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[ CAS No. 453566-15-9 ] {[proInfo.proName]}

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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 453566-15-9
Chemical Structure| 453566-15-9
Chemical Structure| 453566-15-9
Structure of 453566-15-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 453566-15-9 ]

CAS No. :453566-15-9 MDL No. :MFCD16620379
Formula : C9H6BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DNNTVDNUUQKALF-UHFFFAOYSA-N
M.W : 240.05 Pubchem ID :21942615
Synonyms :

Calculated chemistry of [ 453566-15-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.14
TPSA : 50.09 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) : -5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.11
Log Po/w (MLOGP) : 2.0
Log Po/w (SILICOS-IT) : 2.37
Consensus Log Po/w : 2.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.162 mg/ml ; 0.000677 mol/l
Class : Soluble
Log S (Ali) : -3.29
Solubility : 0.123 mg/ml ; 0.000512 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.0915 mg/ml ; 0.000381 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 453566-15-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P280-P305+P351+P338-P311 UN#:3439
Hazard Statements:H302+H312-H315-H319-H331-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 453566-15-9 ]

* 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 [ 453566-15-9 ]
  • Downstream synthetic route of [ 453566-15-9 ]

[ 453566-15-9 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 453566-15-9 ]
  • [ 453566-14-8 ]
YieldReaction ConditionsOperation in experiment
85% With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; To methyl 3-bromo-5-carbamoyl-benzoate (2.8 g, 10.8 mmol, 1.0 eq) was added POCI3 (30 mL) and the reaction heated at 100 °C overnight. The POCI3 was removed under reduced pressure, water was added and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo to afford a crude residue which was purified by column chromatography (petroleum ethenEtOAc, 20:1 ) to give methyl 3-bromo-5-cyano-benzoate (2.5 g, 96 percent). This material was dissolved in THF (30 mL) and LiOH.H20 (1.7 g, 41.6 mmol, 1.54 eq) and H20 (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the aqueous phase acidified with diluted HC1 and extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2C12: MeOH, 50: 1) to give the title compound as a white solid (2 g, 85 percent).LC-MS: m z 248.0, 249.9 [M+Na1H NMR (400 MHZ, DMSO) δ 13.67 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.24 (s, 1H).
Reference: [1] Patent: WO2013/37705, 2013, A2, . Location in patent: Page/Page column 139
  • 2
  • [ 1427407-54-2 ]
  • [ 453566-15-9 ]
YieldReaction ConditionsOperation in experiment
96% at 100℃; To methyl 3-bromo-5-carbamoyl-benzoate (2.8 g, 10.8 mmol, 1.0 eq) was added POCI3 (30 mL) and the reaction heated at 100 °C overnight. The POCI3 was removed under reduced pressure, water was added and the aqueous layer extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo to afford a crude residue which was purified by column chromatography (petroleum ethenEtOAc, 20:1 ) to give methyl 3-bromo-5-cyano-benzoate (2.5 g, 96 percent). This material was dissolved in THF (30 mL) and LiOH.H20 (1.7 g, 41.6 mmol, 1.54 eq) and H20 (10 mL) were added. The mixture was stirred at room temperature overnight. The THF was removed under reduced pressure and the aqueous phase acidified with diluted HC1 and extracted with EtOAc. The combined organic extracts were dried (Na2SC>4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (CH2C12: MeOH, 50: 1) to give the title compound as a white solid (2 g, 85 percent).LC-MS: m z 248.0, 249.9 [M+Na1H NMR (400 MHZ, DMSO) δ 13.67 (br s, 1H), 8.40 (s, 1H), 8.24 (s, 1H), 8.24 (s, 1H).
Reference: [1] Patent: WO2013/37705, 2013, A2, . Location in patent: Page/Page column 139
  • 3
  • [ 188813-07-2 ]
  • [ 453566-15-9 ]
Reference: [1] Patent: US2003/55085, 2003, A1,
  • 4
  • [ 51760-21-5 ]
  • [ 453566-15-9 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
  • 5
  • [ 23351-91-9 ]
  • [ 453566-15-9 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
  • 6
  • [ 161796-10-7 ]
  • [ 453566-15-9 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
  • 7
  • [ 439937-35-6 ]
  • [ 453566-15-9 ]
Reference: [1] Patent: WO2013/37705, 2013, A2,
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