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Product Details of [ 61601-54-5 ]

CAS No. :61601-54-5 MDL No. :MFCD02752204
Formula : C12H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :QBPAUIDFWFXLKB-UHFFFAOYSA-N
M.W : 183.21 Pubchem ID :6454228
Synonyms :

Safety of [ 61601-54-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 61601-54-5 ]

* 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 [ 61601-54-5 ]

[ 61601-54-5 ] Synthesis Path-Downstream   1~34

  • 2
  • [ 61601-54-5 ]
  • [ 70377-05-8 ]
YieldReaction ConditionsOperation in experiment
85% With potassium dihydrogenphosphate; potassiuim nitrosodisulfonate In water; acetone for 0.5h; Ambient temperature;
80% With salcomine; oxygen In acetonitrile at 20℃; for 4h; Inert atmosphere;
With potassium dihydrogenphosphate; potassiuim nitrosodisulfonate; water; acetone
  • 4
  • [ 4544-87-0 ]
  • [ 61601-54-5 ]
YieldReaction ConditionsOperation in experiment
86% With boron tribromide In dichloromethane at -78℃; for 16h;
65% With boron tribromide In dichloromethane at -78 - 20℃; for 5h; Inert atmosphere; 1-Hydroxycarbazole (7) General procedure: To a solution of 1-methoxycarbazole (21a) (85 mg, 0.43 mmol) in CH2Cl2 (2mL) was added BBr3 (169 μL, 1.72 mmol) at -78 oC. After stirring at rt for 5 h, the reaction mixture waspoured into ice water. The mixture was extracted with EtOAc. The EtOAc phase was washed with waterand brine, dried with Na2SO4, and concentrated under reduced pressure. The residue was purified bycolumn chromatography (silica gel, 20 g; EtOAc/hexane, 1/4 v/v) to give the 1-hydroxycarbazole (7) (51mg, 0.28 mmol, 65%) as a white solid, mp 165-167 oC (CHCl3) (Lit.,20 mp 163-165 oC). IR (ATR): 3429,3197 cm-1. 1H NMR (300 MHz, CDCl3): δ 4.99 (br. s, 1H), 6.83 (d, J = 7.9 Hz, 1H), 7.08 (t, J = 7.9 Hz,1H), 7.21-7.26 (m, 1H), 7.40-7.48 (m, 2H), 7.69 (d, J = 7.9 Hz, 1H), 8.06 (d, J = 7.9 Hz, 1H), 8.24 (br. s,1H). 13C NMR (75 MHz, CDCl3): δ 110.63, 110.94, 113.25, 119.44, 119.68, 120.59, 123.57, 125.34,125.93, 128.95, 139.41, 141.00. MS (EI): m/z 183 [M]+. HRMS (EI): calcd. for C12H9NO: 183.0684;found 183.0706.
32% With hydrogen bromide; hypophosphorous acid at 75 - 80℃; for 72h;
With water; hydrogen bromide; acetic acid

  • 5
  • [ 5796-98-5 ]
  • [ 111960-23-7 ]
  • [ 61601-54-5 ]
  • 6
  • [ 61601-54-5 ]
  • [ 557-21-1 ]
  • [ 171918-27-7 ]
YieldReaction ConditionsOperation in experiment
82% With hydrogenchloride In diethyl ether at -5 - 0℃; for 4.5h;
  • 7
  • [ 61601-54-5 ]
  • [ 621-82-9 ]
  • [ 756482-78-7 ]
YieldReaction ConditionsOperation in experiment
55% With aluminium trichloride; trichlorophosphate at 20℃; for 24h;
With zinc(II) chloride; trichlorophosphate
  • 8
  • [ 61601-54-5 ]
  • [ 118-92-3 ]
  • [ 15351-42-5 ]
  • 12,13-dihydro-indolo[3,2-<i>c</i>]acridin-7-one [ No CAS ]
  • 9
  • [ 86-74-8 ]
  • [ 61601-54-5 ]
  • [ 148519-91-9 ]
YieldReaction ConditionsOperation in experiment
1: 39.3% 2: 46.8% With Escherichia coli JM109 harbouring pJ31BP-Q282Y In dimethyl sulfoxide at 30℃; for 18h; L-medium; Enzymatic reaction;
  • 10
  • [ 61601-54-5 ]
  • [ 609-67-6 ]
  • [ 1341186-28-4 ]
YieldReaction ConditionsOperation in experiment
58% With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
  • 11
  • [ 61601-54-5 ]
  • [ 7154-66-7 ]
  • [ 1341186-27-3 ]
YieldReaction ConditionsOperation in experiment
72% With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
  • 12
  • [ 61601-54-5 ]
  • [ 3433-80-5 ]
  • [ 1343478-09-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In acetone for 3h; Reflux; 25 General procedure for the synthesis of 1-(2-bromo-benzyloxy)-9H-carbazole (6): General procedure: A mixture of the respective 1-hydroxycarbazoles (5, 1 mmol), 2-bromobenzylbromide (1 mmol) and dried K2CO3 in acetone was refluxed in a steam bath for 3 h. The reaction mixture was monitored by TLC. After completion of the reaction the excess solvent was removed and dissolved in ice water and neutralized with ice cold 1:1 HCl. The solid separated was filtered, washed with water and dried. Then, it was purified by column chromatography over silica gel using petroleum ether and ethyl acetate (99:1) to get the respective 1-(2-bromo-benzyloxy)-9H-carbazole (6).
  • 13
  • [ 2033-24-1 ]
  • [ 61601-54-5 ]
  • [ CAS Unavailable ]
  • [ 1361944-20-8 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydrogencarbonate at 20℃; for 0.166667h; neat (no solvent);
  • 14
  • [ 61601-54-5 ]
  • [ CAS Unavailable ]
  • [ 109-77-3 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydrogencarbonate at 20℃; for 0.166667h; neat (no solvent);
  • 15
  • [ 61601-54-5 ]
  • [ 762-42-5 ]
  • [ 1431462-42-8 ]
YieldReaction ConditionsOperation in experiment
95% With triphenylphosphine In dichloromethane at -5 - 20℃; for 24h;
  • 16
  • [ 61601-54-5 ]
  • [ CAS Unavailable ]
  • [ 109-77-3 ]
  • [ 1620750-22-2 ]
YieldReaction ConditionsOperation in experiment
95% With indium(III) chloride In acetonitrile at 70℃; for 0.166667h; Microwave irradiation; Green chemistry; Procedure for the Preparation of Pyrano[2,3-a]carbazoles (2a) InCl3 (25 mol%) dissolved in CH3CN was added to a mixture of 1-hydroxycarbazole (1 mmol), malononitrile (1 mmol), and benzaldehyde (1 mmol) and subjected to microwave irradiation (Biotage microwave oven, 70 °C, 2 bar pressure) for 10 min. The progress of the reaction was monitored by TLC. Upon cooling, the product precipitated from the reaction mixture, which was filtered, dried, and recrystallized from ethanol.
  • 17
  • [ 61601-54-5 ]
  • [ 91-56-5 ]
  • [ 109-77-3 ]
  • [ 1620750-26-6 ]
YieldReaction ConditionsOperation in experiment
93% With indium(III) chloride In acetonitrile at 70℃; for 0.166667h; Microwave irradiation; Green chemistry; General procedure for the preparation of pyrano[2,3-a]carbazoles (2/3 a-d) General procedure: To a mixture of 1-hydroxycarbazole (1 mmol), Malononitrile (1 mmol) and benzaldehyde/Isatin (1 mmol), InCl3 (25 mol %) was dissolved in CH3CN and subjected to microwave irradiation (Biotage microwave oven, 70°C, 2 bar pressure) for 10 min. The progress of the reaction was monitored by thin-layer chromatography. Upon cooling, the product precipitated from the reaction mixture, which was filtered, dried, and recrystallized from ethanol.
  • 18
  • [ 61601-54-5 ]
  • [ 637-44-5 ]
  • [ 1637596-53-2 ]
YieldReaction ConditionsOperation in experiment
89% With zinc(II) chloride; trichlorophosphate at 20℃; for 24h; regiospecific reaction; Reaction of 1-hydroxycarbazoles with phenylpropiolic acid in ZnCl2/POCl3; general procedure General procedure: A mixture of 1-hydroxycarbazole (1, 0.001 mmol) and phenylpropiolic acid (2, 0.001 mmol) was treated with fused ZnCl2/POCl3 (1.5 g/6 mL) at room temperature for 24 h. The reaction was monitored by TLC. After completion of the reaction the mixture was poured onto crushed ice, the solid that separated was filtered off, dried and recrystallised from ethanol to obtain the respective 4-phenylpyrano[2,3-a]carbazol-2-one 4 as the sole product in high yield.
  • 19
  • [ 61601-54-5 ]
  • [ 637-44-5 ]
  • [ 1637596-53-2 ]
  • [ 756482-82-3 ]
YieldReaction ConditionsOperation in experiment
1: 42% 2: 34% With trifluoroacetic acid for 5h; Reflux; Reaction of 1-hydroxycarbazoles with phenylpropiolic acid intrifluroacetic acid; general procedure General procedure: A mixture of 1-hydroxycarbazole (1, 0.001 mol) and phenylpropiolic acid (2, 0.001 mol) in trifluroacetic acid (10 mL) was refluxed ina steam bath for 5 h. The reaction was monitored by TLC. After the completion of reaction the excess solvent was removed andthe reaction mixture was poured onto ice water. The brown solid thus obtained was found to be a mixture of two products. The crude products were separated by column chromatography over silica gel using petroleum ether and ethyl acetate (98 : 2 and 90 : 10) as the eluants to yield the respective 2-phenylpyrano[2,3-a]carbazol-4-one3 and 4-phenylpyrano[2,3-a]carbazole-2-one 4. The compounds thus obtained were recrystallised from ethanol.
  • 20
  • [ 61601-54-5 ]
  • [ 637-44-5 ]
  • [ 756482-82-3 ]
YieldReaction ConditionsOperation in experiment
86% With phosphorus pentoxide; trichlorophosphate at 100℃; regiospecific reaction; Reaction of 1-hydroxycarbazoles with phenylpropiolic acid in P2O5/POCl3; general procedure General procedure: A mixture of 1-hydroxycarbazole (1, 0.001 mmol) and phenylpropiolic acid (2, 0.001 mmol) was treated with P2O5/POCl3 (1.4 g/6 mL) and heated to 100 °C. The reaction was monitored by TLC. After completion of the reaction the mixture was poured onto crushed ice,the solids that separated were filtered off, dried and crystallised from ethanol to yield the respective 2-phenylpyrano[2,3-a]carbazol-4-one 3as the sole product.
  • 21
  • [ 1219637-88-3 ]
  • [ 61601-54-5 ]
YieldReaction ConditionsOperation in experiment
82% With dihydrogen peroxide In tetrahydrofuran; water at 0 - 23℃; for 12h; Inert atmosphere;
77% With dihydrogen peroxide In tetrahydrofuran; water at 20℃; Inert atmosphere;
  • 22
  • [ 108-86-1 ]
  • [ 61601-54-5 ]
  • [ 1916473-27-2 ]
YieldReaction ConditionsOperation in experiment
69% With copper; caesium carbonate In acetonitrile at 80℃; for 4h; Inert atmosphere; Intermiediate 1-phenoxy-9H-carbazole (D-1) synthesis The flask was added 100 mL three 1-hydroxy-9H-carbazole (1.83g, 10mmol) was dissolved in 50ml of acetonitrile, add cesium carbonate (6·51g, 20mmol), copper (12mg, 0.2mmol), of 1-bromobenzene (1·73g, 11mmol) under the protection of nitrogen, 80 °C reaction 4h, evaporated after the reaction was extracted organic phase column chromatography to obtain intermediate D-1 (1.79g, y = 69%),
  • 23
  • [ 61601-54-5 ]
  • [ 74-88-4 ]
  • [ 4544-87-0 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 1-hydroxycarbazole With sodium hydride In N,N-dimethyl-formamide at 0 - 23℃; for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 23℃; for 3h; Inert atmosphere;
  • 24
  • [ 61601-54-5 ]
  • [ 22979-35-7 ]
  • [ 2089148-96-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 1-hydroxycarbazole With bis(benzonitrile)palladium(II) dichloride; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate; 2,6-bis((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)pyridine In chloroform for 0.0833333h; Molecular sieve; Inert atmosphere; Stage #2: Methyl phenyldiazoacetate In chloroform at 40℃; for 5h; Molecular sieve; Inert atmosphere; enantioselective reaction;
  • 25
  • [ 2265883-70-1 ]
  • [ 61601-54-5 ]
YieldReaction ConditionsOperation in experiment
89% With magnesium In tetrahydrofuran; methanol at 70℃; for 5h;
  • 26
  • [ CAS Unavailable ]
  • [ 61601-54-5 ]
  • [ 102721-76-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
66% In neat (no solvent) for 0.0833333h; Heating; Microwave irradiation; General procedure for the preparation of compounds (9a-j and 11a-f) General procedure: A mixture of 4-hydroxycarbazole (6) (1 mmol) or 2-hydroxycarbazole (10) (1 mmol), aromatic aldehydes (7) (1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (8) (1 mmol) were heated under microwave irradiation (360 W) for 5 min. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed with ethanol (5 mL) and dried to afford the pure products 9a-j or 11a-f (yields: 66-89 %).
  • 27
  • [ 61601-54-5 ]
  • [ 102721-76-6 ]
  • [ 1122-91-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
68% In neat (no solvent) for 0.0833333h; Heating; Microwave irradiation; General procedure for the preparation of compounds (9a-j and 11a-f) General procedure: A mixture of 4-hydroxycarbazole (6) (1 mmol) or 2-hydroxycarbazole (10) (1 mmol), aromatic aldehydes (7) (1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (8) (1 mmol) were heated under microwave irradiation (360 W) for 5 min. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed with ethanol (5 mL) and dried to afford the pure products 9a-j or 11a-f (yields: 66-89 %).
  • 28
  • [ 61601-54-5 ]
  • [ 102721-76-6 ]
  • [ 555-16-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
70% In neat (no solvent) for 0.0833333h; Heating; Microwave irradiation; General procedure for the preparation of compounds (9a-j and 11a-f) General procedure: A mixture of 4-hydroxycarbazole (6) (1 mmol) or 2-hydroxycarbazole (10) (1 mmol), aromatic aldehydes (7) (1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (8) (1 mmol) were heated under microwave irradiation (360 W) for 5 min. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed with ethanol (5 mL) and dried to afford the pure products 9a-j or 11a-f (yields: 66-89 %).
  • 29
  • [ 61601-54-5 ]
  • [ 102721-76-6 ]
  • [ 591-31-1 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
71% In neat (no solvent) for 0.0833333h; Heating; Microwave irradiation; General procedure for the preparation of compounds (9a-j and 11a-f) General procedure: A mixture of 4-hydroxycarbazole (6) (1 mmol) or 2-hydroxycarbazole (10) (1 mmol), aromatic aldehydes (7) (1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (8) (1 mmol) were heated under microwave irradiation (360 W) for 5 min. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed with ethanol (5 mL) and dried to afford the pure products 9a-j or 11a-f (yields: 66-89 %).
  • 30
  • [ 61601-54-5 ]
  • [ 102721-76-6 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
76% In neat (no solvent) for 0.0833333h; Heating; Microwave irradiation; General procedure for the preparation of compounds (9a-j and 11a-f) General procedure: A mixture of 4-hydroxycarbazole (6) (1 mmol) or 2-hydroxycarbazole (10) (1 mmol), aromatic aldehydes (7) (1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (8) (1 mmol) were heated under microwave irradiation (360 W) for 5 min. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed with ethanol (5 mL) and dried to afford the pure products 9a-j or 11a-f (yields: 66-89 %).
  • 31
  • [ 61601-54-5 ]
  • [ 102721-76-6 ]
  • [ 105-07-7 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
67% In neat (no solvent) for 0.0833333h; Heating; Microwave irradiation; General procedure for the preparation of compounds (9a-j and 11a-f) General procedure: A mixture of 4-hydroxycarbazole (6) (1 mmol) or 2-hydroxycarbazole (10) (1 mmol), aromatic aldehydes (7) (1 mmol) and (E)-N-methyl-1-(methylthio)-2-nitroethenamine (8) (1 mmol) were heated under microwave irradiation (360 W) for 5 min. After completion of the reaction (confirmed by TLC), the reaction mixture was cooled to room temperature. The precipitated solid was filtered, washed with ethanol (5 mL) and dried to afford the pure products 9a-j or 11a-f (yields: 66-89 %).
  • 32
  • [ 61601-54-5 ]
  • [ 625-99-0 ]
  • [ 2780322-74-7 ]
YieldReaction ConditionsOperation in experiment
80 % With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; 1.3 (3) Synthesis of Sub-1-1 To Sub-1-1-d (15.0 g, 81.9 mmol) obtained in the above reaction, Sub-1-1-e (18.9 g, 81.9 mmol),After adding Pd2(dba)3 (2.3 g, 2.5 mmol), P(t-Bu)3 (1.0 g, 4.9 mmol), NaOt-Bu (15.7 g, 163.7 mmol), and toluene (409 mL), at 80 proceed with the reaction. After the reaction was completed, extraction was performed with CH2Cl2 and water, and the organic layer was dried with MgSO4, concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 17.1 g of the product. (Yield: 80%)
  • 33
  • [ 2780322-61-2 ]
  • [ 61601-54-5 ]
YieldReaction ConditionsOperation in experiment
72 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl acetamide Reflux; 1.2 (2) Synthesis of Sub-1-1-d After dissolving Sub-1-1-c (30.0 g, 113.6 mmol) obtained in the above reaction with DMAC (Dimethylacetamide) (1136 mL), K2CO3 (31.4 g, 227.2 mmol), Pd(PPh3)4 (2.63 g, 2.3 mmol) was added and refluxed. After dissolving in CHCl3, washing with water, about 50% of the solvent was removed under reduced pressure. Thereafter, the mixture was crystallized by adding Ethylacetate in a reflux state, cooled to room temperature, and the resulting crystals were filtered. The obtained solid was recrystallized with silicagel column to obtain 15.0 g of product. (Yield: 72.0%)
72 % With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl acetamide Reflux; 1.I.1.2 (2) Synthesis of Sub-1-1-d After dissolving Sub-1-1-c (30.0 g, 113.6 mmol) obtained in the above reaction with DMAC (Dimethylacetamide) (1,136 mL), K2CO3 (31.4 g, 227.2 mmol), Pd(PPh3)4 (2.63 g, 2.3 mmol) was added and refluxed. After dissolving in CHCl3, washing with water, about 50% of the solvent was removed under reduced pressure. Thereafter, the mixture was crystallized by adding Ethylacetate in a reflux state, cooled to room temperature, and the resulting crystals were filtered. The obtained solid was recrystallized with silicagel column to obtain 15.0 g of product. (Yield: 72%)
  • 34
  • [ 61601-54-5 ]
  • [ 615-41-8 ]
  • [ 2780322-77-0 ]
YieldReaction ConditionsOperation in experiment
71 % With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃; 1.I.1.3 (3) Synthesis of Sub-1-1 Sub-1-1-e (18.9 g, 81.9 mmol), Pd2(dba)3 (2.3 g, 2.5 mmol), P(t After adding -Bu)3 (1.0 g, 4.9 mmol), NaOt-Bu (15.7 g, 163.7 mmol), and toluene (409 mL), the reaction proceeds at 80 °C. After the reaction was completed, extraction was performed with CH2Cl2 and water, and the organic layer was dried with MgSO4, concentrated, and the resulting organic material was recrystallized using a silica gel column to obtain 17.1 g of the product. (Yield: 71%)
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