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Product Details of [ 85864-82-0 ]

CAS No. :85864-82-0 MDL No. :MFCD09909583
Formula : C11H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :BMUGYUZLQXTNAA-UHFFFAOYSA-N
M.W : 235.08 Pubchem ID :13067255
Synonyms :

Safety of [ 85864-82-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 85864-82-0 ]

* 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.

  • Downstream synthetic route of [ 85864-82-0 ]

[ 85864-82-0 ] Synthesis Path-Downstream   1~50

  • 2
  • [ 4856-13-7 ]
  • [ 85864-82-0 ]
  • [ 85865-00-5 ]
YieldReaction ConditionsOperation in experiment
72% at 160℃; for 2h;
  • 3
  • [ 85864-82-0 ]
  • [ 1576-35-8 ]
  • [ 85864-83-1 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride In ethanol
  • 4
  • [ 85864-82-0 ]
  • [ 4039-83-2 ]
  • [ 335164-63-1 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 3-(4-methoxybenzyloxy)propyne With n-butyllithium In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 8-bromonaphthalene-1-carbaldehyde In tetrahydrofuran at -78℃; for 3h; Further stages.;
  • 5
  • [ 518-05-8 ]
  • [ 85864-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 2: 86 percent / thionyl chloride / methanol / 6 h / Heating 3: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 4: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents
  • 6
  • [ 56268-44-1 ]
  • [ 85864-82-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 2: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents
  • 8
  • [ 85864-82-0 ]
  • [ 10397-12-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 72 percent / 2 h / 160 °C 2: 87 percent / hydrochloric acid / methanol / Heating 3: 1.) sodium hydride / 1.) dichloromethane, 2.) benzene, reflux, 1 h
  • 9
  • [ 85864-82-0 ]
  • [ 85865-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 72 percent / 2 h / 160 °C 2: 87 percent / hydrochloric acid / methanol / Heating 3: 39 percent / sodium methoxide / methanol / 2 h / Heating
  • 10
  • [ 85864-82-0 ]
  • [ 85865-01-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / 2 h / 160 °C 2: 87 percent / hydrochloric acid / methanol / Heating
  • 11
  • [ 85864-82-0 ]
  • [ 232-89-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 94 percent / hydrochloric acid / aq. ethanol 2: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 3: lithium aluminum hydride / diethyl ether / Ambient temperature
  • 12
  • [ 85864-82-0 ]
  • [ 54125-15-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 94 percent / hydrochloric acid / aq. ethanol 2: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h
Multi-step reaction with 2 steps 1.1: hydrogenchloride / lithium hydroxide monohydrate; ethanol / 0.08 h / 75 °C 2.1: sodium hydride / dichloromethane; mineral oil / 0.5 h / 20 °C 2.2: 0.5 h / 120 °C
  • 13
  • [ 85864-82-0 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 1037295-10-5 ]
YieldReaction ConditionsOperation in experiment
77% In tetrahydrofuran at 20℃; for 4h;
  • 14
  • [ 948592-78-7 ]
  • [ 85864-82-0 ]
  • [ 1255216-86-4 ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 8-bromonaphthalene-1-carbaldehyde With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2-(pyrrolidin-1-yl)phenylboronic acid With sodium carbonate In 1,2-dimethoxyethane at 90℃; Reflux;
  • 15
  • [ 17135-74-9 ]
  • [ 33513-42-7 ]
  • [ 85864-82-0 ]
YieldReaction ConditionsOperation in experiment
53% A solution of <strong>[17135-74-9]1,8-dibromonaphthalene</strong> (1.0 g, 3.5 mmol) in THF (18 mL) was cooled to -70 C. To this solution was added n-butyllithium (2.1 N in hexanes, 2.0 mL, 4.2 mmol) dropwise. After the mixture was stirred at -70 C for 30 minutes, N,N-dimethylformamide (0.6 mL) was added dropwise. The solution warmed to room temperature over one hour. The reaction was quenched with saturated aqueous NLLCl, the organics were separated, and the aqueous phase was extracted twice with DCM. The organics were dried over MgSCri and condensed. The material was purified by flash chromatography (RediSep Gold 24g column, 0-10% EtO Ac/hexane) to afford 8-bromo-l-naphthaldehyde (0.44 g, 53%). 1HNMR (400 MHz, CDCb): d 11.44 (s, 1H), 8.01 (d, J= 8.2 Hz, 1H), 7.91 (q, J= 7.6 Hz, 3H), 7.57 (t, J= 7.7 Hz, 1H), 7.40 (t, J= 7.7 Hz, 1H).
  • 16
  • [ 85864-82-0 ]
  • [ 108-00-9 ]
  • C15H17BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In dichloromethane at 20℃; for 1h; (1-C10H6-8-Br)CH=NCH2CH2N(CH3)2 (A): 21 mg (0.24 mmol) of N,N-dimethylethylenediamine and 56 mg (0.24 mmol) of 8-bromo-1-naphthyladehyde werecombined in CH2Cl2 (15 mL) at room temperature for one hour. The solvent wasremoved to produce a light-brown oil. Yield: 64 mg (87%). 1H NMR (400 MHz, CDCl3):δ = 2.35 [s, 6H, Ha]; 2.74 [m, 2H, Hb]; 3.82 [m, Hc]; {7.26-7.97 [m, 6H], aromatics}; 9.60[s, 1H, Hd]. 13C NMR (100 MHz, CDCl3): δ = 45.7 [Ca, Cb]; 59.55 [Cc]; {126.17;126.24; 128.95; 129.71; 130.98; 132.99, aromatics}; 163.9 [Cd]. FTIR (neat): 2938, 1679(cm-1).
  • 17
  • [ 85864-82-0 ]
  • [ 269409-70-3 ]
  • 8-(4-hydroxyphenyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 12h; Inert atmosphere; Reflux;
  • 18
  • 2-(4-methoxy-naphthalen-1-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
  • [ 85864-82-0 ]
  • 4’-methoxy-[1,1’-binaphthalene]-8-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 21h; Inert atmosphere;
  • 19
  • 2-(3-(tert-butyl)-4-methoxynaphthalen-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 85864-82-0 ]
  • 3'-(tert-butyl)-4'-methoxy-[1,1'-binaphthalene]-8-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 17h; Inert atmosphere;
  • 20
  • [ 85864-82-0 ]
  • [ 62-53-3 ]
  • C17H12BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With magnesium sulfate In dichloromethane at 20℃; for 24h; 1 3.3.1 [(C10H6Br)CH=N(C6H5)], L1 Both 8-bromo-1-napthaldehdyde (0.508 g, 2.16 mmol) and aniline (0.201 g, 2.16 mmol) were dissolved in 10 mL anhydrous methylene chloride. MgSO4 was added to the flask and the mixture was allowed to stir at room temperature for 24 h. The solution was then filtered and the solvent evaporated yielding an orange oil which was washed with 10. mL anhydrous pentane. The resulting compound crystallized into a yellow solid after one week. Final yield was 0.442 g of imine (1.42 mmol, 65% yield). 1H NMR (400 MHz, CDCl3): δ = 7.29-7.47 (m, 6H), 7.57 (t, J(H-H) = 5.6 Hz, 1H) 7.88 (t, J (H-H) = 6.6 Hz, 2H), 7.94 (d, J (H-H) = 10.6 Hz, 1H), 8.08 (d, J (H-H) = 7.4 Hz, 1H), 9.81 (s, 1H, CHN). 13C NMR (100.3 MHz, CDCl3): δ = 118.9, 121.2, 126.0, 126.2, 126.4, 129.0, 129.2, 129.2, 130.0, 131.6, 133.1, 134.7, 135.9, 151.9, 161.6 (CHN).
  • 21
  • [ 85864-82-0 ]
  • [ 104-86-9 ]
  • C18H13BrClN [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With magnesium sulfate In dichloromethane at 20℃; for 24h; 1 3.3.1 [(C10H6Br)CH=N(C6H5)], L1 General procedure: Both 8-bromo-1-napthaldehdyde (0.508 g, 2.16 mmol) and aniline (0.201 g, 2.16 mmol) were dissolved in 10 mL anhydrous methylene chloride. MgSO4 was added to the flask and the mixture was allowed to stir at room temperature for 24 h. The solution was then filtered and the solvent evaporated yielding an orange oil which was washed with 10. mL anhydrous pentane. The resulting compound crystallized into a yellow solid after one week. Final yield was 0.442 g of imine (1.42 mmol, 65% yield).
  • 22
  • [ 1679-18-1 ]
  • [ 85864-82-0 ]
  • C17H11ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 24h; Reflux; 1-1 1-1) Synthesis of intermediate 1-a 8-bromo-1-naphthaldehyde (30.0 g, 128 mmol), (4-chlorophenyl) boronic acid (24.0 g, 153 mmol) was completely dissolved in 1000 mL of tetrahydrofuran, and then 200 mL of an aqueous solution of potassium carbonate (53.1 g, 384 mmol) was added. Tetrakis- (triphenylphosphine) palladium (8.8 g, 7.65 mmol), and the mixture was refluxed for 24 hours and stirred. After completion of the reaction, the reaction mixture was cooled to room temperature, and extracted with water and ethyl acetate to separate an organic layer. The organic layer was treated with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain intermediate 1-a (28.7 g, yield: 84%).
  • 23
  • [ 85864-82-0 ]
  • C32H23BrClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / ethanol; water 2: C31H44N4O4; scandium tris(trifluoromethanesulfonate); potassium carbonate / dichloromethane / 12 h / 30 °C / Glovebox
  • 24
  • [ 85864-82-0 ]
  • C32H19BrClNO2 [ No CAS ]
  • C32H19BrClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water 2: C31H44N4O4; scandium tris(trifluoromethanesulfonate); potassium carbonate / dichloromethane / 12 h / 30 °C / Glovebox 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 30 °C
  • 25
  • [ 85864-82-0 ]
  • C32H19BrClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydroxide / ethanol; water 2: C31H44N4O4; scandium tris(trifluoromethanesulfonate); potassium carbonate / dichloromethane / 12 h / 30 °C / Glovebox 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 30 °C
  • 26
  • [ 85864-82-0 ]
  • [ 98-86-2 ]
  • C19H13BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In ethanol; water
  • 27
  • [ 249762-98-9 ]
  • [ 85864-82-0 ]
  • C28H19BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With oxalic acid In ethanol for 12h; 1.1 Step 1: Preparation of compound Int-1 At room temperature, 0.50 mol of bis(2-indolyl) methane was dissolved in 200 mL of ethanol, 0.25 mol of acid was added, and 0.50 mol of 8-bromo-1-naphthaldehyde was added. The reaction was stirred for 12 hours, filtered, and filtered. The cake was washed with ethanol to obtain a white solid compound Int-1 with a yield of 93%.
  • 28
  • 3-(benzofuran-2-ylmethyl)-1H-indole [ No CAS ]
  • [ 85864-82-0 ]
  • C28H18BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol for 12h; 7.3 The third step: Preparation of compound Int-17 General procedure: 10.0mmol of intermediate Int-16 was dissolved in 100mL of ethanol, 5.0mmol of acid was added, and 10.0mmol of 8-bromo-1-naphthaldehyde was added, the reaction was stirred for 12 hours, filtered, and the filter cake was washed with ethanol to obtain a white solid , The yield is 90-95%.
  • 29
  • [ 85864-82-0 ]
  • [ 14938-58-0 ]
YieldReaction ConditionsOperation in experiment
99% With sodium tetrahydroborate; ethanol; at 0 - 20℃; 8-Bromo-l-naphthaldehyde (0.24 g, 1.0 mmol) was suspended in ethanol (5 mL). After the mixture was cooled to 0 C, NaBHi (57 mg, 1.5 mmol) was added. The mixture was warmed to room temperature, diluted with EtO Ac, and quenched with saturated aqueous MHCl. The organics were separated and the aqueous phase was extracted with ethyl acetate. The combined organics were dried over MgS04 and condensed to afford (8-bromonaphthalen- l-yl)methanol (0.24 g, 99%). NMR (400 MHz, CDCb): d 7.89- 7.83 (m, 3H), 7.71 (d, J= 7.0 Hz, 1H), 7.48 (t, J= 7.6 Hz, 1H), 7.28 (t, J= 7.7 Hz, 1H), 5.47 (d, J = 7.0 Hz, 2H).
  • 30
  • [ 85864-82-0 ]
  • [ 766-97-2 ]
  • 8-(p-tolylethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 31
  • [ 85864-82-0 ]
  • [ 79887-14-2 ]
  • 8-((4-ethoxyphenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 32
  • [ 67237-53-0 ]
  • [ 85864-82-0 ]
  • 8-(thiophen-3-ylethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 33
  • [ 873-73-4 ]
  • [ 85864-82-0 ]
  • 8-((4-chlorophenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 34
  • [ 766-83-6 ]
  • [ 85864-82-0 ]
  • 8-((3-chlorophenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 35
  • [ 873-31-4 ]
  • [ 85864-82-0 ]
  • 8-((2-chlorophenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 36
  • [ 766-96-1 ]
  • [ 85864-82-0 ]
  • 8-((4-bromophenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 37
  • [ 766-98-3 ]
  • [ 85864-82-0 ]
  • 8-((4-fluorophenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 38
  • [ 2561-17-3 ]
  • [ 85864-82-0 ]
  • 8-((3-fluorophenyl)ethynyl)-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 39
  • [ 3032-92-6 ]
  • [ 85864-82-0 ]
  • 4-((8-formylnaphthalen-1-yl)ethynyl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 70 - 80℃; Inert atmosphere;
  • 40
  • [ 61-54-1 ]
  • [ 85864-82-0 ]
  • C21H17BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With acetic acid In 1,2-dichloro-ethane for 10h; Reflux; 2.1 Step 1: Preparation of compound Int-3 47.6mmol tryptamine, 150mL dichloroethane,57.0mmol of 1-bromo-8-naphthaldehyde and a few drops of acetic acid, heated and refluxed and reacted for 10 hours, then cooled to room temperature and stirred for 1 hour, then concentrated to dryness under reduced pressure, added petroleum ether, filtered and washed with petroleum ether to obtain yellow The solid was separated and purified with a silica gel column to obtain a white solid. Yield: 75%.
  • 41
  • [ 72758-17-9 ]
  • [ 85864-82-0 ]
YieldReaction ConditionsOperation in experiment
68% With 2-nitropropane; sodium methylate In methanol at 20℃; for 16h; Inert atmosphere; 9.2 Second step 9b (6.50 g, 21.80 mmol) was dissolved in methanol (100 mL), and 30% sodium methoxide methanol solution (5 mL) and 2-nitropropane (2.91 g, 32.77 mmol) were added. After nitrogen replacement three times, the reaction was carried out at room temperature for 16 hours. Adjust the pH to about 5 with 2N dilute hydrochloric acid, concentrate under reduced pressure to remove methanol, then add water (50 mL) and ethyl acetate (50 mL) and stir, filter, and concentrate under reduced pressure to obtain a residue. The residue is subjected to column chromatography (petroleum ether: Ethyl acetate=0-100%) was purified to obtain compound 9c (3.50g), yield: 68%.
  • 42
  • [ 85864-82-0 ]
  • C11H7BrF2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With diethylamino-sulfur trifluoride In ethanol; dichloromethane at 80℃; for 48h; Sealed tube; 9.3 third step Compound 9c (3.50g, 15.02mmol) was dissolved in dichloromethane (20mL) and ethanol (20mL), diethylaminosulfur trifluoride (9.70g, 75.11mmol) was added, and the tube was sealed and the reaction was heated to 80°C Stir for 48 hours. Dichloromethane (30mL) and water (50mL) were added to separate the liquids, and the aqueous phase was extracted with dichloromethane (30mL x 2). After the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a residue. The residue was purified by column chromatography (ethyl acetate: petroleum ether=0-100%) to obtain compound 9d (2.20 g) with a yield of 57%.
  • 43
  • [ 120-72-9 ]
  • [ 85864-82-0 ]
  • 6,12-bis(8-bromonaphthalen-1-yl)-5,11-dihydroindolo[3,2-b]carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: indole; 8-bromo-1-naphthaldehyde With hydrogen iodide In acetonitrile at 80℃; for 16h; Inert atmosphere; Stage #2: With iodine In acetonitrile at 80℃; for 10h; Inert atmosphere;
  • 44
  • [ 120-72-9 ]
  • [ 85864-82-0 ]
  • benzo[kl]benzo[2,3]naphtho[1',8':5,6,7]indolizino[1,8-ab]indolo[3,2,1-de]acridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogen iodide / acetonitrile / 16 h / 80 °C / Inert atmosphere 1.2: 10 h / 80 °C / Inert atmosphere 2.1: copper (I) iodide; tetra(n-butyl)ammonium hydroxide / N,N-dimethyl-formamide; methanol / 24 h / 120 °C / Inert atmosphere
  • 45
  • [ 85864-82-0 ]
  • potassium trifluoro(methyl)boranuide [ No CAS ]
  • [ 35699-44-6 ]
YieldReaction ConditionsOperation in experiment
84% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; silver(I) acetate; 3-aminobenzenesulfonic acid; acetic acid; silver(I) bis(trifluoromethanesulfonyl)imide at 90℃; Inert atmosphere;
  • 46
  • [ 85864-82-0 ]
  • C12H9ClO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; 3-aminobenzenesulfonic acid; silver(I) acetate; silver(I) bis(trifluoromethanesulfonyl)imide; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)] / 90 °C / Inert atmosphere 2: (2,2,2-trifluoroacetyl)oxysilver; N-chloro-succinimide; palladium diacetate; anthranilic acid; trifluoroacetic acid / 1,2-dichloro-ethane / 24 h / 60 °C / Sealed tube
  • 47
  • [ 85864-82-0 ]
  • 8-methoxy-2-methyl-1-naphthaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; 3-aminobenzenesulfonic acid; silver(I) acetate; silver(I) bis(trifluoromethanesulfonyl)imide; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)] / 90 °C / Inert atmosphere 2: 3-trifluoromethylaniline; potassium peroxodisulfate; palladium diacetate / dichloromethane / 36 h / 60 °C / Sealed tube
  • 48
  • [ 85864-82-0 ]
  • C12H9BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; 3-aminobenzenesulfonic acid; silver(I) acetate; silver(I) bis(trifluoromethanesulfonyl)imide; bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)] / 90 °C / Inert atmosphere 2: (2,2,2-trifluoroacetyl)oxysilver; N-Bromosuccinimide; 4-Nitroanthranilic acid; trifluorormethanesulfonic acid; palladium diacetate / 1,2-dichloro-ethane / 24 h / 90 °C / Sealed tube
  • 49
  • [ 2537-48-6 ]
  • [ 85864-82-0 ]
  • C13H8BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 8-bromo-1-naphthaldehyde With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: diethyl 1-cyanomethylphosphonate In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; 42.2 Step 2: Diethyl (cyanomethyl) phosphonate (4.29 g, 24.3 mmol) was added dropwise to a suspension of NaH (1.94 g, 48.5 mmol) in THF (57 mL) at 0 C under N2 atmosphere. The resulting mixture was stirred at 0 C for 1 hour. A solution of 123-1 (1.9 g, 8.09 mmol) in THF (23 mL) was added at 0 C under N2 atmosphere. The mixture was allowed to warm to room temperature. After 1 hour, the reaction was quenched with sat. aq. NH4Cl solution, diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 10/1) to afford 123-2.
  • 50
  • [ 85864-82-0 ]
  • [ 1576-35-8 ]
  • [ 85864-83-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In ethanol; lithium hydroxide monohydrate at 75℃; for 0.0833333h; Step B: N'-((8-Bromonaphthalen-l-yl)methylene)-4-methylbenzenesulfonohydrazide (Int K2) HC1 (37%, 57 μL, 0.69 mmol) was added to a solution of 8-bromo-l -naphthaldehyde (Int KI) (3.28 g, 13.9 mmol) and NH2NHTs (2.65 g, 14.2 mmol) in EtOH (19.8 mL) and water (1.04 mL) at 75 °C. The reaction stirred vigorously at 75 °C for 5 min. The reaction was cooled to room temperature, filtered, and washed with EtOH (5 x 10 mL). The resulting solid was dried under reduced pressure to provide N'-((8-bromonaphthalen- l-yl)m ethyl ene)-4- methylbenzenesulfonohydrazide (Int K2), which was used in the subsequent step without further purification. MS (ESI) [M+H]+ m/z: 403.
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