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[ CAS No. 72716-87-1 ] {[proInfo.proName]}

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Chemical Structure| 72716-87-1
Chemical Structure| 72716-87-1
Structure of 72716-87-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 72716-87-1 ]

CAS No. :72716-87-1 MDL No. :MFCD06410680
Formula : C7H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VOCKNCWQVHJMAE-UHFFFAOYSA-N
M.W : 137.14 Pubchem ID :2762996
Synonyms :

Calculated chemistry of [ 72716-87-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.12
TPSA : 39.19 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) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.2
Log Po/w (XLOGP3) : 0.83
Log Po/w (WLOGP) : 0.9
Log Po/w (MLOGP) : -0.08
Log Po/w (SILICOS-IT) : 1.48
Consensus Log Po/w : 0.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.53
Solubility : 4.09 mg/ml ; 0.0298 mol/l
Class : Very soluble
Log S (Ali) : -1.24
Solubility : 7.97 mg/ml ; 0.0581 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.07
Solubility : 1.16 mg/ml ; 0.00849 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.51

Safety of [ 72716-87-1 ]

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 [ 72716-87-1 ]

* 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 [ 72716-87-1 ]
  • Downstream synthetic route of [ 72716-87-1 ]

[ 72716-87-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 123148-66-3 ]
  • [ 72716-87-1 ]
YieldReaction ConditionsOperation in experiment
646 mg With chromium trioxide pyridine In dichloromethane at 20℃; for 2 h; LiAlH4 (1.9 g, 49 mmol) was added portionwise to a solution of 2-methoxy isonicotinic acid (5.0 g, 33 mmol) in tetrahydrofuran (40 mL) at 0 °C. The reaction mixture was continuously stirred at 0 °C for 1 h, then saturated sodium sulphate solution was added dropwise slowly. After filtration, the filtrate was extracted with ethyl acetate, and the organic layer was washed with brine, and concentrated under vacuum. The resulting residue was dissolved in dichloromethane (30 mL), and chromium trioxide pyridine (10.6 g, 49 mmol) was added. The resulting mixture was stirred at room temperature for 2 h, then poured onto the short silica gel column and eluted with ethyl acetate. The resulting solution was concentrated under vacuum to remove the solvent. The residue was purified by column chromatography (petroleum ether : ethyl acetate = 10:1) to afford the title compound (646 mg, 14 percent). 1H NMR (CDCl3): δ 10.01 (1H, s), 8.36 (1H, d, J = 5.2 Hz), 7.29 (1H, dd, J = 1.2 Hz, 5.2 Hz), 7.14 (1H, d, J = 1.2 Hz), 3.99 (3H, s).
260 mg With manganese(IV) oxide In ethyl acetate for 3 h; Reflux Manganese dioxide (1.04 g) was added to a solution of (2-methoxypyridin-4-yl)methanol (417 mg) in ethyl acetate (5 mL), followed by refluxing for 1.5 hours. Manganese dioxide (1.04 g) was added thereto, followed by refluxing for 1.5 hours. The reaction mixture was cooled to room temperature, the insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:6), whereby 2-methoxyisonicotinic aldehyde (260 mg) was obtained as a colorless oily material
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5580 - 5585
[2] Patent: EP2816032, 2014, A1, . Location in patent: Paragraph 0458
[3] Patent: EP2862571, 2015, A1, . Location in patent: Paragraph 0103; 0104
[4] Patent: US2016/168139, 2016, A1, . Location in patent: Paragraph 0942; 0943
  • 2
  • [ 72716-86-0 ]
  • [ 563-41-7 ]
  • [ 72716-87-1 ]
YieldReaction ConditionsOperation in experiment
35% With formaldehyd; sodium acetate In hydrogenchloride; ethanol; water (b)
A mixture of 2-methoxy-4-cyanopyridine (57.2 g), semicarbazide hydrochloride (71.24 g), sodium acetate (69.86 g), ethanol (1,200 ml) and water (370 ml) was hydrogenated at 344 kPa using Raney nickel catalyst (1.0 g).
The mixture was evaporated to a volume of 450 ml, water (900 ml) was added and the mixture was allowed to stand at 0° overnight.
The mixture was filtered and the solid was washed with water and was dissolved in 10percent hydrochloric acid (950 ml).
Formaldehyde solution (36percent w/v, 420 ml) was added and the mixture was warmed for 30 minutes, allowed to cool and was added to a solution of sodium acetate (280 g) in water (840 ml).
The mixture was extracted with ether (3*500 ml) and the combined extracts were successively washed with aqueous potassium carbonate and water and were dried out evaporated to give 2-methoxypyridine-4-carboxaldehyde (20.53 g, 35percent) m.p. 33-5°.
A sample recrystallized from petroleum ether had m.p. 33-36°.
35% With formaldehyd; sodium acetate In hydrogenchloride; ethanol; water (ii)
A mixture of 2-methoxy-4-cyanopyridine (57.2 g), semicarbazide hydrochloride (71.24 g), sodium acetate (69.86 g), ethanol (1200 ml) and water (370 ml) was hydrogenated at 344 kPa using Raney nickel catalyst (1.0 g).
The mixture was evaporated to a volume of 450 ml, water (900 ml) was added and the mixture was allowed to stand at 0° overnight.
The mixture was filtered and the solid was washed with water and was dissolved in 10percent hydrochloric acid (950 ml).
Formaldehyde solution (36percent w/v, 420 ml) was added and the mixture was warmed for 30 minutes, allowed to cool and was cooled to a solution of sodium acetate (280 g) in water (840 ml).
The mixture was extracted with ether (3*500 ml) and the combined extracts were successively washed with aqueous potassium carbonate and water and were dried and evaporated to give 2-methoxypyridine-4-carboxyaldehyde (20.53 g, 35percent) m.p. 33°-35°.
A sample recrystallized from petroleum ether had m.p. 33°-36°.
Reference: [1] Patent: US4255428, 1981, A,
[2] Patent: US4234588, 1980, A,
  • 3
  • [ 105596-63-2 ]
  • [ 72716-87-1 ]
YieldReaction ConditionsOperation in experiment
14%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1 h;
Stage #2: With pyridine; chromium(VI) oxide In dichloromethane at 20℃; for 2 h;
LiAlH4(1.9 g, 49 mmol) was added portionwise to a solution of 2-methoxy isonicotinic acid (5.0 g, 33 mmol) in tetrahydrofuran (40 mL) at 0° C. The reaction mixture was continuously stirred at 0° C. for 1 h, then saturated sodium sulphate solution was added drop wise slowly. After filtration, the filtrate was extracted with ethyl acetate, and the organic layer was washed with brine, and concentrated under vacuum. The resulting residue was dissolved in dichloromethane (30 mL), and chromium trioxide pyridine (10.6 g, 49 mmol) was added. The resulting mixture was stirred at room temperature for 2 h, then poured onto the short silica gel column and eluted with ethyl acetate. The resulting solution was concentrated under vacuum to remove the solvent. The residue was purified by column chromatography (petroleum ether:ethyl acetate=10:1) to afford the title compound (646 mg, 14percent). 1H NMR (CDCl3): δ10.01 (1H, s), 8.36 (1H, d, J=5.2 Hz), 7.29 (1H, dd, J=1.2 Hz, 5.2 Hz), 7.14 (1H, d, J=1.2 Hz), 3.99 (3H, s).
Reference: [1] Patent: US2015/166559, 2015, A1, . Location in patent: Paragraph 0152; 0153
[2] Patent: EP2862571, 2015, A1,
  • 4
  • [ 33252-30-1 ]
  • [ 72716-87-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 1993, vol. 28, # 7-8, p. 601 - 608
  • 5
  • [ 26156-51-4 ]
  • [ 72716-87-1 ]
Reference: [1] Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5580 - 5585
[2] Patent: EP2816032, 2014, A1,
  • 6
  • [ 72716-86-0 ]
  • [ 72716-87-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 1993, vol. 28, # 7-8, p. 601 - 608
  • 7
  • [ 6313-54-8 ]
  • [ 72716-87-1 ]
Reference: [1] Patent: EP2816032, 2014, A1,
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