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[ CAS No. 3528-58-3 ] {[proInfo.proName]}

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Chemical Structure| 3528-58-3
Chemical Structure| 3528-58-3
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Product Details of [ 3528-58-3 ]

CAS No. :3528-58-3 MDL No. :MFCD00010849
Formula : C5H9N3 Boiling Point : -
Linear Structure Formula :- InChI Key :FSJOLBAFVKSQQJ-UHFFFAOYSA-N
M.W : 111.15 Pubchem ID :337310
Synonyms :

Calculated chemistry of [ 3528-58-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.4
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.7
TPSA : 43.84 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.05
Log Po/w (XLOGP3) : 0.19
Log Po/w (WLOGP) : 0.49
Log Po/w (MLOGP) : 0.14
Log Po/w (SILICOS-IT) : -0.05
Consensus Log Po/w : 0.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.05
Solubility : 10.0 mg/ml ; 0.0901 mol/l
Class : Very soluble
Log S (Ali) : -0.67
Solubility : 23.8 mg/ml ; 0.214 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.78
Solubility : 18.4 mg/ml ; 0.166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 3528-58-3 ]

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 [ 3528-58-3 ]

* 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 [ 3528-58-3 ]
  • Downstream synthetic route of [ 3528-58-3 ]

[ 3528-58-3 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 58793-47-8 ]
  • [ 3528-58-3 ]
Reference: [1] Patent: WO2005/80359, 2005, A1, . Location in patent: Page/Page column 91
  • 2
  • [ 75-07-0 ]
  • [ 107-13-1 ]
  • [ 3528-58-3 ]
YieldReaction ConditionsOperation in experiment
15%
Stage #1: With hydrazine hydrate In tetrahydrofuran at 0 - 20℃;
Stage #2: at 20℃;
Stage #3: With potassium <i>tert</i>-butylate In butan-1-ol at 20 - 120℃;
Hydrazine hydrate (98.7 gm, 1.97 moles) was added drop wise to a solution of acrylonitrile (100 gm, 1.88 moles) in tetrahydrofuran (350 ml) at 0-50C. The reaction mixture was stirred at room temperature for about 3 hrs and acetaldehyde (86.9 gm, 1.9 moles) was added drop wise followed by stirring at room temperature for about 3 hrs. The solvent was removed at reduced pressure to give yellow oil, which was dissolved in n- butanol (100 ml) and further, n-butanol (250 ml) containing potassium t-butoxide (221 gm, 1.9 moles) was added. The resulting mixture was gradually heated from room temperature to 1200C and heating was continued for about 3 hrs. The reaction mixture was cooled to room temperature and water (500 ml) was added. Extraction was done with ethyl acetate (3x 500 ml). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude compound was purified by column chromatography using silica gel (100-200 mesh) saturated with triethyl amine. Elution was done by using 20percent ethyl acetate in hexane. Yield: 66.0 gm (15percent) m/z: (M+H) 111.98
Reference: [1] Patent: WO2010/46791, 2010, A1, . Location in patent: Page/Page column 30-31
  • 3
  • [ 42066-48-8 ]
  • [ 3528-58-3 ]
Reference: [1] Patent: WO2008/9735, 2008, A1, . Location in patent: Page/Page column 110
[2] Journal of Combinatorial Chemistry, 2010, vol. 12, # 4, p. 510 - 517
[3] Patent: WO2008/15416, 2008, A1, . Location in patent: Page/Page column 168-169
  • 4
  • [ 137968-19-5 ]
  • [ 3528-58-3 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 5, p. 1563 - 1567
  • 5
  • [ 71-36-3 ]
  • [ 3528-58-3 ]
Reference: [1] Patent: US5942520, 1999, A,
  • 6
  • [ 71-36-3 ]
  • [ 3528-58-3 ]
Reference: [1] Patent: US5488055, 1996, A,
  • 7
  • [ 137968-12-8 ]
  • [ 3528-58-3 ]
Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 5, p. 1563 - 1567
  • 8
  • [ 624-80-6 ]
  • [ 6162-76-1 ]
  • [ 3528-58-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2340 - 2343
  • 9
  • [ 75-07-0 ]
  • [ 353-07-1 ]
  • [ 3528-58-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 938 - 942
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