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Chemical Structure| 90-11-9 Chemical Structure| 90-11-9

Structure of 1-Bromonaphthalene
CAS No.: 90-11-9

Chemical Structure| 90-11-9

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Product Details of [ 90-11-9 ]

CAS No. :90-11-9
Formula : C10H7Br
M.W : 207.07
SMILES Code : BrC1=C2C=CC=CC2=CC=C1
MDL No. :MFCD00003868
InChI Key :DLKQHBOKULLWDQ-UHFFFAOYSA-N
Pubchem ID :7001

Safety of [ 90-11-9 ]

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

Computational Chemistry of [ 90-11-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 51.65
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.36
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

3.62
Log Po/w (WLOGP)?

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

3.6
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.

4.05
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

3.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.47

Water Solubility

Log S (ESOL):?

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

-4.08
Solubility 0.0173 mg/ml ; 0.0000837 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-3.31
Solubility 0.102 mg/ml ; 0.000492 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

-4.93
Solubility 0.00243 mg/ml ; 0.0000117 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

Low
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.

-4.99 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<2.0
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)

1.28

Application In Synthesis of [ 90-11-9 ]

* 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 [ 90-11-9 ]

[ 90-11-9 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 90-11-9 ]
  • [ 75-36-5 ]
  • [ 46258-62-2 ]
YieldReaction ConditionsOperation in experiment
91% With aluminum (III) chloride; In 1,2-dichloro-ethane; at 0 - 20℃; for 24h; A solution of 1-Bromo-naphthalene (10 g, 48.3 mmol) and acetyl chloride (4.2 ml, 58 mmol) in 1,2-dichloroethane (100 ml) was cooled to 0C and aluminum chloride (14.4 g, 108 mmol) was added portion wise. The mixture was stirred at RT for 24 hours. The reaction mixture was poured into ice-water (100 ml). The two layers were separated and the water layer was extracted with diethyl ether (3 x 150 ml). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to give an orange colored oil. The 1- (4-bromo-naphtalen-1-yl)-ethanone was purified by flash chromatography (cyclohexane/ethylacetate: 95/5), yielding an yellow oil (91% yield). The 1- (4-bromo-naphtalen-1-yl)-ethanone oxime was prepared according to the procedure described for Compound 22, yielding a white powder (98% yield). Activated zinc dust (24.7 g, 379 mmol) was added portion wise to a suspension of the oxime (10.0 g, 37.9 mmol) in acetic acid (40 ml). The mixture was stirred at RT for 2 hours. The zinc dust was removed by filtration and acetic acid was removed under reduced pressure. Water (100 ml) was added and the pH was adjusted to pH = 13 with 1N NaOH. The water layer was extracted with EtOAc (3 x 100 ml). The combined organic layers were dried over MgS04, filtered and the solvent was removed under reduced pressure, yielding a yellow oil (70% yield). Boc20 (7.1 g, 31.8 mmol) was added to a solution of the amine (6.6 g, 26.5 mmol) in 1,4-dioxane (50 ml). The reaction mixture was stirred at RT for 2 hours. The solvent was removed under reduced pressure and the product was purified by flash chromatography (cyclohexane/EtOAc: 95/5), yielding a yellow powder (75% yield). The bromide (350 mg, 1 mmol) was dissolved in THF (13 ml) /water (2 ml). Potassium acetate (100 mg, 1 mmol), 1,3-bis-diphenylphosphinopropane (9.0 mg, 0.02 mmol) and palladium- (11)-acetate (9.0 mg, 0.04 mmol) were added. The mixture was stirred at 50 atm CO pressure and 150C for 3 hours. The reaction mixture was filtered, the filtrate dried over MgS04 and the solvent was removed under reduced pressure to give a yellow- greenish oil (300 mg). The 4- (l-tert-butoxycarbonylamino-ethyl)-naphthalene-l- carboxylic acid was purified by flash chromatography (DCM/MeOH : 90/10), yielding a white powder (14% yield). The title product was prepared according to the procedure of Compound 31, starting from 4- (1-tert-butoxycarbonylamino-ethyl)-naphthalene-1-carboxylic acid (44 mg) and 4-amino-pyridine (67% yield).'H NMR (300 MHz, , DMSO-d6): 1.64 ppm (d, 3H, J = 6.6 Hz); 5.3 ppm (q, 1H, J = 6.5 Hz), 7.71 ppm (m, 1H), 8.00 ppm (d, 1H, J = 7.7 Hz), 8.32 ppm (m, 1H), 8. 35 ppm (d, 1H, J = 7.3 Hz), 8.81 ppm (d, 2H, J = 7.2 Hz), 12.2 ppm (s, 1H).
91% aluminum (III) chloride; In 1,2-dichloro-ethane; at 0 - 20℃; for 24h; Section IExample I-IPreparation of Compound 301 and 302General Procedure I-AA solution of 1-Bromo-naphthalene (I-Ia; 2 g, 9.6 mmol) and acetyl chloride (0.84 mL, 11.6 mmol) in 1,2-dichloroethane (30 mL) was cooled to 0 C. and aluminum chloride (2.88 g, 21.6 mmol) was added portion wise. The mixture was stirred at r.t. for 24 hours. The reaction mixture was poured into ice-water (100 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (150 mL×3). The combined organic layers were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure to give compound I-Ib as an orange oil (2.16 g, yield 91%). 1H NMR (400 MHz, CDCl3) delta 8.6 (m, 1H), 8.3 (m, 1H), 7.8 (d, J=8.0 Hz, 1H), 7.66 (d, J=7.6 Hz, 1H), 7.58 (m, 2H), 2.63 (s, 3H). MS (ESI) m/z (M+H)+ 250.
62% With aluminum (III) chloride; In carbon disulfide; at 0 - 20℃; for 120h;Inert atmosphere; To a stirred solution of 1.00 g (4.8 mmol) of 1-bromonaphthalene in 15 mL of carbon disulfide at 0 C in a flame-dried flask under N2 was added 0.42 g (5.3 mmol) of acetyl chloride. This solution was stirred at 0 C for 10 min and 0.84 g (6.3 mmol) of AlCl3 was added. The reaction was stirred at 0 C for 3 days followed by 2 days of stirring at ambient temperature. The reaction mixture was poured over ice and concentrated HCl, extracted with ether, washed with NaHCO3 and brine. After drying (MgSO4) the solution was concentrated in vacuo and purified by chromatography (petroleum ether/ether, 95:5) to give 0.75 g (62%) of 1-acetyl-4-bromonaphthalene as a brown oil: 1H NMR (300 MHz, CDCl3) delta 2.74 (s, 3H), 7.65-7.69 (m, 2H), 7.74 (d, J = 6 Hz, 1H), 7.83 (d, J = 6 Hz, 1H), 8.32-8.35 (m, 1H), 8.72-8.75 (m, 1H); 13C NMR (75.5 MHz, CDCl3) delta 30.1, 126.4, 127.5, 127.8, 128.2, 128.4, 128.7, 128.7, 131.2, 132.3, 135.2, 201.0; GC/MS (EI) m/z (rel intensity) 248 (46), 233 (100), 205 (44). The data agree in all respects with those reported previously.
  • 2
  • [ 90-11-9 ]
  • [ 108-24-7 ]
  • [ 46258-62-2 ]
  • 3
  • [ 3167-63-3 ]
  • [ 90-11-9 ]
  • [ 53575-08-9 ]
  • 5
  • [ 90-11-9 ]
  • [ 771-15-3 ]
  • 6
  • [ 75-15-0 ]
  • [ 7446-70-0 ]
  • [ 90-11-9 ]
  • [ 75-36-5 ]
  • [ 46258-62-2 ]
  • 7
  • [ 90-11-9 ]
  • [ 326-64-7 ]
  • (5-chloro-2-trifluoromethoxy-phenyl)-naphthalen-1-yl-amine [ No CAS ]
  • 8
  • [ 1455-20-5 ]
  • [ 90-11-9 ]
  • [ 1044231-45-9 ]
YieldReaction ConditionsOperation in experiment
96% With dibromo[1-benzyl-3-(2,3,5,6-tetramethylbenzyl)benzimidazole-2-ylidene]pyridine palladium(II); potassium acetate; In N,N-dimethyl acetamide; at 130℃; for 1h;Schlenk technique; Inert atmosphere; General procedure: KOAc (1.0 mmol), aryl-bromide derivatives (1.0 mmol), heteroaryl derivatives (2-nbutylthiazole,<strong>[1455-20-5]2-<strong>[1455-20-5]n-butylthiophene</strong></strong> and 2-n-butylfuran) (2.0 mmol) and Pd-NHC-PEPPSIcomplexes 2a-e (0.01 mmol) were dissolved in N,N-dimethylacetamide (DMAc) (2 mL)in a small Schlenk tube under argon as described in literature [49]. The reaction mixturewas stirred in an oil bath at 130 C for 1 h, then cooled to room temperature, andthe solvent was removed under vacuum. The obtained residue was purified by columnchromatography (silica gel 60-120 mesh) by using diethyl ether/n-hexane (1:5) as eluentto afford the pure product. The purity of the compounds was checked by gaschromatography (GC) and gas chromatography-mass spectrometry (GC-MS).Conversions were calculated by taking into account the conversion of aryl bromidesto products.
  • 10
  • [ 4805-22-5 ]
  • [ 90-11-9 ]
  • [ 148875-83-6 ]
  • 5,5'-bis(1-naphthyl)-2,2'-bithiophene [ No CAS ]
  • 11
  • [ 90-11-9 ]
  • [ 1626-24-0 ]
  • [ 604-53-5 ]
  • [ 605-02-7 ]
  • 12
  • [ 90-11-9 ]
  • [ 870778-88-4 ]
  • [ 1246888-95-8 ]
  • 13
  • [ 98-01-1 ]
  • [ 90-11-9 ]
  • [ 51792-36-0 ]
  • 14
  • [ 90-11-9 ]
  • [ 219834-96-5 ]
  • (R)-2-(benzyloxy)-1,1'-binaphthalene [ No CAS ]
  • 2-benzyloxy-[1,1']binaphthalenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(benzonitrile)palladium(II) dichloride; cesium fluoride; (R)-4-phenyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine; In tetrahydrofuran; at 70℃; for 4h;Inert atmosphere; Schlenk technique; General procedure: A Schlenk tube was charged with 0.25 mmol of naphthyl halide, 0.0025 mmol of Pd precursor, 0.00375 mmol of the appropriate chiral ligand, 0.5 mmol of boronic acid, and 1.25 mmol of base. Anhydrous solvent was added, the flask was sealed and the mixture was stirred and heated at the corresponding temperature. The reaction mixture was treated with 10 mL of distilled water, extracted with 3 x10 mL of CH2Cl2, dried over MgSO4, and purified by flash chromatography to obtain the corresponding products. The conversion and selectivity was monitored by gas chromatography. The ee values were determined by High Performance Liquid Chromatography.
  • 15
  • [ 90-11-9 ]
  • [ 1533519-92-4 ]
  • 17
  • [ 381-98-6 ]
  • [ 90-11-9 ]
  • [ 78622-62-5 ]
  • 19
  • [ 90-11-9 ]
  • [ 19616-28-5 ]
  • [ 865-48-5 ]
  • [ 50337-75-2 ]
  • [ 1609171-46-1 ]
  • 20
  • [ 90-11-9 ]
  • [ 22237-13-4 ]
  • 1-(4-ethoxyphenyl)naphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With bis[1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene]palladium(II) iodide; potassium tert-butylate; In ethanol; at 20℃; for 3h;Inert atmosphere; General procedure: Bromo compound (0.5 mmol, 1eq), boronic acid ( 0.6mmol, 1.2 eq )was dissolved in absolute ethanol (10 mL) in a 25 mL two neck flask . The contents of the flask were degassed with nitrogen. Potassium t-butoxide (0.75 mmol, 1.5 eq) was added followed by (0.5 mol %) of the complex, [Bis[1-((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)-3-methyl-4-phenyl-1,2,3-triazol-5-ylidene]palladium (II) iodide (11)]. The contents of the flask were stirred at room temperature under nitrogen atmosphere. The reaction was monitored by thin layer chromatography. After completion of the reaction (disappearance of the bromo compound) solvent was evaporated and the residue was dissolved in water (20 mL) and extracted with dichloromethane (3 x 20 mL). The dichloromethane layer was washed with saturated sodium chloride solution (20 mL) and water (20 mL). The organic layer was evaporated; the compound was purified by column chromatography using hexane as solvent.
  • 21
  • [ 90-11-9 ]
  • [ 633-70-5 ]
  • [ 914306-89-1 ]
YieldReaction ConditionsOperation in experiment
83.1% a) 2,6-Dibromo-9,10-bis(naphth-1-yl)anthracene The corresponding Grignard reagent is prepared from 30.5 ml (220 mmol) of 1-bromonaphthalene and 5.5 g (225 mmol) of magnesium in 500 ml of THF. 36.6 g (100 mmol) of 2,6-dibromoanthraquinone are added to this Grignard reagent, the mixture is refluxed for 6 h and allowed to cool, 15 ml of acetic acid are added, the mixture is evaporated to dryness, the residue is taken up in 500 ml of DMF, 56.9 g (300 mmol) of tin(II) chloride are added, and the mixture is refluxed for 5 h. After cooling, 200 ml of 2N hydrochloric acid are added, the mixture is stirred for a further 1 h, the solid is filtered off with suction, washed three times with 200 ml of 2N hydrochloric acid each time, three times with 300 ml of water each time, and three times with 200 ml of ethanol each time, dried under reduced pressure and recrystallised once from DMF. Yield: 48.9 g (83 mmol), 83.1% of theory; purity: 98% according to 1H-NMR.
  • 23
  • [ 90-11-9 ]
  • [ 90766-48-6 ]
  • 24
  • [ 90-11-9 ]
  • [ 219834-96-5 ]
  • [ 1451092-92-4 ]
  • 25
  • [ 90-11-9 ]
  • [ 34907-53-4 ]
  • C20H21BO [ No CAS ]
 

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