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Chemical Structure| 85199-06-0 Chemical Structure| 85199-06-0
Chemical Structure| 85199-06-0

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Product Details of 2,5-Dimethylphenylboronic acid

CAS No. :85199-06-0
Formula : C8H11BO2
M.W : 149.98
SMILES Code : C1=C(C=CC(=C1B(O)O)C)C
MDL No. :MFCD01863525
InChI Key :OOMZKLJLVGQZGV-UHFFFAOYSA-N
Pubchem ID :2734347

Safety of 2,5-Dimethylphenylboronic acid

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

Application In Synthesis of 2,5-Dimethylphenylboronic acid

* 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 [ 85199-06-0 ]

[ 85199-06-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 57310-39-1 ]
  • [ 85199-06-0 ]
  • [ 7495-37-6 ]
YieldReaction ConditionsOperation in experiment
51% With N,N-dimethyl acetamide; palladium diacetate; potassium carbonate; tricyclohexylphosphine; Trimethylacetic acid; at 150℃; for 10h;Inert atmosphere; In a reactor equipped with a reflux condenser, a mixture of 3-bromo-4-chlorotoluene (compound CM20a above, 30.82 g, 150 mmol), 2,5-dimethylphenylboronic acid (compound CM20b above, 24.75 g, 165 mmol), anhydrous potassium carbonate (124.39 g, 900 mmol), palladium(II) acetate (0.67 g, 6 mmol), tricyclohexylphosphine (1.68 g, 12 mmol), dimethylacetamide (commercially available dehydrated product, 600 ml) and pivalic acid (15.32 g and 150 mmol) was stirred for 10 hours under an argon gas atmosphere while heating in an oil bath set to 150 C. After diluting with toluene (500 ml), rinsing and liquid separation were carried out 3 times using ion-exchanged water. Next, there was repeated twice a procedure of adding active white clay (product of Wako Pure Chemical Industries, Ltd., 60 g) to the obtained oil layer, stirring the mixture for 2 hours, and then passing it through Celite and a silica gel pad to remove the insolubles. After removing the solvent from the obtained solution by concentration under reduced pressure, recrystallizing purification was carried out (with a mixed solvent of chloroform and ethanol), and the deposited crystals were filtered out and dried under reduced pressure to obtain the target CM20c (35.5 g) as a solid with a faint yellow-white appearance. Yield: 51%. The HPLC-area percent value of the obtained compound CM20c measured under analysis conditions 1 was 99.3% (UV254 nm)
  • 2
  • [ 16657-07-1 ]
  • [ 85199-06-0 ]
  • 4-(2,5-dimethylphenyl)indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 90℃; for 16h; 38 g (180 mmol) of tripotassium phosphate, 100 mL of distilled water, 100 mL of DME, 10 g (66.7 mmol) of 2,5-dimethylphenylboronic acid, 10.8 g (55.4 mmol) of <strong>[16657-07-1]7-bromo-1H-indene</strong>, 969 mg (1.38 mmol) of dichlorobis(triphenylphosphine)palladium, and 1.30 g (4.96 mmol) of triphenyl phosphine were put into a 500-mL glass reactor in that order, and then heated under reflux at 90 C. for 16 hours. This was left cooled to room temperature, and the reaction liquid was poured into 100 mL of distilled water, transferred into a separatory funnel, and extracted three times with hexane. 6 mL of concentrated hydrochloric acid was added to the hexane solution at room temperature, then stirred at room temperature for 30 minutes, the palladium compound was precipitated, filtered away through filter paper, and the filtrate was washed three times each with saturated saline water and distilled water, and then dried with sodium sulfate. Sodium sulfate was filtered away, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent, hexane/diisopropyl ether=20/1) to give 12.2 g (yield 100%) of 4-(2,5-dimethylphenyl)indene as a colorless liquid.
  • 3
  • [ 16657-07-1 ]
  • [ 85199-06-0 ]
  • 2,2-bis(4-(2,5-dimethylphenyl)-inden-1-yl)propane [ No CAS ]
  • 4
  • [ 6277-17-4 ]
  • [ 85199-06-0 ]
  • [ 799765-72-3 ]
YieldReaction ConditionsOperation in experiment
99% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In toluene; at 90℃; for 12h;Schlenk technique; Inert atmosphere; Sealed tube; General procedure: The preparation of substituted 2-nitrobiphenyls: An oven-dried Schlenk flask containing amagnetic stir bar was charged with the appropriate aryl iodide (1.0 equiv), Pd2dba3 (2.0 mol%),S-Phos (8.0 mol%), the aryl boronic acid (1.5 equiv) and anhydrous powdered K3PO4 (3.0equiv). The Schlenk flask was capped with a rubber septum and then evacuated and backfilledwith argon (this sequence was repeated three times). Dry toluene (0.15 M) was added throughthe septum via syringe and the resulting mixture was stirred at room temperature for ~2 min.The Schlenk flask was sealed. The reaction mixture was heated at 90 C with vigorous stirringfor 24 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate,filtered through a thin pad of silica gel (eluting with ethyl acetate) and concentrated underreduced pressure. The crude material was purified by flash chromatography on silica gel.
  • 5
  • [ 66127-01-3 ]
  • [ 85199-06-0 ]
  • 3-(2,5-dimethylphenyl)-1,10-phenanthroline [ No CAS ]
 

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