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[ CAS No. 27149-27-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 27149-27-5
Chemical Structure| 27149-27-5
Chemical Structure| 27149-27-5
Structure of 27149-27-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 27149-27-5 ]

CAS No. :27149-27-5 MDL No. :MFCD09997917
Formula : C9H6BrNS Boiling Point : -
Linear Structure Formula :- InChI Key :AGSWRPPPAGUIOZ-UHFFFAOYSA-N
M.W : 240.12 Pubchem ID :13546651
Synonyms :

Calculated chemistry of [ 27149-27-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.25
TPSA : 41.13 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 3.46
Log Po/w (WLOGP) : 3.57
Log Po/w (MLOGP) : 2.56
Log Po/w (SILICOS-IT) : 4.38
Consensus Log Po/w : 3.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.12
Solubility : 0.0182 mg/ml ; 0.0000757 mol/l
Class : Moderately soluble
Log S (Ali) : -4.01
Solubility : 0.0237 mg/ml ; 0.0000988 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.67
Solubility : 0.00513 mg/ml ; 0.0000214 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.08

Safety of [ 27149-27-5 ]

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

Application In Synthesis of [ 27149-27-5 ]

* 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 [ 27149-27-5 ]
  • Downstream synthetic route of [ 27149-27-5 ]

[ 27149-27-5 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 3034-53-5 ]
  • [ 589-87-7 ]
  • [ 27149-27-5 ]
YieldReaction ConditionsOperation in experiment
18.3 g
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran for 1 h; Cooling with ice; Inert atmosphere
Stage #2: With zinc(II) chloride-TMEDA In tetrahydrofuran at 20℃; for 1 h; Cooling with ice; Inert atmosphere
Stage #3: With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 1.5 h; Reflux; Inert atmosphere
A flask which in 2-bromothiazole (16.4 g) and 50 ml of THF solution were put was cooled in an iced bath, and then 55 ml of a THF solution of 2 M isopropylmagnesium chloride was added dropwise there to under in a in nitrogen atmosphere while stirring the solution. After dropewise addition the rection mixture was stirred for 1 hour, and then a zinc chloride-tetramethylethylenediamine complex (30.3 g) was added. the resuting mixture was stirring for 1 hour at room temperature, and then 1-bromo-4-iodobenzene (28.3 g) and Pd(PPh3)4 (3.5 g) were added and then heated and stirred for 1.5 hours at reflux temperature. After cooling the reaction solution to room temperature, to remove the metal ions of the catalyst, a solution prepared by dissolving the compound ethylenediamine Inc. acid, use the sodium salt dihydrate equivalent to approximately 2-fold molar with respect to the objective to the appropriate amount of water (after and it stirred to fall abbreviated) EDTA · 4Na in an aqueous solution. Then, after removing also separated by adding toluene, and the solvent was distilled off under reduced pressure to the solution, and purified by silica gel column chromatography (eluent: toluene / ethyl acetate = 50/1 (volume ratio)) to give 2-(4-bromophenyl)thiazole (18.3g).
Reference: [1] Patent: KR2015/138163, 2015, A, . Location in patent: Paragraph 0333; 0334
  • 2
  • [ 96159-83-0 ]
  • [ 27149-27-5 ]
Reference: [1] Chemistry - An Asian Journal, 2013, vol. 8, # 7, p. 1408 - 1411
  • 3
  • [ 589-87-7 ]
  • [ 121359-48-6 ]
  • [ 27149-27-5 ]
Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[2] Tetrahedron Letters, 2006, vol. 47, # 4, p. 599 - 603
  • 4
  • [ 623-00-7 ]
  • [ 27149-27-5 ]
Reference: [1] Chemistry - An Asian Journal, 2013, vol. 8, # 7, p. 1408 - 1411
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