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Limited Quantity | USD 15-60 |
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CAS No. : | 3336-18-3 | MDL No. : | MFCD22988323 |
Formula : | C7H3Cl2NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LIDUSYSXQFAHHK-UHFFFAOYSA-N |
M.W : | 188.01 | Pubchem ID : | 21323083 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.2 |
TPSA : | 44.02 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) : | -5.45 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 2.81 |
Log Po/w (WLOGP) : | 2.57 |
Log Po/w (MLOGP) : | 1.97 |
Log Po/w (SILICOS-IT) : | 2.6 |
Consensus Log Po/w : | 2.33 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.18 |
Solubility : | 0.124 mg/ml ; 0.000661 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.39 |
Solubility : | 0.0763 mg/ml ; 0.000406 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.14 |
Solubility : | 0.136 mg/ml ; 0.000721 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 | UN#: | 3439 |
Hazard Statements: | H301+H311+H331-H315-H319 | Packing Group: | Ⅲ |
GHS Pictogram: |
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* 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 |
---|---|---|
With nitric acid; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
2.5-Dichlor-4-brom-phenolacetat, CuCN, 1.) Δ, DMF; 2.) NH3/H2O; | ||
2.5-Dichlor-4-brom-anisol, CuCN, 1.) Δ, DMF; 2.) Py., HCl, Δ; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i) NaNO2, aq. HCl, (ii) /BRN= 4652394/, aq. CuSO4 2: AlCl3 / toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 12h; | 26 Example 26; 3-(2,5-Dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo [ 1 ,2-a] pyridin-2-yl)- 1 ,2,4- oxadiazol-3-yl)phenoxy)-2-hydroxypropanoic acid; 2-(2,5-Dichloro-4-(5-(8-chlor o-6-(trifluoromethyl)imidazo [ 1 ,2-β] pyridin-2-yl)- l,2,4-oxadiazol-3-yl)phenoxy)ethanol.; To a stirred solution of 2,5-dichloro-4-(5-(8-chloro-6- (trifluoromethyl)imidazo(l,2-α)pyridine-2-yl)-l,2,4-oxadiazole-3-yl) phenol (1.0 g, 2.4 mmol), prepared as described in Example 13, in DMF (10 mL) was added K2CO3 (1.66 g, 12.0 mmol) and 2-bromoethanol (1.5 g, 12 mmol). The reaction mixture was stirred at 800C for 12 h and then quenched with ice water and extracted with EtOAc. The organic layer was washed with water and saturated NaCl solution, dried over Na2SO4 and concentrated in vacuo to afford of intermediate 127 (0.70 g, 59% yield) as a yellowish-brown solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 2,5-dichloro-4-hydroxybenzonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 3h; | 1 Example 1: Synthesis of (S)-5-((2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo [1,2- al pyridin-2-yl)- 1 ,2,4-oxadiazol-3-yl)phenoxy)methyl)pyrrolidin-2-one (11) To a stirred solution of 2,5-dichloro-4-hydroxybenzonitrile (2) (35.0 g, 186 mmol) in DMF (150 mL) was added NaH (13.7 g, 347 mmol) in small portions at 0°C and the mixture was stirred for 30 mill at 0°C. Methyl iodide (35 mL, 560 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was cooled to 0°C and ice-water was added carefully. The resulting precipitate was collected by filtration, washed with water and dried to afford compound (3) (29 g, 78%) as a white solid. |
78% | Stage #1: 2,5-dichloro-4-hydroxybenzonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 3h; | [00251] To a stirred solution of 2,5-dichloro-4-hydroxybenzonitrile (2) (35.0 g, 186 mmol) in DMF (150 mL) was added NaH (13.7 g, 347 mmol) in small portions at 0°C and the mixture was stirred for 30 min at 0°C. Methyl iodide (35 mL, 560 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was cooled to 0°C and ice-water was added carefully. The resulting precipitate was collected by filtration, washed with water and dried to afford compound (3) (29 g, 78%) as a white solid. |
78% | Stage #1: 2,5-dichloro-4-hydroxybenzonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 3h; | 9 To a stirred solution of 2,5-dichloro-4-hydroxybenzonitrile (27) (35.0 g, 186 mmol) in DMF (150 mL) was added NaH (13.7 g, 347 mmol) in small portions at 0°C and the mixture was stirred for 30 mm at 0°C. Methyl iodide (35 mL, 560 mmol) was added dropwise and the reaction mixture was allowed to warm to room temperature and stirred for 3 h. The mixture was cooled to 0°C and ice-water was added carefully. The resulting precipitate was collected by filtration, washed with water and dried to afford compound (28) (29 g, 78%) as a white solid. |
54% | Stage #1: 2,5-dichloro-4-hydroxybenzonitrile With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; | 13 2,5-Dichloro-4-methoxy benzonitrile (72).; To a stirred solution of 2,5-dichloro-4- cyanophenol 71 (11.0 g, 58.5 mmol) in DMF (40 mL) was added NaH (4.3 g, 109 mmol) in small portions at 0 0C and stirred for 30 min at 0 0C. Methyl iodide (11 rnL, 176 mmol) was added dropwise and after addition the reaction was allowed to warm to room temperature and was stirred for 3 h. After completion, the reaction mixture was cooled to 0 0C and quenched with ice water. The precipitated solid was collected by filtration, washed well with water and dried completely to afford the title intermediate 72 as a white solid (6.4 g, yield 54%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: 2,5-dichloro-4-hydroxybenzonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333h; Stage #2: allyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 14 Example 14; 3-(2,5-Dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo[l,2-a]pyridin-2-yl)-l,2,4- oxadiazol-3-yl)phenoxy)propane-l,2-diol[00406] 4-(Allyloxy)-2,5-dichlorobenzonitrile (75).; To intermediate 71 (1.72 g, 9.15 mmol) in dry DMF (20 mL), was added NaH (475 mg, 0.011 mole, 60% dispersion in oil) at 0 0C and stirred for 20 min. To the resulting reaction mixture, allyl bromide (1.5 ml, 0.018 mol) was added dropwise at 0 0C and the mixture stirred for an additional 3 h at room temperature. Excess NaH was quenched by ice, and the resulting mixture extracted with EtOAc. The combined extracts were washed with water, saturated NaCl, dried over Na2SO4, and concentrated. The resulting residue was purified by column chromatography using EtOAc:hexane as eluent to give intermediate 75 (1.22 g, 59.0%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In N,N-dimethyl-formamide at 150℃; for 3h; | 13 Example 13; 2,5-Dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo(l,2-«)pyridine-2-yl)-l,2,4- oxadiazole-3-yl) phenol; 2,5-Dichloro-4-hydroxy benzonitrile (71).; To a stirred solution of 2,5-dichloro-4- bromophenol 70 (10 g, 41 mmol) in DMF (50 mL) was added cuprous cyanide (4.83 g, 53.8 mmol) and the reaction was stirred at 150 0C for 3 h. After completion, the reaction mixture was concentrated in vacuo. To the residue, water and EtOAc were added and the biphasic mixture filtered through celite. The filtrate was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography, using 15% EtOAc/hexane as eluent, to afford the title intermediate 71 as a white solid (7.7 g, yield 100%). |
57% | In N,N-dimethyl-formamide at 150℃; for 4h; | 1 Example 1: Synthesis of (S)-5-((2,5-dichloro-4-(5-(8-chloro-6-(trifluoromethyl)imidazo [1,2- al pyridin-2-yl)- 1 ,2,4-oxadiazol-3-yl)phenoxy)methyl)pyrrolidin-2-one (11) To a stirred solution of 2,5-dichloro-4-bromophenol (1) (210.0 g, 0.86 mol) in DIMF(1000 mL) was added cuprous cyanide (101.5 g, 1.13 mmol) at room temperature. The reactionmixture was stirred at 150°C for 4 h. The mixture was concentrated under vacuum. Water andEtOAc were added to the residue and then filtered through a pad of celite. The filtrate wasextracted with EtOAc and the combined organic layers were dried over anhydrous Na2504 andconcentrated under vacuum. The residue was recrystallized from petroleum ether/EtOAc (10:1,1400 mL) to afford 2,5-dichloro-4-hydroxybenzonitrile (2) (93.0 g, 57%) as a white solid. |
57% | In N,N-dimethyl-formamide at 150℃; for 4h; | [00250] To a stirred solution of 2,5-dichloro-4-bromophenol (1) (210.0 g, 0.86 mol) in DMF (1000 mL) was added cuprous cyanide (101.5 g, 1.13 mmol) at room temperature. The reaction mixture was stirred at 150°C for 4 h. The mixture was concentrated under vacuum. Water and EtOAc were added to the residue and then filtered through a pad of celite. The filtrate was extracted with EtOAc and the combined organic layers were dried over anhydrous Na2S04 and concentrated under vacuum. The residue was recrystallized from petroleum ether/EtOAc (10: 1, 1400 mL) to afford 2,5-dichloro-4-hydroxybenzonitrile (2) (93.0 g, 57%) as a white solid. |
57% | In N,N-dimethyl-formamide at 150℃; for 4h; | 9 To a stirred solution of 2,5-dichloro-4-bromophenol (26) (210.0 g, 0.86 mol) in DMF (1000 mL) was added cuprous cyanide (101.5 g, 1.13 mmol) at room temperature. The reaction mixture was stirred at 150°C for 4 h. The mixture was concentrated under vacuum. Water and EtOAc were added to the residue and then filtered through a pad of celite. The filtrate was extracted with EtOAc and the combined organic layers were dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was recrystallized from petroleum ether/EtOAc (10:1, 1400 mL) to afford 2,5-dichloro-4-hydroxybenzonitrile (27) (93.0 g, 57%) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 20 - 80 °C 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 100 °C | ||
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C | ||
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 20 - 80 °C 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C 5.1: potassium carbonate / acetonitrile / 13 h / 76 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C 5.1: potassium carbonate / acetonitrile / 13 h / 76 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C 5.1: potassium carbonate / acetonitrile / 18 h / 76 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C 5.1: potassium carbonate / acetonitrile / 18 h / 76 °C 6.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 6.2: 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C 5.1: potassium carbonate / acetonitrile / 18 h / 76 °C | ||
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 20 - 80 °C 3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere 5.1: potassium carbonate / acetonitrile / 18 h / 76 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C 5.1: potassium carbonate / acetonitrile / 18 h / 76 °C 6.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C 6.2: 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 4 h / 80 °C | ||
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: hydroxylamine hydrochloride; triethylamine / ethanol / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: sodium hydroxide / ethanol / 0.17 h / 20 °C 5.2: 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: sodium hydroxide / ethanol / 0.17 h / 20 °C 5.2: 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 80 °C 6.1: barium hydroxide octahydrate / ethanol; water / 1 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 2.25 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 8 h / 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: sodium hydroxide / ethanol / 1 h / 20 °C 5.2: 16 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere 5.1: pyridine / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere 5.1: pyridine / dichloromethane / 0 - 20 °C 6.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere 5.1: pyridine / dichloromethane / 0 - 20 °C 6.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 7.1: sulfuric acid / water / 6 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 12 h / 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 2.5 h / 5 - 10 °C / Inert atmosphere 5.1: pyridine / dichloromethane / 0 - 20 °C 6.1: tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 15 h / 80 °C / Inert atmosphere 7.1: sulfuric acid / water / 6 h / Reflux 8.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h 8.2: 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 20 - 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: triethylamine; hydroxylamine hydrochloride / ethanol / 4.5 h / 20 - 80 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.25 h 3.2: 20 - 100 °C 4.1: aluminum (III) chloride / dichloromethane / 0.17 h / 10 °C / Inert atmosphere 4.2: 3 h / 5 °C / Inert atmosphere 5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6.1: diisobutylaluminium hydride / dichloromethane; tetrahydrofuran / 2.25 h / -10 °C |
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