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[ CAS No. 618-95-1 ] {[proInfo.proName]}

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Chemical Structure| 618-95-1
Chemical Structure| 618-95-1
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Product Details of [ 618-95-1 ]

CAS No. :618-95-1 MDL No. :MFCD00007250
Formula : C8H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :AXLYJLKKPUICKV-UHFFFAOYSA-N
M.W : 181.15 Pubchem ID :69260
Synonyms :

Calculated chemistry of [ 618-95-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.54
TPSA : 72.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.59
Log Po/w (XLOGP3) : 1.89
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : -0.45
Consensus Log Po/w : 1.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.3
Solubility : 0.913 mg/ml ; 0.00504 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.17 mg/ml ; 0.00094 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.85
Solubility : 2.54 mg/ml ; 0.014 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.79

Safety of [ 618-95-1 ]

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 [ 618-95-1 ]

* 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 [ 618-95-1 ]
  • Downstream synthetic route of [ 618-95-1 ]

[ 618-95-1 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 618-95-1 ]
  • [ 334952-09-9 ]
Reference: [1] Patent: US2015/284327, 2015, A1,
  • 2
  • [ 618-95-1 ]
  • [ 14192-26-8 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2015, vol. 58, # 7, p. 308 - 312
[2] Patent: US2015/284327, 2015, A1,
  • 3
  • [ 618-95-1 ]
  • [ 6307-87-5 ]
YieldReaction ConditionsOperation in experiment
86% at 20℃; for 2 h; Inert atmosphere; Schlenk technique Methyl 3-bromo-5-nitrobenzoate 51) methyl 3-nitrobenzoate (50) (85.4 g; 471 mmol, 1 eq.) were dissolved in concentrated sulfuric acid (500 mL). Then a solution of dibromoisocyanuric acid (67.6 g; 235 mmol, 0.5 eq.) in concentrated sulfuric acid (850 mL) was added. After stirring the clear solution for 2 hours the whole mixture were poured on 5 kg ice. The slurry was extracted 5 times with each 2 L of dichloromethane. The combined organic phases were dried over sodium sulfate. After evaporating of the solvent the crude product were recrystallized- from methanol to yield the title compound (105.8 g 406 mmol, 86percent) as large pale yellow crystals. Rf silica gel 60; chloroform/methanol 95:5 = 0.87. mp. 74.1°C. 1H NMR (300 MHz; CHC13): 6 = 8.75 (dd, 1H, 4JH-H I = 2.0 Hz, JH.H 2 = 1.4 Hz, CH-6); 8.51 (dd, 1H, 4JH-H I = 4JH-H 2 = 2.0 Hz, Ar-CH-4); 8.45 (dd, 1H, JH-H I = 1.7 Hz, 4JH-H 2 = 1.5 Hz, Ar-CH-2); 3.96 (s, 3H, OCH3) ppm. 13C NMR (75 MHz; CHC13): δ = 163.7 (COOMe), 148.7 (Ar-C-NO2), 138.2 (Ar-CH-2), 133.2 (Ar-CCOOMe), 130.4 (Ar-CH-4), 123.1 (Ar-CH-6), 123.0 (Ar-C-Br), 53.1 (OCH3) ppm. IR (ATR) : v (Trd) = 3096 (w), 3082 (m), 2955 (w), 2917 (w), 2870 (w), 2847 (w), 1725 (s), 1607 (w), 1527 (m), 1446 (m), 1434 (m), 1420 (m), 1345 (s), 1284 (s), 1243 (m), 1197 (m), 1146 (m), 1087 (m), 980 (m), 919 (m), 902 (s), 842 (m), 770 (m), 733 (s), 726 (s), 653 (m) cm"1. EI-MS (EI+, 70 eV) : m/z = 259/261 (65) [M]'+,.228/230 (100), 213/215 (8), 182/184 (22), 172/172 (6), 154/156 (6), 75 (31), 74 (30). HRMS (ESI+) calc. for C8H6N79Br04 [M+H]+: 258.9486, found 258.9480 amu.
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 18, p. 4764 - 4774
[2] Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17408 - 17416
[3] Patent: WO2014/19685, 2014, A1, . Location in patent: Page/Page column 13; 39
[4] Journal of Molecular Structure, 2013, vol. 1036, p. 505 - 509
[5] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 3496 - 3505
[6] Tetrahedron Letters, 2003, vol. 44, # 7, p. 1469 - 1472
  • 4
  • [ 67-56-1 ]
  • [ 618-95-1 ]
  • [ 6307-87-5 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 42, p. 8254 - 8260
  • 5
  • [ 618-95-1 ]
  • [ 6307-87-5 ]
  • [ 6307-83-1 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 42, p. 8254 - 8260
  • 6
  • [ 618-95-1 ]
  • [ 6307-87-5 ]
  • [ 6307-83-1 ]
Reference: [1] Tetrahedron, 2010, vol. 66, # 42, p. 8254 - 8260
  • 7
  • [ 618-95-1 ]
  • [ 6307-83-1 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1973, vol. 38, p. 3496 - 3505
  • 8
  • [ 618-95-1 ]
  • [ 35998-96-0 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 10, p. 3148 - 3162
  • 9
  • [ 618-95-1 ]
  • [ 42753-75-3 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 1930
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 56
  • 10
  • [ 865-47-4 ]
  • [ 618-95-1 ]
  • [ 3816-62-4 ]
  • [ 3987-92-6 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 4878 - 4888
  • 11
  • [ 618-95-1 ]
  • [ 118535-52-7 ]
  • [ 3816-62-4 ]
  • [ 3987-92-6 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 4878 - 4888
  • 12
  • [ 618-95-1 ]
  • [ 3816-62-4 ]
  • [ 3987-92-6 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 4878 - 4888
  • 13
  • [ 618-95-1 ]
  • [ 706791-83-5 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 7, p. 1469 - 1472
[2] Journal of Molecular Structure, 2013, vol. 1036, p. 505 - 509
[3] Journal of the American Chemical Society, 2013, vol. 135, # 46, p. 17408 - 17416
[4] Patent: WO2014/19685, 2014, A1,
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