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[ CAS No. 35472-56-1 ] {[proInfo.proName]}

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Chemical Structure| 35472-56-1
Chemical Structure| 35472-56-1
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Product Details of [ 35472-56-1 ]

CAS No. :35472-56-1 MDL No. :MFCD11174593
Formula : C10H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WBSWYVBUGLBCOV-UHFFFAOYSA-N
M.W : 179.22 Pubchem ID :101365
Synonyms :

Calculated chemistry of [ 35472-56-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.83
TPSA : 38.33 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) : -5.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 3.24
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 1.94
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 2.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.07
Solubility : 0.153 mg/ml ; 0.000851 mol/l
Class : Soluble
Log S (Ali) : -3.72
Solubility : 0.0343 mg/ml ; 0.000191 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.0866 mg/ml ; 0.000483 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 35472-56-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 35472-56-1 ]

* 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 [ 35472-56-1 ]
  • Downstream synthetic route of [ 35472-56-1 ]

[ 35472-56-1 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 64-17-5 ]
  • [ 119-68-6 ]
  • [ 35472-56-1 ]
YieldReaction ConditionsOperation in experiment
100% for 20 h; Inert atmosphere; Reflux Concentrated sulfuric acid (2 mL, 37 mmol, 98percent) was added to a stirred solution of 2-(methylamino)-benzoic acid 7 (1.1 g, 7.5 mmol) in anhydrous ethanol (16.5 mL). The solution was refluxed for 20 hours, or until the reaction was complete. The solvent was removed under reduced pressure and the residue was re-dissolved in water (20 mL) and neutralised with sodium hydroxide (5 M). The aqueous phase was extracted with chloroform (3 x 20 mL), the organic layers were combined, washed with brine (40 mL), dried over anhydrous magnesium sulfate and the solvent evaporated to yield a brown oil 8 in quantitative yield (1.3 g, 7.5 mmol, 100percent). Rf 0.40 (1/10 v/v ethyl acetate/hexane); IR (ZnSe cell, oil) vmax: 3378 (w, aromatic R2NH), 2981, 2906 (w, C-H), 1677 (s, C=O), 1579, 1517 (m, aromatic C=C), 1233 (s, aromatic R2NH, ester C-O), 1125, 1085 (m, aromatic C=C) cm-1; 1H NMR (300 MHz, d6-DMSO): δ 7.79 (1H, dd, 3J6-5 = 8.1 Hz, 4J6-4 = 1.4 Hz, 6-CH), 7.56 (1H, br, d, 3JNH-10 = 4.2 Hz, NH) 7.40 (1H, ddd, 3J5-6 ~ 3J5-4 = 7.8 Hz, 4J5-3=1.2 Hz, 5-CH), 6.71 (1H, d, 3J3-4 = 8.4 Hz, 3-CH), 6.57 (1H, dd, 3J4-3 ~ 3J4-5 = 7.8 Hz, 4-CH), 4.25 (2H, q, 3J8-9 = 7.02 Hz, 8-CH2-), 2.91 (3H, d, 3J10-NH = 5.1 Hz, 10-CH3), 1.30 (3H, t, 3J9-8 = 7.2 Hz, 9-CH3) ppm; 13C NMR (125 MHz, CDCl3): δ 168.0 (7-C=O), 151.4 (2-C), 133.8 (4-CH), 130.9 (6-CH), 113.6 (5-CH), 110.0 (3-CH), 109.5 (1-C), 59.5 (8-CH2-), 28.8 (10-CH3), 13.7 (9-CH3) ppm; LRMS (+ ESI) m/z: 180 ([M + H]+, 100percent), 162 ([M – C3H5O2 + MeOH + Na + H]+ 56percent), 134 ([M - OCH2CH3]+, 47percent), 130 ([M - (CO2CH2CH3) + Na + H]+, 48percent)
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 29 - 34
[2] Chemische Berichte, 1901, vol. 34, p. 1645
[3] Chem. Zentralbl., 1906, vol. 77, # II, p. 1007
[4] Chemische Berichte, 1920, vol. 53, p. 2354
[5] Archiv der Pharmazie (Weinheim, Germany), 1925, p. 494
[6] Organic and Biomolecular Chemistry, 2011, vol. 9, # 20, p. 7113 - 7125
  • 2
  • [ 64-17-5 ]
  • [ 10328-92-4 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17490 - 17493,4
  • 3
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 100-61-8 ]
  • [ 35472-56-1 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 6, p. 1397 - 1400
[2] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 4
  • [ 10328-92-4 ]
  • [ 122-51-0 ]
  • [ 35472-56-1 ]
Reference: [1] Organic Letters, 2018,
  • 5
  • [ 100-61-8 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17490 - 17493,4
[2] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17490 - 17493,4
[3] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17490 - 17493,4
  • 6
  • [ 55426-74-9 ]
  • [ 35472-56-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 4, p. 687 - 692
  • 7
  • [ 76393-16-3 ]
  • [ 72368-50-4 ]
  • [ 35472-56-1 ]
  • [ 29055-08-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2750 - 2753
  • 8
  • [ 118-48-9 ]
  • [ 35472-56-1 ]
Reference: [1] Organic Letters, 2018,
  • 9
  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 100-61-8 ]
  • [ 35472-56-1 ]
  • [ 10328-92-4 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 10
  • [ 79228-33-4 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 16, p. 3699 - 3701
  • 11
  • [ 33923-02-3 ]
  • [ 35472-56-1 ]
  • [ 85-91-6 ]
Reference: [1] Journal of Organic Chemistry, 1987, vol. 52, # 16, p. 3699 - 3701
  • 12
  • [ 616-38-6 ]
  • [ 87-25-2 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7374 - 7378
  • 13
  • [ 23310-36-3 ]
  • [ 64-17-5 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 369 - 373
  • 14
  • [ 87-25-2 ]
  • [ 74-88-4 ]
  • [ 35472-56-1 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1891, vol. <2> 43, p. 444
[2] Tetrahedron Letters, 1990, vol. 31, # 20, p. 2869 - 2972
  • 15
  • [ 62-53-3 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 16
  • [ 3422-01-3 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 17
  • [ 28131-24-0 ]
  • [ 35472-56-1 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 18
  • [ 118-92-3 ]
  • [ 35472-56-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 95, p. 29 - 34
  • 19
  • [ 62-53-3 ]
  • [ 35472-56-1 ]
  • [ 10328-92-4 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 20
  • [ 3422-01-3 ]
  • [ 35472-56-1 ]
  • [ 10328-92-4 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 21
  • [ 28131-24-0 ]
  • [ 35472-56-1 ]
  • [ 10328-92-4 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263
  • 22
  • [ 141814-27-9 ]
  • [ 87-25-2 ]
  • [ 35472-56-1 ]
  • [ 55426-74-9 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 7, p. 2476 - 2485
  • 23
  • [ 2621-79-6 ]
  • [ 35472-56-1 ]
  • [ 10541-82-9 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1988, # 4, p. 671 - 680
  • 24
  • [ 4214-38-4 ]
  • [ 10328-92-4 ]
  • [ 35472-56-1 ]
  • [ 81235-51-0 ]
Reference: [1] Synlett, 2007, # 8, p. 1269 - 1273
  • 25
  • [ 76393-16-3 ]
  • [ 72368-50-4 ]
  • [ 35472-56-1 ]
  • [ 29055-08-1 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 11, p. 2750 - 2753
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