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Chemical Structure| 91270-69-8 Chemical Structure| 91270-69-8
Chemical Structure| 91270-69-8

7-Bromonaphthalen-1-ol

CAS No.: 91270-69-8

4.5 *For Research Use Only !

Cat. No.: A119332 Purity: 97%

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Product Details of [ 91270-69-8 ]

CAS No. :91270-69-8
Formula : C10H7BrO
M.W : 223.07
SMILES Code : OC1=C2C=C(Br)C=CC2=CC=C1
MDL No. :MFCD17012439
Boiling Point : No data available
InChI Key :STJXOXMPODAEAK-UHFFFAOYSA-N
Pubchem ID :13215711

Safety of [ 91270-69-8 ]

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

Calculated chemistry of [ 91270-69-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 53.67
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.05
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

2.99
Log Po/w (WLOGP)?

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

3.31
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.

3.24
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

3.16
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.95

Water Solubility

Log S (ESOL):?

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

-3.72
Solubility 0.0422 mg/ml ; 0.000189 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.

-3.08
Solubility 0.186 mg/ml ; 0.000834 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

-4.36
Solubility 0.0098 mg/ml ; 0.000044 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

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.

-5.54 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

1.0
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)

1.23

Application In Synthesis of [ 91270-69-8 ]

* 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 [ 91270-69-8 ]

[ 91270-69-8 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 871888-40-3 ]
  • [ 91270-69-8 ]
  • [ 15719-64-9 ]
  • 2
  • [ 91270-69-8 ]
  • [ 102878-44-4 ]
  • 3
  • [ 88-14-2 ]
  • [ 90500-15-5 ]
  • [ 91270-69-8 ]
  • [ 91270-68-7 ]
  • 4
  • [ 477907-60-1 ]
  • [ 91270-69-8 ]
  • [ 91270-68-7 ]
  • 5
  • [ 91270-69-8 ]
  • [ 77-78-1 ]
  • [ 33295-53-3 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate;tetrabutylammomium bromide; In acetonitrile; for 2.75h;Heating / reflux; Preparation of 7-Bromo-1-methoxynaphthalene. [CHEMMOL-00140] [0466] A slurry of <strong>[91270-69-8]7-bromo-1-naphthol</strong> (8.89 g, 39.9 mmol), potassium carbonate (8.26 g, 59.8 mmol), dimethyl sulfate (5.66 mL, 59.8 mmol) and tetrabutylammonium bromide (0.085 g, 0.264 mmol) in acetonitrile (160 mL) was heated at reflux for 2 h 45 min. The reaction was cooled to room temperature, and water was added (200 mL). The mixture was then extracted (1.x.100, 1.x.40 mL) with CH2Cl2. The combined organic layers were washed (1.x.40 mL) with saturated aqueous NaHCO3 solution, dried over MgSO4, and concentrated. The residue was purified by medium pressure chromatography (100percent hexanes) to give the intermediate title compound as a yellow oil (8.42 g, 89percent). FDMS m/e=236 M+.
  • 7
  • γ-<4-bromo-phenyl>-paraconic acid [ No CAS ]
  • [ 91270-69-8 ]
  • 8
  • 2,7-dibromo-3,4-dihydro-2<i>H</i>-naphthalen-1-one [ No CAS ]
  • [ 91270-69-8 ]
  • 9
  • [ 88-14-2 ]
  • polymeric 1-(2-carboxyaryl)-triazene [ No CAS ]
  • [ 91270-69-8 ]
  • [ 91270-68-7 ]
  • 10
  • [ 580-13-2 ]
  • [ 91270-69-8 ]
  • 11
  • [ 91270-69-8 ]
  • 2-(8-methoxynaphthalin)-phosphonsaeurediethylester [ No CAS ]
  • 12
  • [ 20776-50-5 ]
  • [ 91270-69-8 ]
  • 13
  • [ 21740-00-1 ]
  • [ 91270-69-8 ]
  • 14
  • [ 91270-69-8 ]
  • [ 99971-69-4 ]
  • 15
  • [ 91270-69-8 ]
  • [ 859450-54-7 ]
  • 16
  • [ 91270-69-8 ]
  • [ 33295-55-5 ]
  • 17
  • [ 91270-69-8 ]
  • [ 5773-97-7 ]
  • 18
  • [ 91270-69-8 ]
  • [ 33295-54-4 ]
  • 19
  • [ 91270-69-8 ]
  • [ 33295-66-8 ]
  • 20
  • [ 345995-25-7 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
27.3% With lithium chloride; In DMF (N,N-dimethyl-formamide); for 0.5h;Heating / reflux; The crude mixture of 2,5-dibromo-1-tetralone (16.08 g, 52.9 mmol,), LiCl (5.61 g, 132 mmol), and 120 mL of dry DMF were combined under an N2 atmosphere and heated to reflux (155° C.). The mixture turned dark brown. HPLC showed complete consumption of the starting material in just 0.5 h. After cooling to room temperature, the mixture was diluted with 1 N HCl (200 mL) and extracted three times with Et2O (100 mL, 25 mL, 25 mL). The Et2O layers were combined to give a brown hazy mixture (some emulsion). After stirring with decolorizing carbon (10 g, Calgon ADP) and filtration through hyflo supercel, a clear light yellow solution was obtained. This solution was extracted with 3 N NaOH (100 mL, 25 mL), leaving the non-naphtholic byproducts behind. The brown NaOH extracts were combined, acidified to pH 1 with conc. HCl, and extracted with CH2Cl2 (100 mL, 25 mL). The combined CH2Cl2 layers formed a deep red solution. After stirring with decolorizing carbon (5 g, Darco G-60) and filtration through hyflo supercel, the solution was again light yellow. An equal volume of heptane was added, and the CH2Cl2 was distilled away. When the temperature reached 75° C., gray precipitate became evident. This increased substantially on cooling to room temperature. Following filtration and drying in vacuo at 50° C., a product mixture of gray solid (5.92 g, 50.2percent) was obtained. HPLC showed this to be a mixture of 7-bromo-1-naphthol (48.3percent) and 5-bromo-1-naphthol (50.8percent). However, 1H NMR (CDCl3) integration showed that the actual ratio was about 9/1 5-Br/7-Br. Preparative reverse phase HPLC gave one peak of 5-bromo-1-naphthol as a white solid (3.22 g, 27.3percent).
27.3% The crude mixture of 2,5-dibromo-1-tetralone (16.08 g, 52.9 mmol,), LiCl (5.61 g, 132 mmol), and 120 mL of dry DMF were combined under an N2 atmosphere and heated to reflux (?155 C.). The mixture turned dark brown. HPLC showed complete consumption of the starting material in just 0.5 h. After cooling to room temperature, the mixture was diluted with 1 N HCl (200 mL) and extracted three times with Et2O (100 mL, 25 mL, 25 mL). The Et2O layers were combined to give a brown hazy mixture (some emulsion). After stirring with decolorizing carbon (10 g, Calgon ADP) and filtration through hyflo supercel, a clear light yellow solution was obtained. This solution was extracted with 3 N NaOH (100 mL, 25 mL), leaving the non-naphtholic byproducts behind. The brown NaOH extracts were combined, acidified to pH 1 with conc. HCl, and extracted with CH2Cl2 (100 mL, 25 mL). The combined CH2Cl2 layers formed a deep red solution. After stirring with decolorizing carbon (5 g, Darco G-60) and filtration through hyflo supercel, the solution was again light yellow. An equal volume of heptane was added, and the CH2Cl2 was distilled away. When the temperature reached 75 C., gray precipitate became evident. This increased substantially on cooling to room temperature. Following filtration and drying in vacuo at 50 C., a product mixture of gray solid (5.92 g, 50.2percent) was obtained. HPLC showed this to be a mixture of 7-bromo-1-naphthol (48.3percent) and 5-bromo-1-naphthol (50.8percent). However, 1H NMR (CDCl3) integration showed that the actual ratio was about 9/15-Br/7-Br. Preparative reverse phase HPLC gave one peak of 5-bromo-1-naphthol as a white solid (3.22 g, 27.3percent).
  • 21
  • [ 148378-71-6 ]
  • [ 345995-25-7 ]
  • [ 52927-23-8 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
27.3% With lithium chloride; In DMF (N,N-dimethyl-formamide); at 155℃; for 0.5h;Heating / reflux; of 5-Bromo-1-naphthalenol. [0096] The crude mixture of 2,5-dibromo-1-tetralone (16.08 g, 52.9 mmol,), LiCl (5.61 g, 132 mmol), and 120 mL of dry DMF were combined under an N2 atmosphere and heated to reflux (155° C.). The mixture turned dark brown. HPLC showed complete consumption of the starting material in just 0.5 h. After cooling to room temperature, the mixture was diluted with 1 N HCl (200 mL) and extracted three times with Et2O (100 mL, 25 mL, 25 mL). The Et2O layers were combined to give a brown hazy mixture (some emulsion). After stirring with decolorizing carbon (10 g, Calgon ADP) and filtration through hyflo supercel, a clear light yellow solution was obtained. This solution was extracted with 3 N NaOH (100 mL, 25 mL), leaving the non-naphtholic byproducts behind. The brown NaOH extracts were combined, acidified to pH 1 with conc. HCl, and extracted with CH2Cl2 (100 mL, 25 mL). The combined CH2Cl2 layers formed a deep red solution. After stirring with decolorizing carbon (5 g, Darco G-60) and filtration through hyflo supercel, the solution was again light yellow. An equal volume of heptane was added, and the CH2Cl2 was distilled away. When the temperature reached 75° C., gray precipitate became evident. This increased substantially on cooling to room temperature. Following filtration and drying in vacuo at 50° C., a product mixture of gray solid (5.92 g, 50.2percent) was obtained. HPLC showed this to be a mixture of 7-bromo-1-naphthol (48.3percent) and 5-bromo-1-naphthol (50.8percent). However, 1H NMR (CDCl3) integration showed that the actual ratio was about 9/1 5-Br/7-Br. Preparative reverse phase HPLC gave one peak of 5-bromo-1-naphthol as a white solid (3.22 g, 27.3percent).
  • 22
  • [ 91270-69-8 ]
  • [ 74-88-4 ]
  • [ 33295-53-3 ]
YieldReaction ConditionsOperation in experiment
88% With potassium carbonate; In acetone; at 65℃; for 2h; Step E: Potassium carbonate (3.3 g, 23.9 mmol) and methyl iodide (1.5 ml, 23.9 mmol) were added to a solution of the product from Step D (2.7 g, 11.9 mmol) in acetone (40 ml) at room temperature and the mixture was stirred at 65° C. for 2 hours. The solids were filtered, rinsed with ethyl acetate and the filtrate was evaporated. The residue was dissolved in ethyl acetate and washed with water twice. The aqueous layers were extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulfate to give 7-bromo-1-methoxynaphthalene (2.5 g, 88percent) after chromatography (19:1 heptane/ethyl acetate): 1H NMR (300 MHz, CDCl3) delta 8.49 (d, J=2.1 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.59 (dd, J=8.7, 2.1 Hz, 1H), 7.39-7.43 (m, 2H), 6.85 (dd, J=5.4, 3.0 Hz, 1H), 3.15 (s, 3H).
  • 23
  • [ 32281-97-3 ]
  • [ 91270-69-8 ]
YieldReaction ConditionsOperation in experiment
56% Step D: A solution of tetrabutylammonium tribromide (11.8 g, 24.4 mmol) in dichloromethane (80 ml) was added dropwise to a solution of the product from Step C (5.0 g, 22.2 mmol) in dichloromethane (20 ml) and methanol (20 ml) at room temperature over 1 hour. At completion of the addition, the mixture was stirred at room temperature for 15 hours and was then concentrated. The residue was taken into dichloromethane and was washed with saturated sodium bicarbonate three times. The organic layer was concentrated and the residue was dissolved in dimethylformamide (100 ml). Lithium carbonate (5.3 g, 71.1 mmol) and lithium bromide (4.1 g, 46.6 mmol) were added and the resulting mixture was stirred at 140° C. for 1.5 hours. After cooling to room temperature, the solids were filtered and rinsed with ethyl acetate. The filtrate was washed with water four times and dried over sodium sulfate to give 7-bromonaphthalen-1-ol (2.7 g, 56percent): 1H NMR (300 MHz, CDCl3) delta 8.41 (d, J=1.8 Hz, 1H), 7.68 (d, J=8.7 Hz, 1H), 7.57 (dd, J=8.7, 1.8 Hz, 1H), 7.41 (d, J=8.4 Hz, 1H), 7.28-7.35 (m, 1H), 6.62 (d, J=7.2 Hz, 1H), 5.80 (br s, 1H).
  • 24
  • [ 91270-69-8 ]
  • [ 96-32-2 ]
  • [ 1149374-96-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h; A mixture of <strong>[91270-69-8]7-bromonaphthalen-1-ol</strong> (0.10 g), lambda/,lambda/-dimethylformamide (2.0 mL) and potassium carbonate (0.081 g) was treated with methyl bromoacetate (0.048 mL), and the resulting mixture was stirred at room temperature for 1 hour. The mixture was diluted with water, extracted with diethyl ether and the combined extracts were washed with a saturated aqueous sodium hydrogen carbonate solution and water and then dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography on silica gel, eluting <n="22"/>T/GB2008/003758with a mixture of petroleum ether and dichloromethane (5:1 by volume) to afford the title compound as a colourless oil (0.10 g).1H NMR (DMSO-d6): delta 3.69 (s, 3H), 5.00 (s, 2H), 6.97 (d, J = 7.4 Hz, 1H), 7.41 (t, J = 8.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.63 (dd, J = 2.1 , 8.7 Hz, 1H), 7.85 (d, J = 8.7 Hz, 1 H), 8.29 (d, J = 2.1 Hz1 IH).
  • 25
  • [ 91270-69-8 ]
  • [ 93267-04-0 ]
  • methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(8-hydroxynaphthalen-2-yl)propanoate [ No CAS ]
  • 26
  • [ 91270-69-8 ]
  • (S)-2-((tert-butoxycarbonyl)amino)-3-(8-hydroxynaphthalen-2-yl)propanoic acid [ No CAS ]
  • 27
  • [ 91270-69-8 ]
  • (S)-2-amino-N-((R)-6-benzyl-1,2,3,4-tetrahydroquinolin-4-yl)-3-(8-hydroxynaphthalen-2-yl)propanamide [ No CAS ]
  • 28
  • [ 91270-69-8 ]
  • C34H37N3O4 [ No CAS ]
 

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