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[ CAS No. 13466-41-6 ] {[proInfo.proName]}

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Chemical Structure| 13466-41-6
Chemical Structure| 13466-41-6
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Product Details of [ 13466-41-6 ]

CAS No. :13466-41-6 MDL No. :MFCD00134298
Formula : C6H7NO Boiling Point : -
Linear Structure Formula :NC5H3(OH)CH3 InChI Key :YBDRFJXGJQULGH-UHFFFAOYSA-N
M.W : 109.13 Pubchem ID :280741
Synonyms :

Calculated chemistry of [ 13466-41-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 31.23
TPSA : 33.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.39
Log Po/w (XLOGP3) : 0.89
Log Po/w (WLOGP) : 1.1
Log Po/w (MLOGP) : 0.54
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 2.54 mg/ml ; 0.0233 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 7.37 mg/ml ; 0.0676 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.77
Solubility : 1.84 mg/ml ; 0.0169 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.15

Safety of [ 13466-41-6 ]

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

Application In Synthesis of [ 13466-41-6 ]

* 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 [ 13466-41-6 ]
  • Downstream synthetic route of [ 13466-41-6 ]

[ 13466-41-6 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 695-34-1 ]
  • [ 13466-41-6 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With sulfuric acid; sodium nitrite In water at 0 - 95℃; for 2.25 h;
Stage #2: With sodium hydroxide In water at 20℃;
Synthesis of intermediate V-a: 4-Methyl-pyridin-2-olIntermediate V-a was prepared using the method of Adger et al, in J. Chem. Soc. Perkin Trans. 1, 1988, p2791 -2796. A 1 L flask containing water (240 mL) was treated with cone. H2S04 (32 mL) and cooled to 0°C then treated with the 2-amino-4-picoline in one portion (30 g, 277 mmol). A solution of NaN02 (20.6 g, 299 mmol) in water (40 mL) was added dropwise over 1 h such that the internal temperature never rose above 5°C. The reaction was stirred at 0°C for lh then heated to 95°C and after 15 min at this temperature cooled to room temperature. The solution was taken to pH 6-7 with 50percent NaOH aq (exotherm) and extracted whilst hot with EtOAc (4 x 120 mL). The combined organics were dried (MgS04), filtered and evaporated to afford a beige crystalline solid (24.5 g, 81percent) of intermediate V-a.1H NMR (300 MHz, DMSO-d6) δ 1 1.31 (s, 1H), 7.23 (d, J= 6.7 Hz, 1H), 6.10 (s, 1H), 6.00 (dd, J= 6.7, 1.2 Hz, lH), 2.10 (s, 3H).
Reference: [1] Patent: WO2013/14170, 2013, A1, . Location in patent: Page/Page column 77-78
[2] Chemische Berichte, 1924, vol. 57, p. 794
[3] Organic Syntheses, 2002, vol. 78, p. 51 - 51
  • 2
  • [ 108-89-4 ]
  • [ 13466-41-6 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 794
[2] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 10-11
[3] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 11
[4] Patent: EP1801102, 2007, A1, . Location in patent: Page/Page column 11
  • 3
  • [ 13466-41-6 ]
  • [ 3678-62-4 ]
YieldReaction ConditionsOperation in experiment
98.7% With sodium carbonate In chloroform; water; trichlorophosphate (1)
Synthesis of 2-chloro-4-methylpyridine
2-Hydroxy-4-methylpyridine (20.3 g, 0.186 mol) was heated to 100° C. with stirring in 50 ml of phosphorus oxychloride for 4 hours.
The reaction solution was poured into iced water, followed by adding sodium carbonate so as to be weak alkalinity and extracting 2 times with 200 ml of chloroform.
After the extract solution was washed with saturated saline solution, it was dried with sodium sulfate and the solvent was distilled off in vacuum.
The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10) to give a liquid.
Yield: 23 g, percent yield: 98.7percent IR NaCl liq.
Film cm-1: 1596, 1554, 1473, 1383, 1086, 870, 825. 1H-NMR (60 MHz, CDCl3, δ): 2.26 (3H, s, CH3), 6.8-7.1 (2H, m, pyridine ring H), 8.1 (1H, d, J=4 Hz, pyridine ring H).
Reference: [1] Patent: US6610853, 2003, B1,
[2] Patent: US6159901, 2000, A,
[3] Patent: US6200933, 2001, B1,
  • 4
  • [ 13466-41-6 ]
  • [ 3678-62-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
  • 5
  • [ 13466-41-6 ]
  • [ 10026-13-8 ]
  • [ 3678-62-4 ]
Reference: [1] Chemische Berichte, 1924, vol. 57, p. 794
  • 6
  • [ 13466-41-6 ]
  • [ 75-25-2 ]
  • [ 4926-28-7 ]
Reference: [1] Patent: US6005112, 1999, A,
  • 7
  • [ 13466-41-6 ]
  • [ 74-88-4 ]
  • [ 100848-70-2 ]
YieldReaction ConditionsOperation in experiment
71% With silver carbonate In chloroform at 20℃; for 48 h; To a stirred solution OF 2-HYDROXY-4-METHYLPYRIDINE (10 g, 92 mmol) in chloroform (350 mL) was added at room temperature silver carbonate (34.2 g, 124 mmol) and iodomethane (130 g, 920 mmol). The reaction mixture was stirred in the dark for 48 h, and then filtered through Celite and washed with ether. The filtrate was concentrated below 20 oC, and the residue was purified by chromatography with PENTANE/ETHER (5: 1) to afford 2-methoxy-4-methylpyridine as a colorless oil (8.0 g, 71percent). LH NMR (CDC13) 8 8. 02 (d, 1H, J = 5.4 Hz), 6.69 (d, 1H, J= 5.4 Hz), 6.55 (s, 1H), 3.91 (s, 3H), 2. 28 (s, 3H) ;"C NMR (CDC13) 8 164.40, 149. 72,146. 31, 118. 21,110. 88,53. 17, 20. 81. MS M/Z (percent): 123 (M+, 76), 122 (100).
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 35, p. 6153 - 6156
[2] Patent: WO2005/806, 2005, A2, . Location in patent: Page 72
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 921 - 924
  • 8
  • [ 13466-41-6 ]
  • [ 100848-70-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 2791 - 2796
  • 9
  • [ 33245-30-6 ]
  • [ 13466-41-6 ]
  • [ 21901-40-6 ]
  • [ 6635-86-5 ]
Reference: [1] Australian Journal of Chemistry, 1983, vol. 36, # 6, p. 1159 - 1166
  • 10
  • [ 33245-30-6 ]
  • [ 13466-41-6 ]
  • [ 21901-40-6 ]
  • [ 6635-86-5 ]
Reference: [1] Australian Journal of Chemistry, 1983, vol. 36, # 6, p. 1159 - 1166
  • 11
  • [ 13466-41-6 ]
  • [ 56100-19-7 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 26, p. 10048 - 10051
[2] Organic Syntheses, 2002, vol. 78, p. 51 - 51
  • 12
  • [ 13466-41-6 ]
  • [ 89581-53-3 ]
Reference: [1] Synlett, 2003, # 11, p. 1678 - 1682
  • 13
  • [ 13466-41-6 ]
  • [ 89581-53-3 ]
  • [ 164513-38-6 ]
  • [ 18368-59-7 ]
Reference: [1] Synlett, 2003, # 11, p. 1678 - 1682
  • 14
  • [ 13466-41-6 ]
  • [ 89581-53-3 ]
  • [ 164513-38-6 ]
  • [ 18368-59-7 ]
Reference: [1] Synlett, 2003, # 11, p. 1678 - 1682
  • 15
  • [ 13466-41-6 ]
  • [ 188554-13-4 ]
Reference: [1] Journal of the American Chemical Society, 1997, vol. 119, # 15, p. 3619 - 3620
  • 16
  • [ 13466-41-6 ]
  • [ 188554-13-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 12, p. 1533 - 1540
[2] Tetrahedron, 2008, vol. 64, # 22, p. 5072 - 5078
  • 17
  • [ 13466-41-6 ]
  • [ 717843-51-1 ]
Reference: [1] Patent: WO2013/14170, 2013, A1,
  • 18
  • [ 13466-41-6 ]
  • [ 1420998-43-1 ]
Reference: [1] Patent: WO2013/14170, 2013, A1,
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