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[ CAS No. 580-13-2 ] {[proInfo.proName]}

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Chemical Structure| 580-13-2
Chemical Structure| 580-13-2
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Quality Control of [ 580-13-2 ]

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Product Citations

Product Citations

Lim, Taeho ; Ryoo, Jeong Yup ; Han, Min Su DOI: PubMed ID:

Abstract: In this study, we developed a simple transition-metal-free borylation reaction of aryl bromides. Bis-boronic acid (BBA), was used, and the borylation reaction was performed using a simple procedure at a mild temperature. Under mild conditions, aryl bromides were converted to arylboronic acids directly without any deprotection steps and purified by conversion to trifluoroborate salts. The functional group tolerance was considerably high. The mechanism study suggested that this borylation reaction proceeds via a radical pathway.

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Product Details of [ 580-13-2 ]

CAS No. :580-13-2 MDL No. :MFCD00004051
Formula : C10H7Br Boiling Point : No data available
Linear Structure Formula :- InChI Key :APSMUYYLXZULMS-UHFFFAOYSA-N
M.W : 207.07 Pubchem ID :11372
Synonyms :

Calculated chemistry of [ 580-13-2 ]      Expand+

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 : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 3.65
Log Po/w (WLOGP) : 3.6
Log Po/w (MLOGP) : 4.05
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.1
Solubility : 0.0166 mg/ml ; 0.0000802 mol/l
Class : Moderately soluble
Log S (Ali) : -3.34
Solubility : 0.0949 mg/ml ; 0.000458 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.93
Solubility : 0.00243 mg/ml ; 0.0000117 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.28

Safety of [ 580-13-2 ]

Signal Word:Warning Class:
Precautionary Statements:P501-P270-P264-P280-P337+P313-P301+P312+P330 UN#:
Hazard Statements:H302-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 580-13-2 ]

* 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 [ 580-13-2 ]

[ 580-13-2 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 81-16-3 ]
  • [ 580-13-2 ]
  • 2
  • [ 3167-63-3 ]
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  • [ 57277-25-5 ]
  • 3
  • [ 580-13-2 ]
  • [ 62171-59-9 ]
  • [ 72040-90-5 ]
  • 2-(8,8-Dimethyl-bicyclo[4.2.0]octa-1(6),2,4-trien-2-yl)-naphthalene [ No CAS ]
  • 4
  • [ 256652-04-7 ]
  • [ 580-13-2 ]
  • 6
  • [ 580-13-2 ]
  • [ 91270-69-8 ]
  • 7
  • [ 18711-15-4 ]
  • [ 580-13-2 ]
  • [ 259667-62-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; Reference Example 23 4,6-Dichloro-3-hydroxy-3-(2-naphthyl)oxindole To a solution of 2-bromonaphthalene (2.952 g) in anhydrous THF (25 mL) was added portion wise a solution of n-butyl lithium in n-hexane (1.55 N, 10.12 mL) at -78 C. The reaction solution was stirred for 30 minutes. To the mixture was then added portion wise a solution of <strong>[18711-15-4]4,6-dichloroisatin</strong> (1.54 g) in anhydrous THF (25 ml) for 50 minutes. The reaction mixture was stirred for 2 hours. Then the mixture was allowed to warm to room temperature. To the mixture was added 1N HCl and extracted by ethyl acetate. The organic phase was separated, washed with 1N HCl and brine and dried over MgSO4 and concentrated. Purification was carried out by silica gel chromatography (hexane:ethyl acetate, 2:1 to 1:1 gradient) to give the title compound (0.652 g, yield: 27%). 1H NMR (DMSO-d6, 300 MHz) delta 6.93 (1H, s), 6.96 (1H, d, J=1.7 Hz), 7.12 (1H, d, J=1.7 Hz), 7.23 (1H, m), 7.49 (2H, m), 7.80-7.94 (4H, m), 10.80 (1H, brs).
  • 9
  • [ 580-13-2 ]
  • [ 61676-62-8 ]
  • [ 256652-04-7 ]
YieldReaction ConditionsOperation in experiment
73% (1) Synthesis of Intermediate 1-1 (0232) 20.0 g (20 mmol) of 2-bromonaphthalene was dissolved in 50 mL of tetrahydrofuran (THF), and then 8.8 mL (22.0 mmol) of n-BuLi (2.5 M in hexane) was slowly dropwise added thereto at about -78 C. After the reaction solution was stirred at the same temperature for about 1 hour, 4.65 mL (25.0 mmol) of 2-isoproxy-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane was slowly dropwise added to the reaction solution, stirred at about -78 C. for about 1 hour, and then further stirred at ambient temperature for about 24 hours. After termination of the reaction, 30 mL of a 10% HCl aqueous solution and 30 mL of H2O were added thereto, followed by extraction three times with 50 ml of diethyl ether. An organic phase was collected and dried using magnesium sulfate, followed by evaporating the solvent. The resulting residue was purified by silica gel column chromatography to obtain 3.7 g of Intermediate 1-1 (Yield: 73%). This compound was identified by liquid chromatography-mass spectrometry (LC-MS). C16H19BO2: M+ 255.1
41% To a 500 mL 3 -necked round bottomed flask, charged were THF (300 mL) and 2-bromonaphthalene (10 g, 48.3 mmol) , and the mixture was chilled to -78C by using liquefied nitrogen. Then, n-BuLi (14.73 g, 53.1 mmol) was slowly added dropwise thereto. After stirring at ambient temperature for 1 hour, 2- isopropoxy-4, 4, 5, 5-tetramethyl- [1, 3, 2] -dioxaborolane (9.87 g) was slowly added dropwise at -78C to the mixture. After 12 hours, water is poured thereto, to quench the reaction. The reaction mixture was extracted with ether, dried over MgSO4 and evaporated by using a rotary evaporator to remove the solvent. The product was isolated via column chromatography (eluent: hexane/EA = 5/1) .Yield: 4.05 g (41%) m.p. : 93 C1H NMR (300 MHz, CDCl3, ppm): 7.81 (d, 4H), 7.29 (t, 3H), 1. 26 (m , 12H).
  • 10
  • [ 580-13-2 ]
  • [ 25015-63-8 ]
  • [ 91-20-3 ]
  • [ 256652-04-7 ]
  • 11
  • [ 580-13-2 ]
  • [ 201230-82-2 ]
  • [ 2243-82-5 ]
  • 12
  • [ 580-13-2 ]
  • [ 90767-17-2 ]
  • [ 771-15-3 ]
  • 13
  • [ 680192-98-7 ]
  • [ 580-13-2 ]
  • [ 91-20-3 ]
  • [ 256652-04-7 ]
  • 14
  • [ 580-13-2 ]
  • [ 73183-34-3 ]
  • [ 256652-04-7 ]
YieldReaction ConditionsOperation in experiment
87.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In tetrahydrofuran; at 80℃; for 5h;Inert atmosphere; (1)In a 250mL three-vial bottle,With nitrogen,Add 0.02mol 2-bromonaphthalene dissolved in 100ml tetrahydrofuran (THF),Then add 0.024 mol of bis(pinacolato)diboron,0.0002mol(1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and 0.05 mole of potassium acetate were added,Stir the mixture,The above mixed solution of the reactants was heated to reflux at a reaction temperature of 80C for 5 hours;After the reaction is over,Cool and add 100 ml of water,The mixture was filtered and dried in a vacuum oven.The residue obtained is separated and purified through a silica gel column.Obtained 2-naphthaleneboronic acid pinacol ester; HPLC purity 99.8%, yield87.8%.
83% With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate; In 1,4-dioxane; at 110℃; for 6h; General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 mol%) was added, and the contents were refluxed on preheatedoil bath at 110 C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent.
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; for 24h; Sub B (3) (4.14g, 20mmol) then dissolved in toluene, bis pinacolato Todai boron ( 5.58g , 22mmol ) , Pd ( dppf ) Cl2 catalyst(0.44g, 0.6mmol), KOAc (5.89g, 60mmol) was added to a stirred for 24 hours and then by synthesizing the borate compound and then in the orderIn , then the resulting compound was separated through a silicagel column and recrystallized to obtain 3.8g of Sub B - 3 . (Yield: 75%)
75% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In toluene; for 24h; Sub 2-1-3 (4.14g, 20mmol) was dissolved in toluene, bis-pinacolato diboron (5.58g, 22mmol), Pd(dppf)Cl2 catalyst (0.44g, 0.6mmol), KOAc (5.89g, 60mmol )was added. A borate compound was synthesized by stirring for 24 hours after the addition, as, after the thus obtained compound was separated over a silicagel column and recrystallized to obtain 3.8g of Sub 2 (3). (Yield: 75%)
61% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 120℃; for 8h;Inert atmosphere; Fill a dry 500mL double-neck round bottom flask with nitrogen.Add 2-naphthalene bromide (20.6g, 0.1mol),Bis (pinacolato) diboron (25.4g, 0.1mol),Potassium acetate (19.6g, 0.2mol),[1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (0.005mol),1,4-dioxane (200 mL), reacted at 120 C for 8 hours;After the reaction was completed, it was cooled to room temperature, quenched with water, and extracted with dichloromethane (three times with 200 mL extraction). The extract was dried over anhydrous magnesium sulfate and spin-dried.The crude product was separated by silica gel column chromatography.2-naphthoboronic acid pinacol ester (15.5 g, yield 61%) was obtained.
47% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,2-dimethoxyethane; for 4h;Inert atmosphere; Reflux; 2eBromonaphthalene (299 mg, 1.14 mmol) KAcO (416 mg,4.24 mmol) and bis(pinacolato)diboron (558 mg,2.20 101 mmol) were dissolved in 50 mL of 1,2-dimethoxyethane (DME) and the mixture was purged with N2 gas. [1,10-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)complex with dichloromethane (Pd(dppf)Cl2CH2Cl2) (49 mg,5.94 102 mmol)was added to the resulting solution and refluxedfor 4 h. The mixture was extracted with ethyl acetate. The solutionwas washed withwater, and passed through phase separator paper.After the solvent was removed, the crude mixture was purified bysilica gel column chromatography (ethyl acetate:hexane 1:40) togive 1 as a yellow solid (170 mg, yield: 47%). 1H NMR (400 MHz,CDCl3): delta 8.37 (s, 1H), 7.89 (d, J 7.6 Hz 3H), 7.86e7.79 (m, 3H), 1.39(s, 12H). HRMS (ESI-TOF) calculated for C16H19BO2 [MNa] :276.1421, found: 276.1407.
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate; In 1,4-dioxane; at 20 - 80℃;Inert atmosphere; General procedure: The appropriate 2-iodothiophene (100mg,0.47mmol), bis(pinacolato)diboron(137mg, 0.57mmol), andbis(triphenylphosphine)palladium (II) dichloride (33.4mg,0.04mmol) were dissolved in dry 1,4-dioxane in an inertatmosphere. Potassium acetate (93.4mg,0.9521mmol) was then added at room temperature, and the mixturewas heated at 80C for 5-6 h. After solvent evaporation, water was added to theresidue extracted with ethyl acetate. The organic layer was washed with brine,and dried by distillation to obtain a crude product, which was used withoutfurther purification. Other aryl halide, 2-bromonaphthalene andbromoahthracene, also followed same procedure with 2-iodothiophene.

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[ 580-13-2 ]

Chemical Structure| 1262053-54-2

A1440475[ 1262053-54-2 ]

2-Bromonaphthalene-1,2,3,4,4a,8a-13C6

Reason: Stable Isotope

; ;