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Chemical Structure| 644-08-6 Chemical Structure| 644-08-6
Chemical Structure| 644-08-6

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4-Methylbiphenyl is an endogenous metabolite.

Synonyms: 4-Phenyltoluene

4.5 *For Research Use Only !

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Product Details of 4-Methylbiphenyl

CAS No. :644-08-6
Formula : C13H12
M.W : 168.23
SMILES Code : CC1=CC=C(C2=CC=CC=C2)C=C1
Synonyms :
4-Phenyltoluene
MDL No. :MFCD00008544
InChI Key :ZZLCFHIKESPLTH-UHFFFAOYSA-N
Pubchem ID :12566

Safety of 4-Methylbiphenyl

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of 4-Methylbiphenyl

* 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 [ 644-08-6 ]

[ 644-08-6 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 15499-27-1 ]
  • [ 29540-83-8 ]
  • [ 960-16-7 ]
  • [ 644-08-6 ]
  • [ 37909-95-8 ]
  • 2
  • phenylboron dihydroxide [ No CAS ]
  • [ 106-43-4 ]
  • argon [ No CAS ]
  • [ 224311-51-7 ]
  • [ 644-08-6 ]
YieldReaction ConditionsOperation in experiment
palladium diacetate; In tetrahydrofuran; EXAMPLE 26 General Procedure for Determining the Effect of Various Additives on the Preparation of 4-methylbiphenyl via Suzuki Coupling An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (4.5 mg, 0.015 mmol, 1.5 mol percent), phenylboron dihydroxide (183 mg, 1.5 mmol), additive (3.0 mmol), and 4-chlorotoluene (0.12 mL, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (2 mL) was added through a rubber septum. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was then diluted with ethyl acetate (30 mL) and poured into a separatory funnel. The mixture was washed with 2.0M NaOH (20 mL), followed by brine (20 mL). The organic layer was submitted for GC analysis giving the results tabulated below.
palladium diacetate; In tetrahydrofuran; Example 26 General Procedure for Determining the Effect of Various Additives on the Preparation of 4-methylbiphenyl via Suzuki Coupling An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (4.5 mg, 0.015 mmol, 1.5 mol percent), phenylboron dihydroxide (183 mg, 1.5 mmol), additive (3.0 mmol), and 4-chlorotoluene (0.12 mL, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (2 mL) was added through a rubber septum. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was then diluted with ethyl acetate (30 mL) and poured into a separatory funnel. The mixture was washed with 2.0M NaOH (20 mL), followed by brine (20 mL). The organic layer was submitted for GC analysis giving the results tabulated below.
  • 3
  • phenylboron dihydroxide [ No CAS ]
  • [ 106-43-4 ]
  • [ 224311-51-7 ]
  • KF [ No CAS ]
  • [ 644-08-6 ]
YieldReaction ConditionsOperation in experiment
158 mg (94%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; EXAMPLE 29 Optimized synthesis of 4-methylbiphenyl utilizing KF An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 4-chlorotoluene (0.12 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 158 mg (94percent) of the title compound.
158 mg (94%) With potassium fluoride;palladium diacetate; In tetrahydrofuran; Example 29 Optimized Synthesis of 4-methylbiphenyl Utilizing KF An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), phenylboron dihydroxide (183 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 4-chlorotoluene (0.12 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with 1.0 M NaOH (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 158 mg (94percent) of the title compound.
  • 4
  • [ 1625-92-9 ]
  • [ 92-52-4 ]
  • [ 7116-95-2 ]
  • [ 644-08-6 ]
  • [ 5707-44-8 ]
  • [ 37909-95-8 ]
  • [ 10289-45-9 ]
  • 5
  • [ 6843-66-9 ]
  • [ 106-49-0 ]
  • [ 644-08-6 ]
YieldReaction ConditionsOperation in experiment
General procedure: The concentration of0.25mol aniline was dissolved in the mixture of 63 ml HCl and 63 ml water in600 ml beaker. After cooled to 0-5 oC with stirring, anilinehydrochloride crystallization. Aqueous solution of sodium nitrite (18gdissolved in 40 ml water) was added into beaker dropwise with stirring, keepingthe temperature under 5 oC. 40 g of sodium tetrafluoroboratesolution dissolved in 80 ml water was added to the diazonium salt solution, andthen continue to stir for 10 minutes. The solid was immediately washed by 10 ml5 % solution of sodium tetrafluoroborate for three times after filtered, andthen washed by 15 ml methanol twice to afford diazonium salt.A mixture of arenediazonium tetrafluoroborate salt(0.5 mmol), Pd(OAc)2 (5 mol%), TBAF (0.5 mmol) and aryl silanes (0.6mmol) was stirred in water (1 mL) at room termperature for 6 h. Afterwards, thereaction solution was filtered through a filter paper and the solution wasextracted by Et2O (1 mL) for three times. The organic phase wascombined and evaporated under reduced pressure. The residue was purified on aSiO2 column to afford the desired product.
  • 6
  • [ 6843-66-9 ]
  • [ 824-79-3 ]
  • [ 644-08-6 ]
 

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