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Chemical Structure| 1625-92-9 Chemical Structure| 1625-92-9

Structure of 1625-92-9

Chemical Structure| 1625-92-9

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Product Details of [ 1625-92-9 ]

CAS No. :1625-92-9
Formula : C16H18
M.W : 210.31
SMILES Code : CC(C1=CC=C(C2=CC=CC=C2)C=C1)(C)C
MDL No. :MFCD00222366
InChI Key :CDOYZTOFTGTGBC-UHFFFAOYSA-N
Pubchem ID :137120

Safety of [ 1625-92-9 ]

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

Application In Synthesis of [ 1625-92-9 ]

* 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 [ 1625-92-9 ]

[ 1625-92-9 ] Synthesis Path-Downstream   1~5

  • 1
  • potassium phosphate [ No CAS ]
  • phenylboron dihydroxide [ No CAS ]
  • [ 3972-65-4 ]
  • [ 224311-51-7 ]
  • [ 1625-92-9 ]
YieldReaction ConditionsOperation in experiment
tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; 1,2-dimethoxyethane; EXAMPLE 27 Synthesis of 4-t-butylbiphenyl using K3PO4 as Base with 0.1 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and DME (1.5 mL) and 1-bromo-4-t-butylbenzene (0.17 mL, 1.0 mmol) were added through a rubber septum. A separate flask was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-(di-tert-butylphosphino)biphenyl (4.5 mmol, 0.015 mmol), and DME (1 mL). The mixture was stirred for 1 minute at room temperature, then 100 muL of this solution (0.1 mol percent Pd, 0.15 mol percent 2-(di-tert-butylphosphino)biphenyl) was added to the Schlenk tube followed by additional THF (1.5 mL). The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 2 minutes, then heated to 80° C. with stirring until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 199 mg 95percent) of a glassy solid.
199 mg (95%) tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; 1,2-dimethoxyethane; Example 27 Synthesis of 4-t-butylbiphenyl using K3PO4 as base with 0.1 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and DME (1.5 mL) and 1-bromo-4-t-butylbenzene (0.17 mL, 1.0 mmol) were added through a rubber septum. A separate flask was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-(di-tert-butylphosphino)biphenyl (4.5 mmol, 0.015 mmol), and DME (1 mL). The mixture was stirred for 1 minute at room temperature, then 100 muL of this solution (0.1 mol percent Pd, 0.15 mol percent 2-(di-tert-butylphosphino)biphenyl) was added to the Schlenk tube followed by additional THF (1.5 mL). The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 2 minutes, then heated to 80° C. with stirring until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 199 mg (95percent) of a glassy solid.
  • 2
  • phenylboron dihydroxide [ No CAS ]
  • [ 3972-65-4 ]
  • [ 224311-51-7 ]
  • [ 1625-92-9 ]
YieldReaction ConditionsOperation in experiment
202 mg (96%) With cesium fluoride;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; EXAMPLE 28 Synthesis of 4-t-butylbiphenyl using CsF as Base with 0.05 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboron dihydroxide (183 mg, 1.5 mmol), and cesium fluoride (456 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1.5 mL) and 1-bromo-4-t-butylbenzene (0.17 mL, 1.0 mmol) were added through a rubber septum. A separate flask was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-(di-tert-butylphosphino)biphenyl (4.5 mmol, 0.015 mmol), and THF (1 mL). The mixture was stirred for 1 minute at room temperature, then 50 muL of this solution (0.05 mol percent Pd, 0.075 mol percent 2-(di-tert-butylphosphino)biphenyl) was added to the Schlenk tube followed by additional THF (1.5 mL). The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 2 minutes, then heated to 80° C. with stirring until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 202 mg (96percent) of a glassy solid.
202 mg (96%) With cesium fluoride;tris-(dibenzylideneacetone)dipalladium(0); In tetrahydrofuran; Example 28 Synthesis of 4-t-butylbiphenyl using CsF as base with 0.05 mol percent Pd An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with phenylboron dihydroxide (183 mg, 1.5 mmol), and cesium fluoride (456 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1.5 mL) and 1-bromo-4-t-butylbenzene (0.17 mL, 1.0 mmol) were added through a rubber septum. A separate flask was charged with Pd2(dba)3 (4.6 mg, 0.005 mmol), 2-(di-tert-butylphosphino)biphenyl (4.5 mmol, 0.015 mmol), and THF (1 mL). The mixture was stirred for 1 minute at room temperature, then 50 muL of this solution (0.05 mol percent Pd, 0.075 mol percent 2-(di-tert-butylphosphino)biphenyl) was added to the Schlenk tube followed by additional THF (1.5 mL). The septum was removed, the tube was sealed with a teflon screw cap and the mixture was stirred at room temperature for 2 minutes, then heated to 80° C. with stirring until the starting aryl bromide had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (20 mL) and poured into a separatory funnel. The mixture was washed with 1M NaOH (20 mL), and the layers were separated. The aqueous layer was extracted with ether (20 mL), and the combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude material was then purified by flash chromatography on silica gel to give 202 mg (96percent) of a glassy solid.
  • 3
  • [ 1625-92-9 ]
  • [ 92-52-4 ]
  • [ 7116-95-2 ]
  • [ 644-08-6 ]
  • [ 5707-44-8 ]
  • [ 37909-95-8 ]
  • [ 10289-45-9 ]
  • 4
  • [ 3972-65-4 ]
  • [ 56-33-7 ]
  • [ 253185-03-4 ]
  • [ 1625-91-8 ]
  • [ 1625-92-9 ]
  • 5
  • [ 3972-65-4 ]
  • [ 56-33-7 ]
  • [ 1625-91-8 ]
  • [ 1625-92-9 ]
 

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