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Chemical Structure| 766-96-1 Chemical Structure| 766-96-1
Chemical Structure| 766-96-1

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Synonyms: 1-Bromo-4-ethynylbenzene

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Product Details of 4-Bromophenylacetylene

CAS No. :766-96-1
Formula : C8H5Br
M.W : 181.03
SMILES Code : C1=C(C=CC(=C1)Br)C#C
Synonyms :
1-Bromo-4-ethynylbenzene
MDL No. :MFCD00168822
InChI Key :LTLVZQZDXQWLHU-UHFFFAOYSA-N
Pubchem ID :136603

Safety of 4-Bromophenylacetylene

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H319-H372-H410
Precautionary Statements:P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330
Class:9
UN#:3077
Packing Group:

Application In Synthesis of 4-Bromophenylacetylene

* 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 [ 766-96-1 ]

[ 766-96-1 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 766-96-1 ]
  • [ 591-50-4 ]
  • [ 13667-12-4 ]
YieldReaction ConditionsOperation in experiment
93% With copper(l) iodide; potassium carbonate; In ethanol; for 3h;Reflux; General procedure: A flame-dried 50mL round-bottom flask equipped with amagnetic stirbar and a rubber septum were charged witharyl halide (1.0mmol), terminal alkyne (1.1mmol), CuI(0.05mmol), K2CO3(2.0mmol) and CL-salen-Pd(II) (1.0%mmol). Ethanol (5.0mL) was then added and the mixturewas heated to reflux under air atmosphere for 3h. Afterextraction with ethyl acetate, drying over anhydrous MgSO4,filtration and concentration, the crude product was purifiedby column chromatography.
86% With piperidine; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; General procedure: To a stirred solution of 1.0 mmol of aryl halide in 4 mL of DMF,1.0 mmol of terminal alkyne, 1.5 mmol of piperidine and 0.2 mol%of Pd/Fe3O4NPs were added and the mixture was heated on anoil bath at 110C for 24 h under inert atmosphere (N2). After com-pletion of the reaction (as monitored by TLC), the reaction mixturewas cooled to room temperature and the catalyst was separatedusing a magnetic separator. The solvent was evaporated at reducedpressure, and the residue was subjected to gel permeation chro-matography to afford pure products. All the products are knowncompounds and the spectral data and melting points were identicalto those reported in the literature.
86% With piperidine; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; Green chemistry; General procedure: To a stirred solution of 1.0 mmol of aryl halide in 4 mL of DMF,1.0 mmol of terminal alkyne, 1.5 mmol of piperidine and 0.2 mol%of Pd/Fe3O4NPs were added and the mixture was heated on anoil bath at 110C for 24 h under inert atmosphere (N2). After com-pletion of the reaction (as monitored by TLC), the reaction mixturewas cooled to room temperature and the catalyst was separatedusing a magnetic separator. The solvent was evaporated at reducedpressure, and the residue was subjected to gel permeation chro-matography to afford pure products. All the products are knowncompounds and the spectral data and melting points were identicalto those reported in the literature
48.2% With C19H25CuN5(1+)*F6P(1-); potassium carbonate; In N,N-dimethyl-formamide; at 135 - 140℃;Sealed tube; General procedure: A 20mL scintillation vial was charged with a Teflon stir bar, copper complex (0.1mmol), 76 potassium carbonate (0.75mmol), aryl iodide (0.5mmol), 77 phenylacetylene (0.75mmol) in 5mL non-anhydrous DMF in air. The vial was sealed and placed in an oil bath with pre-adjusted temperature at 135-140C. After the allowed time, the reaction mixture was cooled down, diluted with 25-30mL ethyl acetate, and filtered through a pad of silica gel. The solvent was then removed under vacuum and the residue was purified by column chromatography using mixtures of hexane and ethyl acetate to obtain analytically pure product.

  • 2
  • [ 766-96-1 ]
  • [ 19591-17-4 ]
  • N-(2-((4-bromophenyl)ethynyl)phenyl)acetamide [ No CAS ]
  • 3
  • [ 766-96-1 ]
  • [ 4181-20-8 ]
  • tris-4,4',4''-(4-bromophenylethynyl)triphenylamine [ No CAS ]
  • 4
  • [ 40263-57-8 ]
  • [ 766-96-1 ]
  • [ 934328-77-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 90℃; for 4h;Product distribution / selectivity; To 4-bromophenylactetylene (4.3 g) was added <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (5.25 g), bis(triphenylphosphine)palladium dichloride (1.5 g), copper (I) iodide (0.58 g) and triethylamine (100 ml_). The reaction was stirred at 9O0C1 under nitrogen, for 4 h. The reaction was cooled, diluted with EtOAc (400 ml.) and washed twice with saturated ammonium chloride solution, brine and then concentrated. The crude product was dissolved in DCM, filtered and purified by ISCO companion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane (30-100%) to give the title compound. MS calcd for (C13H8BrNO + H)+: 274/276 MS found (electrospray): (M+H)+ = 274/276
A suspension of bis(triphenylphosphine)palladium dichloride (92 mg) and copper (I) iodide (430 mg) in DMF (7.5 ml.) was treated with triethylamine (4.6 mL) and heated to 7O0C. 4- Bromophenylacetylene (3.98 g) and <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (6.12 g) were dissolved in DMF (13 mL) and added dropwise to the mixture over 80 min. The mixture was heated at 7O0C for 19 h and cooled to 370C. Water (45 mL) was added over 10 min and the resulting suspension was filtered, washing with 1 :1 DMF:water (2 x 60 mL) and then water (40 mL). The wet solid was suspended in 3:1 toluene: MeOH (70 mL), heated to reflux for ~ 30 mins and cooled. Charcoal (1.13 g) was added and the mixture was refluxed for 1 h. The mixture was cooled, filtered through silica (11.3 g) and washed with 3:1 toluene:MeOH (2 x 20 mL). The filtrate was concentrated to 80% of its volume and iso-propanol (60 mL) was added. The mixture was further concentrated to 80% of its volume, and the suspension was then allowed to cool to ambient temperature overnight. The mixture was cooled further to 50C, filtered and washed with cold iso-propanol (2 x 9 mL). The solid was dried in vacuo to give the title compound.1H NMR (d6-DMSO):. δ 8.51 (1 H, bd), 8.05 (1 H, d), 7.93 (2H, d), 7.8-7.7 (3H, m), 7.35 (1 H, dd).
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 90℃; for 4h; To 4-bromophenylactetylene (4.3 g) was added <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (5.25 g), bis(triphenylphosphine)palladium dichloride (1.5 g), copper (I) iodide (0.58 g) and triethylamine (100 ml_). The reaction was stirred at 9O0C, under nitrogen, for 4 h. The reaction was cooled, diluted with EtOAc (400 ml.) and washed twice with saturated ammonium chloride solution, brine and then concentrated. The crude product was dissolved in DCM, filtered and purified by ISCO companion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane (30-100%) to give the title compound. MS calcd for (C13H8BrNO + H)+: 274/276 MS found (electrospray): (M+H)+ = 274/276
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 50℃; for 3h; Intermediate 39 2-(4-Bromophenyl)furo[3,2-b]pyridineTo 4-bromophenylactetylene (1.65 g) was added <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (2.02 g), bis(triphenylphosphine)palladium dichloride (575 mg), copper (I) iodide (225 mg) and triethylamine (35 ml_). The reaction was stirred at 5O0C, under nitrogen, for 3 h. The reaction was cooled, diluted with DCM (250 ml_) and washed with saturated ammonium chloride solution, brine and then concentrated. The crude product was purified by ISCO companion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane to give the title compound.MS calcd for (C13H8BrNO + H)+: 274/276MS found (electrospray): (M+H)+ = 274/276
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 50℃; for 3h; Intermediate 4 2-(4-Bromophenyl)furo[3,2-]pyridineTo 4-bromophenylactetylene (1.65 g) was added <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (2.02 g), bis(triphenylphosphine)palladium dichloride (575 mg), copper (I) iodide (225 mg) and triethylamine (35 mL). The reaction was stirred at 5O0C, under nitrogen, for 3 h. The reaction was cooled, diluted with DCM (250 mL) and washed with saturated ammonium chloride solution, brine and then concentrated. The crude product was purified by ISCOCompanion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane to give the title compound.MS calcd for (C13H8BrNO + H)+: 274/276 MS found (electrospray): (M+H)+ = 274/276
With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; at 90℃; for 4h;Neat (no solvent); Intermediate 3 2-(4-Bromophenyl)furo[3,2-b]pyridineT )> <( ))- BrTo 4-bromophenylactetylene (4.3 g) was added <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (5.25 g), bis(triphenylphosphine)palladium dichloride (1.5 g), copper (I) iodide (0.58 g) and triethylamine (100 mL). The reaction was stirred at 9O0C, under nitrogen, for 4 h. The reaction was cooled, diluted with EtOAc (400 mL) and washed twice with saturated ammonium chloride solution, brine and then concentrated. The crude product was dissolved in DCM, filtered and purified by ISCO Companion silica chromatography eluting with a gradient of ethyl acetate in cyclohexane (30-100%) to give the title compound. MS calcd for (Ci3H8BrNO + H)+: 274/276 MS found (electrospray): (M+H)+ = 274/276

  • 5
  • [ 766-96-1 ]
  • [ 19337-60-1 ]
  • [ 934330-97-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 50℃; for 2.5h; Dichloropalladium bistriphenylphosphine (0.14 g) and copper (I) iodide (0.036 g) were added to a degassed solution of Intermediate 68 (0.89 g), bromophenyl acetylene (1.02 g) and triethylamine (2.11 mL) in THF (12 ml_). The mixture was heated at 5O0C under nitrogen for 2.5 h. The reaction was allowed to cool and was evaporated in vacuo. The residue was partitioned between DCM and water. The organics were separated using a hydrophobic frit and were evaporated in vacuo. The crude material was purified by ISCO Companion silica <n="64"/>chromatography, eluting with a gradient 0-70percent EtOAc in cyclohexane to give the title compound.1H NMR (d6-DMSO) delta 9.57 (1 H, s), 9.07 (1H, s), 7.61 (2H, d), 7.46 (2H, d), 6.83 (2H, dt),6.04 (1 H, t).
  • 6
  • [ 1075-35-0 ]
  • [ 766-96-1 ]
  • [ 941-55-9 ]
  • [ 1283598-90-2 ]
  • 7
  • [ 766-96-1 ]
  • [ 98-80-6 ]
  • [ 13667-12-4 ]
  • 8
  • [ 766-96-1 ]
  • [ 61676-62-8 ]
  • [ 1034287-04-1 ]
  • 9
  • [ 766-96-1 ]
  • phenyl(triphenyl-λ5-phosphanyl)gold [ No CAS ]
  • [ 13667-12-4 ]
  • 10
  • [ 766-96-1 ]
  • [ 75-75-2 ]
  • [ 64-19-7 ]
  • [ 7500-37-0 ]
  • [ 19826-89-2 ]
YieldReaction ConditionsOperation in experiment
86% With 8-methylquinoline 1-oxide; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); at 20℃; for 8h; General procedure: A mixture of 8-methylquinoline 1-oxide (62.0 mg, 0.39 mmol), MsOH (32.4 mg, 0.33 mmol), and Ph3PAuNTf2 (11.4 mg, 0.015mmol) was added to a soln of the appropriate alkyne 1 (0.30 mmol) in AcOH (5 mL), and the mixture was stirred at r.t. until the reaction was complete (TLC). The mixture was then concentrated and the residue was purified by chromatography (silica gel, hexanes-EtOAc).
  • 11
  • [ 766-96-1 ]
  • [ 154237-70-4 ]
  • [ 1560949-47-4 ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80℃; for 4h;Inert atmosphere; To a solution of <strong>[154237-70-4]4-bromo-nicotinonitrile</strong> (1.10 g, 6.00 mmol) in DMF (20 ml) are added bis(triphenylphosphine)-palladium(ll)-chloride (211 mg, 0.30 mmol), copper(l) iodide (34 mg, 0.18 mmol), triethylamine (1.66 ml, 12.0 mmol) and 1-bromo-4-ethynyl-benzene (1.19 g, 6.6 mmol). The mixture is flushed with nitrogen, heated to 80C and stirred in a closed reaction vial at this temperature for 4 hours. The reaction mixture is allowed to cool to room temperature and partitioned between water and dichloromethane. The organic phase is washed with 1 N HCI, dried over sodium sulfate and evaporated under vacuum. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to give 4-(4-bromo- phenylethynyl)-nicotinonitrile as light yellow powder; HPLC/MS 2.09 min (B), [M+H] 283/285.
  • 12
  • [ 766-96-1 ]
  • [ 100-63-0 ]
  • [ 13667-12-4 ]
  • 13
  • [ 766-96-1 ]
  • benzenediazonium o-benzenedisulfonimide [ No CAS ]
  • [ 13667-12-4 ]
  • 15
  • [ 766-96-1 ]
  • [ 160976-02-3 ]
  • 5-bromo-2-((4-bromophenyl)ethynyl)-1,3-difluorobenzene [ No CAS ]
  • 16
  • [ 766-96-1 ]
  • [ 14752-66-0 ]
  • (E)-1-bromo-4-(2-((4-chlorophenyl)sulfonyl)-1-iodovinyl)benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With di-tert-butyl peroxide; iodine; In ethanol; water; at 60℃; for 2h;Green chemistry; General procedure: I2 (0.5 mmol) was added to a solution of alkynes (0.5 mmol),sodium benzenesulfnates (1.0 mmol) and DTBP (1.0 mmol)in C2H5OH: H2O (2 mL:2 mL), and the reaction mixture wasstirred and heated at 60C for 2.0 h. Then, the mixture wascooled to room temperature, quenched by Na2S2O3, dilutedwithwaterandextractedbyCH2Cl2 (10mL ×3).Thecombined organic layer was washed with water and dried over anhydrousNa2SO4. The solvent was removed in vacuum and the targetcompound was obtained by column chromatography on silicagel (petroleum ether: ethyl acetate = 15: 1, v: v).
  • 17
  • [ 766-96-1 ]
  • [ 84868-02-0 ]
  • C25H35BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% The obtained 5.51 g of 1-bromo-4-ethynylbenzene and 735 mg of NaH coated with 60 wt% of mineral oil were dissolved in 47 mL of dried THF and stirred for 30 minutes. After confirming that hydrogen gas no longer escapes from the reaction mixture, a solution of 2.56 g of 4- (trans-4'-n-pentylcyclohexyl) cyclohexanone dissolved in 47 ml of dry THF was added. The reaction mixture was stirred at room temperature for 20 hours, and the reaction was terminated with aqueous NH4Cl solution. Extracted with CH2Cl2, and the combined organic layers were washed with brine. The organic layer was dried over MgSO4 and filtered, and the resulting filtrate was concentrated under reduced pressure. Purification by column chromatography (SiO2, Hexanes: EtOAc = 6: 1) yielded 3.12 g of Compound 5.
  • 18
  • [ 766-96-1 ]
  • [ 80-17-1 ]
  • [ 13667-12-4 ]
  • 19
  • [ 766-96-1 ]
  • [ 1147-23-5 ]
  • C17H16BrN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 - 80℃;Inert atmosphere; <strong>[1147-23-5]5-<strong>[1147-23-5]iodocytidine</strong></strong>(0.48 g, 2 mol) was added to 100 ml of the reaction tube under nitrogen atmosphere,4-bromophenylacetylene (0.54 g 3 mol),Bis triphenylphosphine palladium dichloride (0.03g, 0.1mmol),Cuprous iodide (0.03 g, 0.12 mmol), 40 ml of triethylamine and 15 ml of N, N-dimethylformamide were reacted at 50 to 80 C for 6 to 10 hours. The solvent was removed in vacuo, diluted with 30 ml of methanol, and the insoluble solid was removed by filtration. Silica gel was added and the solvent was removed by rotary evaporation. The solvent was removed by methanol / dichloromethane mixed solvent to give 0.41 g of nucleoside derivative 3 (yellow solid) in a yield of 86%.
  • 20
  • [ 766-96-1 ]
  • [ 211029-67-3 ]
  • tert-butyl 3-((4-bromophenyl)ethynyl)pyridin-4-ylcarbamate [ No CAS ]
 

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