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[ CAS No. 4583-55-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 4583-55-5
Chemical Structure| 4583-55-5
Chemical Structure| 4583-55-5
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Product Details of [ 4583-55-5 ]

CAS No. :4583-55-5 MDL No. :MFCD00850844
Formula : C10H10BrN Boiling Point : -
Linear Structure Formula :- InChI Key :IOGAIEWEHFPGNO-UHFFFAOYSA-N
M.W : 224.10 Pubchem ID :12793097
Synonyms :

Calculated chemistry of [ 4583-55-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.2
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.93
TPSA : 15.79 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 3.5
Log Po/w (WLOGP) : 3.55
Log Po/w (MLOGP) : 2.89
Log Po/w (SILICOS-IT) : 4.12
Consensus Log Po/w : 3.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.99
Solubility : 0.023 mg/ml ; 0.000102 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0685 mg/ml ; 0.000306 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.92
Solubility : 0.00271 mg/ml ; 0.0000121 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 4583-55-5 ]

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 [ 4583-55-5 ]

* 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 [ 4583-55-5 ]
  • Downstream synthetic route of [ 4583-55-5 ]

[ 4583-55-5 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 622-88-8 ]
  • [ 78-93-3 ]
  • [ 4583-55-5 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 96 h; Inert atmosphere A 500 ml_ three neck round bottomed flask equipped with a stir bar, thermocouple, heat mantle, and water condenser with nitrogen inlet was charged with 3-bromophenylhydrazine hydrochloride (19.84 g, 88.77 mmol) and isopropanol (240 ml_). 2-Butanone (8.0 ml_, 89.32 mmol) was added and the reaction was heated to 80 °C. After 4 days the reaction was allowed to cool to room temperature. The solvent was removed by rotary evaporation and the red residue dissolved in ethyl acetate (200 ml_). The organic layer was washed with 1 N hydrochloric acid (100 ml_) and saturated aqueous sodium bicarbonate (100 ml_). The organic layer was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation to give 5- bromo-2,3-dimethyl-1 H-indole as a red solid (1 5.94 g, 71 .1 mmol, 80percent). 1 H NMR (400 MHz, CDCIs) δ 7.70 (s, 1 H), 7.59 - 7.55 (m, 1 H), 7.1 7 (dd, J = 8.5, 1 .9 Hz, 1 H), 7.1 1 (dd, J = 8.4, 0.6 Hz, 1 H), 2.35 (d, J = 0.8 Hz, 3H), 2.17 (q, J = 0.7 Hz, 3H). 13C NMR (1 01 MHz, CDCIs) δ 133.77, 132.10, 131 .27, 123.54, 120.61 , 1 12.26, 1 1 1 .35, 107.02, 1 1 .58, 8.35.
67% for 22 h; Reflux Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL).
The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl.
The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated.
The crude residue was purified by chromatography (SiO2, 0-20percent EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67percent).
1H NMR (CDCl3, 500 MHz) δ 7.69 (br s, 1H), 7.55 (d, 1H, J=2.0 Hz), 7.15 (dd, 1H, J=2.0, 8.5 Hz), 7.09 (dd, 1H, J=0.5, 8.5 Hz), 2.34 (s, 3H), 2.15 (d, 3H, J=0.5 Hz)
ESI m/z 224.0 ([M+H]+, C10H11BrN requires 224.0)
Reference: [1] Heterocycles, 2007, vol. 72, p. 373 - 383
[2] Patent: WO2018/89181, 2018, A1, . Location in patent: Page/Page column 20
[3] Journal of the American Chemical Society, 2011, vol. 133, # 5, p. 1428 - 1437
[4] Patent: US9095571, 2015, B2, . Location in patent: Page/Page column 104
[5] Organic Letters, 2012, vol. 14, # 8, p. 2066 - 2069
  • 2
  • [ 27246-81-7 ]
  • [ 78-93-3 ]
  • [ 4583-55-5 ]
YieldReaction ConditionsOperation in experiment
80% at 80℃; for 96 h; Inert atmosphere A 500 mL three neck round bottomed flask, equipped with a stir bar, thermocouple, heat mantle, and water condenser, and with a nitrogen inlet, was charged with 3-bromophenylhydrazine hydrochloride (17) (19.84 g, 88.77 mmol) and isopropanol (240 mL) . 2-Butanone (18) (8.0 mL, 89.32 mmol) was added and the reaction was heated to 80. After 4 days, the reaction was allowed to cool to room temperature. The solvent was removed by rotary evaporation and the red residue dissolved in ethyl acetate (200 mL) . The organic layer was washed with 1N HCl (100 mL) and saturated aqueous sodium bicarbonate (100 mL) . The organic layer was dried over magnesium sulfate, filtered, and concentrated by rotary evaporation to give indole compound (19) as red solids (15.94 g, 71.1 mmol, 80) .1H NMR (400 MHz, Chloroform-d) δ 7.70 (s, 1H) , 7.59 –7.55 (m, 1H) , 7.17 (dd, J 8.5, 1.9 Hz, 1H) , 7.11 (dd, J 8.4, 0.6 Hz, 1H) , 2.35 (d, J 0.8 Hz, 3H) , 2.17 (q, J 0.7 Hz, 3H) .13C NMR (101 MHz, CDCl3) δ 133.77, 132.10, 131.27, 123.54, 120.61, 112.26, 111.35, 107.02, 11.58, 8.35.
Reference: [1] Patent: WO2016/107459, 2016, A1, . Location in patent: Paragraph 00158
  • 3
  • [ 78-93-3 ]
  • [ 589-21-9 ]
  • [ 4583-55-5 ]
YieldReaction ConditionsOperation in experiment
73% Reflux Preparation of 5-bromo-2,3~dimethylindole A mixture of 4-bromophenylhydrazine (5.0 g, 22.3 mmoi) and methyl ethyl ketone (1.6 g, 22.3 mmoi) was heated in ethanof (60 mL) at refiux overnight. The solvent was removed under vacuum and the residue recrystaliized from ethanol/water, to give the target compound (3.6 g, 73percent). NMR (400 MHz, d6-DMSO): δ 10.87 (s, 1 H), 7.51 (d. J = 1 .2 Hz, 1 H), 7.18 (d, J = 6.3 Hz, 1 H), 7.07 (dd, J = 6.3 Hz, 1 ,2 Hz, 1 H), 2.31 (s, 3H), 2.13 (s, 3H).
Reference: [1] Patent: WO2015/74123, 2015, A1, . Location in patent: Page/Page column 47
  • 4
  • [ 1417407-56-7 ]
  • [ 4583-55-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 2, p. 620 - 623
  • 5
  • [ 598-30-1 ]
  • [ 673-40-5 ]
  • [ 4583-55-5 ]
Reference: [1] Synthesis, 2011, # 1, p. 23 - 29
  • 6
  • [ 1075-34-9 ]
  • [ 124-38-9 ]
  • [ 4583-55-5 ]
Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10476 - 10480[2] Angew. Chem., 2014, vol. 126, # 39, p. 10644 - 10648,5
  • 7
  • [ 1417407-98-7 ]
  • [ 4583-55-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 2, p. 620 - 623
  • 8
  • [ 1417408-14-0 ]
  • [ 4583-55-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 2, p. 620 - 623
  • 9
  • [ 1417408-30-0 ]
  • [ 4583-55-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 2, p. 620 - 623
  • 10
  • [ 1417408-44-6 ]
  • [ 4583-55-5 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 2, p. 620 - 623
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