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[ CAS No. 1984-49-2 ] {[proInfo.proName]}

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Chemical Structure| 1984-49-2
Chemical Structure| 1984-49-2
Structure of 1984-49-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1984-49-2 ]

CAS No. :1984-49-2 MDL No. :MFCD11046470
Formula : C24H16N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PUMOFXXLEABBTC-UHFFFAOYSA-N
M.W : 332.40 Pubchem ID :12462601
Synonyms :

Calculated chemistry of [ 1984-49-2 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 26
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 2.0
Molar Refractivity : 110.6
TPSA : 31.58 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.68
Log Po/w (XLOGP3) : 6.48
Log Po/w (WLOGP) : 6.62
Log Po/w (MLOGP) : 4.75
Log Po/w (SILICOS-IT) : 6.63
Consensus Log Po/w : 5.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.66
Solubility : 0.0000732 mg/ml ; 0.00000022 mol/l
Class : Poorly soluble
Log S (Ali) : -6.94
Solubility : 0.0000383 mg/ml ; 0.000000115 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.01
Solubility : 0.0000000326 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.03

Safety of [ 1984-49-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1984-49-2 ]

* 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 [ 1984-49-2 ]
  • Downstream synthetic route of [ 1984-49-2 ]

[ 1984-49-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 86-74-8 ]
  • [ 1984-49-2 ]
YieldReaction ConditionsOperation in experiment
84% With iron(III) chloride In chloroform at 20℃; for 0.5 h; Carbazole (10 g, 59.8 mmol), iron (III) chloride (38.8 g, 239.3 mmol) and chloroform (200 mL) were sequentially added to a 400 mL four-necked flask and stirred at room temperature for 30 minutes.After completion of the reaction, the organic solvent was removed under reduced pressure, and the solid obtained was washed by adding methanol.The solid was collected by filtration, and then the same methanol washing was repeated twice to obtain Intermediate 3 (16.7 g, yield 84percent).
62% With iron(III) chloride In chloroform at 20℃; Bicarbazole (BCz) was prepared by chemical oxidation of 9H-carbazole in the presence of FeCl3. To a solution of 9H-carbazole (8.35 g, 100 mmol) in chloroform (150 ml) Iron chloride (anhydrous FeCl 3, 20 g, 120 mmol) was added thereto and stirred at room temperature for 30 minutes. The chloroform was removed from the reaction mixture and concentrated.After filtration with an excess amount of water, BCz (5.5 g, 62percent) was obtained through column chromatography (hexane: ethyl acetate = 2: 1 to 1: 1).
22%
Stage #1: With iron(III) chloride In chloroform at 20℃; for 0.5 h; Inert atmosphere
Stage #2: With acetic acid; zinc In methanol; chloroform; ethyl acetate at 50℃; Inert atmosphere
Carbazole (12.0 g, 72.0 mmol) and anhydrous FeCl3 (47.0 g, 288 mmol) were dissolved in 240 mLof chloroform and stirred for 30 min under nitrogen. The solution was subsequently poured into alarger quantity of methyl alcohol. The precipitated green powder and zinc powder (18.7 g, 288 mmol)were dissolved in a solution of acetic acid and ethyl acetate (180 mL, 1:1) under nitrogen. The mixturewas heated at 50 °C overnight. The reaction mixture was filtered and washed with hot ethyl acetate.The filtered solution was poured into water and extracted with ethyl acetate. The organics werecombined, washed with brine, and dried with sodium sulfate. After solvent removal, 5.94 g of a brownpowder was obtained. This crude product was purified via vacuum sublimation. Obtained as a whilesolid was 2.53 g (8.0 mmol, 22percent) of BCz. 1H-NMR (400 MHz, DMSO-d6): δ (ppm) 11.28 (s, 2H), 8.51(s, 2H), 8.25 (d, J = 7.7 Hz, 2H), 7.81 (dd, J = 8.4 Hz, J = 1.4 Hz, 2H), 7.58 (d, J = 8.4 Hz, 2H), 7.51 (d,J = 8.1 Hz, 2H), 7.41 (t, J = 7.6 Hz, 2H), 7.19 (t, J = 7.4 Hz, 2H). 13C-NMR (100 MHz, DMSO-d6): δ (ppm)140.7, 139.2, 132.8, 126.1, 125.4, 123.6, 123.2, 120.9, 119.0, 118.6, 111.7, 111.5.
11% With iron(III) chloride In methanol at 20℃; for 22 h; In a 300 mL eggplant flask, 20 g of iron chlorideAnd 5 g of carbazole, and the mixture was vigorously stirred.After disappearance of carbazole was confirmed by TLC (thin layer chromatograph), the reaction mixture was added to 2 L of methanol. This operation was carried out ten times, and the mixture was stirred in methanol at room temperature for 22 hours. The green solid was collected by suction filtration to obtain a dark green solid. The obtained solid was treated with a large sublimation purifier at 1.2 × 10 -2 torr, at a heating rate of 1 ° C./min,Purification was carried out at a sublimation temperature of 250 ° C. to obtain a white solid (yield 2.8 g, yield 11percent). Identification of the target product was carried out by 1 H-NMR (400 MHz, DMSO). A chart of 1 H-NMR is shown in FIG. 1.
14 g
Stage #1: With iron(III) chloride In chloroform at 20℃; for 22 h; Inert atmosphere
Stage #2: for 1 h;
Stage #3: for 0.5 h; Reflux
Under nitrogen flow , at room temperature, the32.0 g of cardazole, Anhydrous ferric chloride [III] 93.13g with 400 ml of chloroform mixture solution was stirred for 22h. The mixed solution wasplaced in 1000 ml of methanol, stirred for 1 hour and then filtered. Into the resultingpowder added tetrahydrofuran (600 rrd) then mixture was refluxed for 30 minutesand followed by filtration to remove the insoluble matter. After evaporation,the mixture was dissolved in 100 ml of DMI (l, 3-Dimethyl-2-Imidazolidinone)and recrystallized at 5 ° C to obtain 14.0 g of 9H, 9'H-3,3'- Dicarbazole

Reference: [1] Patent: TWI540129, 2016, B, . Location in patent: Paragraph 0090-0092
[2] Patent: KR101802423, 2017, B1, . Location in patent: Paragraph 0153 - 0156
[3] Molecules, 2018, vol. 23, # 4,
[4] Patent: JP5727237, 2015, B2, . Location in patent: Paragraph 0123
[5] J. Gen. Chem. USSR (Engl. Transl.), 1992, vol. 62, # 1.2, p. 164 - 168[6] Zhurnal Obshchei Khimii, 1992, vol. 62, # 1, p. 199 - 203
[7] Journal of the Chemical Society, 1927, p. 1391
[8] Molecular Crystals and Liquid Crystals, 2008, vol. 497, p. 241/[573]-253/[585]
[9] RSC Advances, 2016, vol. 6, # 39, p. 33212 - 33220
[10] Patent: TWI523840, 2016, B, . Location in patent: Page/Page column 52
  • 2
  • [ 1592-95-6 ]
  • [ 1126522-69-7 ]
  • [ 1984-49-2 ]
YieldReaction ConditionsOperation in experiment
59% With tris-(dibenzylideneacetone)dipalladium(0) In water; toluene A mixture solution of 3-bromo-9H-carbazole (6.75 g, 27.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12.15 g, 32.9 mmol), Pd2(dba)3 (0.251 g, 0.274 mmol), SPhos (0.450 g, 1.097 mmol) and K3PO4 (25.3 g, 110 mmol) in toluene (500 mL) and water (50 mL) was refluxed under nitrogen for 10 h.
After cooling to room temperature, the reaction mixture was extracted with dichloromethane and washed with brine.
The combined organic solutions were dried over Na2SO4, filtered, and the solvent was evaporated to yield a crude product, which was recrystallized from DCM/hexane (1/1, v/v, 1200 mL) to yield 9H,9'H-3,3'-bicarbazole (6.66 g, 59percent) as a yellow solid.
Reference: [1] Patent: US2013/26909, 2013, A1, . Location in patent: Page/Page column
  • 3
  • [ 1160823-44-8 ]
  • [ 1984-49-2 ]
Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 12, p. 4490 - 4498
[2] RSC Advances, 2015, vol. 5, # 46, p. 36374 - 36384
  • 4
  • [ 591-50-4 ]
  • [ 1984-49-2 ]
  • [ 1060735-14-9 ]
YieldReaction ConditionsOperation in experiment
5.59 g With copper; potassium carbonate In nitrobenzene at 180℃; for 4 h; Inert atmosphere Then under a nitrogen stream, the 14.0g of 9H, 9'H-3,3'- Dicarbazole,Iodine benzene 8.59 g, nitrobenzene 400ml, 5.72 g of copper powder with 12.44 g of potassium carbonate mixturesolution heated to 180 ° C for 4 hours. After coolingto room temperature, the nitrobenzene was removed by distillation under reducedpressure, followed by purification by silica gel chromatography, vacuum dryingto obtain 5.59g of 9-phenyl-9H, 9H-3,3-dicarbazole.
Reference: [1] Patent: TWI523840, 2016, B, . Location in patent: Page/Page column 52
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