*Storage:
*Shipping:
4.5
*For Research Use Only !
Change View
Size | Price | USA Stock *0-1 Day | Global Stock *5-7 Days | In Stock |
250mg | łÇǶÊÊ | Inquiry | Inquiry | |
1g | łË˶ÊÊ | Inquiry | Inquiry | |
5g | łÍ§¶ÊÊ | Inquiry | Inquiry | |
10g | łóǶÊÊ | Inquiry | Inquiry | |
25g | łËÊʶÊÊ | Inquiry | Inquiry | |
100g | łďÇò¶ÊÊ | Inquiry | Inquiry |
łÇǶÊÊ
łË˶ÊÊ
łÍ§¶ÊÊ
łóǶÊÊ
łËÊʶÊÊ
łďÇò¶ÊÊ
In Stock
- +
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 136888-20-5 |
Formula : | C5H3FN2O3 |
M.W : | 158.09 |
SMILES Code : | O=C1C([N+]([O-])=O)=CC(F)=CN1 |
MDL No. : | MFCD05662412 |
InChI Key : | BLFUHTOZIOQGBU-UHFFFAOYSA-N |
Pubchem ID : | 10583047 |
GHS Pictogram: | ![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 11 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 4.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 35.84 |
TPSA ? Topological Polar Surface Area: Calculated from | 78.68 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from | 0.45 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by | 0.06 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from | 0.84 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from | -0.42 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by | -0.13 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions | 0.16 |
Log S (ESOL):? ESOL: Topological method implemented from | -1.2 |
Solubility | 10.1 mg/ml ; 0.0637 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (Ali)? Ali: Topological method implemented from | -1.27 |
Solubility | 8.57 mg/ml ; 0.0542 mol/l |
Class? Solubility class: Log S scale | Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by | -1.58 |
Solubility | 4.16 mg/ml ; 0.0263 mol/l |
Class? Solubility class: Log S scale | Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg | High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg | No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) | No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) | No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) | No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) | No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) | No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) | No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from | -7.22 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from | 0.0 |
Ghose? Ghose filter: implemented from | None |
Veber? Veber (GSK) filter: implemented from | 0.0 |
Egan? Egan (Pharmacia) filter: implemented from | 0.0 |
Muegge? Muegge (Bayer) filter: implemented from | 1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat | 0.55 |
PAINS? Pan Assay Interference Structures: implemented from | 0.0 alert |
Brenk? Structural Alert: implemented from | 2.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from | No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) | 2.02 |
* 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 |
---|---|---|
43% | With sulfuric acid; nitric acid; at 85℃;Cooling with ice; | a) 5-Fluoro-3-nitropyridin-2-ol A mixture of concentrated sulphuric acid (1 mL) and fuming nitric acid (1 mL) was added dropwise to a stirred, cooled (ice-bath) mixture of 5-fluoropyridin-2-ol (1.20 g, 10.6 mmol) and concentrated sulphuric acid (2.7 mL). The mixture was warmed to ambient temperature and then to 85 C. After 2 hours, the mixture was cooled and poured onto ice-water. The precipitate was filtered and dried to give the title compound (0.72 g, 43%) as a yellow solid. LRMS (m/z): 157 (M-1)+. 1H NMR delta (300 MHz, DMSO-d6): 8.28 (s, 1H), 8.67 (s, 1H). |
43% | With sulfuric acid; nitric acid; at 85℃; for 2h;Cooling with ice; | 5-Fluoro-2-methoxypyridin-3 -amine a) 5-Fluoro-3-nitropyridin-2-olA mixture of concentrated sulphuric acid (1 mL) and fuming nitric acid (1 mL) was added dropwise to a stirred, cooled (ice-bath) mixture of 5-fluoropyridin-2-ol (1 .20 g, 10.6 mmol) and concentrated sulphuric acid (2.7 mL). The mixture was warmed to ambient temperature and then heated to 85 C. After 2 hours, the mixture was cooled and poured onto ice-water. The precipitate was filtered and dried to give the title compound (0.72 g, 43%) as a yellow solid.LRMS (m/z): 157 (M-1 )+.1H NMR delta (300 MHz, DMSO-d6): 8.28 (s, 1 H), 8.67 (s, 1 H). |
40% | With sulfuric acid; nitric acid; at 28 - 65℃; for 2.75h; | To a solution of 5-fluoro-2-hydroxypyridine (200 mg, 1.77 mmol) in concentrated sulfuric acid (900 mul) was added, dropwise over 15 minutes, a premixed solution of concentrated sulfuric acid (900 mul) and fuming nitric acid (170 mul). The internal temperature rose by up to 280C. The reaction mixture was then heated at 650C for 2.5 hours. The cooled mixture was poured onto ice-water, and the pH of the mixture was adjusted to 2.5 with sodium carbonate. It was then extracted with ethyl acetate (2 x 25 ml). The aqueous layer was concentrated and extracted again with a mixture of tetrahydrofuran (25 ml) and ethyl acetate (25 ml). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title compound (112 mg, 40%) as a solid. 1H NMR (400MHz, DMSO-D6): delta 8.22 (dd, 1 H), 8.60 (dd, 1 H); LRMS APCI" m/z 157 [M-H]'. |
With sulfuric acid; nitric acid; In water; at 65 - 80℃; for 1h; | The solid from above containing (4-80) was divided in 4 batches and treated with H2SO4 and fuming HNO3 as shown below. The amounts used were: Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed 4-80 and something else (discarded)). [1493] The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80 [1494] Total:117.0+3.6+6.23 =126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). [1495] Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. [1496] Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEtA different product was obtained. No desired product in these extracts. | |
With sulfuric acid; nitric acid; at 20 - 80℃; for 1h; | Intermediate 3 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed intermediate 4 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford intermediate 4 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of intermediate 4; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product intermediate 4. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. | |
With sulfuric acid; nitric acid; In water; at 65 - 80℃; | Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM showed 4-80 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEt A different product was obtained. No desired product in these extracts. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With benzyltrimethylammonium chloride; trichlorophosphate; In acetonitrile; at 80℃; for 6h; | a) Synthesis of 2-chloro-5-fluoro-3-nitro-pyridine 5-fluoro-3-nitro-pyridin-2-ol (2 g, 12.7 mmol) and benzyltrimethyl ammonium chloride (1.17 g, 6.35 mmol) were dissolved in acetonitrile, and phosphorus oxychloride (3.5 ml, 38.1 mmol) was added thereto and stirred at 80 C. for 6 hours. The reaction mixture was cooled and poured into ice water to quench the reaction, and extracted with dichloromethane. The combined organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluding with a solvent of dichloromethane:methanol=30:1. The fractions containing the product were collected and evaporated to obtain yellow liquid (1.57 g, 70%). 1H-NMR (CDCl3, 300 MHz); delta=8.56 (d, J=2.7 Hz, 1H), 8.40 (dd, J=6.5 Hz, 2.7 Hz, 1H). MS (ESI); 176.9 (M++1). |
69% | With tetraethylammonium chloride; trichlorophosphate; In acetonitrile; at 90℃; for 24h; | PREPARATION 53 2-Chloro-5-fluoro-3-nitropyridine 5-Fluoro-3-nitro-pyridin-2-ol (1.00 g, 5.33 mmol) was dissolved in acetonitrile (40 mL) and tetraethylammonium chloride (2.10g, 12.65 mmol) was added. The mixture became clear, phosphorous oxytrichloride (1.94 g, 12.65 mmol) was added at room temperature and the mixture was heated at 90 ºC for 24h. The reaction mixture was evaporated to dryness; the residue was taken up with water (100 mL) and extracted with ethyl acetate (2x100 mL). The organic layer was dried with sodium sulfate, filtered and evaporated to dryness. A yellow solid (0.90 g, 69%) was isolated, pure enough to perform the next synthetic step. LRMS (m/z): 177 (M+1)+ |
41% | With trichlorophosphate;N,N-dimethyl-formamide; at 110℃; for 18h; | A mixture of the pyridine of preparation 55 (105 mg, 0.66 mmol), phosphorus oxychloride (1 ml) and Lambda/,Lambda/-dimethyIformamide (10 mul, catalytic) was heated at 11O0C for 18 hours. The cooled reaction mixture was then concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using dichloromethane/acetonitrile as eluant (100:0 to 50:50 v/v) to yield the title compound (48 mg, 41%) as a solid. 1H NMR (400MHz, CDCI3): delta 8.03 (dd, 1 H), 8.55 (d, 1 H). |
With trichlorophosphate; In 1,2-dimethoxyethane; at 110℃; for 5h; | In Step B, compound zz2' (500 mg, 3.16 mmol) was dissolved in phosphorous oxychloride (1.7 mL, 18.9 mmol) and dimethoxyethane at room temperature. The reaction was heated to 110 C. for 5 hours. The excess phosphorous oxychloride was then removed by concentrating the reaction mixture in vacuo. The residue was chromatographed on silica gel, eluted with chloroform (100%) to afford 176 mg of product zz3'. | |
With tetraethylammonium chloride; trichlorophosphate; In acetonitrile; at 20 - 90℃; for 24h; | 5-Fluoro-3-nitro-pyridin-2-ol (1 .00 g, 5.33 mmol) was dissolved in acetonitrile (40 mL) and tetraethylammonium chloride (2.1 Og, 12.65 mmol) was added. The mixture became clear, phosphorous oxytrichloride (1 .94 g, 12.65 mmol) was added at room temperature and the mixture was heated at 90 C for 24h. The reaction mixture was evaporated to dryness; the residue was taken up with water (100 mL) and extracted with ethyl acetate (2x100 mL). The organic layer was dried with sodium sulphate, filtered and evaporated to dryness. A yellow solid (0.90 g, 69%) was isolated, pure enough to perform the next synthetic step.LRMS (m/z): 177 (M+1 )+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With N,N-dimethyl-formamide; phosphorus(V) oxybromide; at 20 - 110℃; for 3.08333h; | A total of 117 g of 5-80 was divided in 4 batches of 30 g×3 and 27 g×1 and treated with POBr3 (3 equiv.; 163 g×3 and 155 g×1) and a catalytic amount of DMF (15 ml) at rt (DMF was added carefully gas evolution). After 5 min. at room temperature, the solutions were heated at 110 C. for 3 hr. LC/MS showed starting material had been consumed. The reaction mixtures were allowed to cool to rt. The reaction flasks were placed in an ice bath; and then ice was added very slowly and carefully portionwise into the flask, gas evolution was due to HBr formation; the liquid and black solid that formed was poured into a beaker with ice. EtOAc was added and the mixture was then extracted several times with EtOAc. The organic layer was washed with saturated aq. NaHCO3; H2O and brine; dried over Na2SO4 and filtered. The product was dried in the pump overnight to provide 123 g of 6-80 as a brown solid (77% yield). [1498] Note: Reaction is completed within 1 h. [1499] 1HNMR(delta, CDCl3):8.52 (m, 1H), 7.93 (m, 1H). |
77 - 97% | With phosphorus(V) oxybromide;N,N-dimethyl-formamide; at 20 - 110℃; for 3h; | A total of 117 g of intermediate 4 was divided in 4 batches of 30 g×3 and 27 g×1 and treated with POBr3 (3 equiv.; 163 g×3 and 155 g×1) and a catalytic amount of DMF (15 ml) at rt (DMF was added carefullygas evolution). After 5 min. at room temperature, the solutions were heated at 110 C. for 3 hr. LC/MS showed starting material had been consumed. The reaction mixtures were allowed to cool to rt. The reaction flasks were placed in an ice bath; and then ice was added very slowly and carefully portionwise into the flask, gas evolution was due to HBr formation; the liquid and black solid that formed was poured into a beaker with ice. EtOAc was added and the mixture was then extracted several times with EtOAc. The organic layer was washed with saturated aq. NaHCO3; H2O and brine; dried over Na2SO4 and filtered. The product was dried in the pump overnight to provide 123 g of intermediate 5 as a brown solid (77% yield). Note: Reaction is completed within 1 h. 1HNMR(delta, CDCl3):8.52 (m, 1H), 7.93 (m, 1H). |
77% | With phosphorus(V) oxybromide;N,N-dimethyl-formamide; at 110℃; for 3h; | A total of 117 g of 5-80 was divided in 4 batches of 30 g×3 and 27 g×1 and treated with POBr3 (3 equiv.; 163 g×3 and 155 g×1) and a catalytic amount of DMF (15 ml) at rt (DMF was added carefully gas evolution). After 5 min. at room temperature, the solutions were heated at 110 C. for 3 hr. LC/MS showed starting material had been consumed. The reaction mixtures were allowed to cool to rt. The reaction flasks were placed in an ice bath; and then ice was added very slowly and carefully portionwise into the flask, gas evolution was due to HBr formation; the liquid and black solid that formed was poured into a beaker with ice. EtOAc was added and the mixture was then extracted several times with EtOAc. The organic layer was washed with saturated aq. NaHCO3; H2O and brine; dried over Na2SO4 and filtered. The product was dried in the pump overnight to provide 123 g of 6-80 as a brown solid (77% yield). Note: Reaction is completed within 1 h. 1HNMR(delta, CDCl3):8.52 (m, 1H), 7.93 (m, 1H). |
With phosphorus(V) oxybromide; In DMF (N,N-dimethyl-formamide); at 110℃; | Intermediate 4,4-fluoro-7-bromo-6-azaindole, was prepared according to the following scheme: [CHEMMOL-00081] [0364] A) fuming HNO3, H2SO4; [0365] B) POBr3/DMF, 110 C.; [0366] C) vinylmagnesium bromide, THF, -78 C. -20 C. [0367] Intermediate 4 was isolated as a brownish solid. MS m/z: (M+H)+ calcd for C7H5BrFN2: 214.96; found 214.97. HPLC retention time: 1.28 minutes (column G). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid; In water; at 85℃; for 1h; | In Step A, compound zzl' (1.2 g, 0.01 mol) was dissolved in sulfuric acid (2.7 mL) at room temperature. Premixed fuming nitric acid (1 mL) and sulfuric acid was added dropwise at 5-10 C. to the solution of compound zzl'. The reaction mixture was then heated at 85 C. for 1 hour, then was cooled to room temperature and poured into ice (20 g). The yellow solid precipitate was collected by filtration, washed with water and air dried to provide 1.01 g of compound zz2'. | |
With nitric acid;sulfuric acid; | Intermediate 4,4-fluoro-7-bromo-6-azaindole, was prepared according to the following scheme: [CHEMMOL-00081] [0364] A) fuming HNO3, H2SO4; [0365] B) POBr3/DMF, 110 C.; [0366] C) vinylmagnesium bromide, THF, -78 C. -20 C. [0367] Intermediate 4 was isolated as a brownish solid. MS m/z: (M+H)+ calcd for C7H5BrFN2: 214.96; found 214.97. HPLC retention time: 1.28 minutes (column G). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | The combined extracts were dried (MgSO4) and concentrated to yield an additional amount of the title compound (1.71 g, 11%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58.5% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 2h; | 5-Fluoro-3-nitropyridin-2-ol (10 g, 63.3 mmol) was dissolved in ethanol (300 mL), 1 0% Pd/C (1 .8 g) was added and the mixture wasstirred at room temperature under atmospheric pressure of hydrogen for2 h. Pd/C was removed by filtration and the solvent was evaporated invacuum to obtain the title compound as an off-white solid (7,5 g, 58.5mmol, Y=92%). LC-MS (M-H) = 129.0 |
Step 4. 3-amino-5-fluoropyridin-2-olA mixture of <strong>[136888-20-5]5-fluoro-3-nitropyridin-2-ol</strong> (73 mg, 0.46 mmol; prepared according to procedure reported in WO 2006/114706) and iron (130 mg, 2.3 mmol), in ethanol (1.0 mL), acetic acid (0.76 mL), water (0.38 mL) and c. HCl (1 drop) was heated to 100 C. for 20 min. After cooling to RT, the solution was diluted with water (10 mL), filtered, and the filtrate was concentrated. The residue was then treated with saturated sodium bicarbonate solution to near pH 7, and the product was extracted with 6×40 mL of 20% isopropanol/DCM. The extracts were dried over sodium sulfate, filtered and concentrated and the product was used without further purification in the following step. LCMS (M+H)+: 129.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With dmap; triethylamine; In dichloromethane; at 25℃; for 16h;Inert atmosphere; | To a mixture of <strong>[136888-20-5]5-fluoro-3-nitropyridin-2-ol</strong> (24.2 g, 153 mmol, CAS 136888-20-3), tosyl-chloride (33.4 g, 176 mmol) in dichloromethane (1000 mL) was added at room temperature, under nitrogen atmosphere, triethyl amine (44 mL, 304 mmol). At the end of the addition, DMAP (3.7 g, 30 mmol) was added. The resulting mixture was stirred at 25C for 16 h. Dichloromethane (500 mL) was added and the mixture was successively washed with an aqueous solution IN of hydrochloric acid (2 X 500 mL) and brine (500 mL). The separated aqueous layer was extracted with CH2CI2 (400 mL). The combined organic layers were dried over Na2S04 and filtered through a silica pad (50 g). The filtrate was purified by flash chromatography (eluent: CH2CI2) to give intermediate 22-1 (34 g, 67 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With silver carbonate; In hexane; at 150℃; for 1h;Microwave irradiation; | Method xxi-pyridyl amine 1: To a solution of <strong>[136888-20-5]5-fluoro-3-nitropyridin-2-ol</strong> (158 mg, 1 mmol) in n-hexane (1 mL) was added silver carbonate (331 mg, 1.2 mmol) and methyl iodide (0.2 mL, 2 mmol). The resulting mixture was stirred at 150 C under microwave irradiation (Power 250 W) for 1 hour. Solvent was removed and the residue was dissolved in ethyl acetate (2 ml) and washed with water (2x). Solvent was removed and the residue was purified on ISCO affording 5-fluoro-2-methoxy-3-nitropyridine (100 mg, 58%) as a colorless oil. 1H NMR (400 MHz, CDC13) delta 8.31 (d, J = 2.8 Hz, 1H), 8.09 (dd, J = 7.2, 2.8 Hz, 1H), 4.11 (s, 3H). |
55% | With silver carbonate; In chloroform; at 20℃; | b) 5-Fluoro-2-methoxy-3-nitropyridine Iodomethane (1.97 mL, 31.7 mmol) was added to a suspension of <strong>[136888-20-5]5-fluoro-3-nitropyridin-2-ol</strong> (Preparation 5a, 0.500 g, 3.2 mmol) and silver(I) carbonate (1.04 g, 3.8 mmol) in chloroform (15 mL) and the mixture was stirred overnight at ambient temperature. The mixture was filtered through Celite, the filtrate was evaporated and the residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (0.300 g, 55%) as a white solid. LRMS (m/z): 173 (M+1)+. 1H NMR delta (300 MHz, CDCl3): 4.17 (s, 3H), 8.15 (dd, 1H), 8.37 (d, 1H). |
55% | With silver carbonate; In chloroform; at 20℃; | b) 5-Fluoro-2-methoxy-3-nitropyridinelodomethane (1 .97 mL, 31.7 mmol) was added to a suspension of 5-fluoro-3- nitropyridin-2-ol (Preparation 5a, 0.500 g, 3.2 mmol) and silver(l) carbonate (1 .04 g, 3.8 mmol) in chloroform (15 mL) and the mixture was stirred overnight at ambient temperature. The mixture was filtered through Celite, the filtrate was evaporated and the residue was purified by flash chromatography (2:1 hexanes/ethyl acetate) to give the title compound (0.300 g, 55%) as a white solid. LRMS (m/z): 173 (M+1 )+.1H NMR delta (300 MHz, CDCI3): 4.17 (s, 3H), 8.15 (dd, 1 H), 8.37 (d, 1 H). |
Tags: 136888-20-5 synthesis path| 136888-20-5 SDS| 136888-20-5 COA| 136888-20-5 purity| 136888-20-5 application| 136888-20-5 NMR| 136888-20-5 COA| 136888-20-5 structure
A457985 [1616526-85-2]
5-Fluoro-1-methyl-3-nitropyridin-2(1H)-one
Similarity: 0.95
A107577 [33252-64-1]
3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one
Similarity: 0.71
A140048 [25892-08-4]
N-(2,6-Difluoro-3-nitrophenyl)acetamide
Similarity: 0.67
A178118 [132679-61-9]
(S)-2-((5-Fluoro-2,4-dinitrophenyl)amino)-3-methylbutanamide
Similarity: 0.66
A125594 [51173-06-9]
5-Fluoro-1-methylpyridin-2(1H)-one
Similarity: 0.65
A457985 [1616526-85-2]
5-Fluoro-1-methyl-3-nitropyridin-2(1H)-one
Similarity: 0.95
A251862 [88511-57-3]
4-Amino-3-nitropyridin-2(1H)-one
Similarity: 0.74
A115913 [21901-18-8]
4-Methyl-3-nitropyridin-2(1H)-one
Similarity: 0.72
A280340 [15862-34-7]
5-Bromo-2-hydroxy-3-nitropyridine
Similarity: 0.72
A457985 [1616526-85-2]
5-Fluoro-1-methyl-3-nitropyridin-2(1H)-one
Similarity: 0.95
A251862 [88511-57-3]
4-Amino-3-nitropyridin-2(1H)-one
Similarity: 0.74
A115913 [21901-18-8]
4-Methyl-3-nitropyridin-2(1H)-one
Similarity: 0.72
A280340 [15862-34-7]
5-Bromo-2-hydroxy-3-nitropyridine
Similarity: 0.72
A457985 [1616526-85-2]
5-Fluoro-1-methyl-3-nitropyridin-2(1H)-one
Similarity: 0.95
A251862 [88511-57-3]
4-Amino-3-nitropyridin-2(1H)-one
Similarity: 0.74
A115913 [21901-18-8]
4-Methyl-3-nitropyridin-2(1H)-one
Similarity: 0.72
A280340 [15862-34-7]
5-Bromo-2-hydroxy-3-nitropyridine
Similarity: 0.72
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
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.
Home
* Country/Region
* Quantity Required :
* Cat. No.:
* CAS No :
* Product Name :
* Additional Information :
Total Compounds: mg
The concentration of the dissolution solution you need to prepare is mg/mL