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Chemical Structure| 52427-05-1 Chemical Structure| 52427-05-1

Structure of 52427-05-1

Chemical Structure| 52427-05-1

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CAS No.: 52427-05-1

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Product Details of [ 52427-05-1 ]

CAS No. :52427-05-1
Formula : C6H4BrNO3
M.W : 218.01
SMILES Code : OC1=C(Br)C=CC(=C1)[N+]([O-])=O
MDL No. :MFCD00466299
Boiling Point : No data available
InChI Key :KNJNITQHVLIWBN-UHFFFAOYSA-N
Pubchem ID :12867136

Safety of [ 52427-05-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 52427-05-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 44.99
TPSA ?

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

66.05 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.43
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

2.71
Log Po/w (WLOGP)?

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

2.06
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.

1.05
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

-0.1
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.43

Water Solubility

Log S (ESOL):?

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

-3.24
Solubility 0.126 mg/ml ; 0.00058 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.

-3.75
Solubility 0.0387 mg/ml ; 0.000178 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

-2.06
Solubility 1.89 mg/ml ; 0.00867 mol/l
Class?

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

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

 No
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

 Yes
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.

-5.71 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

2.0 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)

 1.92

Application In Synthesis of [ 52427-05-1 ]

* 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.

  • Downstream synthetic route of [ 52427-05-1 ]

[ 52427-05-1 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 554-84-7 ]
  • [ 52427-05-1 ]
YieldReaction ConditionsOperation in experiment
51% With bromine; In acetic acid; at 125℃; for 16h; To a solution of 3-nitrophenol (25.0 g, 179.8 mmol) in acetic acid (250 mL) was added bromine (28.8 g, 179.8 mmol) dropwise and the mixture was heated to 125 °C for 16 h. Upon completion of the reaction the volatiles were carefully removed under reduced pressure to dryness. The residue was partitioned betweenwater (100 mL) and ethyl acetate (150 mL). The organic layer was separated and washed with sodium thiosulfate (100 mL), brine solution (100 mL), dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. This was purified by silica gel column chromatography to afford 2-bromo-5- nitrophenol (20.0 g, 51percent yield) as a brown solid: LCMS (ESI) m/e 216.0 [(M),calcd for C6H3BrNO3, 215.9]; LC/MS retention time (method A): tR = 1.52 min.
49.1% With bromine; acetic acid; at 120℃; for 1.5h; To a solution of 3-nitrophenol (1.00 g, 7.19 mmol) in acetic acid (10 mL) at rt, was added bromine (0.37 mL, 7.19 mmol), dropwise. The reaction mixture was heated at 120°C for 1.5 h, then was cooled to rt and concentrated. The product was partitioned betweenwater and EtOAc. The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography (0-8percent EtOAc / pet. ether) to afford Intermediate 6A (0.86 g, 3.53 mmol, 49.1percent yield) as a pale yellow solid. ?H NMR (300MHz, CDC13) oe 7.89 (d, J=2.3 Hz, 1H), 7.76 - 7.64 (m, 2H), 5.91 (s, 1H).
  • 2
  • [ 52427-05-1 ]
  • [ 55065-94-6 ]
  • 3
  • [ 52427-05-1 ]
  • [ 55120-56-4 ]
YieldReaction ConditionsOperation in experiment
93% With iron; ammonium chloride; In ethanol; water; at 80℃; for 5h; 5-Amino-2-bromophenol 2-Bromo-5-nitrophenol (450 mg, 2.06 mmol) was initially charged in water (13.5 ml) and ethanol (13.5 ml). Ammonium chloride (596 mg, 11.15 mmol) and iron filings (691 mg, 12.39 mmol) were added and the mixture was stirred at 80° C. for 5 h. The reaction mixture was then cooled to RT and filtered through kieselguhr, and the filtrate was concentrated. Subsequent workup by means of column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:1) gave 359 mg (93percent of theory) of the title compound. LC/MS (Method 3, ESIpos): Rt=0.41 min, m/z=188 [M+H]+.
  • 4
  • [ 52427-05-1 ]
  • benzoic acid-(2-bromo-5-nitro-phenyl ester) [ No CAS ]
  • 5
  • [ 52427-05-1 ]
  • toluene-4-sulfonic acid-(2-bromo-5-nitro-phenyl ester) [ No CAS ]
  • 6
  • [ 860209-11-6 ]
  • [ 52427-05-1 ]
  • 7
  • [ 52427-05-1 ]
  • [ 108-24-7 ]
  • acetic acid-(2-bromo-5-nitro-phenyl ester) [ No CAS ]
  • 8
  • [ 52427-05-1 ]
  • [ 100-44-7 ]
  • [ 6345-68-2 ]
  • 9
  • [ 52427-05-1 ]
  • [ 77-78-1 ]
  • [ 77337-82-7 ]
YieldReaction ConditionsOperation in experiment
100% To a solution of <strong>[52427-05-1]2-bromo-5-nitrophenol</strong> (20 g, 92.2 mmol) in THF (300 mL) cooled to 0 °C was added lithium hydroxide (3.87 g, 92.2 mmol) and the mixture wasstirred for 1 h. To this mixture dimethylsulfate (17.5 mL, 184.4 mmol) was added dropwise and the mixture was warmed to room temperature. Stirring was continued overnight. Upon completion of the reaction, the mixture was quenched by the addition of water (200 mL) and extracted using ethyl acetate (3 x 200 mL). The combined organic layers were washed with brine solution (100 mL), dried oversodium sulfate and concentrated under reduced pressure to afford 1 -bromo-2-methoxy-4-nitrobenzene (23.0 g, quantitative yield) as a pale yellow solid: GC-MS(El) m/e 230.9 [(M), calcd for C7H6BrNO3, 230.9]; GC/MS retention time (methodA): tp. = 7.61 mm (GC-MS was performed using Agilent GCMS Module-7890 (GC)5975C(MSD) fitted with column - HP-5M5, 30m x 0.25mm ID x 0.25um Film thickness with helium flow of 0.9 mL/min. Column gradient 50 °C for 1 mm and raised to 300 °C at the rate of 25 °C/min).
  • 11
  • [ 186581-53-3 ]
  • [ 52427-05-1 ]
  • [ 77337-82-7 ]
  • 13
  • [ 77337-82-7 ]
  • [ 52427-05-1 ]
YieldReaction ConditionsOperation in experiment
99% With boron tribromide; In dichloromethane; at 0 - 20℃; for 24h;Inert atmosphere; To a charged round-bottom flask, backfilled with argon, was added 1-bromo-2-methoxy-4-nitrobenzene (10 g, 43.098 mmol) followed by boron tribromide solution (1.0 M in DCM, 107.5 mL) at 0°C. The reaction mixture was stirred for 24 h at room temperature before quenching with DI water. The organic layer was washed with DI water, dried over Na2SO4, filtered, and concentrated under reduced pressure. It was used in the next step without further purification (9.2 g, 99percent yield). 1H NMR (400 MHz, CDCl3) delta 7.84 (s, 1H), 7.79-7.59 (m, 2H), 5.92 (bs, 1H). 13C NMR (101 MHz, CDCl3) delta 152.97, 148.49, 132.62, 117.44, 116.43, 111.20.
83.39% With aluminum (III) chloride; In dichloromethane; at 0 - 50℃; for 16h;Inert atmosphere; To a solution of 23.1 (0.97 g 4.1 mmol, 1.0 eq.) in dry CH2Cl2 (6.0 mL) was added anhydrous AlCl3 (1.66 g, 12.5 mmol, 3.0 eq) at 0° C. under argon atmosphere. The reaction mixture was stirred at 50° C. for 16 hours. After completion of the reaction, mixture was poured into diluted HCl to adjust pH to 4, and extracted using CH2Cl2. Organic layer was washed with brine and dried over sodium sulfate. Organic layer was concentrated under reduced pressure and crude was purified by column chromatography to afford pure 23.2 (0.76 g, 83.39percent). MS (ES): m/z 219.1 [M+H]+.
78% Method 9 2-Bromo-5-nitrophenol. To a 500 niL round bottom flask charged with 2-bromo-5-nitroanisole (11.0 g, 47 mmol) was added 100 mL of anhydrous DCM. Aluminum chloride (25 g, 150 mmol) was then added to the reaction mixture. The resulting suspension was heated overnight under nitrogen at 50 0C. The reaction was allowed to cool to rt, poured over ice, and acidified to pH 4 with the addition of aqueous 10 percent HCl. The resulting mixture was filtered through a bed of Celite and the filtrate was transferred to a separatory funnel. The aqueous phase was extracted with methylene chloride (~ 2 x 200 mL). The combined organic phase was dried over Na2SO4 and cone in vacuo giving the crude title compound which was purified by silica gel chromatography (330 g) using EtOAc/hexanes (1:1) as eluent to afford the title compound (8.0 g, 78 percent) m/z: 211.
78% To a 500 niL round bottom flask charged with 2-bromo-5-nitroanisole (11.0 g, 47 mmol) was added 100 mL of anhydrous DCM. Aluminum chloride (25 g, 150 mmol) was then added to the reaction mixture. The resulting suspension was heated overnight under nitrogen at 50 0C. The reaction was allowed to cool to rt, poured over ice, and acidified to pH 4 with the addition of aqueous 10 percent HCl. The resulting mixture was filtered through a bed of Celite and the filtrate was transferred to a separatory funnel. The aqueous phase was extracted with methylene chloride (~ 2 x 200 mL). The combined organic phase was dried over Na2SO4 and cone in vacuo giving the crude title compound which was purified by silica gel chromatography (330 g) using EtOAc/hexanes (1 : 1) as eluent to afford the title compound (8.0 g, 78 percent) m/z: 217
71% To a solution of l-bromo-2-methoxy-4-nitrobenzene (3 g, 12.93 mmol) in CH2CI2 (5 niL) at -78 °C was added tribromoborane (38.8 niL, 38.8 mmol). The resulting mixture was stirred at room temperature overnight and then diluted with EtOAc and water. The separated organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography on silica to yield 16A (2.0 g, 71percent yield). MS (ES): m/z= 218.0 [M+H]+. 3/4 NMR (500 MHz, DMSO-d6) delta ppm 7.55-7.60 (m, 1 H) 7.61-7.66 (m, 1 H) 7.79 (d, J=2.20 Hz, 1 H).
65% With boron tribromide; In dichloromethane; at 0 - 20℃; BBr3 (8.58 mL of 1.0M solution, 8.6 mmol) was added to the DCM (10 mL) solution of 1-bromo-2-methoxy-4-nitrobenzene (1.0 g, 4.3 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. The mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The combined extracts were dried and the crude was purified by flash column chromatography to get the desired compound as pale brown powder in 65percent yield (600 mg). [0227] 1H NMR (400 MHz, CDCl3) delta 7.84 (s, 1H), 7.79-7.59 (m, 2H), 5.92 (br s, 1H). [0228] 13C NMR (101 MHz, CDCl3) delta 152.97, 148.49, 132.62, 117.44, 116.43, 111.20.
63% With hydrogen bromide; In water; for 20h;Reflux; INTERMEDIATE PREPARATION 164-bromo-3-[ -methylethyl)oxy]aniline2-bromo-5-nitrophenolA mixture of 2-bromo-5-nitrophenyl methyl ether (5 g, 2.17 mmol) in HBr (10 mL) was heated to reflux for 20 h. The reaction mixture was poured into ice cold water (100 mL) and filtered. The solid was collected by filtration, dissolved in ethyl acetate (50 mL), dried over Na2S04, filtered, and concentrated in vacuo. The crude product was purified via column chromatography (30:1-20:1 petroleum ether/ethyl acetate) to afford 2-bromo-5-nitrophenol (9.49 g, 63percent yield) as a yellow solid
27.4 g (125.6 mmol, 100%) With boron tribromide; In dichloromethane; Step 1 2-Bromo-5-nitrophenol A mixture of 29.1 g (125.6 mmol) of 2-bromo-5-nitroanisole and 250 mL CH2Cl2 was stirred at -44° C. in a dry ice acetonitrile bath under a nitrogen atmosphere. Boron tribromide (18 mL) was added dropwise to the reaction mixture. The resulting black reaction was stirred while allowing the cooling bath to slowly rise to room temperature over 20 h. TLC analysis indicated complete reaction, so the reaction mixture was transferred to an addition funnel and added cautiously to a mixture of ice, water and 75 g solid KH2PO4. The layers were separated, the aqueous layer was washed with CH2Cl2, the combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered, concentrated to give 27.4 g (125.6 mmol, 100percent) of 2-bromo-5-nitrophenol as a black solid. 1H NMR (400 MHz) CDCl3 7.85 (s, 1H), 7.62-7.70 (m, 2H), 5.88 (s, 1H).

  • 17
  • [ 554-84-7 ]
  • [ 7726-95-6 ]
  • [ 64-19-7 ]
  • [ 52427-05-1 ]
  • 18
  • diazotized 5-nitro-2-amino-phenol [ No CAS ]
  • [ 52427-05-1 ]
  • 19
  • [ 52427-05-1 ]
  • ammonium hydroxide [ No CAS ]
  • iron(II) sulfate [ No CAS ]
  • [ 55120-56-4 ]
  • 20
  • [ 860209-11-6 ]
  • sulfate sodium nitrite [ No CAS ]
  • [ 52427-05-1 ]
  • 21
  • [ 75-30-9 ]
  • [ 52427-05-1 ]
  • [ 423165-35-9 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate; In acetonitrile; for 2h;Reflux; To a solution of <strong>[52427-05-1]2-bromo-5-nitro-phenol</strong> (2 g, 9.174 mmol) in acetonitrile (10.0 mL) was added 2-iodopropane (approximately 2.495 g, 14.68 mmol), and potassium carbonate (approximately 2.536 g, 18.35 mmol). The resulting mixture was heated to reflux for approximately 2 hours. The reaction mixture was diluted with dichloromethane. After filtration, the filtrate was concentrated under reduced pressure to afford 1-bromo-2-isopropoxy-4-nitro-benzene (2.35 g, 93percent). 1H NMR (300 MHz, CDCl3) delta 7.75 (d, J = 2.6 Hz, 1H), 7.73 - 7.69 (m, 2H), 4.72 (dt, J = 12.1, 6.1 Hz, 1H), 1.46 (d, J = 6.1 Hz, 6H) ppm. ESI-MS m/z calc. 258.9844, found 260.23 (M+l)+; Retention time: 0.98 minutes.
With potassium carbonate; In acetonitrile; for 2h;Reflux; 2-bromo-5-nitrophenyl 1-methylethyl etherTo a solution of <strong>[52427-05-1]2-bromo-5-nitrophenol</strong> (8.8 g, 42.55 mmol) in acetonitrile (100 mL), was added potassium carbonate (1 1 .19 g, 81.1 mmol) followed by isopropyl iodide (10.34 g, 64.85 mmol). The resulting mixture was heated to reflux for 2 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, dried over Na2S04, filtered and concentrated in vacuo to afford 2-bromo-5-nitrophenyl 1-methylethyl ether (10.5 g) as a yellow oil. This material was used in the next step without further purification. MS (m/z) 259.9 (M+H+)
  • 22
  • [ 615-37-2 ]
  • [ 52427-05-1 ]
  • [ 292638-85-8 ]
  • 6-[(methoxycarbonyl)methyl]-7-methyl-3-nitro-6H-dibenzopyran [ No CAS ]
  • 23
  • [ 554-84-7 ]
  • 2,4-dibromo-3-nitrophenol [ No CAS ]
  • [ 52427-05-1 ]
  • [ 101870-35-3 ]
  • [ 100477-78-9 ]
  • 24
  • [ 554-84-7 ]
  • 2,4-dibromo-3-nitrophenol [ No CAS ]
  • [ 52427-05-1 ]
  • [ 69076-62-6 ]
  • [ 100477-78-9 ]
  • 26
  • [ 52427-05-1 ]
  • [ 753031-08-2 ]
  • 27
  • [ 52427-05-1 ]
  • [ 3189-13-7 ]
  • 28
  • [ 52427-05-1 ]
  • [ 111795-95-0 ]
 

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