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[ CAS No. 151230-42-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 151230-42-1
Chemical Structure| 151230-42-1
Chemical Structure| 151230-42-1
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Product Details of [ 151230-42-1 ]

CAS No. :151230-42-1 MDL No. :MFCD06659628
Formula : C8H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZCGXHOLCXPKKBO-UHFFFAOYSA-N
M.W :212.04 Pubchem ID :10036077
Synonyms :

Calculated chemistry of [ 151230-42-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.68
TPSA : 26.03 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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 2.85
Log Po/w (WLOGP) : 2.9
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 3.02
Consensus Log Po/w : 2.65

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.56
Solubility : 0.059 mg/ml ; 0.000278 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.187 mg/ml ; 0.00088 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.16
Solubility : 0.0147 mg/ml ; 0.0000692 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.29

Safety of [ 151230-42-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 151230-42-1 ]

* 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 [ 151230-42-1 ]
  • Downstream synthetic route of [ 151230-42-1 ]

[ 151230-42-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 38191-34-3 ]
  • [ 78-39-7 ]
  • [ 151230-42-1 ]
YieldReaction ConditionsOperation in experiment
88.5% at 25℃; for 0.166667 h; 2-Amino-5-bromophenol (561 mg, 3.00 mmol)Was added to triethyl orthoacetate (656 μL, 3.6 mmol),1,3-Dibromo-5,5-dimethylhydantoin (17.2 mg, 6.00 × 10 -2 mmol) was added,And the mixture was stirred at room temperature for 10 minutes.And extracted with ethyl acetate (50 mL × 2).The organic layer was washed with saturated brine,After dehydration with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure,The residue was subjected to silica gel column chromatography using ethyl acetate / hexane (1/4 (volume ratio)) as an elution solvent,Compound 16 was obtained in a yield of 560 mg (88.5percent).
65% for 0.5 h; Reflux To 2-amino-5- bromophenol ( l .OOg, 5.32 mmol) , acetic acid ((0.006 ml) and triethylorthoacetate ( 1.75 ml, 9.58 mmol) were added and refluxed for 3o min. The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was column chromatographed with ethyl acetate : petroleum ether to afford the title compound as a orange solid ((0.756 g, 65percent). -NMR (δ ppm, CDC13, 400 MHz): δ 7.64 (d, 7 = 1.7 Hz, 1 H), 7.51 (d, 7 = 8.4 Hz, 1 H), 7.43 (dd, 7 = 8.4, 1.7 Hz, 1 H), 2.67 (s, 3H).
65% for 0.5 h; Reflux Intermediate 126
6-bromo-2-methylbenzo[d]oxazole:
To 2-amino-5-bromophenol (1.00 g, 5.32 mmol), acetic acid ((0.006 ml) and triethylorthoacetate (1.75 ml, 9.58 mmol) were added and refluxed for 30 min.
The reaction mixture was quenched with water, extracted with ethyl acetate, dried over sodium sulphate and concentrated.
The crude product was column chromatographed with ethyl acetate:
petroleum ether to afford the title compound as a orange solid ((0.756 g, 65percent).
1H-NMR (δ ppm, CDCl3, 400 MHz): δ 7.64 (d, J=1.7 Hz, 1H), 7.51 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 1.7 Hz, 1H), 2.67 (s, 3H).
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7241 - 7257
[2] Patent: JP2016/79108, 2016, A, . Location in patent: Paragraph 0063
[3] Patent: WO2012/151525, 2012, A1, . Location in patent: Page/Page column 128
[4] Patent: US2012/289496, 2012, A1, . Location in patent: Page/Page column 113
  • 2
  • [ 1445-45-0 ]
  • [ 38191-34-3 ]
  • [ 151230-42-1 ]
YieldReaction ConditionsOperation in experiment
85% for 0.5 h; Reflux To an AcOH (1.521 μl, 0.027 mmol) were added 2-amino-5-bromophenol 23 (500 mg, 2.66 mmol) and 1,1,1-trimethoxyethane (600 μl, 4.79 mmol), then the reaction mixture was refluxed for 30 minutes. To the reaction solution was added water, then the reaction solution was extracted with ethyl acetate. The extraction was washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The obtained residue was purified by column chromatography to give Compound 24 (481 mg, 85percent).Compound 24; 1H-NMR (CDCl3) δ: 2.63 (s, 3H), 7.42 (dd, J=8.62, 2.03 Hz, 1H), 7.51 (d, J=8.62 Hz, 1H), 7.64 (d, J=2.03 Hz, 1H).
Reference: [1] Patent: US2012/253040, 2012, A1, . Location in patent: Page/Page column 31
  • 3
  • [ 16394-40-4 ]
  • [ 151230-42-1 ]
Reference: [1] Monatshefte fuer Chemie, 1993, vol. 124, # 4, p. 367 - 380
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