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[ CAS No. 444796-09-2 ] {[proInfo.proName]}

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Chemical Structure| 444796-09-2
Chemical Structure| 444796-09-2
Structure of 444796-09-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 444796-09-2 ]

CAS No. :444796-09-2 MDL No. :MFCD28147705
Formula : C18H11Br2N Boiling Point : -
Linear Structure Formula :- InChI Key :MDXCDMSVFQIDGN-UHFFFAOYSA-N
M.W : 401.10 Pubchem ID :22392517
Synonyms :

Calculated chemistry of [ 444796-09-2 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 19
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 96.18
TPSA : 4.93 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.7
Log Po/w (XLOGP3) : 6.38
Log Po/w (WLOGP) : 6.31
Log Po/w (MLOGP) : 5.61
Log Po/w (SILICOS-IT) : 5.38
Consensus Log Po/w : 5.48

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -6.95
Solubility : 0.000045 mg/ml ; 0.000000112 mol/l
Class : Poorly soluble
Log S (Ali) : -6.28
Solubility : 0.000213 mg/ml ; 0.000000531 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.28
Solubility : 0.00000213 mg/ml ; 0.0000000053 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.95

Safety of [ 444796-09-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P273-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H412 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 444796-09-2 ]

* 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 [ 444796-09-2 ]
  • Downstream synthetic route of [ 444796-09-2 ]

[ 444796-09-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 591-50-4 ]
  • [ 136630-39-2 ]
  • [ 444796-09-2 ]
YieldReaction ConditionsOperation in experiment
80% With palladium diacetate; tris-(o-tolyl)phosphine; sodium t-butanolate In toluene 2.5 g (8 mmol) 4,4’-dibromo biphenyl was used(utilized) to perform a cyclization reaction to synthesize 2.08g (80percent) of 4,4’-dibromo carbazole. The 4,4’-dibromo carbazole and iodinated phenyl were dissolved in 40 ml of toluene to synthesize Intermediate C through a buchwald reaction.
78% With copper; potassium carbonate In N,N-dimethyl-formamide at 130℃; Inert atmosphere Synthesis of 2,7-dibromo-9-phenyl-9H-carbazole
A mixture of 32.5 g (100 mmole) 2,7-dibromo-9H-carbazole, 20.4 g (100 mmole) iodobenzene, 9.5 g (150 mmole) of copper powder, 27.6 g (200 mmole) of potassium carbonate, and 600 ml dimethylformamide were heated at 130° C. under nitrogen overnight, then cooled to room temperature, the solution was filtered.
The filtrate was extracted three times with dichloromethane and water, dried with anhydrous magnesium sulfate, the solvent was evaporated in vacuum.
The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (31.3 g, 78 mmol, 78percent).
70% With copper; potassium carbonate In 1,2-dichloro-benzene at 140℃; for 12 h; 2,7-dibromo-9H-carbazole (3.0 g, 9.32 mmol), iodobenzene (2.1 g, 10.25 mmol), copper powder (1.8 g,27.95 mmol) and potassium carbonate (4.1 g, 29.81 mmol) were added to stirred 60 mL o-dichlorobenzene, the system at 140 °C Reflow for 12 hours. At the end of the reaction, 20 mL of distilled water was added thereto, followed by extraction with ethyl acetate, and the organic phases were combined. After drying over anhydrous magnesium sulfate, it was concentrated and column chromatography afforded 2,7-dibromo-9-phenyl-carbazole (2.4 g, 70percent yield).
Reference: [1] Patent: KR2015/144421, 2015, A, . Location in patent: Paragraph 0312; 0313; 0315
[2] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[3] Patent: US2016/204345, 2016, A1, . Location in patent: Paragraph 0034-035
[4] Patent: CN107827808, 2018, A, . Location in patent: Paragraph 0080; 0081; 0082; 0083; 0094; 0095; 0096; 0097
[5] Journal of Materials Chemistry, 2011, vol. 21, # 15, p. 5638 - 5644
[6] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
[7] Patent: US9166177, 2015, B2,
  • 2
  • [ 568592-11-0 ]
  • [ 444796-09-2 ]
Reference: [1] Polymer, 2011, vol. 52, # 8, p. 1748 - 1754
  • 3
  • [ 108-86-1 ]
  • [ 136630-39-2 ]
  • [ 444796-09-2 ]
Reference: [1] Patent: CN108203427, 2018, A, . Location in patent: Paragraph 0119; 0120
  • 4
  • [ 136630-39-2 ]
  • [ 444796-09-2 ]
Reference: [1] Polymer, 2011, vol. 52, # 8, p. 1748 - 1754
  • 5
  • [ 350-46-9 ]
  • [ 444796-09-2 ]
Reference: [1] Polymer, 2011, vol. 52, # 8, p. 1748 - 1754
  • 6
  • [ 92-86-4 ]
  • [ 444796-09-2 ]
Reference: [1] Journal of Materials Chemistry, 2011, vol. 21, # 13, p. 4918 - 4926
[2] Patent: KR2015/144421, 2015, A,
  • 7
  • [ 439797-69-0 ]
  • [ 444796-09-2 ]
Reference: [1] Patent: KR2015/144421, 2015, A,
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