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[ CAS No. 129013-83-8 ] {[proInfo.proName]}

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Chemical Structure| 129013-83-8
Chemical Structure| 129013-83-8
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Product Details of [ 129013-83-8 ]

CAS No. :129013-83-8 MDL No. :MFCD04116232
Formula : C11H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :FCHUOBPHXDXZBK-UHFFFAOYSA-N
M.W : 234.09 Pubchem ID :1515241
Synonyms :

Calculated chemistry of [ 129013-83-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.37
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 3.17
Log Po/w (WLOGP) : 3.51
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.1

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.91
Solubility : 0.0291 mg/ml ; 0.000124 mol/l
Class : Soluble
Log S (Ali) : -3.11
Solubility : 0.181 mg/ml ; 0.000774 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.00093 mg/ml ; 0.00000397 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 129013-83-8 ]

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

Application In Synthesis of [ 129013-83-8 ]

* 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.

  • Upstream synthesis route of [ 129013-83-8 ]
  • Downstream synthetic route of [ 129013-83-8 ]

[ 129013-83-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 589-87-7 ]
  • [ 1692-25-7 ]
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YieldReaction ConditionsOperation in experiment
56% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water for 5 h; Inert atmosphere; Heating In the three-necked flask, Join p-Bromoiodobenzene (28g, 0.1mol),3-pyridyl boronic acid (12.3g, 0.1mol),Potassium carbonate (27.2g, 200mmol),Tetrakistriphenylphosphine palladium (0.8g),Tetrahydrofuran (200ml) and water (50ml),Heated under a nitrogen atmosphere for 5 hours.cool down,filter,The crude product was purified by column chromatography to give the product 13g,Yield 56percent.
38% With sodium carbonate In 1,2-dimethoxyethane; ethanol; water at 80℃; for 12 h; A synthetic scheme of 3- (4-broniophenyl)pyridine is shown in (C-1).
In a 100 mL three-necked flask were placed 2.4 g (20 mmol) of 3-pyridineboronic acid, 5.6 g (19 mmol) of para-bromoiodobenzene, and 4.5 g (42 mmol) of sodium carbonate.
The atmosphere in the flask was replaced with nitrogen, and to the flask were added 15 mL of water, 25 mL of DME, and 10 mL of ethanol.
The mixture was degassed by being stirred under reduced pressure, to which 0.22 g (0.19 mmol) of tetrakis(triphenylphosphine)palladium(0) was added.
The mixture was stirred under nitrogen stream at 80 °C for 12 hours.
After a predetermined time, water was added to the mixture, and an organic substance was extracted with chloroform from the aqueous layer.
The obtained extract was washed with a saturated aqueous sodium chloride solution together with the organic layer and then dried over magnesium sulfate.
The mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and the filtrate was condensed to obtain an oily substance.
The obtained substance was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1); thus, 1.8 g of the target yellow oily substance was obtained with a yield of 38 percent.
Reference: [1] Patent: CN105753849, 2016, A, . Location in patent: Paragraph 0056; 0057
[2] Chemistry - A European Journal, 2017, vol. 23, # 60, p. 15089 - 15097
[3] Patent: EP2065378, 2009, A1, . Location in patent: Page/Page column 141
  • 2
  • [ 589-87-7 ]
  • [ 129013-83-8 ]
Reference: [1] Patent: US2004/102472, 2004, A1, . Location in patent: Page 34
  • 3
  • [ 589-87-7 ]
  • [ 59020-09-6 ]
  • [ 129013-83-8 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 19, p. 6999 - 7008
  • 4
  • [ 106-37-6 ]
  • [ 1692-25-7 ]
  • [ 129013-83-8 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4430 - 4442
[2] Patent: CN105601613, 2016, A, . Location in patent: Paragraph 0093; 0094; 0095
  • 5
  • [ 1008-88-4 ]
  • [ 129013-83-8 ]
YieldReaction ConditionsOperation in experiment
48.5 g at 20℃; for 4 h; Compound 1 50.0g (0.32mol) was added 150mL of concentrated sulfuric acid, and added Ag2SO4(50.0g0.16mol), liquid bromine (51.2g, 0.32mol) was slowly added dropwise to the reaction mixture, after the addition was complete, the reaction at room temperature for 4 hours, the insoluble was filtered off, the filtrate was slowly added to 300mL ice-water mixture, and continued stirring, solid precipitated solid was filtered off, dried in vacuo at 45 , pale yellow 48.5g.
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981, vol. 17, # 1, p. 69 - 72[2] Khimiya Geterotsiklicheskikh Soedinenii, 1981, # 1, p. 85 - 88
[3] Patent: CN106854176, 2017, A, . Location in patent: Paragraph 0034; 0035
  • 6
  • [ 626-55-1 ]
  • [ 589-87-7 ]
  • [ 129013-83-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1999, vol. 42, # 18, p. 3572 - 3587
  • 7
  • [ 39795-60-3 ]
  • [ 129013-83-8 ]
Reference: [1] Patent: US5554613, 1996, A,
  • 8
  • [ 72287-26-4 ]
  • [ 589-87-7 ]
  • [ 497-19-8 ]
  • [ 129013-83-8 ]
Reference: [1] Patent: US2003/96829, 2003, A1,
  • 9
  • [ 72287-26-4 ]
  • [ 589-87-7 ]
  • [ 497-19-8 ]
  • [ 129013-83-8 ]
Reference: [1] Patent: US2003/114478, 2003, A1,
  • 10
  • [ 63996-36-1 ]
  • [ 129013-83-8 ]
Reference: [1] Patent: US5714496, 1998, A,
  • 11
  • [ 110-86-1 ]
  • [ 589-87-7 ]
  • [ 63996-36-1 ]
  • [ 39795-60-3 ]
  • [ 129013-83-8 ]
Reference: [1] Heterocycles, 2004, vol. 64, p. 499 - 504
[2] Tetrahedron, 2006, vol. 62, # 33, p. 7824 - 7837
  • 12
  • [ 110-86-1 ]
  • [ 622-88-8 ]
  • [ 63996-36-1 ]
  • [ 129013-83-8 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 54, p. 7124 - 7127
  • 13
  • [ 129013-83-8 ]
  • [ 73183-34-3 ]
  • [ 929203-04-3 ]
YieldReaction ConditionsOperation in experiment
93% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In 1,4-dioxane for 5 h; Inert atmosphere; Reflux In a flask,Intermediate 2-4 (13g, 56mmol),United pinacolato ester (21.3g, 84mmol),Potassium acetate (20g, 200mmol),Dioxane (300ml) and bistriphenylphosphine palladium dichloride (1g),Under nitrogen was heated to reflux for 5 hours.cool down,concentrate,The crude product was purified by column chromatography to give the product 14.6g,Yield 93percent.
15.0 g for 4 h; Inert atmosphere; Reflux 3-(4-bromophenyl)pyridine 14.0g, bis(pinacolato)diboron 18.3g, 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane complex 1.5g, potassium acetate 11.8g, cyclopentylmethyl ether(CPME) 100 ml in a flask, under nitrogen atmosphere this mixture was stirred for 4 hours at reflux temperature. The liquid water addition, toluene liquid to room temperature by cooling the reaction. The organic layer is concentrated, activated carbon dissolved in toluene at column chromatography is purified (soln.: toluene), 3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridine (15.0g) is obtained.
Reference: [1] Patent: CN105753849, 2016, A, . Location in patent: Paragraph 0058; 0059
[2] Organic Electronics: physics, materials, applications, 2018, vol. 62, p. 5 - 11
[3] Chemistry - A European Journal, 2017, vol. 23, # 60, p. 15089 - 15097
[4] Patent: JP5907069, 2016, B2, . Location in patent: Paragraph 0186
  • 14
  • [ 129013-83-8 ]
  • [ 1476776-55-2 ]
Reference: [1] Patent: CN106854176, 2017, A,
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