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[ CAS No. 89642-49-9 ] {[proInfo.proName]}

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Chemical Structure| 89642-49-9
Chemical Structure| 89642-49-9
Structure of 89642-49-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 89642-49-9 ]

CAS No. :89642-49-9 MDL No. :MFCD00982006
Formula : C7H3BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :FXRMUJPWDOLCLX-UHFFFAOYSA-N
M.W :227.02 Pubchem ID :3926861
Synonyms :

Calculated chemistry of [ 89642-49-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.68
TPSA : 69.61 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) : -6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 2.16
Log Po/w (WLOGP) : 2.23
Log Po/w (MLOGP) : 1.02
Log Po/w (SILICOS-IT) : 0.33
Consensus Log Po/w : 1.43

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.91
Solubility : 0.278 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.126 mg/ml ; 0.000557 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.72
Solubility : 0.429 mg/ml ; 0.00189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 89642-49-9 ]

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

Application In Synthesis of [ 89642-49-9 ]

* 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 [ 89642-49-9 ]
  • Downstream synthetic route of [ 89642-49-9 ]

[ 89642-49-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 89642-49-9 ]
  • [ 6393-40-4 ]
Reference: [1] Chemische Berichte, 1916, vol. 49, p. 2230
  • 2
  • [ 89642-49-9 ]
  • [ 3272-08-0 ]
Reference: [1] Chemische Berichte, 1917, vol. 50, p. 1354
  • 3
  • [ 60-35-5 ]
  • [ 89642-49-9 ]
  • [ 7732-18-5 ]
  • [ 127-09-3 ]
  • [ 3272-08-0 ]
Reference: [1] Chemische Berichte, 1917, vol. 50, p. 1354
  • 4
  • [ 623-00-7 ]
  • [ 89642-49-9 ]
YieldReaction ConditionsOperation in experiment
56% at 0 - 20℃; for 3 h; To a solution of 4-bromobenzonitrile (4.0 g, 22 mmol) in conc. H2SO4 (10 mL) was added dropwise at 0° C. nitric acid (6 mL).
The reaction mixture was stirred at 0° C. for 30 min, and then at room temperature for 2.5 h.
The resulting solution was poured into ice-water.
The white precipitate was collected via filtration and washed with water until the washings were neutral.
The solid was recrystallized from an ethanol/water mixture (1:1, 20 mL) twice to afford 4-bromo-3-nitrobenzonitrile as a white crystalline solid (2.8 g, 56percent).
1H NMR (300 MHz, DMSO-d6) δ 8.54 (s, 1H), 8.06 (d, J=8.4 Hz, 1H), 7.99 (d, J=8.4 Hz, 1H); 13C NMR (75 MHz, DMSO-d6) δ 150.4, 137.4, 136.6, 129.6, 119.6, 117.0, 112.6; HPLC ret. time 1.96 min, 10-100percent CH3CN, 5 min gradient; ESI-MS 227.1 Ink (MH+).
Reference: [1] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 0673
[2] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36
[3] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 106,107
[4] Chemische Berichte, 1916, vol. 49, p. 2224
[5] Chemische Berichte, 1890, vol. 23, p. 3442
[6] Patent: US2011/98311, 2011, A1,
  • 5
  • [ 106-40-1 ]
  • [ 89642-49-9 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1922, vol. 41, p. 36
  • 6
  • [ 89642-49-9 ]
  • [ 17626-40-3 ]
Reference: [1] Chemische Berichte, 1916, vol. 49, p. 2230
  • 7
  • [ 89642-49-9 ]
  • [ 72635-78-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 369[2] Chem.Abstr., 1948, vol. 42, p. 148
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