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[ CAS No. 849833-56-3 ] {[proInfo.proName]}

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Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
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3d Animation Molecule Structure of 849833-56-3
Chemical Structure| 849833-56-3
Chemical Structure| 849833-56-3
Structure of 849833-56-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 849833-56-3 ]

CAS No. :849833-56-3 MDL No. :MFCD00464225
Formula : C4H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 102.14 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 849833-56-3 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 28.46
TPSA : 58.61 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) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.11
Log Po/w (XLOGP3) : 0.44
Log Po/w (WLOGP) : 0.39
Log Po/w (MLOGP) : 0.42
Log Po/w (SILICOS-IT) : -0.42
Consensus Log Po/w : 0.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.68
Solubility : 21.1 mg/ml ; 0.207 mol/l
Class : Very soluble
Log S (Ali) : -1.24
Solubility : 5.9 mg/ml ; 0.0577 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.21
Solubility : 167.0 mg/ml ; 1.63 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 4.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 849833-56-3 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P405-P501 UN#:2811
Hazard Statements:H301-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 849833-56-3 ]

* 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 [ 849833-56-3 ]
  • Downstream synthetic route of [ 849833-56-3 ]

[ 849833-56-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 78-82-0 ]
  • [ 849833-56-3 ]
YieldReaction ConditionsOperation in experiment
98% With hydroxylamine In ethanol; water for 5 h; Heating / reflux A solution of isobutyronitrile (276 g, 4.0 mol) in ETOH (2.0 L) was combined with hydroxylamine (50percent aqueous solution, 1.1 L, 16 mol), and refluxed for 5 h. The solvent was then removed in vacuo, and the residual water was azeotropically removed with toluene. The residue was then taken up in CH2CL2, dried over MGSO4, and the solvent was removed to afford a white solid (402 g, 98percent YIELD). H NMR (CDCIS) 8 7.94 (br s, 1 H), 4.55 (br s, 2 H), 2.47 (M, 1 H), 1.20 (d, 6 H, J= 7.1 Hz).
98% With hydroxylamine In ethanol; water for 5 h; Heating / reflux A solution of isobutyronitrile (276 g, 4. 0 mol) in ETOH (2. 0 L) was combined with hydroxylamine (50percent aqueous solution, 1. 1 L, 16 mol), and refluxed for 5 h. The solvent was then removed in vacuo, and the residual water was azeotropically removed with toluene. The residue was then taken up in CH2C12, dried over MGS04, and the solvent was removed to afford a white solid (402 g, 98percent yield).'H NMR (CDC13) 8 7. 94 (br s, 1 H), 4. 55 (br s, 2 H), 2. 47 (m, 1 H), 1. 20 (d, 6 H, J= 7. 1 Hz).
98% With hydroxylamine In ethanol; water for 3 h; Reflux A mixture of 2-methylpropanenitrile (10 mL, 110 mmol), 50percent hydroxylamine in water (30 mL, 440 mmol) and ethanol (50 mL) was stirred at reflux for 3 h, then cooled to ambient temperature, and concentrated to give N-hydroxy-2-methylpropanimidamide (11.05 g, 98percent) as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 8.67 (s, 1H), 5.21 (s, 2H), 2.31-2.11 (m, 1H), 1.02 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 103 (M+H).
93% With hydroxylamine In water for 5 h; Reflux Intermediate 8: N-Hydroxy-isobutyramidine; Loosely following the procedure of A. Hamze et al. (J. Org. Chem. 2003, 68, 7316-7321), a mixture of isobutyronitrile (15 g, 217 mmol) and 50percent aqueous hydroxylamine (60 mL, 908 mmol) was heated at reflux for 5 h. The solvent was evaporated and the residue was co-evaporated with toluene to remove water. Dichloromethane (100 mL) was added and the solution was dried (sodium sulfate), filtered, evaporated, and dried under high vacuum to give N-hydroxy-isobutyramidine (17.5 g, 93percent) as a white solid which was used directly in the subsequent step without further purification.
90% With water; hydroxylamine In methanol at 50℃; for 22 h; Reflux Example 1: Synthesis of isobutyroamidoxime (V, R = isopropyl)Isobutyronitrile (104 g, 1.50 mol) is dissolved in methanol (300 ml), then treated with 50percent hydroxylamine aqueous solution (100 g, 1.51 mol) and the resulting solution is heated at 50°C for 18 hours, then under reflux of the solvent for 4 hours. The reaction mixture is then concentrated under reduced pressure, diluted with toluene and coevaporated under reduced pressure. The residue is taken up with toluene while warm, then the solution is slowly cooled to obtain an abundant precipitate. The solid is filtered and washed with toluene to afford 138 g of isobutyroamidoxime in 90percent yield.
69% With hydroxylamine hydrochloride; potassium carbonate In ethanol; water at 80℃; for 16 h; To a solution of isobutyronitrile (2.6 mL; 29 mmol) in EtOH (30 mL) and water(10 mL) was added hydroxylamine hydrochloride (2.01 g, 29 mmol) and potassiumcarbonate (4 g, 29 mmol). The resulting suspension was heated at 80 °C for 16 h. Thesolvent was removed under vacuo. The residue was co-evaporated with toluene. Thecrude material was washed with EtOH and filtered to remove the sodium chloride. The filtrate was evaporated, co-evaporated with toluene several times and dried under vacuo to give 2 g (69percent) of N-hydroxybutyramidine.
69% With hydroxylamine hydrochloride; potassium carbonate In ethanol; water at 80℃; for 16 h; To a solution of isobutyronitrile (2.6 mE; 29 mmol) in EtOH (30 mE) and water (10 mE) was added hydroxylamine hydrochloride (2.01 g, 29 mmol) and potassium carbonate (4 g, 29 mmol). The resulting suspension was heated at 80° C. for 16 h. The solvent was removed under vacuo. The residue was co-evaporated with toluene. The crude material was washed with EtOH and filtered to remove the sodium chloride. The filtrate was evaporated, co-evaporated with toluene several times and dried under vacuo to give 2 g (69percent) of N-hydroxybutyramidine.
34% With hydroxylamine hydrochloride; sodium hydroxide In ethanol; waterReflux A mixture of 2-methylpropanenitrile (100 g, 1.45 mol), hydroxylamine hydrochloride (111 g, 1.59 mol) and NaOH (64 g, 1.59 mol) in EtOH (2 L) and water (500 mL) was stirred at reflux overnight. The mixture was evaporated to dryness and extracted with dichloromethane. The organic extract was dried over Na2SO4 and concentrated to afford the desired N-hydroxy-2-methylpropanimidamide (50 g, 34percent).

Reference: [1] Patent: WO2005/7647, 2005, A1, . Location in patent: Page/Page column 191
[2] Patent: WO2005/7658, 2005, A2, . Location in patent: Page 199
[3] Patent: US2010/29650, 2010, A1, . Location in patent: Page/Page column 23
[4] Patent: US2009/286812, 2009, A1, . Location in patent: Page/Page column 21
[5] Patent: WO2011/151163, 2011, A1, . Location in patent: Page/Page column 11
[6] Patent: WO2016/205739, 2016, A1, . Location in patent: Paragraph 0369
[7] Patent: US2018/170941, 2018, A1, . Location in patent: Paragraph 1316
[8] Patent: US2010/29650, 2010, A1, . Location in patent: Page/Page column 49
[9] Patent: WO2006/114706, 2006, A1, . Location in patent: Page/Page column 34
[10] Patent: WO2008/8895, 2008, A1, . Location in patent: Page/Page column 116
[11] Patent: WO2012/168315, 2012, A1, . Location in patent: Page/Page column 106-107
[12] Patent: US2013/143892, 2013, A1, . Location in patent: Paragraph 0404; 0405
[13] Patent: WO2016/68453, 2016, A1, . Location in patent: Page/Page column 21
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