771-15-3|2-Bromonaphthalen-1-ol| Ambeed

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Quality Control of [ 771-15-3 ] Purity: 97% SDS Specification

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Product Details of [ 771-15-3 ]

CAS No. :	771-15-3
Formula :	C₁₀H₇BrO
M.W :	223.07
SMILES Code :	OC1=C(Br)C=CC2=C1C=CC=C2
MDL No. :	MFCD00274158
InChI Key :	LOHOSHDZQVKDPS-UHFFFAOYSA-N
Pubchem ID :	150849

Safety of [ 771-15-3 ]

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

Computational Chemistry of [ 771-15-3 ] 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 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.22
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.23
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.31
Log P_o/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 P_o/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 P_o/w? Consensus Log P_o/w: Average of all five predictions	3.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.87
Solubility	0.0298 mg/ml ; 0.000133 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.	-3.33
Solubility	0.105 mg/ml ; 0.00047 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	Yes
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.	-5.37 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)	1.18

Application In Synthesis of [ 771-15-3 ]

* 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 [ 771-15-3 ]

[ 771-15-3 ] Synthesis Path-Downstream 1~35

1
[ 110-86-1 ]
[ 51114-70-6 ]
[ 771-15-3 ]

References: [1]Chemische Berichte,1935,vol. 68,p. 1169,1175.

2
[ 507-19-7 ]
[ 90-15-3 ]
[ 571-57-3 ]
[ 771-15-3 ]

References: [1]Chemistry and industry,1957,p. 660.

3
[ 507-19-7 ]
[ 90-15-3 ]
[ 771-15-3 ]

References: [1]Chemistry and industry,1957,p. 660.

4
[ 90-15-3 ]
[ 771-15-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,2-ethanediylbis(triphenylphosphonium) ditribromide; In methanol; dichloromethane; at 20℃; for 0.0833333h;	General procedure: To a mixture of anilines or phenols (0.7 mmol) the brominatingagent (1) (0.72 g, 0.7 mmol) in dichloromethane(30 ml)-methanol (15 ml) was added. The reactionmixture was stirred at room temperature until decolorizationof the orange solution took place. The progress of thereaction was monitored by TLC (eluent: n-hexane/ethylacetate, 7:3). After completion of the reaction, the solventwas evaporated and diethyl ether (10 ml) was added to theresidue. The supernatant was decanted and the insolubleresidue was washed by ether (3 × 10 ml). The combinedether extracts were dried on magnesium sulfate and also evaporated under vacuum to afford monobromo anilines ormonobromo phenols which was purified by flash columnchromatography over silica gel (n-hexane/ethyl acetate,7:3).
84%	With polyethylene glycol entrapped potassium tribromide; In neat (no solvent); for 0.2h;Green chemistry;	The bromination reactions were carried out in solvent free manner. In a typical reaction, PEG·KBr3 (1mmol, 4.3g) was added to the aromatic substrate (1mmol) in a mortar and was ground for the desired reaction time. The progress of the reaction was monitored by TLC (10% ethyl acetate/hexane). After completion of the reaction, the product was extracted with ethyl acetate and evaporated under vacuum to obtain the pure brominated product. The products were characterized by IR and NMR spectra (see Supporting information).
72.4%	With N-Bromosuccinimide; In dichloromethane; at 40℃;Alkaline conditions;	1-Naphthol (10 g, 69.36 mmol)and diisopropylamine (0.972 mL, 6.94 mmol) was dissolved indichloromethane (100 mL). N-Bromosuccinimide (13.58 g, 76.3 mmol)was carefully added and the reaction mixture was stirred at 40 Covernight. The resulting mixture was allowed to cool to roomtemperature, quenched with 2M H2SO4, and extracted withdichloromethane. The combined organic layer was dried overanhydrous sodium sulfate and concentrated in vacuo. The crudeproduct was purified by silica gel column eluting with petroleumether: ethyl acetate (20/1) to give the desired product (11.2 g, yield72.4%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.23 - 8.21 (m,1H), 7.76 - 7.73 (m, 1H), 7.50 - 7.48 (m, 2H), 7.44 (d, J=8.8 Hz, 1H),7.28 (d, J=8.8 Hz, 1H), 5.97 (s, 1H). ESI-MS: [M-H]- m/z :221.0.

70%	With tetrabutylammomium bromide; isoquinolinium chlorochromate; In water; at 25 - 30℃; for 5h;	General procedure: Phenol (1 mmol, 10 mL) dissolved in 1M PEG-600, isoquinolinium dichromate (IQDC) or isoquinolinium chlorochromate (IQCC) reagent, and tetrabutylammonium halide (TBAX) (1.1 mmol each) were taken in a reaction flask and refluxed with constant stirring at about 25 to 30 C, till the completion of reaction, as as certainedby thin layer chromatography. Then the contents of reaction were diluted with ethyl acetate (10 mL) and separated from aqueous layer. Organic layer was then washed two to three time swith 5 mL water and separated. Finally, the resultant mass is dried over sodium sulphate. The anhydrous ethyl acetate layerwas separated under reduced pressure to give crude product, which was further purified by column chromatography (silicagel, 100-200 mesh) using EtOAc-hexane (3:7). For the separation and recyclization of PEG, aqueous mother liquor (reaction mixture of PEG-600 and water) was treated with ether because PEG is insoluble in ether. The aqueous layer obtained after the removal of ether, was then distilled directly at 100 C to remove water and recover PEG-600. The recovered PEG-600 could be reused for consecutive runs.
69%	With potassium hydrogensulfate; potassium bromide; isoquinolinium chlorochromate; In water; at 20℃;	General procedure: A centimolar (0.01mol) organic substrate (phenols, anilines,or acetanilides), about 0.01 mol of potassium halide (KBr orKI), 0.001 mol hypervalent Cr (VI) reagent (IQCC orIQDC), and solvent (DCE or ACN) were taken in a previouslycleaned round-bottom flask. About 50 mg of KHSO4 isalso added to the reaction flask. The reaction mixture isrefluxed for about 4-5 h at 50-60C. Progress of the reactionwas monitored by TLC technique. After completion, thereaction mixture is treated with 5% sodium thiosulfate solutionfollowed by the addition of ether. The aqueous layer wasseparated, dried, and evaporated under vacuum, and purifiedwith column chromatography using chloroform:n-hexane(9:1) as eluent to get pure product.General.

References: [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1309 - 1315.
[2]Journal of Organic Chemistry,2005,vol. 70,p. 4267 - 4271.
[3]Chinese Journal of Chemistry,2010,vol. 28,p. 2221 - 2225.
[4]RSC Advances,2014,vol. 4,p. 25898 - 25903.
[5]Journal of the Iranian Chemical Society,2016,vol. 13,p. 2019 - 2028.
[6]Tetrahedron Letters,2006,vol. 47,p. 8693 - 8697.
[7]Tetrahedron Letters,2015,vol. 56,p. 5646 - 5650.
[8]Journal of the American Chemical Society,2013,vol. 135,p. 18052 - 18055.
[9]Journal of Organic Chemistry,2014,vol. 79,p. 3725 - 3730.
[10]Chinese Chemical Letters,2013,vol. 24,p. 866 - 868.
[11]Tetrahedron,2005,vol. 61,p. 1863 - 1870.
[12]International Journal of Chemical Kinetics,2018,vol. 50,p. 804 - 812.
[13]Bioorganic and Medicinal Chemistry,2019,vol. 27.
[14]Tetrahedron Letters,2009,vol. 50,p. 4781 - 4784.
[15]Asian Journal of Chemistry,2018,vol. 30,p. 1892 - 1896.
[16]Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry,2016,vol. 46,p. 832 - 837.
[17]Organic Letters,2015,vol. 17,p. 1126 - 1129.
[18]Chemische Berichte,1957,vol. 90,p. 1537,1541.
[19]Journal of Organic Chemistry,1967,vol. 32,p. 2358 - 2360.
[20]Journal fur praktische Chemie (Leipzig 1954),1985,vol. 327,p. 998 - 1006.
[21]Organometallics,2010,vol. 29,p. 478 - 483.
[22]European Journal of Medicinal Chemistry,2013,vol. 68,p. 58 - 71.
[23]European Journal of Organic Chemistry,2014,vol. 2014,p. 4315 - 4326.

5
[ 90-15-3 ]
[ 571-57-3 ]
[ 2050-49-9 ]
[ 771-15-3 ]

References: [1]Gazzetta Chimica Italiana,1987,vol. 117,p. 83 - 86.

6
[ 90-15-3 ]
[ 571-57-3 ]
[ 771-15-3 ]

References: [1]Synlett,1997,vol. 1997,p. 1241 - 1242.
[2]Synlett,1997,vol. 1997,p. 1241 - 1242.
[3]Chemistry - An Asian Journal,2011,vol. 6,p. 2130 - 2146.
[4]Canadian Journal of Chemistry,1988,vol. 66,p. 2556 - 2564.
[5]Synthesis,1980,p. 487 - 489.
[6]Catalysis Letters,2010,vol. 137,p. 190 - 201.

7
[ 51114-70-6 ]
[ 90-15-3 ]
[ 771-15-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 1745 - 1752.

8
[ 771-15-3 ]
(E)-3,3'-Dibromo-[1,1']binaphthalenylidene-4,4'-dione [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1993,vol. 48,p. 1401 - 1407.

9
[ 123674-35-1 ]
[ 771-15-3 ]
2,4-dibromo-7,8-dimethyl-1-naphthol [ No CAS ]

References: [1]Journal of Organic Chemistry,1989,vol. 54,p. 5667 - 5675.

10
[ 136131-47-0 ]
[ 771-15-3 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 6704 - 6708.

11
[ 91348-39-9 ]
[ 771-15-3 ]
[ 909697-44-5 ]

References: [1]Synthetic Communications,2006,vol. 36,p. 1879 - 1886.

12
[ 771-15-3 ]
[ 100-44-7 ]
[ 76939-81-6 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4024 - 4027.

13
[ 771-15-3 ]
3-isopropyl-2-phenylnaphtho[1,2-b]furan [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4024 - 4027.

14
[ 771-15-3 ]
[ 98655-51-7 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4024 - 4027.

15
[ 529-34-0 ]
ethyl halide [ No CAS ]
[ 771-15-3 ]

References: [1]Tetrahedron Letters,2005,vol. 46,p. 4187 - 4191.

16
[ 90-15-3 ]
3.4.5-trimethoxy-benzenediazonium-⁽¹⁾-salt [ No CAS ]
[ 771-15-3 ]

References: [1]Journal of Heterocyclic Chemistry,1996,vol. 33,p. 1371 - 1385.

17
[ 118-92-3 ]
[ 771-15-3 ]

References: [1]Journal of Organic Chemistry,1991,vol. 56,p. 6704 - 6708.

18
[ 4185-62-0 ]
[ 771-15-3 ]

References: [1]Journal of the Chemical Society,1944,p. 538.

19
[ 771-15-3 ]
[ 19938-27-3 ]

References: [1]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 1251 - 1261.

20
[ 771-15-3 ]
[ 19938-26-2 ]

References: [1]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 1251 - 1261.

21
[ 771-15-3 ]
[ 1079-66-9 ]
[ 1158430-75-1 ]

References: [1]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1309 - 1315.
[2]Organometallics,2010,vol. 29,p. 478 - 483.

22
[ 771-15-3 ]
[ 1178529-73-1 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 4781 - 4784.

23
[ 771-15-3 ]
[ 98-59-9 ]
[ 1178529-60-6 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 4781 - 4784.

24
(2S,4R,5S)-(-)-oxazaPB [ No CAS ]
[ 771-15-3 ]
(R(P))-[(1S,2R)-N-ephedrino](1-hydroxy-2-naphthyl)(phenyl)phosphine-P-borane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: To a cold (0 °C) solution of o-bromophenol (74.4 g, 0.43 mol) in diethyl ether (500 mL) was added under stirring n-BuLi (2.1 M in hexanes, 410 mL, 0.86 mol) or NaH (0.45 mol) followed by n-BuLi (2.1 M in hexanes, 0.43 mol).(1) The mixture was stirred at rt overnight (>99percent conversion by GC). To this mixture at -20 °C, a THF (300 mL) solution of (-)-OxazaPB (94.1 g, 0.33 mol) was slowly added and the resulting mixture left to warm up to rt. After 4 h stirring, the reaction was quenched with H2O (20 mL). The residue was partitioned between CH2Cl2 (500 mL) and H2O (500 mL), and the organic layer was dried over Na2SO4 then concentrated. The crystalline solid was washed with hexane/ CH2Cl2 95:5 (200 mL) and dried in vacuum to afford 1a as colorless crystals (115.3 g, 92percent)