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[ CAS No. 298-46-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 298-46-4
Chemical Structure| 298-46-4
Structure of 298-46-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 298-46-4 ]

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Product Details of [ 298-46-4 ]

CAS No. :298-46-4 MDL No. :
Formula : C15H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :FFGPTBGBLSHEPO-UHFFFAOYSA-N
M.W : 236.27 Pubchem ID :2554
Synonyms :
CBZ;NSC 169864;Carbamazepine, Tegretol, Epitol

Calculated chemistry of [ 298-46-4 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.05
TPSA : 46.33 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 1.65
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.125 mg/ml ; 0.00053 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.203 mg/ml ; 0.000858 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.93
Solubility : 0.0278 mg/ml ; 0.000117 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.93

Safety of [ 298-46-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P260-P270-P264-P314-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H373 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 298-46-4 ]

* 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 [ 298-46-4 ]
  • Downstream synthetic route of [ 298-46-4 ]

[ 298-46-4 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 298-46-4 ]
  • [ 260-94-6 ]
  • [ 885-23-4 ]
  • [ 5336-90-3 ]
  • [ 1007228-53-6 ]
Reference: [1] Journal of the American Society for Mass Spectrometry, 2015, vol. 26, # 10, p. 1676 - 1685
  • 2
  • [ 298-46-4 ]
  • [ 3564-73-6 ]
Reference: [1] Pharmazie, 1991, vol. 46, # 7, p. 512 - 517
[2] Pharmazie, 1991, vol. 46, # 7, p. 512 - 517
[3] Journal of the Indian Chemical Society, 1995, vol. 72, # 5, p. 333 - 338
  • 3
  • [ 298-46-4 ]
  • [ 36507-30-9 ]
YieldReaction ConditionsOperation in experiment
91% With peracetic acid; potassium permanganate supported on alumina; sodium carbonate In dichloromethane; acetic acid at 20℃; for 1.66667 h; Heating / reflux Example 1: lla,10b-Dihydro-6H-dibenz/b.f/oxireno[d1 azepine- 6-carboxamide (5); [44] To a stirred suspension of carbamazepine (3) (20Og, 847.5mmol) and sodium carbonate (287.4g, 271 lmmol) in dichloromethane (1000ml) were added tablets of potassium permanganate supported on alumina (3.5percent w/w, 3.46g, 0.77mmol). Thereafter, peroxyacetic acid (39percent solution in acetic acid, 432ml, 2538mmol) was added dropwise over one hour, causing a gradual rise in temperature until gentle reflux of the solvent. The mixture was stirred for twenty minutes and then allowed to stand for twenty minutes. The sodium carbonate and supported catalyst were then removed by filtration and washed by dichloromethane (200ml); the alumina beads were separated from sodium carbonate by screening through a sieve. The combined filtrate was then stirred with an aqueous solution of sodium sulphite (2Og) and sodium bicarbonate (2Og) in water (250ml) for one hour. The phases were then separated and the aqueous phase extracted by dichloromethane (50ml). The combined organic layers were washed by water (100ml), saturated aqueous sodium bicarbonate (100ml), water again (100ml) and brine, then dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent (rotary evaporator, water aspirator pressure, 4O0C) gave the crude epoxide (5) as a beige solid which was crystallised from ethyl acetate (100ml) to give the product as an off-white solid, 194.2g, (91percent yield).
91% With peroxyacetic acid; potassium permanganate on alumina; sodium carbonate; acetic acid In dichloromethane for 1.66667 h; Reflux Step-1 : Synthesis of compound 2: 2 00101) To a stirred suspension of compound 1 (200 g, 847.5 mmol) and sodium carbonate (287.4 g, 271 1 mmol) in dichorometbane (1000 ml) were added tablets of potassium permanganate supported on alumina (3.5percent w/w, 3.46 g, 0.77 mmol). Thereafter, peroxyacetic acid (39percent solution in acetic acid, 432 ml, 2538 mmol) was added dropwise over one hour, causing a gradual rise in temperature until gentle reflux of the solvent. The mixture was stirred for twenty minutes and then allowed to stand for twenty .minutes. The sodium carbonate and supported catalys were then removed by filtration and washed by dichloromethane (200 ml); the alumina beads were separated from sodium carbonate by screening through a sieve. The combined filtrate was then stirred with an aqueous solution of sodium sulphite (20 g) and sodium bicarbonate (20 g) in water (250 ml) for one hour. The phases were then separated and the aqueous phase extracted by dichloromethane (50 ml). The combined organic layers were washed by water (100 ml), saturated aqueous sodium bicarbonate (100 mi), water again (100 ml) and brine, then dried over anhydrous sodium sulphate and fil tered. Evaporation of the solvent (rotary evaporator, water aspirator pressure, 40° C.) gave the crude epoxide 2 as a beige solid which was crystallised from ethyl acetate (100 ml) to give the product as an off-white solid, 194.2 g, (91percent yield).
91% With perpropionic acid; sodium carbonate; acetic acid In dichloromethane at 20℃; for 2 h; Reflux To a stirred suspension of compound 1 (200 g, 847.5 mmol) and sodium carbonate (287.4 g, 2711 mmol) in dichloromethane (1000 ml) were added tablets of potassium permanganate supported on alumina (3.5percent w/w, 3.46 g, 0.77 mmol). Thereafter, peroxyacetic acid (39percent solution in acetic acid, 432 ml, 2538 mmol) was added dropwise over one hour, causing a gradual rise in temperature until gentle reflux of the solvent. The mixture was stirred for twenty minutes and then allowed to stand for twenty minutes. The sodium carbonate and supported catalyst were then removed by filtration and washed by dichloromethane (200 ml); the alumina beads were separated from sodium carbonate by screening through a sieve. The combined filtrate was then stirred with an aqueous solution of sodium sulphite (20 g) and sodium bicarbonate (20 g) in water (250 ml) for one hour. The phases were then separated and the aqueous phase extracted by dichloromethane (50 ml). The combined organic layers were washed by water (100 ml), saturated aqueous sodium bicarbonate (100 ml), water again (100 ml) and brine, then dried over anhydrous sodium sulphate and filtered. Evaporation of the solvent (rotary evaporator, water aspirator pressure, 40° C.) gave the crude epoxide 2 as a beige solid which was crystallised from ethyl acetate (100 ml) to give the product as an off-white solid, 194.2 g, (91percent yield).
66% With peracetic acid; aluminum oxide; potassium permanganate; sodium carbonate In dichloromethane at 20℃; for 2 h; Peroxyacetic acid (2 mL) was added dropwise to the suspension of carbamazepine (954 mg, 4 mmol), Na2CO3 (1.4 g, 13 mmol) and KMnO4/Al2O3 (0.6 mg/18 mg) in dichloromethane (10 mL). The reaction mixture was stirred at room temperature for 2 h. After neutralization with aqueous solution of NaHCO3 (5 g) and NaHSO3 (5g), the mixture was extracted with dichloromethane (2 × 100 mL). The combined organic phase was washed with brine (200 mL) and dried with MgSO4. After evaporation of the solvent, the product was purified by recrystallization from EtOAc as pale yellow powders (662 mg, 66percent).

Reference: [1] Patent: WO2006/75925, 2006, A2, . Location in patent: Page/Page column 9
[2] Patent: WO2013/167985, 2013, A1, . Location in patent: Paragraph 00100; 00101
[3] Patent: US2016/122332, 2016, A1, . Location in patent: Paragraph 0121-0122
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[5] Journal of the American Chemical Society, 1994, vol. 116, # 20, p. 9375 - 9376
[6] Journal of the American Chemical Society, 1994, vol. 116, # 20, p. 9375 - 9376
[7] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1077 - 1088
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[9] Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, # 9, p. 1589 - 1590
[10] Journal of Pharmacy and Pharmacology, 1984, vol. 36, # 12, p. 843 - 844
[11] Journal of the American Chemical Society, 1997, vol. 119, # 27, p. 6269 - 6273
[12] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 5, p. 1221 - 1230
[13] Journal of Pharmaceutical Sciences, 1985, vol. 74, # 8, p. 866 - 870
[14] Arzneimittel-Forschung/Drug Research, 1988, vol. 38, # 5, p. 724 - 726
[15] Journal of the American Chemical Society, 1997, vol. 119, # 27, p. 6269 - 6273
[16] Chemosphere, 2004, vol. 54, # 4, p. 497 - 505
[17] Applied Catalysis A: General, 2011, vol. 408, # 1-2, p. 25 - 30
[18] Angewandte Chemie - International Edition, 2013, vol. 52, # 8, p. 2185 - 2188[19] Angew. Chem., 2013, vol. 125, # 8, p. 2241 - 2244
  • 4
  • [ 298-46-4 ]
  • [ 36507-30-9 ]
  • [ 35079-97-1 ]
Reference: [1] Applied Catalysis A: General, 2011, vol. 408, # 1-2, p. 25 - 30
  • 5
  • [ 298-46-4 ]
  • [ 36507-30-9 ]
  • [ 52618-28-7 ]
Reference: [1] Journal of Pharmacy and Pharmacology, 1984, vol. 36, # 12, p. 843 - 844
  • 6
  • [ 298-46-4 ]
  • [ 256-96-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 6, p. 1759 - 1761
  • 7
  • [ 1220040-57-2 ]
  • [ 298-46-4 ]
  • [ 256-96-2 ]
Reference: [1] Journal of Pharmaceutical Sciences, 2010, vol. 99, # 4, p. 1810 - 1825
  • 8
  • [ 26689-55-4 ]
  • [ 298-46-4 ]
  • [ 256-96-2 ]
Reference: [1] Journal of Pharmaceutical Sciences, 2010, vol. 99, # 4, p. 1810 - 1825
[2] Journal of Pharmaceutical Sciences, 2010, vol. 99, # 4, p. 1810 - 1825
  • 9
  • [ 1220040-58-3 ]
  • [ 298-46-4 ]
  • [ 256-96-2 ]
Reference: [1] Journal of Pharmaceutical Sciences, 2010, vol. 99, # 4, p. 1810 - 1825
  • 10
  • [ 298-46-4 ]
  • [ 29331-92-8 ]
Reference: [1] Patent: WO2013/167985, 2013, A1,
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1077 - 1088
[3] Patent: US2016/122332, 2016, A1,
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