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[ CAS No. 73087-83-9 ] {[proInfo.proName]}

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Chemical Structure| 73087-83-9
Chemical Structure| 73087-83-9
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Product Details of [ 73087-83-9 ]

CAS No. :73087-83-9 MDL No. :MFCD12024284
Formula : C18H10Br3N Boiling Point : -
Linear Structure Formula :- InChI Key :NRTDFHUSNYJENJ-UHFFFAOYSA-N
M.W : 479.99 Pubchem ID :11059889
Synonyms :

Calculated chemistry of [ 73087-83-9 ]

Physicochemical Properties

Num. heavy atoms : 22
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 : 103.88
TPSA : 4.93 Ų

Pharmacokinetics

GI absorption : Low
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) : -4.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.05
Log Po/w (XLOGP3) : 7.07
Log Po/w (WLOGP) : 7.07
Log Po/w (MLOGP) : 6.21
Log Po/w (SILICOS-IT) : 6.04
Consensus Log Po/w : 6.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -7.84
Solubility : 0.00000689 mg/ml ; 0.0000000144 mol/l
Class : Poorly soluble
Log S (Ali) : -6.99
Solubility : 0.000049 mg/ml ; 0.000000102 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -9.05
Solubility : 0.000000428 mg/ml ; 0.0000000009 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.85

Safety of [ 73087-83-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 73087-83-9 ]

* 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 [ 73087-83-9 ]
  • Downstream synthetic route of [ 73087-83-9 ]

[ 73087-83-9 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 57102-42-8 ]
  • [ 73087-83-9 ]
YieldReaction ConditionsOperation in experiment
88% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3 h; To a 100 mL round bottom flask was added 1.61 g (5 mmol) of 9-(4-bromophenyl)carbazole and 20 mL of DMF at room temperature. A solution of 1.78 g (10 mmll) of N-bromosuccinimide in DMF was added dropwise with a constant pressure dropping funnel. he reaction mixture was stirred at room temperature for 3 h, poured in ice water, precipitated a large amount of white precipitate. the resulting white solid was purified by silica gel column (petroleum ether) to give 3,6-dibromo-9-(4-bromophenyl)carbazole in 88percent yield.
78% With N-Bromosuccinimide In dichloromethane at 0℃; for 6 h; Darkness Compound 2 (3.0 g, 0.09 mol) was dissolved in dichloromethane (50 mL) in a three-necked round-bottom flask fitted with a magnetic stirrer. NBS (in dichloromethane, 4.10 g, 0.023 mol) was added dropwise from a dropping funnel at 0 °C and in the darkness. After the addition was completed, the reaction mixture was stirred for 6 h. It was quenched with water and extracted 3 times with dichloromethane. The organic layer was evaporated under reduced pressure. The residue was purified by silica gel chromatography with petroleum ether/dichloromethane (10:1) as the eluent to afford a gossypine solid (16) (3.37 g, 78.0percent). Mp: 195–199 °C; Anal. calcd. for C18H10Br3N (percent): C, 45.05; H, 2.10; N, 2.92. Found: C, 45.24; H, 2.25; N, 2.67.
61% With N-Bromosuccinimide; acetic acid In chloroform at 0 - 20℃; for 10 h; The compound (1)[9- (4-bromo-phenyl) -9H-carbazole] [9- (4-bromo-phenyl) -9H-(10 g, 31 mmol) was dissolved in chloroform (90 ml) and acetic acid (90 ml) was added. N-bromosuccinimide (11.6 g, 65 mmol) was added in small portions at 0 ° C. After the temperature was raised to room temperature, the reaction was allowed to proceed for 10 hours. The solid formed in the reaction was then filtered. The resulting solid was dissolved in a small amount of toluene, and the mixture was allowed to stand at 0 for 3 days to obtain only a needle-like white solid to obtain an intermediate compound (2) (9.1 g, 61percent).
55% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 3 h; Preparation of 3,6-dibromo-9-(4-bromophenyl)-9H-carbazole (0320) To a solution of 9-(4-bromophenyl)-9H-carbazole (0.1 g, 0.31 mmol, 1 eq.) in DMF (3.5 mL), N-Bromosuccinimide (0.12 g, 0.69 mmol, 2.2 eq.) in DMF (3.5 mL) was added dropwise and the mixture was allowed to stir at room temperature for 3 hours. Water was then added to give white precipitate which was recrystallized with hexane to yield white solids (0.082 g, 55percent). (0321) 1H NMR (CDCl3, 400 MHz) δ 7.20 (d, 2H, J=8.5 Hz), 7.37 (d, 2H, J=8.6 Hz), 7.50 (dd, 2H, J=1.9, 8.7 Hz), 7.73 (d, 2H, J=8.5 Hz). 13C NMR (100 MHz, CDCl3) δ 139.8, 136.0, 133.5, 129.7, 128.7, 124.2, 123.5, 121.9, 113.5, 111.4. HRMS (TOF MS ES+): calcd for C18H10 Br3N [M]+ 478.8338. found 478.8349.

Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 10, p. 2961 - 2968
[2] Patent: CN103360416, 2016, B, . Location in patent: Paragraph 0039; 0040
[3] Journal of Materials Chemistry, 2010, vol. 20, # 37, p. 8126 - 8133
[4] Synlett, 2006, # 17, p. 2841 - 2845
[5] Dyes and Pigments, 2013, vol. 96, # 3, p. 705 - 713
[6] Journal of Materials Chemistry, 2012, vol. 22, # 13, p. 6351 - 6355
[7] Patent: KR101594131, 2016, B1, . Location in patent: Paragraph 0090-0091; 0095-0096
[8] Patent: US2016/195519, 2016, A1, . Location in patent: Paragraph 0320; 0321
[9] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[10] Journal of Materials Chemistry C, 2014, vol. 2, # 12, p. 2160 - 2168
[11] Patent: JP2018/35101, 2018, A, . Location in patent: Paragraph 0085
  • 2
  • [ 6825-20-3 ]
  • [ 589-87-7 ]
  • [ 73087-83-9 ]
YieldReaction ConditionsOperation in experiment
75% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 220℃; for 0.5 h; Microwave irradiation General procedure: 9H-Carbazole (1.0 mmol), Cs2CO3 (1.0 mmol), iodobenzene (1.1 mmol), CuI (0.1 mmol), and DMF (2 mL) were added to a 5-mL vial. The vial was sealed with a crimp cap and placed in a Biotage initiator microwave cavity. After irradiation at 220 °C for the appropriate time and subsequent cooling, the reaction mixture was diluted with saturated aqueous ammonium chloride. Products were isolated by extraction into ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. Products were purified by silica gel column chromatography using a hexane/ethyl acetate solvent. N-Phenyl-carbazole (2a)22 was obtained (96percent yield) as a white solid.
Reference: [1] Tetrahedron, 2011, vol. 67, # 26, p. 4820 - 4825
[2] Bulletin of the Korean Chemical Society, 2011, vol. 32, # 7, p. 2461 - 2464
[3] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
  • 3
  • [ 6825-20-3 ]
  • [ 460-00-4 ]
  • [ 73087-83-9 ]
YieldReaction ConditionsOperation in experiment
66% With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24 h; General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200–300 mesh) column.
Reference: [1] Synthesis (Germany), 2016, vol. 48, # 5, p. 737 - 750
  • 4
  • [ 1150-62-5 ]
  • [ 73087-83-9 ]
Reference: [1] Chemische Berichte, 1980, vol. 113, # 2, p. 577 - 585
[2] Patent: JP5663566, 2015, B2, . Location in patent: Paragraph 0162
  • 5
  • [ 106-37-6 ]
  • [ 73087-83-9 ]
Reference: [1] Synlett, 2006, # 17, p. 2841 - 2845
[2] Journal of Materials Chemistry, 2010, vol. 20, # 37, p. 8126 - 8133
[3] Journal of Materials Chemistry, 2012, vol. 22, # 13, p. 6351 - 6355
[4] Dyes and Pigments, 2013, vol. 96, # 3, p. 705 - 713
[5] Patent: KR101594131, 2016, B1,
  • 6
  • [ 86-74-8 ]
  • [ 73087-83-9 ]
Reference: [1] Journal of Materials Chemistry, 2010, vol. 20, # 37, p. 8126 - 8133
[2] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[3] Dyes and Pigments, 2013, vol. 96, # 3, p. 705 - 713
[4] Journal of Materials Chemistry C, 2014, vol. 2, # 12, p. 2160 - 2168
[5] Patent: JP5663566, 2015, B2,
[6] Patent: US2016/195519, 2016, A1,
[7] Patent: KR101594131, 2016, B1,
[8] Patent: CN103360416, 2016, B,
  • 7
  • [ 108-88-3 ]
  • [ 620-83-7 ]
  • [ 713-36-0 ]
  • [ 4316-58-9 ]
  • [ 73087-83-9 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 24, p. 7557 - 7561
  • 8
  • [ 589-87-7 ]
  • [ 73087-83-9 ]
Reference: [1] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4527 - 4534
[2] Journal of Materials Chemistry C, 2014, vol. 2, # 12, p. 2160 - 2168
[3] Patent: CN103360416, 2016, B,
  • 9
  • [ 589-87-7 ]
  • [ 86-74-8 ]
  • [ 73087-83-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 10, p. 2961 - 2968
  • 10
  • [ 583-53-9 ]
  • [ 73087-83-9 ]
Reference: [1] Patent: US2016/195519, 2016, A1,
  • 11
  • [ 108-86-1 ]
  • [ 73087-83-9 ]
Reference: [1] Patent: JP5663566, 2015, B2,
  • 12
  • [ 4316-58-9 ]
  • [ 73087-83-9 ]
Reference: [1] Journal of Physical Chemistry, 1994, vol. 98, # 2, p. 408 - 411
  • 13
  • [ 4316-58-9 ]
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Reference: [1] Journal of Physical Chemistry, 1994, vol. 98, # 2, p. 408 - 411
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