Home Cart 0 Sign in  
X

[ CAS No. 19932-85-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 19932-85-5
Chemical Structure| 19932-85-5
Chemical Structure| 19932-85-5
Structure of 19932-85-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 19932-85-5 ]

Related Doc. of [ 19932-85-5 ]

Alternatived Products of [ 19932-85-5 ]

Product Details of [ 19932-85-5 ]

CAS No. :19932-85-5 MDL No. :MFCD00694727
Formula : C7H4BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DDNKJFBQMQOIKI-UHFFFAOYSA-N
M.W : 214.02 Pubchem ID :29859
Synonyms :

Calculated chemistry of [ 19932-85-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.53
TPSA : 46.0 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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.65
Log Po/w (XLOGP3) : 1.85
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 2.72
Consensus Log Po/w : 1.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.94
Solubility : 0.247 mg/ml ; 0.00115 mol/l
Class : Soluble
Log S (Ali) : -2.44
Solubility : 0.783 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.68
Solubility : 0.0446 mg/ml ; 0.000208 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.44

Safety of [ 19932-85-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 19932-85-5 ]

* 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 [ 19932-85-5 ]
  • Downstream synthetic route of [ 19932-85-5 ]

[ 19932-85-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 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,
  • 2
  • [ 32315-10-9 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In dichloromethane at 0 - 20℃; [0950] To a solution of XXXV-1 (3 g, 16 mmol) in dry DCM (50 mL) was added TEA (3.2 g, 32 mmol). The reaction mixture was cooled to 0°C, triphosgene (1.6 g, 5.3 mmol) was added slowly. The mixture was stuffed overnight at rt, then quenched with water, extracted with DCM (80 mLx3). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (PE/EA=10/1) to afford XXXV-2b (2.7g, 79percent yield).
Reference: [1] Patent: WO2015/153683, 2015, A1, . Location in patent: Paragraph 0950
  • 3
  • [ 59-49-4 ]
  • [ 77-48-5 ]
  • [ 19932-85-5 ]
Reference: [1] Patent: US2002/55631, 2002, A1,
[2] Patent: US2002/86887, 2002, A1,
  • 4
  • [ 65-45-2 ]
  • [ 19932-85-5 ]
Reference: [1] Synthesis, 2001, # 4, p. 541 - 543
  • 5
  • [ 19213-72-0 ]
  • [ 38191-34-3 ]
  • [ 19932-85-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 103, p. 59594 - 59602
  • 6
  • [ 52112-66-0 ]
  • [ 19932-85-5 ]
Reference: [1] Patent: US2895877, 1956, ,
  • 7
  • [ 89-73-6 ]
  • [ 19932-85-5 ]
Reference: [1] Przemysl Chemiczny, 1958, vol. 37, p. 418,419[2] Chem.Abstr., 1959, p. 5246
  • 8
  • [ 95-55-6 ]
  • [ 19932-85-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 37, p. 28 Anm. 1, 31, 38, 46
  • 9
  • [ 19932-85-5 ]
  • [ 74-88-4 ]
  • [ 67927-44-0 ]
YieldReaction ConditionsOperation in experiment
79% With potassium carbonate In acetone at 20℃; for 4 h; Example 3: Scheme B2; To a solution of B2.1 (1 equiv., 23 mmol, 5.0 g) in acetone (230 ml) were successively added potassium carbonate (1.5 equiv., 35 mmol, 5.0 g) and iodomethane (1.2 equiv., <n="37"/>28 mmol, 4.0 g); the mixture was stirred at room temperature for 4 h. The acetone solvent was partially concentrated under reduced pressure; this mixture was poured on a IN aqueous HCl solution, filtered and successively washed with water, isopropanol and isopropyl ether, affording a pink powder B2.2 (4.22 g, yield = 79percent, purity (LC) = 99percent).
Reference: [1] Patent: WO2008/37784, 2008, A1, . Location in patent: Page/Page column 35-36
[2] Patent: US2016/289238, 2016, A1, . Location in patent: Paragraph 0322; 0323
  • 10
  • [ 19932-85-5 ]
  • [ 77-78-1 ]
  • [ 67927-44-0 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 321,326
  • 11
  • [ 19932-85-5 ]
  • [ 38191-34-3 ]
Reference: [1] Journal of the Chemical Society, 1938, p. 321,326
  • 12
  • [ 19932-85-5 ]
  • [ 1016641-53-4 ]
Reference: [1] Patent: US2016/289238, 2016, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 19932-85-5 ]

Bromides

Chemical Structure| 871367-14-5

[ 871367-14-5 ]

7-Bromobenzo[d]oxazol-2(3H)-one

Similarity: 0.85

Chemical Structure| 169303-80-4

[ 169303-80-4 ]

tert-Butyl (2-bromo-5-methoxyphenyl)carbamate

Similarity: 0.83

Chemical Structure| 67927-44-0

[ 67927-44-0 ]

6-Bromo-3-methylbenzo[d]oxazol-2(3H)-one

Similarity: 0.83

Chemical Structure| 401811-77-6

[ 401811-77-6 ]

tert-Butyl (5-bromobenzo[d][1,3]dioxol-4-yl)carbamate

Similarity: 0.78

Chemical Structure| 5579-85-1

[ 5579-85-1 ]

6-Bromo-5-chlorobenzo[d]oxazol-2(3H)-one

Similarity: 0.74

Amides

Chemical Structure| 871367-14-5

[ 871367-14-5 ]

7-Bromobenzo[d]oxazol-2(3H)-one

Similarity: 0.85

Chemical Structure| 169303-80-4

[ 169303-80-4 ]

tert-Butyl (2-bromo-5-methoxyphenyl)carbamate

Similarity: 0.83

Chemical Structure| 67927-44-0

[ 67927-44-0 ]

6-Bromo-3-methylbenzo[d]oxazol-2(3H)-one

Similarity: 0.83

Chemical Structure| 81282-60-2

[ 81282-60-2 ]

7-Aminobenzo[d]oxazol-2(3H)-one

Similarity: 0.80

Chemical Structure| 401811-77-6

[ 401811-77-6 ]

tert-Butyl (5-bromobenzo[d][1,3]dioxol-4-yl)carbamate

Similarity: 0.78

Related Parent Nucleus of
[ 19932-85-5 ]

Benzoxazoles

Chemical Structure| 871367-14-5

[ 871367-14-5 ]

7-Bromobenzo[d]oxazol-2(3H)-one

Similarity: 0.85

Chemical Structure| 67927-44-0

[ 67927-44-0 ]

6-Bromo-3-methylbenzo[d]oxazol-2(3H)-one

Similarity: 0.83

Chemical Structure| 81282-60-2

[ 81282-60-2 ]

7-Aminobenzo[d]oxazol-2(3H)-one

Similarity: 0.80

Chemical Structure| 5579-85-1

[ 5579-85-1 ]

6-Bromo-5-chlorobenzo[d]oxazol-2(3H)-one

Similarity: 0.74

Chemical Structure| 215878-20-9

[ 215878-20-9 ]

3-(4-Piperidinyl)-1,3-benzoxazol-2(3H)-one

Similarity: 0.73