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[ CAS No. 20870-78-4 ] {[proInfo.proName]}

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Chemical Structure| 20870-78-4
Chemical Structure| 20870-78-4
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Product Details of [ 20870-78-4 ]

CAS No. :20870-78-4 MDL No. :MFCD00456998
Formula : C8H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 212.04 Pubchem ID :-
Synonyms :
5-Bromooxindole

Calculated chemistry of [ 20870-78-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.43
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.74
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.37
Log Po/w (MLOGP) : 1.87
Log Po/w (SILICOS-IT) : 2.53
Consensus Log Po/w : 1.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.401 mg/ml ; 0.00189 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.76 mg/ml ; 0.00828 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.75
Solubility : 0.0379 mg/ml ; 0.000179 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 20870-78-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H317-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20870-78-4 ]

* 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 [ 20870-78-4 ]
  • Downstream synthetic route of [ 20870-78-4 ]

[ 20870-78-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 20870-78-4 ]
  • [ 142273-20-9 ]
Reference: [1] European Journal of Organic Chemistry, 2012, # 5, p. 1019 - 1024
  • 2
  • [ 20870-78-4 ]
  • [ 203314-28-7 ]
YieldReaction ConditionsOperation in experiment
80.5%
Stage #1: With hydrogen bromide; sodium nitrite In water at -5 - 0℃; for 0.0025 h;
Stage #2: With hydrogen bromide; copper(I) bromide; copper(ll) bromide In water at 0.5 - 25℃; for 1.5 h;
The 5-bromofluorenone 670.7 g obtained in the previous step,Add 1320ml of water and cool to -5-0 °C in an ice bath.Then add 1100g of hydrogen bromide (48percent) aqueous solution and stir.Most of the raw materials are dissolved, and the temperature is controlled within the range of -5-0 °C.Add 143 g of sodium nitrite to a solution of 286 ml of water.During the period, the control temperature does not exceed 0 °C, about 15 minutes,The incubation reaction was continued for 1 h, and a large amount of brown granular solid (diazonium salt) was precipitated in the reaction solution for use.In another 10000ml four-necked flask, 297g of cuprous bromide, 22g of copper bromide, 13200ml of water, hydrogen bromide(48percent) 1100g of aqueous solution, stirred, the reaction solution was dark red, heated to 20-25 ° C, the diazonium salt obtained in the previous step was added dropwise.After the completion of the dropwise addition, the reaction was continued for 1 h, the temperature was lowered to about 5 ° C, the temperature was kept for 0.5 h, and the filter cake was washed with cold water until the washing liquid was colorless. drying,The solid 2,5-dibromophenylacetic acid 746 g was obtained in a yield of 80.5percent, and the HPLC purity was 98.8percent.
322.5 g
Stage #1: With hydrogen bromide; sodium nitrite In water at -5 - 0℃; for 1 h;
Stage #2: With copper(l) iodide; hydrogen bromide; copper(I) bromide In water at 20 - 25℃; for 1 h;
300.0 g of bromoindolinone (Formula II) prepared in the previous step was put into a reaction flask, 600 ml of water was added, and the temperature was lowered to -5 to 0 ° C in an ice bath,Then 493.5g of hydrogen bromide (48percent) aqueous solution was added and stirred. Most of the raw materials were dissolved and the temperature was controlled at -5-0 ° C. A solution of 65.0g of sodium nitrite dissolved in 130ml of water was added dropwise,During the temperature does not exceed 0 , about 15min plus Bi, continue to heat the reaction 1h,The reaction liquid has a large number of brown granular solid precipitation, stand-by. In another reaction flask, 135.0 g of cuprous bromide, 10.0 g of cupric bromide, 600 ml of water and 500 g of a hydrogen bromide (48percent) aqueous solution were added and the mixture was stirred. The reaction mixture was dark red,The temperature was raised to 20-25 ° C., the diazonium salt obtained from the previous step was added dropwise and the reaction was continued for 1 h after the completion of the incubation.Cool to about 5 , incubated 0.5h, filtered, the filter cake washed with cold water to wash colorless.Drying afforded 322.5g of solid, HPLC purity 99.1percent.
Reference: [1] Patent: CN108794329, 2018, A, . Location in patent: Paragraph 0021; 0022
[2] Patent: CN104693019, 2017, B, . Location in patent: Paragraph 0018; 0023-0026; 0028; 0033-0036; 0038; 0043-0046
  • 3
  • [ 20870-78-4 ]
  • [ 118753-70-1 ]
  • [ 873779-30-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 2945 - 2959
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