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Chemical Structure| 5683-33-0 Chemical Structure| 5683-33-0

Structure of 5683-33-0

Chemical Structure| 5683-33-0

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Product Details of [ 5683-33-0 ]

CAS No. :5683-33-0
Formula : C7H10N2
M.W : 122.17
SMILES Code : CN(C)C1=NC=CC=C1
MDL No. :MFCD00006261
InChI Key :PSHKMPUSSFXUIA-UHFFFAOYSA-N
Pubchem ID :21885

Safety of [ 5683-33-0 ]

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

Application In Synthesis of [ 5683-33-0 ]

* 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 [ 5683-33-0 ]

[ 5683-33-0 ] Synthesis Path-Downstream   1~7

  • 2
  • [ 5683-33-0 ]
  • [ 26163-07-5 ]
YieldReaction ConditionsOperation in experiment
68% With dihydrogen peroxide; 1-butylpyridinium bromide; toluene-4-sulfonic acid; In 1,2-dimethoxyethane; at 80℃; for 24h;Schlenk technique; Inert atmosphere; Green chemistry; General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol,0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1,2-dimethoxyethane (2 mL) under air. Then H2O2 (1.2 mmol, 2.4 equiv) was added. The mixture was stirred at 80C for 24 h. And then the mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the products.
64% With N-Bromosuccinimide; In dichloromethane; for 0.166667h; N-Bromosuccinimide (190 mmol) was added portionwise to a solution of [2- (DIMETHYLAMINO)-PYRIDINE] (200 mmol) in DCM (1.0 L). After 10 min a HPLC- MS indicated complete conversion. The solvent was removed in vacuo and the residue was purified by flash-chromatography (ethyl acetate/heptane 1: 19) to give 25.7 g [(128] mmol, [64%)] of the desired arylbromide as a white solid. LC-MS: rt = 0.46 min, [201] (M+1, ES+).
With N-Bromosuccinimide; ammonium acetate; In acetonitrile; at 20℃; [00158] Pyri(mi)dyl bromides were commercially available (e.g. from SigmaAldrich) (Oakville, Ontario, Canada) or were prepared from commercially available pyridines or pyrimidines (10 mmol) in MeCN (40 mL) at room temperature in the presence of NH OAc (1.0 mmol) and NBS (10.5 mmol), as suggested by Das and co-workers (Das, B.; Venkatswarlu, K.; Majhi, A.; Siddaiah, V.; Reddy, K. J. Mol. Cat. A 2007, 267, 30-33). Reactions were monitored by thin layer chromatography (TLC) and typically were complete within minutes. After removal of acetonitrile in vacuo, water was added (100 mL) and the mixture extracted with EtOAc (3 x 50 mL). Non aqueous layers were combined and washed with 50 mL brine and dried over MgS04. Products were used without further purification. [00172] Compound 27 was prepared in 94% yield from 2-(/V,/V-dimethylamino)-5- bromopyridine (prepared as in Example 5, see also: Nara, S. J.; Jha, M.; Brinkhorst, J.; Zemanek, T. J.; Pratt, D. A. J. Org. Chem. 2008, 73, 9326) and aniline (Aldrich) as outlined in Example 3.
  • 3
  • [ 5683-33-0 ]
  • [ 7664-93-9 ]
  • [ 26163-07-5 ]
  • [ 84539-28-6 ]
  • 4
  • [ 5683-33-0 ]
  • [ 37026-85-0 ]
  • [ 26163-07-5 ]
YieldReaction ConditionsOperation in experiment
72.0% With sodium thiosulfate; In chloroform; water; Example 191-1 Synthesis of 5-bromo-2-dimethylaminopyridine 2-Dimethylaminopyridine (1.0 ml) was dissolved in chloroform (60 ml). After adding tributylammonium bromide (3.88 g) thereto, the resultant mixture was stirred for 7 min. Then the reaction solution was washed with an aqueous solution of sodium thiosulfate and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate-methanol system) to give the title compound (1.097 g) as yellow crystals (yield: 72.0%). 1H-NMR (400 MHz, CDCl3): delta(ppm) 3.05(6H, s), 6.40(1H, dd, J=0.8, 8.8Hz), 7.48(1H, dd, J=2.8, 8.8Hz), 8.16(1H, dd, J=0.8, 2.8Hz).
  • 5
  • [ 5683-33-0 ]
  • [ 1623-93-4 ]
  • [ 33084-49-0 ]
  • N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenyisulfonamide [ No CAS ]
  • [ 166964-10-9 ]
YieldReaction ConditionsOperation in experiment
60% In pyridine; (b) N-(4-Biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenylsulfonamide 5-Amino-4-bromo-3-methylisoxazole (0.179 g, 1.0 mmol) was dissolved in dry pyridine (2 ml). 4-Biphenylsulfonyl chloride (0.509 g, 2.2 mmol) was added with stirring at ambient temperature. N,N-dimethyl-aminopyridine (5 mg) was added, and stirring was continued at 50 C. for 16 h. The reaction mixture was diluted with dichloromethane (75 ml), washed with 1 N HCl (2*50 ml) and the organic phase was dried over magnesium sulfate. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography using 8:2, hexanes/ethyl acetate, to give 0.390 g (60% yield) of N-(4-biphenylsulfonyl)-N-(4-bromo-3-methyl-5-isoxazolyl)-4-biphenyisulfonamide.
  • 6
  • [ 626-64-2 ]
  • [ 337913-25-4 ]
  • [ 5683-33-0 ]
  • [ 2456-81-7 ]
YieldReaction ConditionsOperation in experiment
In dibutylamine; EXAMPLE 1 There are prepared 4-dibutylaminopyridine by adding 0.1 mole of 4-hydroxypyridine and 15 grams of phosphorous pentoxide in the presence of 0.2 mole of dibutylamine at 250° C. for 16 hours. The dimethylaminopyridine was obtained from the Aldrich Chemical Company of Milwaukee, Wis. and the 4-pyrrolidinopyridine was obtained from the Reilley Tar and Chemical Company, Indianapolis, Ind.
In dibutylamine; Example 1. There was prepared 4-dibutylaminopyridine by adding 0.1 mole of 4-hydroxypyridine and 15 grams of phosphorous pentoxide in the presence of 0.2 mole of dibutylamine at 250oC for 16 hours. The dimethylaminopyridine was obtained from the Aldrich Chemical Company of Milwaukee, Wisconsin and the 4-pyrrolidinopyridine was obtained from the Reilley Tar and Chemical Company, Indianapolis, Indiana.
  • 7
  • [ 26163-07-5 ]
  • [ 694-53-1 ]
  • [ 5683-33-0 ]
  • 5-(diphenylsilyl)-N,N-dimethylpyridin-2-amine [ No CAS ]
 

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