Home Cart 0 Sign in  

[ CAS No. 214360-58-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 214360-58-4
Chemical Structure| 214360-58-4
Structure of 214360-58-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 214360-58-4 ]

Related Doc. of [ 214360-58-4 ]

Alternatived Products of [ 214360-58-4 ]

Product Details of [ 214360-58-4 ]

CAS No. :214360-58-4 MDL No. :MFCD03453665
Formula : C12H16BFO2 Boiling Point : -
Linear Structure Formula :- InChI Key :SBWKQMCGTSWDPE-UHFFFAOYSA-N
M.W : 222.06 Pubchem ID :2760593
Synonyms :

Calculated chemistry of [ 214360-58-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.88
TPSA : 18.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.01
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 2.15
Log Po/w (SILICOS-IT) : 2.25
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.105 mg/ml ; 0.000474 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.192 mg/ml ; 0.000866 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.0116 mg/ml ; 0.0000521 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.89

Safety of [ 214360-58-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 214360-58-4 ]

* 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.

  • Upstream synthesis route of [ 214360-58-4 ]
  • Downstream synthetic route of [ 214360-58-4 ]

[ 214360-58-4 ] Synthesis Path-Upstream   1~44

  • 1
  • [ 24424-99-5 ]
  • [ 214360-58-4 ]
  • [ 58656-98-7 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 6, p. 3540 - 3551
[2] Organic Letters, 2014, vol. 16, # 7, p. 1836 - 1839
  • 2
  • [ 73183-34-3 ]
  • [ 460-00-4 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
93% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 1.5 h; Inert atmosphere In the stirring step, potassium acetate (KOAc) (0.073 g, 0.09 mmol) was added to a solution of 1, 1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex (PdCl 2 (dppf) CH 2 Cl 2) Fluorophenyl bromide 1b (R═F, 0.613 g, 3.5 mmol) and bis (pinacolato) diboron 2 (1.161 g, 4.5 mmol) were added to a dimethylsulfoxide (DMSO) solution in which 1.601 g The mixture was stirred at 80 ° C. for 1.5 hours to obtain a reaction solution.In the organic layer extraction step, ice water is added to the reaction solution after the stirring step, and the organic layer is extracted with ethyl acetate (EtOAc) (80 mL × 2) to obtain an extract.In the concentration step, the extract solution subjected to the organic layer extraction step is dried with anhydrous magnesium sulfate (MgSO 4) and concentrated under reduced pressure to obtain a residue.In the purification step, the residue subjected to the concentration step was purified by column chromatography (silica gel, hexane / EtOAc = 9: 1) to obtain the target compound (2- (4-fluorophenyl) -4,4,5,6- Methyl-1, 3, 2-dioxaboron 3b (R = F)) in a yield of 93percent.
81.5% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 2 h; Inert atmosphere A flask charged with 1 (1.226 g, 7.0 mmol), borate 2 (Pin2B2, 2.322 g, 9.0 mmol), PdCl2(dppf)*CH2Cl2 (0.176 g, 0.210 mmol) and KOAc (2.748 g, 28.0 mmol) was flushed with nitrogen. Then DMSO (40 mL) was added. After being stirred at 80 °C for 2.0 h, the reaction mixture was extracted with AcOEt (2 * 80 mL). The combined organic extracts were dried over anhydrous MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography (silica gel, petroleum ethter/AcOEt = 9:1, v/v) to afford the title compound 3. Yield 81.5percent; Colorless liquid; 1H NMR (400 MHz, CDCl3): δ 1.34 (s, 12H), 7.03-7.07 (m, 2H), 7.80 (dd, J = 8.4 Hz, 6.4 Hz, 2H). 13C NMR (100 MHz, CDCl3): δ 25.18, 84.21, 115.15, 137.31, 164.19, 166.68. 19F NMR (376 MHz, CDCl3): δ -108.43 (s, 1F).
Reference: [1] Patent: JP5966165, 2016, B2, . Location in patent: Paragraph 0056-0062
[2] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[4] Journal of Fluorine Chemistry, 2015, vol. 178, p. 195 - 201
[5] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054
[6] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610
[7] Patent: WO2011/149950, 2011, A2, . Location in patent: Page/Page column 136-137
[8] Organic and Biomolecular Chemistry, 2015, vol. 13, # 11, p. 3236 - 3242
[9] Journal of Organic Chemistry, 2015, vol. 80, # 19, p. 9671 - 9681
[10] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 31, p. 5226 - 5231
[11] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 14, p. 2513 - 2517
  • 3
  • [ 371-40-4 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
83% With tert.-butylnitrite; eosin In acetonitrile at 20℃; for 2 h; Irradiation General procedure: tert-Butyl nitrite (155 mg, 1.1 mmol) wasadded drop wise to a mixture of bis(pinacolato)diborane (127 mg, 0.5 mmol),4-anisidine (61 mg, 0.5 mmol) and eosin Y (0.01 mmol) in acetonitrile (3 mL).The resulting mixture was stirred at room temperature under irradiation withblue LED for 2 h (TLC). This mixture after being diluted with ethyl acetate(5 mL) was ltered through celite and the ltrate was extracted with ethylacetate (3 10 mL). The extract was washed with brine, dried over anhydrousNa 2 SO 4 , and evaporated to leave the crude product which was puried bycolumn chromatography over silica gel with hexane–ethyl acetate (98:2) aseluent to furnish pure 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane as a light yellow viscous liquid (3d, 208 mg, 88percent); IR (neat)2978, 2933, 2839, 2526, 2050, 1950, 1911, 1724, 1605, 1570 cm1;1H NMR(500 MHz, CDCl 3 ) d 1.33 (s, 12H), 7.82 (s, 3H), 6.89 (d, J = 8.0 Hz, 2H), 7.75 (d,J = 8.0 Hz, 2H);13C NMR (125 MHz, CDCl 3 ) d 24.9 (4C), 55.2, 83.6 (2C), 113.4(2C), 136.6 (2C), 162.3. The spectroscopic data is in full agreement with thosereported for an authentic sample.14This procedure was followed for all thereactions listed in Table 2. All of these products (3a,143b,143c,16a3d,143e,143f,8a3g,143h,143i,143j,8a3k,8a3l,8a3m,143n,8c3o,16b) are known compounds,and their spectroscopic data are in agreement with those previously reported.
58%
Stage #1: With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1 h;
Stage #2: at 20℃; Sealed tube
General procedure: Aryl amine (10 mmol) was dissolved in a mixture of 5 mL of distilled water and 3.4 mL of 50percent hydrofluoroboric acid. After cooling the reaction mixture to 0 °C using ice bath and the sodium nitrite (0.69 g in 2 mL distilled water), was added dropwise in 5 min interval of time. The resulting mixture was stirred for 1 h and the precipitate was collected by filtration and redissolved in minimum amount of acetone. Diethylether was added until precipitation of aryl diazonium tetrafluoroborate, which is filtered, washed several times with diethyl ether and dried under vacuum. Typical reaction procedure: General procedure: Diazonium tetrafluoroborate salts (0.5 mmol) and B2pin2 (1.5 mmol) were transferred into an oven-dried tube under air. Then acetone/H2O (2/1, 4 mL) were added into the tube via syringe. The sealed tube was keep at 20 °C and stirred for 1-2 h. After the reaction was complete, dichloromethane was added to extract the product and the combined organic solution was dried by Na2SO4. The pure product was isolated after column chromatography on silica gel (petroleum ether/ethyl acetate).
54%
Stage #1: With hydrogenchloride; methanol; sodium nitrite In water at 0 - 5℃; for 0.5 h; Green chemistry
Stage #2: at 20℃; for 1 h; Green chemistry
General procedure: To a solution of arylamine (0.5 mmol, 1.0 equiv) in MeOH(1.0 mL) was added HCl (0.5 mL, 1.5 mmol, 3.0 equiv) followed by H2O (0.5 ml). This mixture was stirred 2 min, and the NaNO2 solution (0.25 mL) was then added. The NaNO2 solution was prepared by dissolving 35 mg of NaNO2 in H2O (0.25 mL). This mixture was stirred 30 minat 0–5 °C followed by B2pin2 (2, 381 mg, 1.5 mmol, 3.0equiv) in MeOH (1.0 mL). This mixture was stirred 60 min.H2O (10 mL) was added to the reaction mixture, then extracted with CH2Cl2 (50 mL, 3×). The combined organic layers were washed with sat. NaHCO3, dried over Na2SO4, followed by evaporation, and the crude residue was purified by flash chromatography.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1551 - 1554
[2] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933
[3] Tetrahedron Letters, 2017, vol. 58, # 40, p. 3851 - 3853
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[5] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[6] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
  • 4
  • [ 352-34-1 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
79% With pyridine; cesium fluoride In dimethyl sulfoxide at 105℃; for 2 h; Inert atmosphere; Schlenk technique General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv) and bispinacolatodiboron (254 mg, 1 mmol, 2 equiv). Under an argon atmosphere, freshly distilled DMSO (0.4 mL), the appropriate aryl iodide (0.5mmol), and pyridine (0.4 to 1 equiv) were added successively. The reaction mixture was heated to 105 °C and stirred for 2 h under argon.
81 %Chromat. With copper(II) ferrite; potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 12 h; Green chemistry General procedure: 4-Iodoanisole (0.813 mmol, 200 mg), bis(pinacolato)diboron (1.219 mmol, 309 mg) were dissolved in 3 mL of dmf followed by copper ferrite nanoparticles (5molpercent with respect to 4-iodoanisole) and potassiumtert-butoxide (1.219 mmol, 137 mg) were added to a 10 mLcapped vial and stirred at RT for time indicated. After stirring, the mixture was diluted with diethyl ether and filtered through celite bed. The filtrate was extracted with water (3 times) and the organic phase was dried over anhydrous MgSO4. The crude product was subjected to analyze by GC–MS. The conversion yield is accurately measured based on the consumption of 4-iodoanisole and the side product formed due to protodeiodination.
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 21, p. 4759 - 4768
[2] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610
[3] Chemical Science, 2016, vol. 7, # 6, p. 3676 - 3680
[4] Catalysis Communications, 2016, vol. 85, p. 61 - 65
  • 5
  • [ 352-34-1 ]
  • [ 78782-17-9 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
63% With sodium t-butanolate In tetrahydrofuran; toluene at 80℃; for 6 h; Sealed tube Fluoro-4-iodobenzene (44 mg, 0.20 mmol), 1,1-diboxomethane (107 mg, 0.40 mmol)And sodium tert-butoxide base (38 mg, 0.40 mmol) was placed in a 4 mL vial.Toluene / tetrahydrofuran (2.0 mL, 1: 1 mixed solution) was then added.This vial was sealed for 6 hours at 80 ° C sealed with a PTFE / silicone coated capThe reaction proceeded. The reaction solution was then filtered through celite using dichloromethane,This organic material was concentrated under reduced pressure. The subsequent productsIn condition Φ 2.0 cm x 8 cm After silica gel column chromatography, n-hexane: diethyl ether,15: 1 eluent.The results showed that 2- (4-Fluorophenyl) -4,4,5,5, -tetramethyl-1,3,2-dioxaborolaneA boronated compound was produced. (28 mg, 63percent yield);
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 975 - 984
[2] Patent: KR2018/12458, 2018, A, . Location in patent: Paragraph 0049; 0050; 0055
  • 6
  • [ 61676-62-8 ]
  • [ 460-00-4 ]
  • [ 214360-58-4 ]
Reference: [1] Organic Process Research and Development, 2013, vol. 17, # 9, p. 1192 - 1208
[2] Chemistry - A European Journal, 2007, vol. 13, # 26, p. 7487 - 7500
[3] Chemistry - A European Journal, 2009, vol. 15, # 47, p. 12978 - 12992
[4] Organic Letters, 2011, vol. 13, # 13, p. 3312 - 3315
[5] Dalton Transactions, 2013, vol. 42, # 24, p. 8939 - 8950
  • 7
  • [ 352-33-0 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[3] ChemCatChem, 2016, vol. 8, # 14, p. 2317 - 2320
[4] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054
[5] ACS Catalysis, 2017, vol. 7, # 5, p. 3199 - 3203
  • 8
  • [ 76-09-5 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
70% With montmorillonite K10 In tetrahydrofuran at 25℃; Molecular sieve General procedure: In a flask containing the appropriate boronic acid 1a-m (0.25 mmol) in tetrahydrofuran (THF; 3 mL) was added montmorillonite K10 (150percent m/m) followed by pinacol(30 mg, 0.25 mmol). The mixture was stirred for 15 minto homogenize the contents, and powdered 4 Å molecularsieves (150percent m/m) were added. The mixture was then stirredat room temperature for the time indicated in Scheme 2.After this period, the mixture was extracted with EtOAc(3 × 10 mL) and the organic phase was washed with water(2 × 15 mL). The organic phase was dried over anhydrousMgSO4, filtered and the solvent was removed in vacuo.
Reference: [1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 9, p. 1777 - 1785
  • 9
  • [ 76-09-5 ]
  • [ 22092-92-8 ]
  • [ 459-45-0 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With ferrocene In acetonitrile at 20℃; for 2.5 h;
Stage #2: With methanol In acetonitrile at 0 - 20℃; for 1 h;
Stage #3: at 20℃; for 4 h;
Example 3: General procedure D for the synthesis of the arylpinacolboronates by arylation of diisopropylaminoborane, catalysed by ferrocene (1percent), followed by methanolysis and transesterification In a dried tube reactor under argon as described in example 2, the arenediazonium salt (1 mmol) and the ferrocene (ΙΟμιηοΙ, 1.8mg) were dissolved in 2mL of anhydrous CH3CN. Diisopropylaminoborane (2mmol, 226mg) was then added to the solution and the mixture was stirred for 2h30 at room temperature. The reaction mixture was quenched by a slow addition of anhydrous MeOH at 0°C (2mL) and stirred for an additional hour at room temperature. After removal of all the volatiles, 1.3eq of pinacol was added in Et20 (2mL), the mixture was stirred 4h at room temperature. The crude mixture was washed with a 50g/L CuCl2 solution (2 x 5mL). The organic layer were separated, dried over Na2S04, filtered and concentrated to dryness. The resulted oil was dissolved with CH2C12 and filtered of a pad of silica gel, eluting with CH2C12 to afford the corresponding boronate. Example 17: synthesis of 2-(4-fluorophenyr)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [CAS 214360-58-4], compound VIA14. 135 mg of 2-(3-iodophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane were obtained following the general procedure D according to example 3, using 210 mg of 4-fluorobenzenediazonium tetrafluoroborate as a pale yellow oil, with an isolated yield of 61percent. 1H NMR (300 MHz, CDC13) δ 7.80 (dd, J = 8.6, 6.3 Hz, 1H), 7.09 - 6.99 (m, 1H), 1.34 (s, 12H) nB NMR (100 MHz, CDC13) δ 30.26 13C NMR (75 MHz, CDC13) δ 166.91, 163.59, 137.18, 137.07, 115.11, 114.84, 84.05, 25.01. MS (EI) tR= 7.07min; m/z: 222 (Μ+', 100percent)
Reference: [1] Patent: WO2014/9169, 2014, A1, . Location in patent: Page/Page column 60
  • 10
  • [ 459-45-0 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
60% With eosin y In neat (no solvent, solid phase) for 1.5 h; Milling; Irradiation General procedure: A mixture of 1 (0.369 mmol), 2 (0.369 or 0.554 mmol) and eosin Y (11.96 mg; 5 mol percent)was mixed in a 25 mL PMMA milling jar with 15 ZrO2 balls of 5 mm in diameter at 25 Hz.Irradiation of the reaction mixture was achieved by wrapping the milling jar with a greenLED strip (90 cm; see picture in section 2). After the milling was stopped, the reactionmixture was recovered from the milling jar and the product was purified by columnchromatography (SiO2, eluent 100:1 n-pentane/ethyl acetate).
Reference: [1] ChemistryOpen, 2017, vol. 6, # 3, p. 345 - 349
[2] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 1463 - 1469
  • 11
  • [ 76-09-5 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
219 mg
Stage #1: at -5 - 20℃; for 1 h;
Stage #2: at 20℃; for 4 h;
In a reaction flask charged with Pd(OAc)2 (4.5 mg, 0.02 mmol), potassium iodide (3.3 mg, 0.02 mmol), and XPhos (28 mg, 0.06 mmol) under argon atmosphere was added, in this following order: anhydrous solvent (2 mL), Et3N (0.4 mL, 3 mmol), l-chloro-4- fluorobenzene (0.16 mL, 1 mmol) and diisopropylaminoborane (0.3 mL, 2 mmol). The reaction was then heated at 50 °C. After total consumption of either starting material, the reaction was cooled at -5 °C, quenched with anhydrous MeOH (2 mL) and stirred for 1 h at room temperature. All volatiles were removed under vacuum before adding pinacol (153 mg, 1.3 mmol) in Et20 (2 mL), and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with Et20 (10 mL), and the organic phase was washed first with a solution of HC1 (0.1 N, 2x10 mL), followed by an aqueous solution of CuCl2 (50g/L, 3x10 mL), dried over anhydrous Na2S04, filtered and concentrated under vacuum. The crude oil was passed through a pad of silica gel, eluting with Et20. The resulting filtrate was concentrated under vacuum to afford 2-(4- fluorophenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (219 mg, 99percent). 1H NMR (300 MHz, CDCls) δ 7.85-7.82 (m, 2H), 7.10-7.06 (m, 2H), 1,39 (s, 12H); 13C NMR (100 MHz, CDCI3) 5 166.19, 164.07, 137.24, 115.33, 83.88, 25.05; nB NMR (96 MHz, CDCI3) δ +30.62; 19F NMR (96 MHz, CDC13) δ -109.65; MS (EI) tR = 7.049 min; m/z: 222 (M+, 100percent).
Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 6, p. 1083 - 1088
[2] Chemistry - A European Journal, 2014, vol. 20, # 19, p. 5573 - 5579
[3] Patent: WO2015/82592, 2015, A2, . Location in patent: Page/Page column 89; 90
  • 12
  • [ 76-09-5 ]
  • [ 1765-93-1 ]
  • [ 214360-58-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 18, p. 3553 - 3557
[2] Chemical Communications, 2015, vol. 51, # 21, p. 4406 - 4409
[3] Angewandte Chemie - International Edition, 2012, vol. 51, # 37, p. 9385 - 9388
[4] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
[5] Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 7, p. 870 - 878
[6] Journal of the American Chemical Society, 2013, vol. 135, # 7, p. 2552 - 2559
[7] Organic Letters, 2018, vol. 20, # 20, p. 6573 - 6577
  • 13
  • [ 371-15-3 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2758 - 2761
[2] Organic Letters, 2016, vol. 18, # 12, p. 2966 - 2969
  • 14
  • [ 96783-59-4 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 17, p. 4560 - 4563
  • 15
  • [ 76-09-5 ]
  • [ 214360-58-4 ]
YieldReaction ConditionsOperation in experiment
219 mg at 20℃; for 4 h; Inert atmosphere In a reaction flask charged with Pd(OAc)2 (4.5 mg, 0.02 mmol), potassium iodide (3.3 mg, 0.02 mmol), and XPhos (28 mg, 0.06 mmol) under argon atmosphere was added, in this following order: anhydrous solvent (2 mL), Et3N (0.4 mL, 3 mmol), 1-chloro-4-fluorobenzene (0.16 mL, 1 mmol) and diisopropylaminoborane (0.3 mL, 2 mmol).
The reaction was then heated at 50 °C.
After total consumption of either starting material, the reaction was cooled at -5 °C, quenched with anhydrous MeOH (2 mL) and stirred for 1 h at room temperature.
All volatiles were removed under vacuum before adding pinacol (153 mg, 1.3 mmol) in Et2O (2 mL), and the mixture was stirred for 4 h at room temperature.
The reaction mixture was diluted with Et2O (10 mL), and the organic phase was washed first with a solution of HCl (0.1 N, 2x10 mL), followed by an aqueous solution of CuCl2 (50g/L, 3x10 mL), dried over anhydrous Na2SO4 filtered and concentrated under vacuum.
The crude oil was passed through a pad of silica gel, eluting with Et2O.
The resulting filtrate was concentrated under vacuum to afford 2-(4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (219 mg, 99percent).
1H NMR (300 MHz, CDCl3) δ 7.85-7.82 (m, 2H), 7.10-7.06 (m, 2H), 1,39 (s, 12H); 13C NMR (100 MHz, CDCl3) δ 166.19, 164.07, 137.24, 115.33, 83.88, 25.05; 11B NMR (96 MHz, CDCl3) δ +30.62; 19F NMR (96 MHz, CDCl3) δ -109.65; MS (EI) tR = 7.049 min; m/z: 222 (M+, 100percent).
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 10, p. 1702 - 1705
[2] Patent: EP2881398, 2015, A1, . Location in patent: Paragraph 0275
  • 16
  • [ 352-33-0 ]
  • [ 25015-63-8 ]
  • [ 214360-58-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2003, vol. 345, # 5, p. 580 - 583
  • 17
  • [ 462-06-6 ]
  • [ 25015-63-8 ]
  • [ 214360-58-4 ]
Reference: [1] Green Chemistry, 2009, vol. 11, # 10, p. 1610 - 1617
[2] Organometallics, 2015, vol. 34, # 10, p. 1911 - 1924
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 41, p. 10336 - 10340
[4] Journal of the American Chemical Society, 2016, vol. 138, # 30, p. 9487 - 9497
  • 18
  • [ 1173294-78-4 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1593 - 1600
  • 19
  • [ 292638-84-7 ]
  • [ 73183-34-3 ]
  • [ 460-00-4 ]
  • [ 1609554-37-1 ]
  • [ 214360-58-4 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 38, p. 12032 - 12036
  • 20
  • [ 1562330-27-1 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 14 - 24
[2] Chemistry - A European Journal, 2015, vol. 21, # 47, p. 16796 - 16800
  • 21
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 22, p. 7440 - 7443
  • 22
  • [ 185990-03-8 ]
  • [ 460-00-4 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 19997 - 20000
  • 23
  • [ 1195-66-0 ]
  • [ 460-00-4 ]
  • [ 214360-58-4 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 43, p. 7009 - 7012
  • 24
  • [ 2714-90-1 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Chemistry - A European Journal, 2016, vol. 22, # 47, p. 16787 - 16790
  • 25
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 50, p. 18730 - 18733
  • 26
  • [ 10085-91-3 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2482 - 2486[2] Angew. Chem., 2017, vol. 129, # 9, p. 2522 - 2526,5
  • 27
  • [ 352-33-0 ]
  • [ 73183-34-3 ]
  • [ 324-74-3 ]
  • [ 214360-58-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003[2] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
  • 28
  • [ 371-40-4 ]
  • [ 214360-58-4 ]
Reference: [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 6, p. 1083 - 1088
[2] Tetrahedron Letters, 2014, vol. 55, # 10, p. 1702 - 1705
[3] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10568 - 10580
[4] Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 14 - 24
  • 29
  • [ 462-06-6 ]
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 38, p. 12211 - 12214
[2] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 332 - 342
[3] Chemistry - A European Journal, 2017, vol. 23, # 24, p. 5663 - 5667
  • 30
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 74, p. 14068 - 14071
  • 31
  • [ 352-33-0 ]
  • [ 214360-58-4 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 19, p. 5573 - 5579
[2] Patent: WO2015/82592, 2015, A2,
[3] Patent: EP2881398, 2015, A1,
  • 32
  • [ 76-09-5 ]
  • [ 31685-21-9 ]
  • [ 214360-58-4 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 14, p. 2878 - 2881
  • 33
  • [ 352-33-0 ]
  • [ 25015-63-8 ]
  • [ 24388-23-6 ]
  • [ 214360-58-4 ]
Reference: [1] Electrochimica Acta, 2005, vol. 50, # 25-26 SPEC. ISS., p. 4897 - 4901
  • 34
  • [ 76-09-5 ]
  • [ 1321604-73-2 ]
  • [ 1321604-76-5 ]
  • [ 214360-58-4 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 29, p. 8005 - 8008
  • 35
  • [ 76-09-5 ]
  • [ 448-59-9 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 7, p. 2116 - 2119
  • 36
  • [ 462-06-6 ]
  • [ 214360-58-4 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 14, p. 2878 - 2881
[2] Chemical Communications, 2015, vol. 51, # 74, p. 14068 - 14071
  • 37
  • [ 456-22-4 ]
  • [ 214360-58-4 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 9, p. 2482 - 2486[2] Angew. Chem., 2017, vol. 129, # 9, p. 2522 - 2526,5
[3] Journal of the American Chemical Society, 2017, vol. 139, # 22, p. 7440 - 7443
  • 38
  • [ 371-41-5 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 4, p. 1593 - 1600
  • 39
  • [ 403-46-3 ]
  • [ 214360-58-4 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 47, p. 16796 - 16800
  • 40
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 975 - 984
  • 41
  • [ 1765-93-1 ]
  • [ 1321604-76-5 ]
  • [ 214360-58-4 ]
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 29, p. 8005 - 8008
  • 42
  • [ 352-34-1 ]
  • [ 73183-34-3 ]
  • [ 99770-93-1 ]
  • [ 24388-23-6 ]
  • [ 214360-58-4 ]
Reference: [1] European Journal of Organic Chemistry, 2013, # 28, p. 6263 - 6266
  • 43
  • [ 73183-34-3 ]
  • [ 214360-58-4 ]
Reference: [1] Organometallics, 2015, vol. 34, # 10, p. 1911 - 1924
  • 44
  • [ 1868-08-2 ]
  • [ 214360-58-4 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 74, p. 14068 - 14071
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 214360-58-4 ]

Fluorinated Building Blocks

Chemical Structure| 936618-92-7

[ 936618-92-7 ]

2-(3-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.98

Chemical Structure| 876062-39-4

[ 876062-39-4 ]

2-(2-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.97

Chemical Structure| 863868-37-5

[ 863868-37-5 ]

2-(2,6-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 1192548-08-5

[ 1192548-08-5 ]

2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 827614-70-0

[ 827614-70-0 ]

4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane

Similarity: 0.90

Organoboron

Chemical Structure| 936618-92-7

[ 936618-92-7 ]

2-(3-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.98

Chemical Structure| 876062-39-4

[ 876062-39-4 ]

2-(2-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.97

Chemical Structure| 863868-37-5

[ 863868-37-5 ]

2-(2,6-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 1192548-08-5

[ 1192548-08-5 ]

2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 827614-70-0

[ 827614-70-0 ]

4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane

Similarity: 0.90

Aryls

Chemical Structure| 936618-92-7

[ 936618-92-7 ]

2-(3-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.98

Chemical Structure| 876062-39-4

[ 876062-39-4 ]

2-(2-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.97

Chemical Structure| 863868-37-5

[ 863868-37-5 ]

2-(2,6-Difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.91

Chemical Structure| 1192548-08-5

[ 1192548-08-5 ]

2-(2-Fluoro-3-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Similarity: 0.90

Chemical Structure| 827614-70-0

[ 827614-70-0 ]

4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane

Similarity: 0.90