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[ CAS No. 59-49-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 59-49-4
Chemical Structure| 59-49-4
Chemical Structure| 59-49-4
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Product Details of [ 59-49-4 ]

CAS No. :59-49-4 MDL No. :MFCD00005716
Formula : C7H5NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ASSKVPFEZFQQNQ-UHFFFAOYSA-N
M.W : 135.12 Pubchem ID :6043
Synonyms :
2-Benzoxazolone;1,3-Benzoxazol-2(3H)-one;2-Hydroxybenzoxazole

Calculated chemistry of [ 59-49-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.03
TPSA : 46.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 1.86
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 0.78
Log Po/w (SILICOS-IT) : 1.46
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.412 mg/ml ; 0.00305 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.476 mg/ml ; 0.00353 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.31
Solubility : 0.666 mg/ml ; 0.00493 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.35

Safety of [ 59-49-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302+H312+H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 59-49-4 ]

* 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 [ 59-49-4 ]
  • Downstream synthetic route of [ 59-49-4 ]

[ 59-49-4 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 89-73-6 ]
  • [ 22353-40-8 ]
  • [ 59-49-4 ]
  • [ 22353-38-4 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h; General procedure: To a solution of N-hydroxysalicylamide (0.5 g, 3.26 mmol) in anhydrous DMF (5 ml) was added 2a or 2b (3.26 mmol) and freshly calcinated K2CO3 (1.35 g, 9.78 mmol) and the mixture was kept, with stirring at the room temperature overnight. DMF was removed in vacuo and the residue was treated with water (10 ml) and then extracted with CH2Cl2 (5 ml). The organic layer was separated, washed with water, dried over anhydrous CaCl2, and purified by flesh chromatography on silica gel using CH2Cl2 as eluent. Dichloromethane was evaporated in vacuo. The resulting residue was benzo[d]oxazol-2(3H)-one 11. The water layer was acidify by hydrochloric acid, filtered and washed with water. The resulting residue was compound 12a(b).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 52, p. 5877 - 5880
  • 2
  • [ 59-49-4 ]
  • [ 19932-85-5 ]
YieldReaction ConditionsOperation in experiment
94% at 20℃; for 4 h; 3H-1,3-Benzoxazol-2-one (5.00 g, 37.00 mmol) was dissolved in acetic acid (50 mL) and bromine (1.9 mL, 37.0 mmol) was added dropwise. The reaction mixture was stirred at 20 °C for 4 h.The reaction mixture was poured onto ice and the precipitate was collected by filtration, washed with water and air-dried to give a pink powder (7.48 g, 34.8 mmol, 94percent). Mp 191.6-192.3 °C. 1H NMR (300 MHz, DMSOd6): δ 11.81 (s, 1H), 7.57 (dd, J = 1.9 Hz, J = 0.3 Hz, 1H), 7.30 (dd, J = 8.3 Hz, J = 1.9 Hz, 1H), 7.04 (dd, J = 8.3 Hz, J = 0.3 Hz, 1H). 13C NMR (75 MHz, DMSOd6): δ 154.5, 144.5, 130.3, 126.9, 113.5, 113.2, 111.7. LCMS m/z calc for [M - H]+: 211.9, 213.9, found: 211.8, 213.8.
84% With bromine In dichloromethane at 20℃; for 19.5 h; To a mixture of 3H-benzooxazol-2-one (20 g, 0.15 mol) in DCM (500 mL) was added bromine (8.34 mL, 0.16 mol). After stirring at room temperature for 19.5 h, the orange precipitate that had formed was filtered off and washed with DCM until the orange color was washed out. The filtrate was concentrated to approximately 33percent of its original volume and filtered and washed as before. The combined solids weighed 28.36 g. 1H NMR indicated the product was clean albeit contained ca. 8-9percent starting material meaning the true yield of product was 26.72 g, 84percent.
70% With N-Bromosuccinimide In acetic acid at 20℃; for 72 h; Step 1: N-Bromosuccinimide (26.6 g, 0.15 mol) was added to a stirred solution of 2-benzoxazolinone (20.0 g, 0.15 mol) in glacial acetic acid (220 mL), and the mixture was stirred at room temperature for 3 days. The reaction mixture was poured into H2O (1.2 L), and the white solid that formed was collected. Recrystallization from hot EtOH (300 mL) gave bromide 1 (22.1 g, 70percent) as an off-white solid: mp 190-195 C.; IR (KBr): 3278, 1779, 1736, 1623 cm?1; 1H NMR (300 MHz, CD3OD): ?7.41 (d, J=2 Hz, 1H), 7.32 (dd, J=5, 2 Hz, 1H), 6.99 (d, J=5 Hz, 1H); CI MS (methane) (m/z): 215 [M+H]+.
31% With N-Bromosuccinimide In acetonitrile at -15 - 20℃; Preparation of 6-Bromo-3H-benzoxazol-2-one.
To a stirred suspension of 3H-benzoxazol-2-one (1.35 g, 10 mmol) in acetonitrile (23 ML) at -15° C. was added portionwise NBS (2.00 g, 11.0 mmol).Following complete addition of NBS the mixture was stirred at -15 to 0° C. for 3 h then allowed to warm to ambient temperature and stirred overnight.The solvent was evaporated in vacuo and the residue was partitioned between CH2Cl2/H2O precipitating the intermediate title compound, 6-bromo-3H-benzoxazol-2-one, (0.67 g, 31percent) as a brown solid. 1HNMR(CDCl3) δ 7.0 (1H, d), 7.15 (1H.,d), 7.3 (1H, s), 11.9 (1H, s).

Reference: [1] European Journal of Medicinal Chemistry, 2018, vol. 159, p. 104 - 125
[2] Patent: US6372933, 2002, B1, . Location in patent: Page column 5 - 6
[3] Patent: US2008/138413, 2008, A1, . Location in patent: Page/Page column 22
[4] Monatshefte fur Chemie, 2011, vol. 142, # 1, p. 67 - 80
[5] Patent: EP1251128, 2002, A1, . Location in patent: Page 38
[6] Patent: US2003/236252, 2003, A1, . Location in patent: Page 14
[7] Monatshefte fuer Chemie, 1993, vol. 124, # 4, p. 367 - 380
[8] Patent: US2003/225127, 2003, A1, . Location in patent: Page 10
[9] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 37, p. 28 Anm. 1, 31, 38, 46
[10] Journal of the Chemical Society, 1934, p. 1186,1190
[11] Chemische Berichte, 1886, vol. 19, p. 2268
[12] Journal of the Chemical Society, 1934, p. 1186,1190
[13] Przemysl Chemiczny, 1958, vol. 37, p. 418,419[14] Chem.Abstr., 1959, p. 5246
[15] Collection of Czechoslovak Chemical Communications, 1979, vol. 44, p. 1790 - 1798
[16] Patent: WO2006/86705, 2006, A1, . Location in patent: Page/Page column 84
[17] Acta Poloniae Pharmaceutica - Drug Research, 2013, vol. 70, # 2, p. 245 - 253
[18] European Journal of Medicinal Chemistry, 2015, vol. 92, p. 575 - 582
[19] Patent: US2003/18021, 2003, A1,
  • 3
  • [ 59-49-4 ]
  • [ 77-48-5 ]
  • [ 19932-85-5 ]
Reference: [1] Patent: US2002/55631, 2002, A1,
[2] Patent: US2002/86887, 2002, A1,
  • 4
  • [ 59-49-4 ]
  • [ 67927-44-0 ]
Reference: [1] Monatshefte fuer Chemie, 1993, vol. 124, # 4, p. 367 - 380
  • 5
  • [ 59-49-4 ]
  • [ 70735-79-4 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1979, vol. 52, p. 1135 - 1138
  • 6
  • [ 615-18-9 ]
  • [ 59-49-4 ]
  • [ 2382-96-9 ]
Reference: [1] Phosphorus and Sulfur and the Related Elements, 1980, vol. 8, p. 205 - 208
  • 7
  • [ 59-49-4 ]
  • [ 121-88-0 ]
Reference: [1] Journal of the Chemical Society, 1926, p. 822
  • 8
  • [ 59-49-4 ]
  • [ 62522-63-8 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2011, vol. 47, # 1, p. 90 - 95
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 20, p. 4875 - 4889
[3] Patent: CN107098846, 2017, A,
  • 9
  • [ 89-73-6 ]
  • [ 939-80-0 ]
  • [ 59-49-4 ]
  • [ 3272-08-0 ]
YieldReaction ConditionsOperation in experiment
84% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18 h; General procedure: To a solution of N-hydroxysalicylamide (0.5 g, 3.26 mmol) in anhydrous DMF (5 ml) was added 2a or 2b (3.26 mmol) and freshly calcinated K2CO3 (1.35 g, 9.78 mmol) and the mixture was kept, with stirring at the room temperature overnight. DMF was removed in vacuo and the residue was treated with water (10 ml) and then extracted with CH2Cl2 (5 ml). The organic layer was separated, washed with water, dried over anhydrous CaCl2, and purified by flesh chromatography on silica gel using CH2Cl2 as eluent. Dichloromethane was evaporated in vacuo. The resulting residue was benzo[d]oxazol-2(3H)-one 11. The water layer was acidify by hydrochloric acid, filtered and washed with water. The resulting residue was compound 12a(b).
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 52, p. 5877 - 5880
  • 10
  • [ 59-49-4 ]
  • [ 1972-28-7 ]
  • [ 162045-53-6 ]
Reference: [1] Patent: US2003/40513, 2003, A1,
  • 11
  • [ 59-49-4 ]
  • [ 1144035-53-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 12, p. 1252 - 1257
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