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Chemical Structure| 5676-56-2 Chemical Structure| 5676-56-2
Chemical Structure| 5676-56-2

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CAS No.: 5676-56-2

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Product Details of [ 5676-56-2 ]

CAS No. :5676-56-2
Formula : C8H6BrNO
M.W : 212.04
SMILES Code : CC1=NC2=CC(Br)=CC=C2O1
MDL No. :MFCD08702771
InChI Key :ZBCCSPFGJDVVJB-UHFFFAOYSA-N
Pubchem ID :10104599

Safety of [ 5676-56-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 5676-56-2 ] Show Less

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 ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.03 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.39
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.85
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.9
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.06
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

3.02
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.64

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.56
Solubility 0.059 mg/ml ; 0.000278 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.06
Solubility 0.187 mg/ml ; 0.00088 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.16
Solubility 0.0147 mg/ml ; 0.0000692 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.57 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 2.29

Application In Synthesis [ 5676-56-2 ]

* 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.

  • Downstream synthetic route of [ 5676-56-2 ]

[ 5676-56-2 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 60-35-5 ]
  • [ 40925-68-6 ]
  • [ 5676-56-2 ]
  • 2
  • [ 95-21-6 ]
  • [ 5676-56-2 ]
  • 3
  • [ 95-55-6 ]
  • [ 5676-56-2 ]
  • 4
  • [ 1445-45-0 ]
  • [ 40925-68-6 ]
  • [ 5676-56-2 ]
YieldReaction ConditionsOperation in experiment
for 1.5h;Heating / reflux; A solution of 2-amino-4-bromophenol (1 g, 5.32 mmol) in trimethyl orthoacetate (20 [ML)] was refluxed for 1.5 hours. The reaction was then cooled and the solvent removed under reduced pressure to give 1.1 g of title compound. [C8H6BRNO] Mass (calculated): [212]; (found): [[M+H+]] = 212,214 (Br). NMR (400 MHz, dmso-d6): 2.55 (3H, s, CH3) ; 7.3 [(1H,] d, J = 8 Hz, aryl-H); 7.35 [(1H,] dd, J = 1 and 8 Hz, aryl-H); 7.75 [(1H,] d, [J] = 2 Hz, aryl-H).
for 1.5h;Reflux; General procedure: The 5-halogeno-2-methylbenzoxazoles were prepared by the treatment of the corresponding 2-amino-4-halogenophenol with either acetic anhydride (X = F or Cl) [14] or trimethylorthoacetate (X = Br) [15]. 2-Amino-4-chlorophenol was commercially available; 2-amino-4-fluorophenol and 2-amino-4-bromophenol were obtained by reduction of the corresponding 2-nitro-4-halogenophenol with H2/Pd [16] and SnCl2·2H2O [17], respectively. Attempts to reduce 2-nitro-4-bromophenol with H2/Pd resulted in debromination of the aromatic ring. The 2-nitro-4-halogenophenols were prepared in batches from the 4-halogenophenols by careful nitration in acetic acid at 15-20 C [18] on a small scale (2-5 g of halogenophenol). Nitration of fluorophenolrequired only 2 min, but nitration of bromophenol required 2-16 h (typically around 3 h); attempts to scale up the reaction resulted in reduced yields. Scheme 3 summarizes these synthetic routes.
  • 5
  • [ 5676-56-2 ]
  • [ 127972-02-5 ]
  • [ 628710-94-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; for 20h;Heating / reflux; A solution of [5-FORMYL-2-METHOXYBENZENEBORONIC] acid [(1] g, 5.6 mmol), 2- methyl-5-bromobenzoxazole (1 g, 4.72 mmol) and [K2CO3] (1.63 g, 11.8 mmol) in ethanol (20 mL) and toluene (40 mL) was degassed prior to addition of Pd (Ph3) 4 (55 mg, 0.047 mmol). The mixture was refluxed for 20 hours then cooled and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, extracted with ethyl acetate, washed with water and the organic layer dried over sodium sulphate. The crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4) to give 1.13 g of title compound. [C16HL3NO4] Mass (calculated): [267]; (found): [M+H+] : 268. NMR (400 MHz, [CDC13)] : 2.6 (3H, s, CH3) ; 3.85 (3H, s, CH30) ; 7.05 [(1H,] d,, JI = [8 HZ, ARYL-H); 7.35 (1H, D, , J = 8 HZ, ARYL-H); 7.45 (1H, D, , J = 8 HZ, ARYL-H);] 7.75 [(1H,] s, aryl-H); 7.8-7. 85 (2H, m, aryl-H); 9.9 [(1H,] s, CHO).
  • 6
  • [ 5676-56-2 ]
  • [ 121-43-7 ]
  • 2-methyl-1,3-benzoxazol-5-yl borate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In tetrahydrofuran; hexane; water; Reference Example 192 In THF (94 ml) was dissolved <strong>[5676-56-2]5-bromo-2-methyl-1,3-benzoxazole</strong> (9.4 g), and to the solution was added dropwise at -78 C. 1.6M n-butyllithium/hexane (30.5 ml). The mixture was stirred for 1 hour, and to the mixture was added dropwise a solution of trimethoxyborane (9.2 ml) in THF (9.2 ml). The mixture was stirred for 30 minutes and warmed to room temperature. To the mixture was added water (37.6 ml), and the mixture was stirred for 15 minutes. The reaction solution was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed, and the residue was washed with hexane/isopropylether to give 2-methyl-1,3-benzoxazol-5-yl borate (5.5 g). 1H-NMR (200 MHz, DMSO-d6) delta 2.17(3H, s), 6.88-6.93(1H, m), 7.14-7.40(1H, m), 7.48-7.56(1H, m), 10.24(2H, br).
  • 7
  • [ 1445-45-0 ]
  • [ 7693-52-9 ]
  • [ 5676-56-2 ]
  • 8
  • [ 5676-56-2 ]
  • [ 1101873-47-5 ]
  • [ 1204664-78-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;copper(l) iodide; 8-quinolinol; In dimethyl sulfoxide; at 160℃; for 0.5h;Microwave irradiation; Step D. Example 5[00133] A mixture of <strong>[5676-56-2]5-bromo-2-methylbenzo[d]oxazole</strong> (81 mg, 0.38 mmol), 4- (l-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(lH)-one (80 mg, 0.25 mmol), quinolin-8-ol (11 mg, 0.076 mmol, Alfa Aesar), potassium carbonate (46 mg, 0.33 mmol), Copper(I) iodide (15 mg, 0.076 mmol, Alfa Aesar) in DMSO (2 mL) was heated under microwave condition 160 0C for 30 min. The resulting mixture was diluted with H2O and extracted with EtOAc (2X). The combined organic layers were concentrated in vacuo to a green oil. The oil was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2) to yield 37 mg of desired product as a light brown solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.30 (s, 2 H) 7.81 (d, J=8.53 Hz, 1 H) 7.74 (d, J=2.01 Hz, 1 H) 7.66 (d, J=7.53 Hz, 1 H) 7.39 (dd, J=8.78, 2.01 Hz, 1 H) 6.05-6.17 (m, 2 H) 4.74-4.89 (m, 1 H) 4.22-4.34 (m, 2 H) 3.49-3.61 (m, 2 H) 2.71 (s, 3 H) 2.44 (t, J=7.53 Hz, 2 H) 2.00-2.16 (m, 2 H) 1.50-1.75 (m, 4 H) 0.94 (t, J=7.28 Hz, 3 H). MS (ESI) 446 (M+H).
  • 9
  • [ 5676-56-2 ]
  • [ 74-88-4 ]
  • [ 1227098-65-8 ]
YieldReaction ConditionsOperation in experiment
In acetone; Fluorescent dye molecule (F) is prepared by reacting 5-bromo-2-methyl-l,3-benzoxazole with iodomethane in acetone to yield an iodo salt, reacting the iodo salt with an appropriate aldehyde in ethanol to yield a dye derivative, and then coupling the dye derivative with an appropriate boronic acid via a Suzuki reaction.
  • 10
  • [ 5676-56-2 ]
  • [ 110556-33-7 ]
  • C13H15NO3 [ No CAS ]
  • 11
  • [ 1450-75-5 ]
  • [ 5676-56-2 ]
  • [ 42524-21-0 ]
YieldReaction ConditionsOperation in experiment
65%; 7% With acetylhydroxamic acid; sulfuric acid; In acetonitrile; at 80℃; under 1292.9 Torr; for 0.166667h;Microwave irradiation; General procedure: 2-Hydroxy acetophenone 4a (1.0 g, 7.4 mmol), acetohydroxamic acid (0.83 g, 11.0 mmol), acetonitrile (3 ml), and conc. H2SO4 (0.2 ml) were taken into a 10 ml pressure tube and subjected to microwave heating (CEM discover, 360 W, 80 C, 25 psi) for 8 min. Next, the reaction mixture was diluted with ethyl acetate (3 ml) and to this; saturated sodium bicarbonate solution (5 ml) was added drop-wise. The mixture was extracted with ethyl acetate (2 × 10 ml) and the combined organic layer was washed with saturated NaCl solution, dried over anhy. Na2SO4, and concentrated under reduced pressure. Purification of the mixture by normal column chromatography (silica gel 60-120 mesh, ethyl acetate/hexane: 1:9) gave benzoxazole 5a (0.67 g, 70%) in the form of a yellow oil and 2-hydroxy acetophenone oxime 6a (68 mg, 6%, mp 104-107 C) in the form of a white powder.
  • 12
  • [ 5676-56-2 ]
  • [ 446-52-6 ]
  • C15H9BrFNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dichloromethane; water;Inert atmosphere; General procedure: The SBOs were prepared by the base-catalysed condensation of the appropriate 5-halogeno-2-methylbenzoxazole with the requisite aromatic aldehyde under phase transfer conditions. In a typical experiment, equimolar quantities (5 mmol) of the starting materials were dissolved in dichloromethane (20-50 ml) in the presence of benzyltriethylammonium chloride (3 mmol) and stirred magnetically under a nitrogen atmosphere as an aqueous solution of sodium hydroxide (50%, w/v, 5 ml) was added dropwise over a period of 10 min. After being stirred for 2-36 h until analytical thin layer chromatography indicated that the reaction was complete, the mixture was diluted with water (50 ml) and the SBO was extracted with dichloromethane (3×20 ml), dried (MgSO4), filtered, evaporated under reduced pressure and recrystallized from aqueous methanol or ethanol.
  • 13
  • [ 5676-56-2 ]
  • [ 456-48-4 ]
  • C15H9BrFNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dichloromethane; water;Inert atmosphere; General procedure: The SBOs were prepared by the base-catalysed condensation of the appropriate 5-halogeno-2-methylbenzoxazole with the requisite aromatic aldehyde under phase transfer conditions. In a typical experiment, equimolar quantities (5 mmol) of the starting materials were dissolved in dichloromethane (20-50 ml) in the presence of benzyltriethylammonium chloride (3 mmol) and stirred magnetically under a nitrogen atmosphere as an aqueous solution of sodium hydroxide (50%, w/v, 5 ml) was added dropwise over a period of 10 min. After being stirred for 2-36 h until analytical thin layer chromatography indicated that the reaction was complete, the mixture was diluted with water (50 ml) and the SBO was extracted with dichloromethane (3×20 ml), dried (MgSO4), filtered, evaporated under reduced pressure and recrystallized from aqueous methanol or ethanol.
  • 14
  • [ 5676-56-2 ]
  • [ 459-57-4 ]
  • C15H9BrFNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide; In dichloromethane; water;Inert atmosphere; General procedure: The SBOs were prepared by the base-catalysed condensation of the appropriate 5-halogeno-2-methylbenzoxazole with the requisite aromatic aldehyde under phase transfer conditions. In a typical experiment, equimolar quantities (5 mmol) of the starting materials were dissolved in dichloromethane (20-50 ml) in the presence of benzyltriethylammonium chloride (3 mmol) and stirred magnetically under a nitrogen atmosphere as an aqueous solution of sodium hydroxide (50%, w/v, 5 ml) was added dropwise over a period of 10 min. After being stirred for 2-36 h until analytical thin layer chromatography indicated that the reaction was complete, the mixture was diluted with water (50 ml) and the SBO was extracted with dichloromethane (3×20 ml), dried (MgSO4), filtered, evaporated under reduced pressure and recrystallized from aqueous methanol or ethanol.
  • 15
  • [ 5676-56-2 ]
  • C44H72B3IrN2O6 [ No CAS ]
  • C44H66B3BrIrN3O7 [ No CAS ]
  • [ 931-88-4 ]
  • 16
  • [ 5676-56-2 ]
  • [ 73183-34-3 ]
  • C50H77B4BrIrN3O9 [ No CAS ]
  • 17
  • [ 5676-56-2 ]
  • [ 73183-34-3 ]
  • [ 1573171-09-1 ]
  • 18
  • [ 5676-56-2 ]
  • [ 73183-34-3 ]
  • [ 1573171-63-7 ]
  • 19
  • [ 40925-68-6 ]
  • [ 123-54-6 ]
  • [ 5676-56-2 ]
  • [ 107986-49-2 ]
  • 20
  • [ 92832-02-5 ]
  • [ 5676-56-2 ]
YieldReaction ConditionsOperation in experiment
83% With [bis(acetoxy)iodo]benzene; triethylamine; In methanol; at 20℃; for 0.5h; Step (1), 5-bromo o-hydroxy acetophenone imine as raw material, iodine diacetate oxidant, triethylamine as an additive, in methanol solvent, according to 5-bromo o-hydroxyacetophenone Imine millimoles: Iodobenzene diacetate Millimole: Triethylamine Millimole: Methanol milliliter ratio 1: 1.5: 0.5: 2 ratio, 5-bromo o-hydroxy acetophenone imine ( (69.7 uL, 0.5 mmol) and finally iodobenzene diacetate (483.2 mg, 1.5 mmol) were added with stirring. After the addition was complete, stirring was continued at room temperature After the oxidative rearrangement reaction for 30 minutes, a reaction liquid of a benzoxazole derivative was prepared. Step (2), the eluent is a mixture of ethyl acetate: petroleum ether ratio of 1:30 to give a white solid 5-bromo-2-Methylbenzoxazole (176.9 mg, yield 83%).
82% With [bis(acetoxy)iodo]benzene; In methanol; at 20℃; for 0.5h; General procedure: To a stirred solution of ortho-hydroxyaryl N-H ketimines 1 (1mmol) in solvent (2mL) was added an additive if specified (0.2-1.0mmol) and PhI(OAc)2 (1.1-2.0mmol). The resulting mixture was stirred at room temperature for 30min and the solvent was removed under reduced pressure. The crude was purified by chromatography on silica gel (pentane/ethyl acetate, 30-100:1) to furnish the desired products 2/3.
  • 21
  • [ 557-21-1 ]
  • [ 5676-56-2 ]
  • [ 903556-80-9 ]
  • 22
  • [ 5676-56-2 ]
  • [ 1066-54-2 ]
  • 2-methyl-5-((trimethylsilyl)ethynyl)benzo[d]oxazole [ No CAS ]
  • 24
  • [ 1450-75-5 ]
  • [ 5676-56-2 ]
  • 5-bromo-N-methylbenzo[d]oxazol-2-amine [ No CAS ]
  • 25
  • [ 1450-75-5 ]
  • [ 5676-56-2 ]
  • [ 42524-21-0 ]
  • [ 6329-74-4 ]
  • 26
  • [ 1450-75-5 ]
  • [ 5676-56-2 ]
  • [ 6329-74-4 ]
 

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