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Chemistry
Organometallic Reagents
Organoboron
9-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-9H-carbazole
Chemistry
Organometallic Reagents
Organic Building Blocks Heterocyclic Building Blocks
Organoboron
Esters Carbazole Series

[ CAS No. 1217891-71-8 ]

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Cat. No.: {[proInfo.prAm]}
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Chemical Structure| 1217891-71-8
Chemical Structure| 1217891-71-8
Structure of 1217891-71-8 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 1217891-71-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1217891-71-8 ]

SDS Specification
Alternatived Products of [ 1217891-71-8 ]

Product Details of [ 1217891-71-8 ]

CAS No. :1217891-71-8 MDL No. :MFCD16294552
Formula : C19H22BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AVCKYKVGQYBADD-UHFFFAOYSA-N
M.W :307.19 Pubchem ID :56924967
Synonyms :

Safety of [ 1217891-71-8 ]

Signal Word:Danger Class:9
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330 UN#:3077
Hazard Statements:H302-H319-H372-H410 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1217891-71-8 ]

* 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 [ 1217891-71-8 ]

[ 1217891-71-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 1484-12-4 ]
  • [ 76-09-5 ]
  • [ 1217891-71-8 ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: N-methylcarbazole With boron trichloride; Dimethyl-p-toluidine In dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; 34 Example 34 - Mono-Borylation of N-Me carbazole1 equiv. BCI3 0.95 equiv.20 °C, 30 min[00143] An oven dried 1 L round-bottomed flask cooled under N2, was charged withAICI3 (14.7 g, 1 10 mmol, 1 .1 equiv.) and N-Me carbazole (17.2 g, 95.0 mmol, 0.95 equiv.). This was then suspended in CH2CI2 (300 ml_) and A ,A/,4-trimethylaniline (18.8 ml_, 130 mmol, 1 .3 equiv.) was added. To the resulting solution was then added a solution of BCI3 (1 .0 M in CH2CI2, 100 ml_, 100 mmol, 1 equiv.). The reaction was stirred for 16 hours before being transferred over 45 minutes via a cannula under a positive pressure of N2 to a solution of pinacol (35.5 g, 300 mmol, 3 equiv.) in triethylamine (209 ml_, 1 .50 mol, 15 equiv.) contained in an oven dried 2 L round-bottomed flask, cooled under N2, with care taken not to allow any significant rise in reaction temperature. After washing the flask with CH2CI2 (2 x 25 ml_) the volatiles were removed in vacuo and the resulting beige solid purified by chromatography on silica gel eluting with a gradient of 0 - 20% EtOAc in petroleum ether 40/60 to give the desired compound (22.3 g, 72.6 mmol, 76%) as a pale yellow solid (M.p. 147 - 149 °C).1 H NMR (CDCI3): 8.60 (s, 1 H), 8.13 (d, J = 7.6 Hz, 1 H), 7.94 (dd, J = 1 .1 , 8.2 Hz, 1 H), 7.47 (ddd, J = 1 .1 , 7.1 , 8.2 Hz, 1 H), 7.39 (d, J = 8.1 Hz, 2 H), 7.25 (td, J = 1 .0, 7.4 Hz, 1 H), 3.84 (s, 3 H), 1 .40 (s, 12 H).13C NMR (CDCI3) : 143.1 , 141 .0, 132.2, 127.7, 125.7, 123.0, 122.5, 120.5, 1 19.3, 108.4, 107.8, 83.6, 29.1 , 24.9.11 B NMR (CD2CI2): 31 .1 (br s).
Reference： [1]Current Patent Assignee: UNIVERSITY OF MANCHESTER - WO2012/25760, 2012, A1 Location in patent: Page/Page column 58
  • 2
  • [ 1217891-71-8 ]
  • [ 1193092-32-8 ]
  • 3-((N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)-9-metyl-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In tetrahydrofuran; water at 80℃; for 24h; Inert atmosphere; 2.3.1 3,6-((Di(N-(2-ethylhexyl)-1,8-naphthalimide)-4-yl)-9-metyl-9H-carbazole (5) General procedure: 4-Bromo-N-(2-ethylhexyl)-1,8-naphthalimide (4) (0.5 g, 1.29 mmol) and 15 mL of dry THF and aqueous K2CO3 solution (0.81 g, 5.85 mmol) in 2 mL H2O were added via a syringe under nitrogen to a three-necked round-bottomed flask (50 mL) equipped with a magnetic stirrer, a reflux condenser and a nitrogen input tube. 9-Methyl-3,6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-9H-carbazole (3a) (0.25 g, 0.59 mmol) and Pd(PPh3)2Cl2 (0.02 g, 0.02 mmol) were successively added and the reaction mixture was refluxed at 80 °C for 24 h under nitrogen atmosphere. After cooling down to the room temperature methylene chloride (200 mL) was added to the reaction mixture. Then it was washed three times with distilled water, and dried with anhydrous magnesium sulfate. The solution was filtered and concentrated. The crude product was purified by column chromatography on silica gel with ethyl acetate and hexane (1:9, V:V) as eluent and crystallized from the eluent mixture of solvents to give 5 as yellow crystals.
Reference： [1]Gudeika, Dalius; Grazulevicius, Juozas Vidas; Volyniuk, Dmytro; Butkute, Rita; Juska, Gytis; Miasojedovas, Arunas; Gruodis, Alytis; Jursenas, Saulius [Dyes and Pigments, 2015, vol. 114, # C, p. 239 - 252]
  • 3
  • [ 91828-08-9 ]
  • [ 61676-62-8 ]
  • [ 1217891-71-8 ]
YieldReaction ConditionsOperation in experiment
70% In an argon atmosphere,3-Bromo-9-methyl-9H-carbazole (10 g, 38.4 mmol)Dissolved in 180 mL refined THF2.4 mL of n-butyllithium (2.4 mL) was gradually added dropwise at -78C.Reaction for 2 hours,Then 12.5 g of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added.The reaction was continued at -78 C for 1 hour.Then warmed to room temperature for 24 hours;The reaction mixture was poured into water, extracted with ethyl acetate, the organic layer was completely washed with brine, and dried over anhydrous magnesium sulfate;After the solution was concentrated, a pale yellow viscous crude product was obtained and purified by silica gel column chromatography.A mixture of petroleum ether and ethyl acetate (8/1, v/v) was used as a rinse to obtain a white solid with a yield of 70%.
Reference： [1]Patent: CN107954921,2018,A .Location in patent: Paragraph 0059-0061
[2]Dyes and Pigments,2015,vol. 114,p. 239 - 252
  • 4
  • [ 1217891-71-8 ]
  • [ 89555-39-5 ]
  • methyl 1-(9-methyl-9H-carbazolyl-3-yl)-2-naphthoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; potassium carbonate In water; toluene at 110℃; for 12h; Inert atmosphere; 3 Example 3 Synthesis of Compound M3Preparation of methyl 1-(9-methyl-9H-carbazolyl-3-yl)-2-naphthoate In an argon atmosphere,In a 500 mL three-necked flask,Methyl 1-bromo-2-naphthalenecarboxylate (10 g, 37.72 mmol) was added,3-(4,4,5,5-tetramethyl-1,3,2-dioxaborinyl)-N-methylcarbazole (12.7 mmol, 41.5 mmol),Tetrabutylammonium bromide (0.61 g, 1.89 mmol),Catalyst tetrakis(triphenylphosphine)palladium (2.18 g, 1.89 mmol) and 200 mL toluene,Stir and heatWhen the temperature is stable at 110°C,52 mL of an aqueous solution of an organic base (20 mL) and K2CO3 (51.06 g, 0.37 mol) was added and reacted for 12 h.The reaction solution was concentrated and purified by silica gel column chromatography. The mixture of petroleum ether and dichloromethane (3/1, v/v) was used as eluent.A white solid is obtained with a yield of
Reference： [1]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN107954921, 2018, A Location in patent: Paragraph 0065-0068

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