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Product Details of 2-Naphthylboronic acid

CAS No. :32316-92-0
Formula : C10H9BO2
M.W : 171.99
SMILES Code : C1=CC2=C(C=C1)C=C(C=C2)B(O)O
MDL No. :MFCD00236051
InChI Key :KPTRDYONBVUWPD-UHFFFAOYSA-N
Pubchem ID :2734375

Safety of 2-Naphthylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 2-Naphthylboronic acid

* 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 [ 32316-92-0 ]

[ 32316-92-0 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 21906-31-0 ]
  • [ 32316-92-0 ]
  • 2-(2-acetonylphenyl)naphthalene [ No CAS ]
  • 2
  • [ 32316-92-0 ]
  • [ 40350-83-2 ]
  • [ 62-53-3 ]
  • [ 298-12-4 ]
  • [ 183742-23-6 ]
  • 2-(2-benzyloxy-4,9-dioxo-octahydro-3a,6,8a-triaza-cyclopenta[<i>b</i>]naphthalen-6-yl)-2-naphthalen-2-yl-<i>N</i>-phenyl-acetamide [ No CAS ]
  • 4
  • [ 591-18-4 ]
  • [ 32316-92-0 ]
  • [ 667940-23-0 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 24h;Heating / reflux; 2- A. Production of compound 2a; [79] After l-bromo-3-iodobenzene (10 g, 35.35 mmol) and 2-naphthalene bromic acid(5.47 g, 31.82 mmol) were dissolved in anhydrous THF (100 mL), Pd(PPh ) (1.2 g, 1.06 mmol) and 50 mL of 2M K CO aqueous solution were added and then refluxed <n="17"/>for 24 hours. The organic layer was extracted by using ethyl acetate and water was removed with magnesium sulfate. The organic layer was filtered at reduced pressure and concentrated, and the solvent was removed. The resulting substance was purified by using column chromatography and then recrystallized in THF and ethanol to obtain a white solid compound 2a (8.5 g, 85%).[80] MS [M + H] = 283
76% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 24h;Inert atmosphere; Reflux; Under an argon gas atmosphere, 243 g (1.41 mol) of 2-naphthaleneboronic acid, 400 g (1.41 mol) of 3-bromoiodobenzene, 3.27 g (28.2 mmol) of tetrakis(triphenylphosphine)palladium(0), 6.4 L of toluene and 3.2 L of aqueous solution of 2M sodium carbonate were added together, and stirred while being refluxed for 24 hours. After the reaction was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was washed by water and dried with magnesium sulfate, the toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 303 g of 2-(3-bromophenyl)naphthalene was obtained at an yield of 76%.
  • 5
  • [ 4805-22-5 ]
  • [ 32316-92-0 ]
  • [ 624744-66-7 ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 85℃; for 48h; A mixture of 5,5'-dibromo-2,2'-bithiophene (6 g, 18.51 mmol) and naphthalene-2-ylboronic acid (2.22 g,12.95 mmol) were added to toluene (80 mL), 2 M K2CO3 (15 mL), and tetrakis(-triphenylphosphine) palladium(0) (0.17 g, 1.47 104 mol). After stirring for 48 h at 85 C, 2 N HCl (40 mL) were added. The crude product was extracted with dichloromethane and purified by column chromatography using hexane as the eluent. Yield: 2.5 g(53%); IR (KBr, cm1); 3031-3064 (aromatic CH), 1H NMR(300 MHz, CDCl3, ppm): d 8.04 (s, 1H), 7.88-7.86 (m, 3H),7.76-7.75 (d, J 1.8 Hz, 1H), 7.52-7.48 (m, 2H), 7.37-7.35 (d,J 3.9 Hz, 1H), 7.15-7.14 (d, J 3.6 Hz 1H), 7.02-6.98 (m, 2H).
45% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 24h;Heating / reflux; Synthesis of Compound 1195,5'-dibromo-2,2'-bothiophene (5.00 g, 15.4 mmol), naphthalene-2-boronic acid (1.86 g, 10.8 mmol) and potassium carbonate (30 mL, 2 M aqueous solution) were suspended in THF (50 mL). Tetrakis(triphenylphosphine)palladium (0.18 g, 0.16 mmol) was added to the suspension. The resulting mixture was stirred at reflux for about 24 hours and thereafter cooled to room temperature. Precipitate was filtered off with suction. The crude product was dissolved in THF, filtered, and washed with THF. The filtrate was concentrated in vacuo and recrystallized from ethyl acetate to give Compound 119 (2.60 g, 45%).
45% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 24h;Heating / reflux; 5,5'-dibromo-2, 2'-bothiophene (5.00 g, 15.4 mmol), naphthalene-2-boronic acid (1.86 g, 10.8 mmol) and potassium carbonate (30 mL, 2 M aqueous solution) were suspended in THF (50 mL). Tetrakis (triphenylphosphine) palladium (0.18 g, 0.16 mmol) was added to the suspension. The resulting mixture was stirred at reflux for about 24 hours and thereafter cooled to room temperature. Precipitate was filtered off with suction. The crude product was dissolved in THF, filtered, and washed with THF. The filtrate was concentrated in vacuo and recrystallized from ethyl acetate to give Compound 119 (2.60 g, 45%).
  • 6
  • [ 108-36-1 ]
  • [ 32316-92-0 ]
  • [ 667940-23-0 ]
YieldReaction ConditionsOperation in experiment
47% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 24h;Heating / reflux; Example 13 : Preparation of compound 30; [196][197] 13-A. Preparation of compound 13a[198] Under N atmosphere, 1,3-dibromophenyl (10 g, 42.2 mmol), 2-naphthyl boronic acid (5.16 g, 42.2 mmol), and Pd(PPh ) (2.4 g, 2.1 mmol) were added to a 2 M aqueous solution of potassium carbonate (50 mL) and THF (300 mL). The mixture was refluxed under stirring for about 24 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, dried over magnesium sulfate, and distilled under reduced pressure. The resultant was purified by column chromatography to prepare a compound 13a (4.6 g, 47%). MS [M] = 233
  • 7
  • [ 32316-92-0 ]
  • [ 33742-70-0 ]
  • [ 1127118-18-6 ]
YieldReaction ConditionsOperation in experiment
71% With sodium carbonate;palladium(II) hydroxide/carbon; In N,N-dimethyl-formamide; at 100℃; for 9.0h; N-methyl-6-(2-naphthyl)-3-nitropyridin-2-amine. To a vial equipped with a teflon-coated cap was added <strong>[33742-70-0]6-chloro-N-methyl-3-nitropyridin-2-amine</strong> (180 mg, 0.96 mmol), sodium carbonate (102 mg, 0.96 mmol) and 2-naphthylboronic acid (198 mg, 1.15 mmol) in anhydrous DMF (5 mL). Nitrogen was bubbled through the reaction mixture for 10 min. Palladium hydroxide (20% on carbon, 13 mg) was added, and the reaction was sealed and heated at 100 C. for 9 h on a shaker block. The reaction was cooled to room temperature and diluted with water (1 mL) and methanol (1 mL). The product precipitated and was collected to yield the titled compound 190 mg (71%) as a gold solid. HPLC (method A): Rt=11.6 min. MS: [M+H-tbutyl]+=280.
  • 8
  • [ 570-02-5 ]
  • [ 32316-92-0 ]
  • [ 1040196-78-8 ]
  • 9
  • [ 1445-39-2 ]
  • [ 32316-92-0 ]
  • [ 157924-74-8 ]
  • 10
  • [ 16932-45-9 ]
  • [ 32316-92-0 ]
  • 2-(2,6-dimethoxyphenyl)naphthalene [ No CAS ]
  • 11
  • [ 1000623-95-9 ]
  • [ 32316-92-0 ]
  • [ 1401102-55-3 ]
YieldReaction ConditionsOperation in experiment
89% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 90℃;Inert atmosphere; Pd(PPh3)4 (35mg, 0.03mmol) was added to a mixture of 3,6-bis(5-bromothiophen-2- yl)-2,5-bis(2-ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (0.35g, 0.51mmol) and 2-naphthyl boronic acid (0.22g, 1.29mmol) in toluene (25mL), ethanol (10mL) and aqueous Na2CO3 solution (2M, 5mL) under N2. After the reaction was heated overnight at 90C, the volatile was evaporated. The residue was treated with water and extracted with CH2Cl2. The organic layer was separated, dried over anhydrous MgSO4, filtered and then concentrated. The crude product was purified by column chromatography using petroleum ether/dichloromethane (v/v=3/1) as eluent to afford a deep mulberry solid in 89% yield (0.36g). 1H NMR (300MHz, CDCl3): delta 9.00 (d, J=4.14Hz, 2H), 8.13 (s, 2H), 7.76-7.90 (m, 8H), 7.60 (d, J=4.14Hz, 2H), 7.48-7.56 (m, 4H), 4.12 (m, 4H), 1.99 (m, 2H), 1.31-1.45 (m, 16H), 0.87-0.96 (m, 12H). 13C NMR (75MHz, CDCl3) delta 10.63, 14.09, 23.14, 23.78, 28.66, 30.46, 39.32, 46.06, 108.35, 123.99, 124.80, 124.95, 126.68, 126.91, 127.80, 128.25, 128.92, 129.06, 130.58, 133.34, 133.52, 136.80, 139.83, 149.72, 161.77. Anal. Calcd. for C50H52N2O2S2: C, 77.28; H, 6.74; N, 3.6; S, 8.25. Found: C, 77.07; H, 6.744; N, 3.57; S, 8.378. MALDI-TOF: m/z 777.631 (100%) M+ (calcd. 777.347).
  • 12
  • [ 10323-39-4 ]
  • [ 32316-92-0 ]
  • [ 1609538-22-8 ]
  • 13
  • [ 618-89-3 ]
  • [ 32316-92-0 ]
  • methyl 3-(naphthalen-2-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 3.5h; To a solution of <strong>[618-89-3]methyl 3-bromobenzoate</strong> 13 (667 μL, 4.65 mmol) in 1,4-dioxane/H2O = 2:1 (15 mL) were added 2-naphthylboronic acid (1.20 g, 6.98 mmol), Na2CO3 (690 mg, 6.51 mmol) and tetrakis(triphenylphosphine)palladium (107 mg, 0.0930 mmol). The reaction mixture was stirred for 3.5 h at 80 C. Then, H2O was added and the whole was extracted with AcOEt x 2. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by means of silica gel column chromatography (eluent: n-hexane/AcOEt) to obtain 14 as a colorless oil (76%). 1H NMR (500 MHz, CDCl3) δ: 8.41 (1H, dd, J = 1.7, 1.7 Hz), 8.09 (1H, d, J = 1.1 Hz), 8.05 (1H, m), 7.92-7.89 (4H, m), 7.77 (1H, dd, J = 8.6, 1.7 Hz), 7.56 (1H, dd, J = 7.7, 7.7 Hz), 7.53-7.51 (2H, m), 3.93 (3H, s).
  • 14
  • [ 32316-92-0 ]
  • [ 479-79-8 ]
  • 5,6-dipropyltetraphene [ No CAS ]
  • 15
  • [ 1120-95-2 ]
  • [ 32316-92-0 ]
  • 3-(naphthalen-2-yl)pyridazine [ No CAS ]
  • 16
  • [ 10485-09-3 ]
  • [ 32316-92-0 ]
  • [ 20924-22-5 ]
YieldReaction ConditionsOperation in experiment
67% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In Dimethyl ether; water; at 90℃; for 6h;Inert atmosphere; (3) Synthesis of 2-(1H-indene-2-yl)naphthalene Finally, 2.7 g (13.8 mmol) of <strong>[10485-09-3]2-bromoindene</strong> was added to a 100 mL Schlenk flask, and dissolved in a mixed solution of 60 mL of DME (dimethyl ether) and 20 mL of water. 3.4 g (18 mmol) of 2-naphthalene boronic acid and 2.8 g (21 mmol) of K2CO3 were added thereto, and argon gas was bubbled therein for 10 min to remove oxygen in the solvent. Thereafter, heating was initiated under an argon atmosphere, and when the temperature reached 90 C., 800 mg (0.7 mmol, 5 mol %) of palladium(0)tetrakis(triphenylphosphine) (Pd/C) was added thereto, and stirred for 6 h. Thereafter, the reaction mixture was cooled to room temperature, and 200 mL of water was poured thereto to filter the resulting brown precipitate, which was washed with about 50 mL of ether, and then dried, thereby obtaining 2.4 g (67%) of a white solid. 1H NMR (500 MHz, CDCl3): δ 3.96 (2H, s), 7.23 (1H, m), 7.31 (1H, m), 7.48-7.54 (4H, m), 7.69-7.74 (1H, m), 7.76-7.83 (4H, m), 8.01 (1H, s).
  • 17
  • [ 166402-16-0 ]
  • [ 32316-92-0 ]
  • 3-(naphthalen-2-yl)quinoxalin-6-amine [ No CAS ]
  • 18
  • [ 88-12-0 ]
  • [ 383-62-0 ]
  • [ 32316-92-0 ]
  • ethyl 2,2-difluoro-4-(naphthalen-2-yl)-4-(2-oxopyrrolidin-1-yl)butanoate [ No CAS ]
  • 19
  • [ 32316-92-0 ]
  • [ 57103-20-5 ]
  • C28H18BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; at 55℃; for 12h; To a round flask was added 1.5 eq of <strong>[57103-20-5]3,6-dibromo-9-phenyl-carbazole</strong> (5 g, 0.01 mol), 1 eq of 2-naphthaleneboronic acid (1.43 g, 8.3 mmol), Pd (PPh3) , 0.415 mmol) and 15 eq of potassium carbonate (17 g, 0.12 mol), and the mixture was stirred with 100 ml of 1,4-dioxane. 20 ml of distilled water was added while raising the temperature, and the reaction was carried out at 55 ° C for 12 hours. After cooling to room temperature and extraction, the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtered organic layer was concentrated under reduced pressure, and recrystallized from dichloromethane / hexane to obtain intermediate A.
  • 20
  • [ 256652-04-7 ]
  • [ 32316-92-0 ]
YieldReaction ConditionsOperation in experiment
A mixture of 3c (762 mg, 3 mmol) and sodium periodate (2.83 g, 9 mmol) in THF (15 mL) andwater (4 mL) was stirred at room temperature for 30 min. To the suspension was added hydrochloricacid (1 N, 2.1 mL, 1.5 mmol), and the reaction mixture was stirred at room temperature for 17 h. Themixture was diluted with water (3 mL) and extracted with ethyl acetate three times. The combinedextracts were washed with water and brine, dried over sodium sulfate, filtered, and concentrated todryness by evaporation. A mixture of the obtained arylboronic acid and anthranilamide (388 mg,2.85 mmol) in toluene (19 mL) was heated under reflux in a Dean-Stark apparatus for 1 h. Aftercooling to room temperature, the precipitates were collected by filtration to give 5c (722 mg, 93%).
  • 21
  • [ 63927-22-0 ]
  • [ 32316-92-0 ]
  • 8-(naphthalen-2-yl)isoquinoline [ No CAS ]
  • 22
  • [ 2631-77-8 ]
  • [ 32316-92-0 ]
  • C27H18O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With lithium hydroxide monohydrate; C36H27N2OPPd; In methanol; water; N,N-dimethyl-formamide; at 80℃; for 24h; General procedure: In a 10 ml round bottom flask, 3,5-dihalosalicylaldehyde(1 mmol), arylboronic acid (2.2 mmol for diiodo precursor or2.5 mmol for dibromo precursor), LiOHH2O (2 mmol) and complex2 (0.01 mol% for diiodo precursor or 0.05 mol% for dibromo precursor)in 0.1 ml dimethylformamide were taken in 2 ml of watermethanol(1:1) mixture. The reaction mixture was then heated at80 C under aerobic condition. Progress of the reaction was monitoredby TLC. On completion, the reaction mixture was cooled toroom temperature and extracted with two 10 ml portions of ethylacetate. The combined extract was washed with water (2 x 10 ml),dried over anhydrous Na2SO4 and finally the solvent was removedunder reduced pressure. The solid obtained was subjected to columnchromatography over silica gel using ethyl acetate and hexanemixture as the eluent to afford the pure product. All the functionalizedtriaryl products obtained were characterized by 1H NMRspectroscopy and high resolution mass spectrometry.
  • 23
  • [ 32316-92-0 ]
  • [ 46258-62-2 ]
  • 1-([1,2'-binaphthalen]-4-yl)ethan-1-one [ No CAS ]
  • 24
  • [ 32316-92-0 ]
  • [ 21193-80-6 ]
  • [ 1252858-01-7 ]
YieldReaction ConditionsOperation in experiment
62% With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; sodium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere; General procedure: 31 (1 eq.), boronic acid (1.5 eq.) or pinacol ester [for compound14 (1.5 eq.)], Na2CO3 (9 eq.), Pd(OAc)2 (0.05 eq.) and TPPTS (0.15 eq.)were added to a 10mL round-bottom flask, equipped with a stir bar.Next, the flask was evacuated and refilled with argon. This procedure was repeated three times in total. Next, degassed MeCN(2 mL/mmol SM) and H2O (4 mL/mmol SM) were added to the solids under argon. After 5 min of stirring, the mixture was heatedto 100 C in a pre-heated oil bath. When the starting material was fully consumed (usually 1e3 h), the mixture was cooled to ambient temperature, and neutralized (pH ~ 7) with 0.5M aq. HCl. Themixture was evaporated till dryness, resuspended in MeOH and evaporated (three times). Next, the mixture was adsorbed onto Celite (fromMeOH) and eluted over a short silica pad (~5 cm) with 20% MeOH/DCM. The liquid was evaporated in vacuo and purified by column chromatography.
  • 25
  • [ 32316-92-0 ]
  • [ 5350-41-4 ]
  • [ 613-59-2 ]
  • 26
  • [ 381-98-6 ]
  • [ 32316-92-0 ]
  • C14H11F3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(l) oxide; In tert-Amyl alcohol; at 50℃; for 20h;Inert atmosphere; General procedure: Amixture of phenylboronic acid (1a) (1 mmol, 122 mg), alpha-trifluoromethylacrylicacid (2) (0.5 mmol, 70 mg), [Cp*RhCl2]2 (0.01 mmol, 6 mg), AgSbF6 (0.1 mmol, 34mg), Ag2O (1 mmol, 232 mg), and 1-methylnaphthalene (ca. 40 mg) as internal standard was stirred in tert-amylalcohol (3 ml) under argon at 50 C for 20 h.Then the reaction mixture was diluted by ethyl acetate (30 ml). The organiclayer was washed by 1 N HCl(30 ml), water 30 (ml), and brine (30 ml) and driedover Na2SO4. After evaporation of the solvents under vacuum, product 3a? (101 mg,93%) was isolated by column chromatography on silica gel usinghexane/EtOAc/AcOH=90/9/1 (v/v/v) as eluent.
  • 27
  • [ 13338-63-1 ]
  • [ 32316-92-0 ]
  • 1-(naphthalen-2-yl)-2-(3,4,5-trimethoxyphenyl)ethan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With [2,2]bipyridinyl; potassium fluoride; palladium diacetate; trifluoroacetic acid; In tetrahydrofuran; water; at 80℃; for 2h;Inert atmosphere; Schlenk technique; General procedure: Under a nitrogen atmosphere, aryl acetonitrile 1 (3mmol), arylboronic acids 2 (6mmol), palladium acetate (5mol %), 2,2′-Bipyridine (10mol %), trifluoroacetic acid (30mmol), potassium fluoride (6mmol), tetrahydrofuran (20mL), and water (10mL) were successively added to a Schlenk reaction tube. The reaction mixture was stirred vigorously at 80C for 2h. After the reaction mixture was cooled to room temperature, saturated sodium bicarbonate (30mL) was added into the solution, and the mixture was extracted with ethyl acetate (10mL) for 3 times. The combined organic layer was concentrated in vacuo. The residue was purified by flash column chromatography to afford desired product 3.
 

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