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[ CAS No. 57103-21-6 ] {[proInfo.proName]}

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Chemical Structure| 57103-21-6
Chemical Structure| 57103-21-6
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Product Details of [ 57103-21-6 ]

CAS No. :57103-21-6 MDL No. :MFCD11521285
Formula : C18H11I2N Boiling Point : -
Linear Structure Formula :- InChI Key :AWGAUYXFWGUFNE-UHFFFAOYSA-N
M.W : 495.10 Pubchem ID :13407347
Synonyms :

Calculated chemistry of [ 57103-21-6 ]

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 : 106.21
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 : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.65
Log Po/w (XLOGP3) : 6.3
Log Po/w (WLOGP) : 5.99
Log Po/w (MLOGP) : 5.83
Log Po/w (SILICOS-IT) : 5.96
Consensus Log Po/w : 5.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -7.48
Solubility : 0.0000163 mg/ml ; 0.000000033 mol/l
Class : Poorly soluble
Log S (Ali) : -6.19
Solubility : 0.000318 mg/ml ; 0.000000642 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.38
Solubility : 0.00000208 mg/ml ; 0.0000000042 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.2

Safety of [ 57103-21-6 ]

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 [ 57103-21-6 ]

* 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 [ 57103-21-6 ]
  • Downstream synthetic route of [ 57103-21-6 ]

[ 57103-21-6 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1150-62-5 ]
  • [ 57103-21-6 ]
YieldReaction ConditionsOperation in experiment
95% With N-iodo-succinimide In acetic acid at 20℃; Firstly, 24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 700 ml of glacial acetic acid, and 44.9 g (200 mmol) of iV-iodosuccinimide was slowly added thereto. The mixture was stirred overnight at a room temperature. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 47.Og (yield 95percent) of 3,6-diiodo-9-phenyl carbazole which was white powder, was obtained.
95% With N-iodo-succinimide In acetic acid at 20℃; 24.3g (100 mmol) of N-phenylcarbazole was dissolved in 700 ml of glacial acetic acid, 44.9 g (200 mmol) of N-iodinesuccinimide was gradually added thereto, and then stirring was carried out at a room temperature overnight. The solution became clouded at 2.5 hours from the reaction started, and precipitation started at 3.5 hours from the reaction started. The obtained precipitate was filtered and was suspended in the aqueous solution of sodium hydro gencarbonate to be neutralized. The solution was filtered. And the obtained material was washed with water and dried to obtain 47 g of off-white powder in a yield of 95 percent.
91% at 100℃; for 1 h; N-phenyl-3,6-diiodocarbazo23.17 g (0.0952 mol, 1.0 eq) of CzP are dissolved in 200 mL of refluxing acetic acid. This solution is then cooled down at 100°C before the subsequent addition of 20.9 g (0.126 mol, 1.32 eq) of KI and 15.9 g (0.074 mol, 0.78 eq) of KIO3. After one hour, the purple iodine disappears what indicates that the reaction is complete. The white solid is filtered, rinsed by 2x100 ml of 5percent Na2S203 aqueous solution, 200 mL of water and then dried to give 42.9 g (0.0867 mol, 91 percent) of ICzP as a white solid.
91%
Stage #1: Reflux
Stage #2: at 100℃;
N phenyl-3, 6-diiodocanbazole - ICzP; [Show Image] 23.17 g (0.0952 mol, 1.0 eq) of CzP are dissolved in 200 mL of refluxing acetic acid. This solution is then cooled down at 100°C before the subsequent addition of 20.9 g (0.126 mol, 1.32 eq) of KI and 15.9 g (0.074 mol, 0.78 eq) of KI03. After one hour, the purple iodine disappears what indicates that the reaction is complete. The white solid is filtered, rinsed by 2x100 ml of 5percent Na2S2O3 aqueous solution, 200 mL of water and then dried to give 42.9 g (0.0867 mol, 91 percent) of ICzP as a white solid.
74.8% at 135℃; for 18 h; A mixture of 9-phenylcarbazole (0.2433 g, 0.1 mmol), potassiumiodide (0.6640 g, 4.0 mmol) and potassium iodate (0.4277 g, 2.0mmol) was refluxed for 18 h in glacial acetic acid (50 mL). The colourof the solution changed from purple to chocolate brown. After thereaction was completed, the mixture was left to cool naturally. Theprecipitate was separated and washed with 10percent sodium hyposulfitesolution (50 mL) and distilled water (30 mL) successively. The whiteneedles obtained were further dried and recrystallised from alcohol togive compound 1 as white crystals: m.p. 185–186 °C; yield 0.3703 g(74.8percent); 1H NMR (400 MHz, Chloroform-d1): δ 8.40 (s, 2H), 7.71–7.58(m, 4H), 7.50 (t, J = 9.4 Hz, 3H), 7.16 (d, J = 8.6 Hz, 2H); FTIR (KBr)(cm−1): 3134(s), 1595(m), 1500(w), 1463(s), 1427(s), 1400(s), 1278(m),1228(s), 1014(m), 867(w), 798(m), 756(m), 696(w), 630(w), 565(w),563(w). Anal. calcd for C18H11I2N: C, 43.67; H, 2.24; N, 2.83; found: C,43.54; H, 2.23; N, 2.84percent
0.1 g at 135℃; for 18 h; A mixture of 9-phenylcarbazole (0.2433 g, 0.1 mmol), potassium iodide (0.6640 g, 4.0 mmol) and potassium iodate (0.4277 g, 2.0 mmol) was mixed with 50 ml of glacial acetic acid at room temperature. Heated to 135 ° C and refluxed for 18 hours. The reaction solution was allowed to cool to room temperature. The precipitate was washed with 50 ml of 10percent sodium thiosulfate solution and 30 ml of distilled water. Weigh 0.1 g of 3,6-diiodo-phenylcarbazole, dissolved in 5 ml of chloroform, filtered and allowed to stand for 3 days to give a colorless block crystal.

Reference: [1] Patent: WO2006/70912, 2006, A1, . Location in patent: Page/Page column 58; 59
[2] Patent: WO2006/43647, 2006, A1, . Location in patent: Page/Page column 59-60
[3] Patent: WO2012/25510, 2012, A1, . Location in patent: Page/Page column 23
[4] Patent: EP2433928, 2012, A1, . Location in patent: Page/Page column 16-17
[5] Journal of Chemical Research, 2017, vol. 41, # 2, p. 79 - 81
[6] European Journal of Inorganic Chemistry, 2007, # 24, p. 3868 - 3880
[7] Patent: US2008/312453, 2008, A1, . Location in patent: Page/Page column 15
[8] Patent: EP2100880, 2009, A1, . Location in patent: Page/Page column 17-18
[9] Dyes and Pigments, 2014, vol. 100, # 1, p. 66 - 72
[10] Patent: CN106631987, 2017, A, . Location in patent: Paragraph 0014-0015
  • 2
  • [ 57103-20-5 ]
  • [ 57103-21-6 ]
YieldReaction ConditionsOperation in experiment
85% at 20℃; [0102] 24.3 g (100 mmol) N-phenyl-3,6-dibromocarbazole in a glacial acetic acid (500 mL) solution was added with 44.9 g (200 mmol) of N-iodine succinimide to be stirred overnight at room temperature. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture until the liquid properties became neutral. The mixture was filtrated and the obtained solid was washed with water and dried to give N-phenyl-3,6-diiodinecarbazole (hereinafter, shown as PhI2Cz) with a yield of 85percent. [0103] By using the obtained PhI2Cz, a coupling reaction was performed with carbazole in the similar manner as described in the synthesis of N-ethyl-3,6-di(N-carbazolyl)carbazole to give the compound in the title, N-phenyl-3,6-di(N-carbazolyl)carbazole as a beige solid (yield: 85percent). NMR data are shown in FIG. 15 (1H NMR) and FIG. 16 (13C NMR). [0104] 1H NMR(300 MHz, CDCl3) δ 7.20-7.80(m, 21H), 8.15(d, J=7.8 Hz, 4H), 8.27(s, 2H). [0105] 13C NMR(75.5 MHz, CDCl3) δ 109.7, 111.3, 119.7, 120.3, 123.2, 123.9, 125.9, 126.3, 127.2, 128.2, 130.2, 130.4, 137.1, 140.7, 141.8. [0106] It had the melting point at 283° C and showed the sublimation point at 410° C under normal pressure. Formation of a uniform film over a substrate by a vacuum evaporation method was confirmed. Absorption maximum was at 341 nm in methanol and 344 nm for the evaporated film. It was fluorescent, showing the maximum of fluorescence at 435 nm in methanol and 409 nm for the evaporated film. The HOMO level was at -5.64 eV, and the LUMO level was at -2.33 eV. The absorption spectra for the methanol solution and evaporated film are shown in FIG. 10. The respective fluorescent spectrum and excitation spectrum are shown in FIG. 11.
Reference: [1] Patent: US2005/31899, 2005, A1, . Location in patent: Page/Page column 18
  • 3
  • [ 86-74-8 ]
  • [ 57103-21-6 ]
Reference: [1] Patent: WO2012/25510, 2012, A1,
[2] Patent: EP2433928, 2012, A1,
  • 4
  • [ 591-50-4 ]
  • [ 57103-21-6 ]
Reference: [1] Patent: WO2012/25510, 2012, A1,
[2] Patent: EP2433928, 2012, A1,
  • 5
  • [ 1150-62-5 ]
  • [ 57103-21-6 ]
  • [ 502161-03-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 933 - 941
[2] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 933 - 941
[3] Tetrahedron Letters, 2006, vol. 47, # 39, p. 6957 - 6960
  • 6
  • [ 1150-62-5 ]
  • [ 57103-21-6 ]
  • [ 502161-03-7 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 933 - 941
[2] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 5, p. 933 - 941
[3] Tetrahedron Letters, 2006, vol. 47, # 39, p. 6957 - 6960
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