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[ CAS No. 654676-12-7 ] {[proInfo.proName]}

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Chemical Structure| 654676-12-7
Chemical Structure| 654676-12-7
Structure of 654676-12-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 654676-12-7 ]

CAS No. :654676-12-7 MDL No. :MFCD29089359
Formula : C18H19Br2N Boiling Point : -
Linear Structure Formula :- InChI Key :YSUUFISKPJBPOH-UHFFFAOYSA-N
M.W : 409.16 Pubchem ID :25150458
Synonyms :

Calculated chemistry of [ 654676-12-7 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 13
Fraction Csp3 : 0.33
Num. rotatable bonds : 5
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 100.14
TPSA : 4.93 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.83 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.27
Log Po/w (XLOGP3) : 6.99
Log Po/w (WLOGP) : 6.9
Log Po/w (MLOGP) : 5.57
Log Po/w (SILICOS-IT) : 6.16
Consensus Log Po/w : 5.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.91
Solubility : 0.0000505 mg/ml ; 0.000000123 mol/l
Class : Poorly soluble
Log S (Ali) : -6.91
Solubility : 0.0000505 mg/ml ; 0.000000124 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.16
Solubility : 0.00000282 mg/ml ; 0.0000000069 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.09

Safety of [ 654676-12-7 ]

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

Application In Synthesis of [ 654676-12-7 ]

* 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 [ 654676-12-7 ]
  • Downstream synthetic route of [ 654676-12-7 ]

[ 654676-12-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 111-25-1 ]
  • [ 136630-39-2 ]
  • [ 654676-12-7 ]
YieldReaction ConditionsOperation in experiment
99% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 80℃; for 14 h; General procedure: A mixture of the corresponding 2,7-disubstituted 9H-carbazole (for the synthesis see Supplementary data) (10mmol), alkylbromide (10.5mmol), BnEt3NCl (0.227g, 1mmol), toluene (20mL) and NaOH solution (0.42g, 10.5mol, in water 50percentw/v) was stirred at 80°C for 14h. Then the reaction mixture was cooled to rt., poured into 50mL of water and acidified with 10percent hydrochloric acid to pH∼2. Organic layer was separated and water phase additionally was extracted with toluene (2×10mL). Combined extracts were washed with water (2×25mL), dried over Na2SO4, filtered and evaporated to dryness. The obtained crude products of the alkylation reaction were purified by column chromatography to give N-alkylcarbazoles 1a–f.
99.8% With sodium hydride In dimethyl sulfoxide at 20 - 30℃; Inert atmosphere Under the protection of argon, in 100 ml of the three-port are sequentially added in the bottle 2,7-dibromo diphenylenimine 4.88g (15mmol), hydrogenated sodium 0.72g, DMSO solvent 30 ml, controlling the reaction temperature 20-30°C, dropwise 1-bromo-hexane, HPLC detection reaction is ended. 100 ml water quenching, with 100 ml dichloromethane extraction, layered, for water 50 ml dichloromethane extraction, combined with the phase, drying by anhydrous magnesium sulphate, pressure reducing and recovering the solvent, the crude solid obtained, using dichloromethane-methanol of performing recrystallization, get white product 2,7-di-bromo-N-hexyl carbazole 5.87g, purity 99.8percent (HPLC), the yield of 95.6percent, melting point 70.6-72.5 °C. 1 HNMR (400MHz, CDCl 3), δ: 0.858-0.906 (3H, t), 1.295-1.351 (6H, m), 1.786-1.885 (2H, m), 4.168-4.217 (2H, t), 7.320-7.354 (2H, dd), 7.525-7.530 (2H, d), 7.875-7.903 (2H, d).
Reference: [1] Dyes and Pigments, 2016, vol. 124, p. 133 - 144
[2] Patent: CN105384679, 2016, A, . Location in patent: Paragraph 0009; 0025; 0026; 0027
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 26, p. 6270 - 6279
[4] Heterocycles, 2010, vol. 81, # 4, p. 977 - 984
[5] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9207 - 9213
[6] Tetrahedron, 2011, vol. 67, # 43, p. 8248 - 8254
[7] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 15065 - 15072
[8] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784
  • 2
  • [ 92-86-4 ]
  • [ 654676-12-7 ]
Reference: [1] Tetrahedron, 2011, vol. 67, # 43, p. 8248 - 8254
[2] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 15065 - 15072
[3] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784
  • 3
  • [ 439797-69-0 ]
  • [ 654676-12-7 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 47, p. 15065 - 15072
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2016, vol. 54, # 17, p. 2774 - 2784
  • 4
  • [ 654676-12-7 ]
  • [ 61676-62-8 ]
  • [ 871696-12-7 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 23, p. 9207 - 9213
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