 g of the expected compound are thus isolated in the form of an orangey powder. 1H NMR (DMSO D6), delta (ppm): 1.9 (m, 4H); 3.79 (m, 4H); 3.88 (s, 3H); 7.62 (s, 1H); 8.69 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With potassium hydroxide; In dimethyl sulfoxide; at 80℃; for 5h; | A mixture of 4-chloro-lH-imidazole (2.72 g, 26.5 mmol), 2- chloro-3-methoxy-5-mtropyridme (5.0 g, 26.5 mmol), and KOH flakes 1.488 g, 26.5 mmol) in anhydrous DMSO (25 mL) was heated at 800C for 5 h. The reaction mixture was allowed to cool to rt and was poured into 1.0 L of water with vigorous stirring. The mixture was stirred at rt for 16 h. The precipitate was collected by vacuum filtration using a coarse sintered glass funnel. The solid was dried under high vacuum for 24 h to provide 2-(4-chloro- 1 H-imidazol- l-yl)-3-methoxy- 5- nitropyridine (5.22 g, 20.50 mmol, 77 % yield) as a light brown solid. LC-MS (M+H)+ = 255.0. 1H NMR (500 MHz, DMSO-^6) delta ppm 8.94 (d, J=2.44 Hz, 1 H) 8.51 (d, J=I.83 Hz, 1 H) 8.42 (d, J=2.44 Hz, 1 H) 8.02 (d, J=I.83 Hz, 1 H) 4.12 (s, 3 H). |
77% | With potassium hydroxide; In dimethyl sulfoxide; at 80℃; for 5h; | 2-(4-chloro- 1 H-imidazol- 1 -yl)-3 -methoxy-5 -nitropyridine A mixture of 4-chloro-lH-imidazole (2.72 g, 26.5 mmol), 2-chloro-3-methoxy-5- nitropyridine (5.0 g, 26.5 mmol), and KOH flakes 1.488 g, 26.5 mmol) in anhydrous DMSO (25 mL) was heated at 80 0C for 5 h. The reaction mixture was allowed to cool to rt and was poured into 1.0 L of water with vigorous stirring. The mixture was stirred at rt for 16 h. The precipitate was collected by vacuum filtration using a coarse sintered glass funnel. The solid was dried under high vacuum for 24 h to provide 2-(4-chloro-lH- imidazol-l-yl)-3-methoxy-5-nitropyridine (5.22 g, 20.50 mmol, 77 % yield) as a light brown solid. LC-MS (M+H)+ = 255.0. 1H NMR (500 MHz, DMSO-d6) delta ppm 8.94 (d, J=2.44 Hz, 1 H) 8.51 (d, J=I.83 Hz, 1 H) 8.42 (d, J=2.44 Hz, 1 H) 8.02 (d, J=I.83 Hz, 1 H) 4.12 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With potassium carbonate; In dimethyl sulfoxide; at 20 - 45℃; | Example 43 b. 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine To a suspension of 4-methyl-lH-imidazole (0.522 g, 6.36 mmol) and potassium carbonate (1.832 g, 13.26 mmol) in DMSO (20 mL) at room temperature was added 2-chloro-3- methoxy-5-nitropyridine (1.0 g, 5.30 mmol). The reaction mixture was stirred at 45C overnight. About 20 mL warm water (heated to 500C) was added to the reaction mixture and the precipitated solid was immediately filtrated and washed with warm water. The solid was dried in the dry vacuum oven at 400C for two days giving 0.914 g of the title compound as an isomeric mixture (74 % Yield). 1H NMR (400 MHz, DMSO-J6) delta ppm 8.90 - 8.94 (m, 1 H), 8.45 (s, 1 H), 8.32 - 8.37 (m, 1 H), 7.66 - 7.70 (m, 1 H), 4.10 (s, 3 H), 2.15 - 2.20 (m, 3 H). MS m/z 235 [M+H] +. |
72% | With potassium carbonate; In dimethyl sulfoxide; at 45℃; for 16h;Inert atmosphere; | Synthesis of 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine [0328] To a stirred solution of <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> (2 g, 10.60 mmol) in DMSO (40 mL) under argon atmosphere were added potassium carbonate (3.65 g, 26.51 mmol) and 4-methyl-lH-imidazole (1 g, 12.72 mmol) at RT. The reaction mixture was stirred at 45 C for 16 h. After consumption of the starting materials (monitored by TLC), the reaction was diluted with hot water (40 mL). The obtained solid was filtered and dried in vacuo to afford 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine (1.8 g, 72%) as a yellow solid. 1H-NMR (DMSO-<, 400 MHz): delta 8.92-8.90 (m, 1H), 8.45 (s, 1H), 8.36-8.32 (m, 1H), 7.68 (s, 1H), 4.10 (s, 3H), 2.20 (s, 3H); LC-MS: 235 (M+l); (column; X-Bridge C- 18 (50 3.0 mm, 3.5 mu); RT 2.09 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH:CH2Cl2 (R 0.4). |
72% | With potassium carbonate; In dimethyl sulfoxide; at 20 - 45℃; for 16h;Inert atmosphere; | To a stirred solution of <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> (2 g, 10.60 mmol) in DMSO (40 mL) under an argon atmosphere were added potassium carbonate (3.65 g, 26.51 mmol) and 4-methyl-1H-imidazole (1 g, 12.72 mmol) at room temperature. The reaction mixture was stirred at 45 oC for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (40 mL) to obtain solid which was filtered and dried in vacuo to afford 3-methoxy-2-(4-methyl-1H-imidazol-1 -yl)-5- nitropyridine (1.8 g, 72%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.92-8.90 (m, 1H), 8.45 (s, 1H), 8.36-8.32 (m, 1H), 7.68 (s, 1H), 4.10 (s, 3H), 2.20 (s, 3H); LC-MS: 235 (M+1); (column; X-Bridge C-18 (50 × 3.0 mm, 3.5 mum); RT 2.09 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/ CH2Cl2 (Rf: 0.4). |
72% | With potassium carbonate; In dimethyl sulfoxide; at 45℃; for 16h;Inert atmosphere; | Synthesis of 3-methoxy-2-(4-methyl-1H-imidazol-1-yl)-5-nitropyridine To a stirred solution of <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> (2 g, 10.60 mmol) in DMSO (40 mL) under an argon atmosphere were added potassium carbonate (3.65 g, 26.51 mmol) and 4-methyl-1H-imidazole (1 g, 12.72 mmol) at room temperature. The reaction mixture was stirred at 45 C. for 16 h. After consumption of the starting material (monitored by TLC), the reaction mixture was diluted with water (40 mL) to obtain solid which was filtered and dried in vacuo to afford 3-methoxy-2-(4-methyl-1H-imidazol-1-yl)-5-nitropyridine (1.8 g, 72%) as a yellow solid. 1H-NMR (DMSO-d6, 400 MHz): delta 8.92-8.90 (m, 1H), 8.45 (s, 1H), 8.36-8.32 (m, 1H), 7.68 (s, 1H), 4.10 (s, 3H), 2.20 (s, 3H); LC-MS: 235 (M+1); (column; X-Bridge C-18 (50*3.0 mm, 3.5 mum); RT 2.09 min. 0.05% aq TFA: ACN; 0.80 mL/min); TLC: 5% MeOH/CH2Cl2 (Rf: 0.4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35.5% | In tetrahydrofuran; at 20℃; | Example 6(3-(2-chlorophenyl)-5-methylisoxazol-4-yl)(4-(3-methoxy-5-nitropyridin-2-yl)piperazin- -yl)methanoneA solution of Amine-E (30 mg, 0.098 mmol), triethylamine (14.89 mg, 0.147 mmol), and <strong>[75711-00-1]2-chloro-3-methoxy-5-nitropyridine</strong> (18.50 mg, 0.098 mmol) in THF (1.5 mL) was stirred at rt overnight. HPLC purification gave the title compound (16.1mg, 0.035 mmol, 35.5 % yield), yellow solid. ^- MR^CDsOD, 500MHz) 88.64 (1H, s), 7.82 (1H, s), 7.48- 7.56(4H, m), 3.92(3H,s), 3.70 (4H,s), 3.36(4H,s), 2.57(3H,s). HPLC/MS (Method K):(ES+) m/z (M+H)+ = 458; Rt = 1.47 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 0 - 27℃; for 0.5h; | Step 1 : Preparation of te/f-butyl (3-methoxy-5-nitropyridin-2-yl)methylcarbamate 2-Chloro-3-methoxy-5-nitropyridine (8.00 g, 43.4 mmol) was added portion-wise to a 35% solution of methylamine in EtOH (14 mL). After standing for 10 min the mixture was cooled to 0C and further 35% methylamine in EtOH (14 mL) was added. After stirring at rt for 20 min ice/water (-28 mL) was added. The mixture was cooled to 0C, stirred vigorously and then allowed to stand for 15 min. The resulting solids were isolation by filtration, washed with H20 and dried to yield crude 3-methoxy-N- methyl-5-nitropyridin-2-amine (7.81 g) which was used without further purification. 1H NMR: (400 MHz, CDCI3) delta: 3.13 (d, J=5.0, 3H), 3.92 (s, 3H), 5.71 (br. s, 1 H), 7.52 (d, J=2.3, 1 H), 8.76 (d, J=2.3, 1 H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium; at 20℃; for 1h; | Freshly cut sodium (0.6 g, 26 mmol) was added portionwise to MeOH (50 mL), and the mixture was stirred at room temperature until the sodium dissolved. Compound 73 (3.0 g, 15.9 mmol) was added, and the reaction mixture was stirred at room temperature for 1 h. Water (100 mL) was added, and the mixture was filtered. The solids were washed with water and dried to give Compound 74 (2.78 g, 95% yield). MS for C7H8N2O4, found 185 (MH+). |
Step 1: 2,3-Dimethoxy-5-nitropyridine A round bottom flask was charged with methanol under nitrogen. Freshly cut sodium (91 mg, 3977 mumol) was added, and the mixture was stirred at RT under nitrogen until the sodium had dissolved. 2-Chloro-3-methoxy-5-nitropyridine (500 mg, 2652 mumol) was added and the reaction mixture was stirred under nitrogen at RT. After ?15 min the mixture became heterogeneous and thick, and GC/MS analysis of a sample taken at 0.5 h indicated complete conversion to the desired product. The mixture was diluted with DCM and water and the layers were separated. The aqueous portion was extracted with additional DCM and the combined organics were dried, filtered and concentrated. The crude solid was passed through a silica plug using 5% MeOH/DCM. The filtrate was concentrated to provide 2,3-dimethoxy-5-nitropyridine as a light yellow solid. MS [M+H]=185. |
Tags: 75711-00-1 synthesis path| 75711-00-1 SDS| 75711-00-1 COA| 75711-00-1 purity| 75711-00-1 application| 75711-00-1 NMR| 75711-00-1 COA| 75711-00-1 structure
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P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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