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CAS No. : | 613656-45-4 | MDL No. : | MFCD06260669 |
Formula : | C10H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SAGRVQMJUPNRRB-UHFFFAOYSA-N |
M.W : | 179.22 | Pubchem ID : | 3871127 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
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59% |
Yield | Reaction Conditions | Operation in experiment |
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Stage #1: methylamine hydrochloride; 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde With sodium hydroxide In methanol at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; | 9.1 1. Methylamine hydrochloride (16.5 g) and sodium hydroxide (9.8 g) were added to a solution of 3 , 4-ethylene- dioxybenzaldehyde (40.0 g) in methanol (700 ml). After stirring at room temperature for one hour, the solution was cooled to O0C prior to addition of sodium borohydride (4,5 g) portion wise. The resulting solution was stirred at room temperature for one hour, after which it was concentrated to dryness. The residue was partitioned between dichloromethane(500 ml) and an aqueous solution of sodium hydroxide (400 ml, 2M) . The dichloromethane phase was separated and extracted with hydrochloric acid (2 X 300 ml, 2M). The aqueous phase was made alkaline (pH 11-12) and extracted with dichloromethane (2 X 300 ml) . The organic phase was dried (sodium sulphate) and concentrated to dryness, leaving N-methyl-3,4- ethylenedioxybenzylamine, which was used without further purification. | |
Stage #1: methylamine hydrochloride; 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde With sodium hydroxide In methanol at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h; | 9.1 Methylamine hydrochloride (16.5 g) and sodium hydroxide (9.8 g) were added to a solution of 3,4-ethylenedioxybenzaldehyde (40.0 g) in methanol (700 ml). After stirring at room temperature for one hour, the solution was cooled to 0° C. prior to addition of sodium borohydride (4.5 g) portion wise. The resulting solution was stirred at room temperature for one hour, after which it was concentrated to dryness. The residue was partitioned between dichloromethane (500 ml) and an aqueous solution of sodium hydroxide (400 ml, 2M). The dichloromethane phase was separated and extracted with hydrochloric acid (2*300 ml, 2M). The aqueous phase was made alkaline (pH 11-12) and extracted with dichloro-methane (2*300 ml). The organic phase was dried (sodium sulphate) and concentrated to dryness, leaving N-methyl-3,4-ethylenedioxybenzylamine, which was used without further purification. |
Yield | Reaction Conditions | Operation in experiment |
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Stage #1: α-acetoxy-3,4,5-trimethoxyphenylacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Heating / reflux; Stage #2: N-methyl-1,4-benzodioxan-7-ylmethylamine In dichloromethane at 20℃; for 2h; | 9.5 5. A solution of α-acetoxy-3 , 4 , 5-trimethoxyphenyl- acetic acid (5.0 g) in dichloromethane (40 ml) was reacted with 1, 1' -carbonyldiimidazole (2,92 g) at room temperature for 30 minutes. The solution was refluxed for 30 minutes, after which N-methyl-3, 4-ethylenedioxybenzylamine (3.26 g) dissolved in dichloromethane (10 ml) was added. The mixture was stirred at room temperature for 2 hours, after which it was washed with aqueous hydrochloric acid (20 ml, IM) followed by aqueous sodium hydrogen carbonate (20 ml, 0.5 M). The organic phase was dried and concentrated to dryness, leaving crude 2- (3, 4,5-trimethoxyphenyl) ~2-acetoxy-N-methyl~ N-3 , 4-ethylenedioxybenzylacetamide (7.27 g) . | |
Stage #1: α-acetoxy-3,4,5-trimethoxyphenylacetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Heating / reflux; Stage #2: N-methyl-1,4-benzodioxan-7-ylmethylamine In dichloromethane at 20℃; for 2h; | 9.5 A solution of α-acetoxy-3,4,5-trimethoxyphenyl-acetic acid (5.0 g) in dichloromethane (40 ml) was reacted with 1,1'-carbonyldiimidazole (2.92 g) at room temperature for 30 minutes. The solution was refluxed for 30 minutes, after which N-methyl-3,4-ethylenedioxybenzylamine (3.26 g) dissolved in dichloromethane (10 ml) was added. The mixture was stirred at room temperature for 2 hours, after which it was washed with aqueous hydrochloric acid (20 ml, 1M) followed by aqueous sodium hydrogen carbonate (20 ml, 0.5 M). The organic phase was dried and concentrated to dryness, leaving crude 2-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-3,4-ethylenedioxybenzylacetamide (7.27 g). |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With sodium tetrahydroborate In methanol for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
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Multi-step reaction with 2 steps 1: methanol / 2 h / 20 °C 2: sodium tetrahydroborate / methanol / 1 h |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C | ||
Stage #1: N-methyl-1,4-benzodioxan-7-ylmethylamine; Cinnamyl bromide With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: With hydrogenchloride In ethyl acetate for 0.0166667h; | 125 Example 125: (E)-N-(1,4-benzodioxan-7-methyl)-N-methyl-3-phenylprop-2-en-1-amine (ID-01) The preparation. 178 mg of Intermediate X, 197 mg of Intermediate IV-01,300 mg of potassium carbonate was added to 5 ml of N,N-dimethylformamide,The reaction was overnight at room temperature. After the reaction is over, water is added to the reaction system.Extract three times with ethyl acetate, wash with saturated brine, and dry over anhydrous sodium sulfate.Filter, concentrate and separate the residue by column chromatography to give the title compound,151 mg of a colorless oil, yield 62%. To purify it,The compound was dissolved in 1 ml of ethyl acetate and hydrogen chloride gas was fed for one minute.It was made into hydrochloride salt, and the solvent was evaporated to dryness. A 1/100 mixture of petroleum ether/ethyl acetate was added to precipitate white solid hydrochloride, which was filtered off with suction and washed.Compound ID-01 hydrochloride was obtained. 1H-NMR is its hydrochloride form data |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C 2: hydrogenchloride / diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
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72% | Stage #1: 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde; methylamine In methanol at 20 - 30℃; Stage #2: With sodium tetrahydroborate In methanol at 50℃; | 124 Example 124: Preparation of N-Methyl-1,4-benzodioxan-7-methylamine (Intermediate X) 162 mg of 2,3-dihydrobenzofuran-6-carbaldehyde was slowly added to 3 ml of methylamine methanol solution and reacted at 20-30[deg.] C. for 2 to 4 hours. 100 mg of sodium borohydride was slowly added to the reaction liquid in portions. Keep the temperature no higher than 50°C and continue stirring for 1 to 3 hours. After the reaction is over, the system is quenched with ammonium chloride, the solvent is distilled off under reduced pressure, and water is added.Extract three times with ethyl acetate, wash with saturated brine, and dry over anhydrous magnesium sulfate.Filtration and concentration gave 129 mg of N-methyl-1,4-benzodioxane-7-methylamine as an intermediate,The yield is 72% |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 - 90 °C 2.1: methanol / 20 - 30 °C 2.2: 50 °C |
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