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[ CAS No. 139-59-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 139-59-3
Chemical Structure| 139-59-3
Chemical Structure| 139-59-3
Structure of 139-59-3 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 139-59-3 ]

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Product Details of [ 139-59-3 ]

CAS No. :139-59-3 MDL No. :MFCD00007862
Formula : C12H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :WOYZXEVUWXQVNV-UHFFFAOYSA-N
M.W : 185.22 Pubchem ID :8764
Synonyms :

Calculated chemistry of [ 139-59-3 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 57.36
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.93
Log Po/w (WLOGP) : 3.07
Log Po/w (MLOGP) : 2.68
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 2.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.34
Solubility : 0.0853 mg/ml ; 0.000461 mol/l
Class : Soluble
Log S (Ali) : -3.33
Solubility : 0.0863 mg/ml ; 0.000466 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.3
Solubility : 0.00937 mg/ml ; 0.0000506 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.42

Safety of [ 139-59-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 139-59-3 ]

* 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 [ 139-59-3 ]
  • Downstream synthetic route of [ 139-59-3 ]

[ 139-59-3 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 101-84-8 ]
  • [ 139-59-3 ]
  • [ 2688-84-8 ]
Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 13, p. 5000 - 5003
[2] Science, 2015, vol. 349, # 6254, p. 1326 - 1330
  • 2
  • [ 101-84-8 ]
  • [ 101-80-4 ]
  • [ 139-59-3 ]
  • [ 2688-84-8 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 3, p. 563 - 567
  • 3
  • [ 67-56-1 ]
  • [ 139-59-3 ]
  • [ 31465-36-8 ]
Reference: [1] Gazzetta Chimica Italiana, 1985, vol. 115, # 6, p. 343 - 346
  • 4
  • [ 139-59-3 ]
  • [ 21567-18-0 ]
Reference: [1] Patent: US4355189, 1982, A,
  • 5
  • [ 139-59-3 ]
  • [ 2050-47-7 ]
Reference: [1] Journal of the Chemical Society, 1955, p. 1274,1277
  • 6
  • [ 75-05-8 ]
  • [ 139-59-3 ]
  • [ 6312-87-4 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With tetrafluoroboric acid In waterInert atmosphere
Stage #2: at 80℃; for 12 h;
General procedure: A mixture of aryl diazonium tetrafluoroborates compounds (0.5 mmol), nitriles (0.5 mmol), H2O (1.5 mmol) and K3PO4 (0.6 mmol) was dissolved in acetonitrile (1.0 mL) or ethyl acetate (1.0 mL) under N2 atmosphere, stirred at 80 oC for 12h. Removal of the solvent under a reduced pressure gave the crude product; pure product was obtained by passing the crude product through a short silica gel column using Hexane/EtOAc (1:1-2:1) as eluent.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 32, p. 3139 - 3142
  • 7
  • [ 108-24-7 ]
  • [ 139-59-3 ]
  • [ 6312-87-4 ]
YieldReaction ConditionsOperation in experiment
4.5 g With triethylamine In dichloromethane at 0 - 20℃; for 1 h; Commercial available 4-phenoxy-aniline (4.16 g, 20.8 mmol) was dissolved in dichloromethane (100 mL), and triethylamine (3.05 g, 31.1 mmol) and acetic anhydride (2.22 g, 20.8 mmol) were added in drops. The mixture was stirred for 1 h at 0° C. to room temperature. After completion of the reaction, the mixture was filtered using dichloromethane and crystallized to give the title compound (4.50 g, 18.6 mmol)
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 9, p. 1826 - 1840
[2] Bulletin of Environmental Contamination and Toxicology, 1995, vol. 55, # 3, p. 446 - 452
[3] Patent: WO2009/25478, 2009, A1, . Location in patent: Page/Page column 42
[4] Patent: US2010/197673, 2010, A1, . Location in patent: Page/Page column 12
[5] Chemical Communications, 2014, vol. 50, # 61, p. 8370 - 8373
[6] Patent: KR101511771, 2015, B1, . Location in patent: Paragraph 0340; 0341
  • 8
  • [ 75-36-5 ]
  • [ 139-59-3 ]
  • [ 6312-87-4 ]
Reference: [1] Photochemical and Photobiological Sciences, 2016, vol. 15, # 1, p. 105 - 116
[2] Journal of the American Chemical Society, 2003, vol. 125, # 50, p. 15395 - 15401
[3] Journal of the American Chemical Society, 2011, vol. 133, # 6, p. 1694 - 1697
  • 9
  • [ 6341-97-5 ]
  • [ 139-59-3 ]
  • [ 6312-87-4 ]
Reference: [1] Macromolecules, 2003, vol. 36, # 6, p. 1815 - 1818
  • 10
  • [ 64-19-7 ]
  • [ 139-59-3 ]
  • [ 6312-87-4 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 2367
  • 11
  • [ 139-59-3 ]
  • [ 60481-02-9 ]
YieldReaction ConditionsOperation in experiment
44%
Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; for 1 h;
Stage #2: at 0℃; for 2 h;
To a solution of 4-phenoxyaniline (2 g, 10.8 mmol, 1 equiv.) in conc. HCl (22 mL) was added dropwise an ice-cold solution of sodium nitrite (1.49 g, 21.6 mmol, 2.0 equiv.) in water (7.6 mL) over 15 min whilst maintaining the temperature below 10 °C. The reaction was then cooled to 0 °C and stirred for 1 h. To the reaction mixture, sulfamic acid (1.05 g, 10.8 mmol, 1 equiv.) was added portion wise over a 20 min period. Then a solution of tin(II) chloride dihydrate (9.78 g, 43.2 mmol, 4 equiv.) in conc. HCl (8.2 mL) was added drop wise over a 20 min period whilst maintaining the temperature below 15 °C. The reaction mixture was stirred at 0 °C for 2 h and basified to pH 14 with 5 M NaOH (aq) whilst maintaining the reaction temperature below 30 °C. The reaction mixture was then rapidly extracted with methylene chloride (2 * 100 mL). The combined organic phases were dried over Na2SO4, filtered and the solvent removed in vacuo. (4-Phenoxyphenyl)hydrazine which is unstable was converted to its hydrochloride by using a solution of 2 M HCl in Et2O (20 mL). The formed precipitate was collected and dried under reduced pressure to give title compound as a pale brown solid (1.2 g, 44percent).
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 58, p. 452 - 463
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3152 - 3162
[3] Patent: CN105061315, 2017, B, . Location in patent: Paragraph 0065; 0067
  • 12
  • [ 1147550-11-5 ]
  • [ 139-59-3 ]
  • [ 65948-19-8 ]
YieldReaction ConditionsOperation in experiment
65% With bromine In formic acid; acetic acid at -3 - 0℃; Inert atmosphere; Darkness General procedure: The synthesis of 6-ethoxy-1,3-benzothiazol-2-amine (1c), obtained following a general procedure for the preparation of aminobenzothiazoles described in the literature [13,14] is described. Aniline 6c (1.0 g, 7.36 mmol) and NH4SCN (1.6 g, 21.9 mmol) were dissolved in a 20percent formic acid–glacial acetic acid mixture (100 mL) and cooled to−3 °C with stirring, under N2. With the exclusion of light from the reaction mixture, bromine (0.30 mL dissolved in 20 mL of glacial acetic acid) was added dropwise, while the reaction temperature was kept between −3°C and 0 °C. The light shield was removed and the mixture was allowed to warm to room temperature overnight. Sodium hydroxide pellets and ice were added with stirring until pH 11 was attained, and the mixture was extracted with EtOAc. The organic layer was separated and filtered through celite to remove polythiocyanogen (SCN)n. The organic layer was then washed with water, saturated NaHCO3 and brine; then, the solvent was evaporated in vacuo. The residue was purified by flash chromatography (EtOAc/petroleum ether 1:1) to give 0.93 g (65percent) of an orange solid:
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 64, p. 357 - 364
  • 13
  • [ 139-59-3 ]
  • [ 65948-19-8 ]
Reference: [1] Patent: US5002942, 1991, A,
  • 14
  • [ 139-59-3 ]
  • [ 65948-19-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 15, p. 4025 - 4037
  • 15
  • [ 333-20-0 ]
  • [ 139-59-3 ]
  • [ 65948-19-8 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 18, p. 9312 - 9320
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