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[ CAS No. 16419-60-6 ] {[proInfo.proName]}

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Chemical Structure| 16419-60-6
Chemical Structure| 16419-60-6
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Product Details of [ 16419-60-6 ]

CAS No. :16419-60-6 MDL No. :MFCD00093526
Formula : C7H9BO2 Boiling Point : -
Linear Structure Formula :- InChI Key :NSJVYHOPHZMZPN-UHFFFAOYSA-N
M.W : 135.96 Pubchem ID :2733267
Synonyms :

Calculated chemistry of [ 16419-60-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.23
TPSA : 40.46 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : -0.33
Log Po/w (MLOGP) : 0.61
Log Po/w (SILICOS-IT) : -0.3
Consensus Log Po/w : 0.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.81
Solubility : 2.1 mg/ml ; 0.0155 mol/l
Class : Very soluble
Log S (Ali) : -1.64
Solubility : 3.15 mg/ml ; 0.0231 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.64
Solubility : 3.09 mg/ml ; 0.0227 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 16419-60-6 ]

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 [ 16419-60-6 ]

* 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 [ 16419-60-6 ]
  • Downstream synthetic route of [ 16419-60-6 ]

[ 16419-60-6 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 288-13-1 ]
  • [ 16419-60-6 ]
  • [ 20157-44-2 ]
Reference: [1] Helvetica Chimica Acta, 2010, vol. 93, # 5, p. 974 - 979
  • 2
  • [ 16419-60-6 ]
  • [ 13764-20-0 ]
Reference: [1] Chemische Berichte, 1992, vol. 125, # 4, p. 929 - 932
  • 3
  • [ 16419-60-6 ]
  • [ 107-14-2 ]
  • [ 22364-68-7 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 1, p. 50 - 53
  • 4
  • [ 16419-60-6 ]
  • [ 6011-14-9 ]
  • [ 22364-68-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
  • 5
  • [ 16419-60-6 ]
  • [ 95-52-3 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 7, p. 2552 - 2559
  • 6
  • [ 16419-60-6 ]
  • [ 62-53-3 ]
  • [ 1205-39-6 ]
YieldReaction ConditionsOperation in experiment
95% With potassium carbonate In water at 20℃; General procedure: In a typical example, phenylboronic acid 1 (1.22 g, 1 mmol) was charged in the flask containing K2CO3 (2 equiv) in water as solvent (2 mL). To this was added aniline 2 (0.93 g, 1 mmol) and Cu–Mn catalyst, and the reaction mixture was allowed to stir at room temperature. The completion of the reaction was monitored by TLC. After completion, the base was neutralized using 2 N HCl and the catalyst was filtered off, thorough washings of water were given, extracted with ethyl acetate, and the organic layer was separated and dried under reduced vacuum. The crude product obtained was purified on silica gel column chromatography (solvents, ratio?), to obtain white crystalline product diphenylamine 3a (1.60 g) with 95percent yield. All reactions were similarly carried out.
88% With potassium carbonate In water at 20℃; for 5 h; General procedure: To a stirred solution of phenylboronic acid (1.0 mmol), aniline (1.0 mmol), and K2CO3 (2.0 mmol) in deionized H2O (10 mL) at room temperature was added an aqueous suspension of FePd nanowires (3.0 mol percent in 3 mL of H2O). The mixture was stirred at room temperature for 5h. After completion of the reaction (as monitored by TLC), 2 M HCl was added and the catalyst was separated by applying an external magnet. The catalyst was washed with EtOAc. The mixture was extracted with EtOAc (2 * 20 mL), dried, and concentrated. The residue was subjected to gel permeation chromatography to afford pure product.
Reference: [1] Tetrahedron Letters, 2013, vol. 54, # 39, p. 5351 - 5354
[2] RSC Advances, 2014, vol. 4, # 90, p. 49273 - 49279
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 5, p. 1785 - 1787
[4] Journal of Organic Chemistry, 2006, vol. 71, # 25, p. 9522 - 9524
[5] Tetrahedron Letters, 2014, vol. 55, # 17, p. 2813 - 2817
[6] RSC Advances, 2014, vol. 4, # 43, p. 22775 - 22778
[7] Organic Letters, 2012, vol. 14, # 17, p. 4326 - 4329
[8] Organic letters, 2001, vol. 3, # 13, p. 2077 - 2079
  • 7
  • [ 16419-60-6 ]
  • [ 149105-19-1 ]
Reference: [1] Synthesis, 2002, # 8, p. 1043 - 1046
[2] Tetrahedron, 1963, vol. 19, p. 821 - 826
[3] J. Prakt. Chem. (2), 1930, vol. 128, p. 153 - 170
[4] Liebigs Annalen der Chemie, 1901, vol. 315, p. 26 - 40
[5] Arkiv foer Kemi, 1957, vol. 10, p. 473 - 482
[6] Arkiv foer Kemi, 1957, vol. 10, p. 513 - 521
[7] Journal of the American Chemical Society, 1934, vol. 56, p. 1865 - 1870
[8] , Gmelin Handbook: B: B-Verb.13, 4.7.2.5, page 209 - 219,
  • 8
  • [ 16419-60-6 ]
  • [ 91983-14-1 ]
YieldReaction ConditionsOperation in experiment
84.6% With bromine In tetrachloromethane for 2 h; Irradiation Was added to the flask, 500mL of o-tolyl boronic acid 14.8g (0.11 mol), was added 380mL of carbon tetrachloride was heated slightly to dissolve, 85mL of carbon tetrachloride was added a solution of 17.9g of bromine under light irradiation, a portion was added rapidly at the start of a few minutes leg color solution, maintaining the solution yellowish 71/92; after the addition the reaction under light irradiation 2h, the basic solution bleaching, filtration, carbon tetrachloride, washed five times, washed three times with n-hexane, and dried in vacuo to afford a white powdery solid 19.97 g, yield: 84.6percent.
Reference: [1] Patent: CN103497211, 2016, B, . Location in patent: Paragraph 0242; 0243
[2] Tetrahedron Letters, 2001, vol. 42, # 34, p. 5875 - 5877
[3] Russian Chemical Bulletin, 2005, vol. 54, # 11, p. 2602 - 2611
[4] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
[5] Chinese Journal of Chemistry, 2011, vol. 29, # 11, p. 2445 - 2450
[6] Journal of the American Chemical Society, 1958, vol. 80, p. 3611,3615
[7] Journal of the American Chemical Society, 1958, vol. 80, p. 835,836
[8] Arkiv foer Kemi, 1957, vol. 10, p. 507,509
[9] Journal of Fluorescence, 2012, vol. 22, # 6, p. 1609 - 1615
  • 9
  • [ 128-08-5 ]
  • [ 16419-60-6 ]
  • [ 91983-14-1 ]
Reference: [1] Russian Chemical Bulletin, 2005, vol. 54, # 11, p. 2602 - 2611
[2] Russian Chemical Bulletin, 2004, vol. 53, # 2, p. 370 - 375
  • 10
  • [ 16419-60-6 ]
  • [ 40138-16-7 ]
Reference: [1] Arkiv foer Kemi, 1957, vol. 10, p. 507,509
  • 11
  • [ 16419-60-6 ]
  • [ 84392-17-6 ]
Reference: [1] Synthesis, 2002, # 8, p. 1043 - 1046
  • 12
  • [ 533-58-4 ]
  • [ 16419-60-6 ]
  • [ 77897-02-0 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 44, p. 14329 - 14335
[2] Organic Letters, 2011, vol. 13, # 20, p. 5504 - 5507
[3] Organic Letters, 2013, vol. 15, # 15, p. 3962 - 3965
  • 13
  • [ 95-56-7 ]
  • [ 16419-60-6 ]
  • [ 77897-02-0 ]
Reference: [1] Chemical Communications, 2016, vol. 52, # 69, p. 10529 - 10532
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 40, p. 10598 - 10601[3] Angew. Chem., 2013, vol. 125, # 40, p. 10792 - 10795,4
  • 14
  • [ 16419-60-6 ]
  • [ 251320-86-2 ]
Reference: [1] Journal of the American Chemical Society, 1999, vol. 121, # 41, p. 9550 - 9561
[2] European Journal of Organic Chemistry, 2012, # 11, p. 2127 - 2131
  • 15
  • [ 16419-60-6 ]
  • [ 255837-19-5 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 36, p. 4686 - 4689
  • 16
  • [ 76-09-5 ]
  • [ 16419-60-6 ]
  • [ 377780-72-8 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: for 2 h; Dean-Stark; Reflux; Inert atmosphere
Stage #2: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In acetonitrile at 90℃; for 2 h; Inert atmosphere
To a three-necked flask equipped with a Dean-Stark trap was added 30 mL of toluene,Then 2-methylbenzeneboronic acid (0.21 g, 1.55 mmol) was added,Pinacol-H2O (0.22 g, 1.86 mmol),The resulting mixture was heated to reflux for two hours.After the reaction,The mixture was washed with water (30 mL x 3)Unreacted pinacol and phenylboronic acid were removed,The separated organic phase was then evaporated under reduced pressure to remove the toluene solvent.The resulting crude product was dissolved with dichloromethane (50 mL)After washing again (30 mL)To the resulting organic phase, anhydrous sodium sulfate was added for drying,The dried solution was evaporated under reduced pressure to give 0.32 g of crude product.The resulting crude product (0.32 g, 1.47 mmol)NBS (N-bromosuccinimide, 0.39 g, 2.2 mmol),AIBN (azobisisobutyronitrile, 0.003 g, 0.018 mmol) dissolved in acetonitrile (10 mL).The resulting reaction solution was refluxed at 90 ° C for two hours.After cooling at room temperature,The solvent was distilled off under reduced pressure,Crude product.The resulting crude product was purified by silica gel column chromatography,With petroleum ether (60 ~ 90 ) / ethyl acetate (v / v) = 1: 1 as eluent,The product was obtained as a white solid (0.53 g, 80percent yield).
Reference: [1] Patent: CN107383078, 2017, A, . Location in patent: Paragraph 0058; 0063; 0064; 0065; 0066; 0067; 0068
  • 17
  • [ 16419-60-6 ]
  • [ 377780-72-8 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 27, p. 9050 - 9058
[2] Chemical Communications, 2017, vol. 53, # 14, p. 2218 - 2221
  • 18
  • [ 16419-60-6 ]
  • [ 62336-24-7 ]
  • [ 402822-72-4 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 11, p. 2025 - 2027
[2] Journal of Organometallic Chemistry, 2008, vol. 693, # 19, p. 3135 - 3140
[3] Journal of Organometalic Chemistry, 2002, vol. 645, # 1-2, p. 14 - 26
[4] Tetrahedron Letters, 2009, vol. 50, # 39, p. 5470 - 5473
[5] Angewandte Chemie - International Edition, 2013, vol. 52, # 45, p. 11892 - 11895[6] Angew. Chem., 2013,
  • 19
  • [ 16419-60-6 ]
  • [ 402822-72-4 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 51, p. 9085 - 9088
[2] Chemical Communications, 2014, vol. 50, # 17, p. 2193 - 2195
[3] Chemical Communications, 2014, vol. 50, # 36, p. 4686 - 4689
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