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Chemical Structure| 930781-28-5 Chemical Structure| 930781-28-5

Structure of 930781-28-5

Chemical Structure| 930781-28-5

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Product Details of [ 930781-28-5 ]

CAS No. :930781-28-5
Formula : C14H22BrN
M.W : 284.24
SMILES Code : CC(C1=C(N(C)C)C(C(C)C)=CC(Br)=C1)C

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Application In Synthesis of [ 930781-28-5 ]

* 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 [ 930781-28-5 ]

[ 930781-28-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 50-00-0 ]
  • [ 64-18-6 ]
  • [ 80058-84-0 ]
  • [ 930781-28-5 ]
YieldReaction ConditionsOperation in experiment
95% Reference Example 4 4-bromo-2,6-diisopropyl-N,N-dimethylaniline ; [Show Image] To a solution of 2,6-diisopropylaniline (25 g, 0.141 moL) in toluene (25 mL) was added dimethyl sulfoxide (12.1 g, 1.1 equivalents), and the mixture was heated to 90°C. 48percent Aqueous hydrobromic acid solution (26.1 g, 1.1 equivalents) was added dropwise to the mixture at the same temperature over 30 min. Then, the mixture was stirred at 86°C for 3 hr and at 100°C for 2 hr. Water (20 mL) was added to the mixture at 0°C, and 1M aqueous sodium hydroxide solution (30 mL) was added dropwise to the mixture. The mixture was partitioned, and the organic layer was washed with 1M aqueous sodium hydroxide solution (50 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered naturally, and the filtrate was concentrated under reduced pressure. The residue was distilled under reduced pressure to give <strong>[80058-84-0]4-bromo-2,6-diisopropylaniline</strong> (29.4 g, pale-yellow liquid). 37percent Formaldehyde (23.1 g, 2.5 equivalents) was added to a solution of <strong>[80058-84-0]4-bromo-2,6-diisopropylaniline</strong> synthesized as mentioned above in formic acid (189 g, 4.11 moL) at 32°C, and the mixture was stirred under refluxing for 2 hr. Toluene (100 mL) and 8M aqueous sodium hydroxide solution (150 mL) were added to the mixture at 0°C, the mixture was partitioned, and the organic layer was successively washed with 1M aqueous sodium hydroxide solution (50 mL) and water (50 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered naturally, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography to give the title compound (35.0 g, colorless solid). yield 95percent. 1H-NMR (300MHz, CDCl3, TMS) delta: 1.20 (d, 12H, J= 6.9Hz), 2.82 (s, 6H), 3.31(septet, 2H, J= 6.9Hz), 7.20 (s, 2H).
  • 2
  • [ 80058-84-0 ]
  • [ 74-88-4 ]
  • [ 930781-28-5 ]
YieldReaction ConditionsOperation in experiment
65% A solution of 12 g (47 mmol) of <strong>[80058-84-0]4-bromo-2,6-diisopropylphenylamine</strong> in 100 ml of DMSO is added to 4.1 g (100 mmol) of sodium hydride in 20 ml of DMSO. The medium is stirred for 1 h and then 6.4 ml (100 mmol) of methyl iodide are added. The medium is heated at 45° C. for 3 hours and then poured into a saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulphate. The residue is purified by silica gel chromatography (90/10 heptane/ethyl acetate). 8.7 g of (4-bromo-2,6-diisopropylphenyl)dimethylamine are obtained in the form of a white solid (yield=65percent).
 

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