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[ CAS No. 16116-78-2 ] {[proInfo.proName]}

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Chemical Structure| 16116-78-2
Chemical Structure| 16116-78-2
Structure of 16116-78-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 16116-78-2 ]

CAS No. :16116-78-2 MDL No. :MFCD01863556
Formula : C11H13BrSi Boiling Point : -
Linear Structure Formula :- InChI Key :RNMSGCJGNJYDNS-UHFFFAOYSA-N
M.W : 253.21 Pubchem ID :4226980
Synonyms :

Calculated chemistry of [ 16116-78-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.37
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.42
Log Po/w (XLOGP3) : 4.81
Log Po/w (WLOGP) : 3.76
Log Po/w (MLOGP) : 4.45
Log Po/w (SILICOS-IT) : 2.55
Consensus Log Po/w : 3.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.78
Solubility : 0.00419 mg/ml ; 0.0000165 mol/l
Class : Moderately soluble
Log S (Ali) : -4.54
Solubility : 0.00726 mg/ml ; 0.0000287 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.6
Solubility : 0.00633 mg/ml ; 0.000025 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.51

Safety of [ 16116-78-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16116-78-2 ]

* 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.

  • Upstream synthesis route of [ 16116-78-2 ]
  • Downstream synthetic route of [ 16116-78-2 ]

[ 16116-78-2 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 16116-78-2 ]
  • [ 7511-49-1 ]
Reference: [1] Arkivoc, 2013, vol. 2013, # 3, p. 49 - 60
  • 2
  • [ 16116-78-2 ]
  • [ 3032-92-6 ]
Reference: [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 18, p. 3056 - 3059
  • 3
  • [ 589-87-7 ]
  • [ 1066-54-2 ]
  • [ 16116-78-2 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: at 20℃; for 0.0833333 h; Inert atmosphere
Stage #2: at 20℃; for 0.5 h; Inert atmosphere
In a two neck rbf containing TEA (200 ml) was added 1-Bromo-4-iodobenzene 5 (24.00 g, 84.83 mmol) at rt under nitrogen. Themixture was stirred for 5 min followed by addition ofethynyltrimethylsilane 2 (13.19 ml, 93.31 mmol), Pd(PPh3)2Cl2(2.98 g, 4.24 mmol) and CuI (1.62 g, 8.48 mmol). The reaction mixturewas stirred for 30 min at the same temperature. The reactionmixture was evaporated in vaccum to remove excess of TEA followedby addition of 1 N HCl until the pH reached to 1. The mixturewas then extracted with EtOAc/water. The organic layer waswashed with brine and dried over anhydrous MgSO4. The solventwas evaporated and the residue was purified by column chromatography(Hexane) to give the desired compound 6 (21.00 g)as a white solid; Yield = 98percent; 1H NMR (CDCl3, 500 MHz): d 7.19–7.06 (4H, m, ArAH), 0.00 (9H, s, ASi(CH3)3); 13C NMR (CDCl3,125 MHz): d 133.5, 131.6, 122.8, 122.3, 104.0, 95.7, 0.00.
96% at 20℃; for 1.5 h; Cooling with ice To an anhydrous triethylamine solution (30 mL), 4-iodo-bromobenzene(2.0 g, 7.07 mmol) was dissolved at room temperature.This solution was cooled in an ice bath, and Pd(PPh3)4 (0.20 g,0.18 mmol) and CuI (34.28 mg, 0.18 mmol) were added. Cold trimethylsilylacetylene solution (1.1 mL, 0.76 g, 7.78 mmol) wasthen added in a dropwise manner. The mixture was stirred in anice bath for 1.5 h, and then saturated NH4Cl aqueous solution(30 mL) was added. The product was extracted with CH2Cl2(3 50 mL), and the organic phases were combined and dried overNa2SO4. Purification by chromatography on silica gel gave a whitesolid (1.73 g, 6.82 mmol, 96percent yield). 1H NMR (CDCl3): d 7.45–7.41(m, 2H), 7.33–7.30 (m, 2H), 0.25 (s, 9H).
95% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 25℃; for 1.5 h; A mixture of 4-iodobromobenzene (2.01 g, 7.10 mmol), trimethylsilylacetylene (1.2 mL, 8.67 mmol), PdCl2(PPh3)2 (52 mg, 0.074 mmol), and CuI (15 mg, 0.079 mmol), NEt3 (5 mL) in THF (20 mL) was stirred at 25 °C. After stirring for 1.5 h, to the mixture was added aqueous 2 M HCl, and extracted with EtOAc (3 times). The organic phase was sequentially washed with brine, aqueous sat.NaHCO3, and brine, and dried with MgSO4. After concentration, the residue was purified with silicagel column chromatography (hexane to hexane/EtOAc = 8/2) to afford 4-(trimethylsilylethynyl)bromobenzene as colorless solids (1.71 g, 95percent). mp 56-59 °C (colorless plates); Rf: 0.65 (hexane); 1H NMR (CDCl3, 400 MHz): 0.06 (s, 9H), 7.13 (d, 2H, J = 8.5 Hz), 7.24 (d, 2H, J = 8.5 Hz); 13C NMR (CDCl3, 100 MHz):  -0.1, 95.6, 103.8, 122.1, 122.7, 131.5, 133.4; IR (KBr): vmax 2956, 2898, 2285, 2157, 1895, 1645, 1580, 1484, 1412, 1392, 1311, 1246, 1209, 1110, 1094, 1070, 1009, 844, 822 cm-1; HRMS (DART): [M+H]+ calcd for C11H13BrSi, 253.00481; found, 252.99518.
95% at 48℃; for 2 h; To a mixture of 1-bromo-4-iodobenzene(1) (3.0 g, 10.06 mmol), dichlorobis(triphenylphosphine)palladium (II) (28 mg, 0.04 mmol),and copper iodide (18 mg, 0.09 mmol) in triethylamine (30 ml) was added trimethylsilylacetylene(1.7 ml, 11.94 mmol), and stirred at 48C for 2 hours. Solvent was evaporatedunder reduced pressure, and the residue was chromatographed on silica gel with hexaneto give 2 (2.42 g, 95percent) in a white solid. 1H NMR (CDCl3, 400 MHz): δ = 0.25 (s, 9H),7.30(d, 2H), 7.40 (d, 2H). Anal. Calcd for C11H13BrSi: C, 52.17percent; H, 5.17percent. Found: C,52.29percent; H, 5.08percent
95% at 0℃; for 3 h; Inert atmosphere 10.0 g of 1-bromo-4-iodobenzene, 400 mg of Pd (OAc) 2, 170 mg of CuI and 250 mg of PPh3 were placed in a 500 mL flask and an argon atmosphere was made. This mixture was diluted with 28.6 g of dry TEA. The mixture was bubbled with argon to remove oxygen and the temperature was lowered to 0 & lt; 0 & gt; C. 4.16 g of (trimethylsilyl) acetylene slowly putThe reaction mixture was stirred for 3 hours. The reaction was quenched with aqueous NH4Cl and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered and concentrated. 8.50 g of [(4-Bromophenyl) ethynyl] (trimethyl) silane was obtained through column chromatography (SiO2, Hexanes: EtOAc = 15: 1)
93% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18 h; Inert atmosphere Compound 76.1. ((4-Bromophenyl)ethynyl)trimethylsiIane. Into a 100-mL three neck round-bottom flask, which was maintained with an inert atmosphere of nitrogen, was placed a solution of l -bromo-4-iodobenzene (1.00 g, 3.53 mmol) in tetrahydrofuran/TEA(9: l) (30 mL). PdCl2(PPh3)2 (50 mg, 0.07 mmol), Cul (13.4 mg, 0.07 mmol), and ethynyltrimethylsilane (748 \xL, 5.29 mmol) were added and the mixture was stirred for 18 h at room temperature, then concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with ethyl acetate (3 x 20 mL), dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield the title compound as a light yellow solid (0.83 g, 93percent
93% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 18 h; Inert atmosphere Compound 76.1. ((4-Bromophenyl)ethynyl)trimethylsilane.
Into a 100-mL three neck round-bottom flask, which was maintained with an inert atmosphere of nitrogen, was placed a solution of 1 -bromo-4-iodobenzene (1.00 g, 3.53 mmol) in tetrahydrofuran/TEA(9: l) (30 mL). PdCl2(PPh3)2 (50 mg, 0.07 mmol), Cul (13.4 mg, 0.07 mmol), and ethynyltrimethylsilane (748 μ, 5.29 mmol) were added and the mixture was stirred for 18 h at room temperature, then concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with ethyl acetate (3 x 20 mL), dried ( a2S04), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with petroleum ether as the eluent to yield the title compound as a light yellow solid (0.83 g, 93percent).
87% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 3 h; Inert atmosphere 1-bromo-4-iodobenzene (200.0 g, 704.8 mmol), (1,1 ‘-bis(diphenylphosphine)ferrocene)dichloropalladium(D) (25.8 g, 35.4 mmol), copper iodide (4.04 g, 21.2 mmol),triethylamine (295.6 ml, 2120 mmol), and tetrahydrofuran(1700 mE) were put in a 3 E round-bottomed flask under anitrogen atmosphere. Then, trimethyl silylacetylene (107.6 ml, 776.6 mmol) was added thereto in a dropwise fashion, and the mixture was stirred at room temperature for 3 hours. The reactant was filtered, and a solvent therein was removed. The resultant was purified through column chromatography to obtain an intermediate 1-11 (155.3 g, a yield:87percent).
71.5% at 0℃; for 5 h; Inert atmosphere 1-Bromo-4-iodobenzene (1a, 300 mg, 1.06 mmol),Pd(PPh34 (61.2 mg, 0.053 mmol), and CuI (20 mg,0.11 mmol) were dissolved in 10 mL of triethylamine and trimethylsilyl acetylene (1b, 176 mL, 1.27 mmol) was added slowly at 0° C. Then, reaction mixture was stirred under N2 atmosphere for 5 h and trimethylamine was distilled off under vacuo. The residue obtained was taken up in ethyl acetate and washed with distilledwater and brine. The organic layer was next driedover anhydrous MgSO4 and evaporated in vacuo togive the crude product. Then the crude product was purified by flash column chromatography on silica gel to give ((4-bromophenyl)ethynyl)trimethylsilane (1) as awhite solid (192 mg, 71.5percent).11 1H NMR (400 MHz,CDCl3: 7.40 (d, 8.4 Hz, 2H), 7.30 (d, 8.4 Hz, 2H),0.24 (s, 0.22 Hz, 9H).

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YieldReaction ConditionsOperation in experiment
86% With 3-aminopropyl-functionalized silica supported MCM-41-immobilized palladium(0)-[(pyridin-2-yl)methylidene]amine complex In tetrahydrofuran at 68℃; for 2 h; Inert atmosphere General procedure: A solution of Ar3In or (RC≡C)3In (0.37mmol, ca. 0.18M in dry THF) was added to a mixture of MCM-41-N,N-Pd(0) (25mg, 1molpercent) and aryl iodide (1mmol) in dry THF (2mL) under Ar. The resulting mixture was refluxed under Ar until the starting material had been consumed (TLC). After being cooled to room temperature, the mixture was diluted with Et2O (30mL) and filtered. The palladium catalyst was washed with DMF (2×5mL), Et2O (2×5mL) and reused in the next run. The filtrate was washed with sat. aq NaHCO3 (5mL), water (3×10mL) and dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash chromatography on silica gel to give the desired cross-coupling product.
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[2] Synthesis, 2005, # 3, p. 485 - 492
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  • 14
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  • 15
  • [ 16116-78-2 ]
  • [ 205877-26-5 ]
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  • [ 630127-51-4 ]
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  • 17
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  • [ 17573-94-3 ]
  • [ 910467-59-3 ]
YieldReaction ConditionsOperation in experiment
66% at 100℃; for 15 h; General procedure: N-(4-(Ethynyl)phenyl)carbazole (5a, 0.53g, 2.0mmol), 4-{2-(trimethylsilyl)ethynyl}-1-bromobenzene (0.76g, 3.0mmol), Cl2Pd(PPh3)2 (0.084g, 0.12mmol), PPh3 (0.052g, 0.20mmol), CuI (0.038g, 0.20mmol), and Et3N (20mL) were placed in a flask, and the mixture was stirred at 100°C for 15h. After stirring, the resulting precipitate was separated by atmospheric filtration, and the filtrate was poured into saturated aqueous NH4Cl solution (20mL). The crude product was extracted with AcOEt (20mL) three times and the combined organic layer was washed with brine (once). The organic layer was collected and dried over anhydrous Na2SO4, which was separated by filtration. The filtrate was evaporated in vacuo and subjected to silica-gel column chromatography (eluent: hexane/CH2Cl2=5/1) to obtain the coupling product 6a in 55percent yield (0.48g, 1.1mmol) as a white solid.
Reference: [1] Journal of Fluorine Chemistry, 2017, vol. 202, p. 54 - 64
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