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[ CAS No. 1192-21-8 ] {[proInfo.proName]}

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Chemical Structure| 1192-21-8
Chemical Structure| 1192-21-8
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Product Details of [ 1192-21-8 ]

CAS No. :1192-21-8 MDL No. :MFCD00068156
Formula : C4H7N3 Boiling Point : -
Linear Structure Formula :- InChI Key :JESRNIJXVIFVOV-UHFFFAOYSA-N
M.W : 97.12 Pubchem ID :136927
Synonyms :

Calculated chemistry of [ 1192-21-8 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.89
TPSA : 43.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.83
Log Po/w (XLOGP3) : -0.11
Log Po/w (WLOGP) : 0.01
Log Po/w (MLOGP) : -0.27
Log Po/w (SILICOS-IT) : -0.26
Consensus Log Po/w : 0.04

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.9
Solubility : 12.2 mg/ml ; 0.125 mol/l
Class : Very soluble
Log S (Ali) : -0.36
Solubility : 42.6 mg/ml ; 0.439 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.35
Solubility : 43.0 mg/ml ; 0.443 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.27

Safety of [ 1192-21-8 ]

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 [ 1192-21-8 ]

* 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 [ 1192-21-8 ]
  • Downstream synthetic route of [ 1192-21-8 ]

[ 1192-21-8 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 60838-50-8 ]
  • [ 60-34-4 ]
  • [ 1192-21-8 ]
YieldReaction ConditionsOperation in experiment
97% With acetic acid In toluene at 120℃; for 1 h; Sealed tube; Microwave irradiation 3.4
5-Amino-1-methyl-1H-pyrazole (9)
A solution of methylhydrazine (2b) (0.25 mL, 4.7 mmol) and 3-methoxyacrylonitrile (1a) (0.20 mL, 2.4 mmol) in toluene/acetic acid (4:1 v/v; 5 mL) was irradiated at 120 °C for 1 h in a sealed, pressure-rated Pyrex tube (10 mL) using a CEM Discover microwave synthesizer by moderating the initial power (100 W).
After cooling in a flow of compressed air, the mixture was neutralized using saturated aqueous NaHCO3 solution and extracted with EtOAc (3*20 mL).
The organic layers were combined, washed successively with water and brine, dried (MgSO4) and evaporated in vacuo to give the title compound (0.22 g, 97percent) as a light brown solid, mp 71-73 °C (lit.
29
mp 71-72 °C) (found: 97.0640. C4H7N3 [M] requires 97.0637); 1H NMR (400 MHz; DMSO-d6) δ 7.60 (1H, d, J 2.0, H-3), 5.15 (1H, d, J 2.0, H-4), 3.85 (2H, br s, exch. D2O, NH2), 3.50 (3H, s, Me); 13C NMR (126 MHz; DMSO-d6) δ 145.6 (C), 138.5 (CH), 90.8 (CH), 34.0 (Me); LRMS (APcI) m/z (rel intensity) 97 (M<ce:glyph name="rad"/>+, 100).
Reference: [1] Tetrahedron, 2013, vol. 69, # 39, p. 8429 - 8438
  • 2
  • [ 31037-02-2 ]
  • [ 1192-21-8 ]
YieldReaction ConditionsOperation in experiment
87% With water; sodium hydroxide In ethanol for 2 h; Reflux; Inert atmosphere Carboxylate 62 (20.0 g, 118 mmol) in ethanol (100 mL) was treated with aqueous sodium hydroxide (50 mL, 3 M). The reaction mixture was heated to reflux and allowed to stir for 2 h and the ethanol removed under reduced pressure. The aqueous solution was cooled to 0 °C and acidified with HCl (3 M) to pH 5. The white precipitate was collected by filtration and heated neat to 185 °C in Kugelrohr oven under vacuum (1 mmHg) to afford titled compound 22 (10.0 g, 87percent) as a light brown solid. MP: 73 – 74 °C; IR (Diamond Cell, neat): 3395, 3134, 1643, 1556, 1517, 1431, 1344, 1268, 1207, 999, 928, 758, 632 cm–1; 1H NMR (300 MHz, Chloroform-d) δ 7.21 (d, J = 2.0 Hz, 1H), 5.49 (d, J = 2.0 Hz, 1H), 3.62 (s, 3H), 3.50 (br. s, 2H); 13C NMR (75 MHz, Chloroform-d) δ 144.6 (C), 138.2 (CH), 91.2 (CH), 34.3 (CH3); LRMS (ESI+) m/z: 98 (100, [M + H]+), 120 (50, [M + Na]+). This data matched that previously reported. 3
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4883 - 4889
[2] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 330 - 333
  • 3
  • [ 50-00-0 ]
  • [ 107-13-1 ]
  • [ 1192-21-8 ]
Reference: [1] Patent: JP2017/19914, 2017, A, . Location in patent: Paragraph 0130
  • 4
  • [ 1225387-53-0 ]
  • [ 74-88-4 ]
  • [ 446866-62-2 ]
  • [ 1192-21-8 ]
Reference: [1] Patent: WO2005/30758, 2005, A1, . Location in patent: Page/Page column 60-61
  • 5
  • [ 5334-41-8 ]
  • [ 1192-21-8 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, # 3, p. 420-428
  • 6
  • [ 128315-64-0 ]
  • [ 1192-21-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, p. 809 - 810
[2] Journal of Organic Chemistry, 1992, vol. 57, # 5, p. 1563 - 1567
[3] Journal of Organic Chemistry, 1992, vol. 57, # 5, p. 1563 - 1567
  • 7
  • [ 871-29-4 ]
  • [ 60-34-4 ]
  • [ 1192-21-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1267 - 1273
  • 8
  • [ 54210-33-2 ]
  • [ 1192-21-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 23, p. 10013 - 10030
  • 9
  • [ 6162-76-1 ]
  • [ 60-34-4 ]
  • [ 1192-21-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 7, p. 2340 - 2343
  • 10
  • [ 1192-21-8 ]
  • [ 3994-46-5 ]
Reference: [1] Patent: US2003/181472, 2003, A1,
  • 11
  • [ 2065-75-0 ]
  • [ 1192-21-8 ]
  • [ 887115-56-2 ]
YieldReaction ConditionsOperation in experiment
27% for 48 h; Heating / reflux Preparation 9; 5-Bromo- 1 -methyl- lH-pyrazolo[3,4-b]pyridine; EPO <DP n="26"/> Dissolve l-methyl-5-aminopyrazole (Butt Park LTD; 1.0 g, 10.3 mmol) and 2- bromomalonaldehyde (Aldrich; 1.55 g, 10.3 mmol) in glacial acetic acid (160 niL) and reflux under nitrogen for 48 h. Concentrate under reduced pressure and purify via chromatography (silica gel, 90percent dichloromethane/10percent diethyl ether) to obtain 610 mg (27percent) of the title compound as an off-white solid. TOF MS ES+ exact mass calculated for C7H7N3Br (p+H): m/z = 21 1.9823, Found: 211.9838.
Reference: [1] Patent: WO2006/52568, 2006, A2, . Location in patent: Page/Page column 24-25
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