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CAS No. : | 2180894-90-8 | MDL No. : | N/A |
Formula : | C27H32BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 478.47 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P302+P352-P305+P351+P338 | 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 |
---|---|---|
82% | Stage #1: 4-bromo-N<SUP>3</SUP>-(2-bromo-5-(dimethylamino)phenyl)-N<SUP>1</SUP>,N<SUP>1</SUP>,N<SUP>3</SUP>-trimethylbenzene-1,3-diamine With magnesium; ethylene dibromide In tetrahydrofuran at 60℃; for 3h; Inert atmosphere; Stage #2: methyl 2,4,6-trimethylbenzoate In tetrahydrofuran at 60℃; for 12h; Inert atmosphere; Stage #3: With hydrogen bromide In tetrahydrofuran; water Inert atmosphere; | General Procedure B General procedure: To a suspension of Mg turnings (1.36 g, 56.0 mmol) in anhyd THF (20.0 mL) at 60 °C was added a solution of 2b (5.98 g, 14.0 mmol) in anhyd THF (60 mL) followed by 1,2-dibromoethane (0.319 mL, 4.20 mmol). The mixture was stirred at 60 °C for 3 h during which the reaction mixture turned yellow. To this solution at 60 °C was added a solution of carboxylic acid ester (10.0 mmol) in anhyd THF (100 mL) and the mixture was stirred at the same temperature for 12 h. Aq HBr (100 mL, 8.8 molL-1) was added and the aqueous phase was extracted with CHCl3/i-PrOH (85:15; 3 * 200 mL). The solvent was removed in vacuo and the residue was recrystallized from H2O (10 mL) to yield acridinium salts 1c and 1d. 3,6-Bis(dimethylamino)-9-mesityl-10-methylacridinium Bromide (1c) Prepared according to the general procedure B using methyl 2,4,6-trimethylbenzoate (1.78 g, 10 mmol) to afford an orange solid; yield: 3.9 g (82%); 192.9 °C (dec.); Rf = 0.13 (CH2Cl2/MeOH 10:1). IR (ATR, neat): 3373w, 2918w, 2170w, 1591s, 1497s, 1435m, 1352s, 1210s, 1148s, 985w, 921s, 807m, 711s cm-1. 1H NMR (500 MHz, CDCl3): δ = 7.26 (d, 3J = 9.5 Hz, 2 H, C1H, C8H), 7.06 (br, 2 H, C3′H, C5′H), 6.95-6.96 (m, 2 H, C4H, C5H), 6.94 (dd, 3J = 9.4 Hz, 4J = 2.1 Hz, 2 H, C2H , C7H), 4.56 (s, 3 H, NCH3), 3.36 [s, 12 H, 2 * N(CH3)2], 2.43 (s, 3 H, CH3) 1.80 (s, 6 H, 2 * CH3). 13C NMR (125 MHz, CDCl3): δ = 155.4 (C3, C6), 154.0 (C9), 143.9 (C4a, C10a), 139.0 (C4′), 136.0 (C2′, C6′), 130.4 (C1, C8, C1′), 128.6 (C3′, C5′), 116.1 (C8a, C9a), 114.3 (C2, C7), 94.3 (C4, C5), 41.1 [2× N(CH3)2], 38.3 (NCH3), 21.2 (CH3), 19.8 (2 * CH3). HRMS (ESI): m/z [M + H+] calcd for C27H32N3+: 398.2591; found: 398.2594. The spectral data were in agreement with literature data.3a |
74% | Stage #1: 4-bromo-N<SUP>3</SUP>-(2-bromo-5-(dimethylamino)phenyl)-N<SUP>1</SUP>,N<SUP>1</SUP>,N<SUP>3</SUP>-trimethylbenzene-1,3-diamine With magnesium In tetrahydrofuran; ethylene dibromide at 60℃; for 3h; Inert atmosphere; Stage #2: methyl 2,4,6-trimethylbenzoate In tetrahydrofuran; ethylene dibromide at 60℃; for 12h; Inert atmosphere; Stage #3: With hydrogen bromide In tetrahydrofuran; water; ethylene dibromide Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 2.2: 2 h / 75 °C / Inert atmosphere 3.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 3.2: 12 h / 60 °C / Inert atmosphere 3.3: Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 2.2: 2 h / 75 °C / Inert atmosphere 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 3.2: 12 h / 60 °C / Inert atmosphere 3.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 2.2: 2 h / 75 °C / Inert atmosphere 3.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 3.2: 12 h / 60 °C / Inert atmosphere 3.3: Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: hydrogenchloride; sodium nitrite / water / 0.33 h / -15 - 0 °C / Inert atmosphere 1.2: 12 h / 0 - 20 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 3.2: 2 h / 75 °C / Inert atmosphere 4.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 4.2: 12 h / 60 °C / Inert atmosphere 4.3: Inert atmosphere | ||
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 2.2: 2 h / 75 °C / Inert atmosphere 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 3.2: 12 h / 60 °C / Inert atmosphere 3.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid; nitric acid / water / 3 h / 0 - 5 °C / Inert atmosphere 2.1: tin(II) chloride dihdyrate; hydrogenchloride / water / 24 h / 20 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 4.2: 2 h / 75 °C / Inert atmosphere 5.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 5.2: 12 h / 60 °C / Inert atmosphere 5.3: Inert atmosphere | ||
Multi-step reaction with 6 steps 1.1: sulfuric acid; nitric acid / water / 3 h / 0 - 5 °C / Inert atmosphere 2.1: tin(II) chloride dihdyrate; hydrogenchloride / water / 24 h / 20 °C / Inert atmosphere 3.1: hydrogenchloride; sodium nitrite / water / 0.33 h / -15 - 0 °C / Inert atmosphere 3.2: 12 h / 0 - 20 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 5.2: 2 h / 75 °C / Inert atmosphere 6.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 6.2: 12 h / 60 °C / Inert atmosphere 6.3: Inert atmosphere | ||
Multi-step reaction with 6 steps 1.1: nitric acid / water; tetrahydrofuran; tert-butyl methyl ether / 1 h / 20 °C / Inert atmosphere 2.1: sulfuric acid / dichloromethane / 1 h / 5 - 20 °C / Inert atmosphere 3.1: ammonium chloride; iron / water; methanol / 1 h / 70 °C / Inert atmosphere 4.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 5.2: 2 h / 75 °C / Inert atmosphere 6.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 6.2: 12 h / 60 °C / Inert atmosphere 6.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium iodide; copper(l) iodide; N,N`-dimethylethylenediamine / N,N-dimethyl-formamide; 1,4-dioxane / 22 h / 110 °C / Inert atmosphere 2.1: bromine / dichloromethane / 0.5 h / 10 - 20 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 4.2: 2 h / 75 °C / Inert atmosphere 5.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 5.2: 12 h / 60 °C / Inert atmosphere 5.3: Inert atmosphere | ||
Multi-step reaction with 5 steps 1.1: sodium iodide; copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 22 h / 110 °C / Inert atmosphere 2.1: bromine / dichloromethane / 1 h / 10 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 4.2: 2 h / 75 °C / Inert atmosphere 5.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 5.2: 12 h / 60 °C / Inert atmosphere 5.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: bromine / dichloromethane / 0.5 h / 10 - 20 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 3.2: 2 h / 75 °C / Inert atmosphere 4.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 4.2: 12 h / 60 °C / Inert atmosphere 4.3: Inert atmosphere | ||
Multi-step reaction with 4 steps 1.1: bromine / dichloromethane / 1 h / 10 °C / Inert atmosphere 2.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 3.2: 2 h / 75 °C / Inert atmosphere 4.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 4.2: 12 h / 60 °C / Inert atmosphere 4.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 1.2: 2 h / 75 °C / Inert atmosphere 2.1: magnesium / tetrahydrofuran; ethylene dibromide / 3 h / 60 °C / Inert atmosphere 2.2: 12 h / 60 °C / Inert atmosphere 2.3: Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 1.2: 2 h / 75 °C / Inert atmosphere 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 2.2: 12 h / 60 °C / Inert atmosphere 2.3: Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid / dichloromethane / 1 h / 5 - 20 °C / Inert atmosphere 2.1: ammonium chloride; iron / water; methanol / 1 h / 70 °C / Inert atmosphere 3.1: tris-(dibenzylideneacetone)dipalladium(0); 1,1'-bis-(diphenylphosphino)ferrocene; sodium t-butanolate / toluene / 14 h / 105 °C / Inert atmosphere 4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 75 °C / Inert atmosphere 4.2: 2 h / 75 °C / Inert atmosphere 5.1: magnesium; ethylene dibromide / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 5.2: 12 h / 60 °C / Inert atmosphere 5.3: Inert atmosphere |