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[ CAS No. 181219-01-2 ] {[proInfo.proName]}

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Chemical Structure| 181219-01-2
Chemical Structure| 181219-01-2
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Product Details of [ 181219-01-2 ]

CAS No. :181219-01-2 MDL No. :MFCD01319051
Formula : C11H16BNO2 Boiling Point : -
Linear Structure Formula :NC5H4BOC(CH3)2C(CH3)2O InChI Key :NLTIETZTDSJANS-UHFFFAOYSA-N
M.W : 205.06 Pubchem ID :2734648
Synonyms :

Calculated chemistry of [ 181219-01-2 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.71
TPSA : 31.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.648 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 1.56 mg/ml ; 0.0076 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0481 mg/ml ; 0.000234 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 181219-01-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 181219-01-2 ]

* 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 [ 181219-01-2 ]
  • Downstream synthetic route of [ 181219-01-2 ]

[ 181219-01-2 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 21369-64-2 ]
  • [ 181219-01-2 ]
  • [ 27876-24-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2205 - 2209[2] Angew. Chem., 2016, vol. 128, # 6, p. 2245 - 2249,5
  • 2
  • [ 181219-01-2 ]
  • [ 13296-04-3 ]
Reference: [1] RSC Advances, 2016, vol. 6, # 63, p. 58516 - 58520
  • 3
  • [ 24424-99-5 ]
  • [ 181219-01-2 ]
  • [ 81660-73-3 ]
Reference: [1] Green Chemistry, 2015, vol. 17, # 6, p. 3540 - 3551
[2] Organic Letters, 2014, vol. 16, # 7, p. 1836 - 1839
  • 4
  • [ 106-37-6 ]
  • [ 181219-01-2 ]
  • [ 113682-56-7 ]
YieldReaction ConditionsOperation in experiment
77% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 48 h; Inert atmosphere; Reflux Example 1
Synthesis of 4,4'-(1,4-phenylene)bis(1-hexylpyridin-1-ium) bis(tetrafluroborate)
A mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (4.34 g, 21.2 mmol), 1,4-dibromobenzene (2.00 g, 8.5 mmol), K2CO3 (2.92 g, 21.2 mmol) and Pd(PPh3)4 (0.49 g, 5 mol percent) in PhMe (30 mL) and EtOH (30 mL) under N2 was heated at reflux for 48 h.
The resulting mixture was poured into water (50 mL), extracted with dichloromethane (2*100 mL), dried (MgSO4) and the solvent removed under reduced pressure.
The residue was chromatographed on silica using MeOH (0-5percent) in dichloromethane as eluent.
The solvent was removed under reduced pressure and the residue crystallised from hot EtOAc/hexanes to give 1,4-di(4-pyridyl)benzene (1.52 g, 77percent) as a pale yellow powder.
71% With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl-formamide; toluene at 130℃; for 48 h; Inert atmosphere Pyridylboronic pinacol ester (3.64 g, 17.8 mmol), 1,4-dibromobenzene (1.40 g, 5.92 mmol), and Cs2CO3 (11.6 g, 35.5 mmol) were added to a 1:1 mixture of dry PhMe/DMF (300 mL), which had been degassed with Ar for 15 min. Next, Pd(PPh3)4 (0.68 g, 0.59 mmol) was added to the reaction mixture and the solution heated to 130° C. under Ar for 48 h. Then, the reaction mixture was cooled to room temperature and the palladium catalyst filtered off using Celite. The organic phase was concentrated under vacuum and then dissolved in CH2Cl2 followed by extraction with H2O three times. The organic layer was made acidic (pH 2-3) by adding dropwise concentrated HCl, which caused the desired product to precipitate from solution. The precipitate was collected by filtration and then dissolved in H2O. Finally, aq. NaOH (10 M) was added dropwise to the water layer until the pH was 8-9, which resulted in precipitation of pure product ExBIPY (973 mg, 71percent) as a white solid. The yield of the product obtained in the reaction was 71percent. 1H NMR (500 MHz, CDCl3, ppm): δH 8.72 (AA′ of AA′XX′, J=4.6, 1.6 Hz, 4H), 7.80 (s, 4H), 7.59 (XX′ of AA′XX′, J=4.6, 1.6 Hz, 4H).
Reference: [1] Patent: US2018/194995, 2018, A1, . Location in patent: Paragraph 0117
[2] Journal of the American Chemical Society, 2013, vol. 135, # 1, p. 183 - 192
[3] Patent: US2014/179017, 2014, A1, . Location in patent: Paragraph 0072
[4] Organic Letters, 2010, vol. 12, # 8, p. 1888 - 1891
[5] Chemistry - A European Journal, 2014, vol. 20, # 3, p. 649 - 652
  • 5
  • [ 108-36-1 ]
  • [ 181219-01-2 ]
  • [ 170165-79-4 ]
Reference: [1] ChemPlusChem, 2016, vol. 81, # 9, p. 985 - 994
  • 6
  • [ 76-09-5 ]
  • [ 1692-15-5 ]
  • [ 181219-01-2 ]
Reference: [1] Journal of Alloys and Compounds, 2013, vol. 555, p. 22 - 27
  • 7
  • [ 110-86-1 ]
  • [ 73183-34-3 ]
  • [ 181219-01-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 17, p. 4853 - 4857[2] Angew. Chem., 2017, vol. 129, # 17, p. 4931 - 4935,5
  • 8
  • [ 110-86-1 ]
  • [ 73183-34-3 ]
  • [ 1012085-50-5 ]
  • [ 181219-01-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 17, p. 4853 - 4857[2] Angew. Chem., 2017, vol. 129, # 17, p. 4931 - 4935,5
  • 9
  • [ 110-86-1 ]
  • [ 73183-34-3 ]
  • [ 181219-01-2 ]
  • [ 329214-79-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299
[2] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651
  • 10
  • [ 76-09-5 ]
  • [ 15854-87-2 ]
  • [ 181219-01-2 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 28, p. 4737 - 4740
  • 11
  • [ 1692-15-5 ]
  • [ 126-30-7 ]
  • [ 181219-01-2 ]
Reference: [1] Journal of Fluorine Chemistry, 2009, vol. 130, # 4, p. 377 - 382
  • 12
  • [ 1120-87-2 ]
  • [ 73183-34-3 ]
  • [ 181219-01-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5053 - 5074
  • 13
  • [ 1120-87-2 ]
  • [ 181219-01-2 ]
Reference: [1] Angewandte Chemie (International Edition in English), 2000, vol. 39, # 21, p. X3843-3845
  • 14
  • [ 76-09-5 ]
  • [ 181219-01-2 ]
Reference: [1] Angewandte Chemie (International Edition in English), 2000, vol. 39, # 21, p. X3843-3845
  • 15
  • [ 110-86-1 ]
  • [ 73183-34-3 ]
  • [ 181219-01-2 ]
  • [ 329214-79-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299
[2] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651
  • 16
  • [ 110-86-1 ]
  • [ 73183-34-3 ]
  • [ 1012085-50-5 ]
  • [ 181219-01-2 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 17, p. 4853 - 4857[2] Angew. Chem., 2017, vol. 129, # 17, p. 4931 - 4935,5
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