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[ CAS No. 81998-04-1 ] {[proInfo.proName]}

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Chemical Structure| 81998-04-1
Chemical Structure| 81998-04-1
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Product Details of [ 81998-04-1 ]

CAS No. :81998-04-1 MDL No. :MFCD02916382
Formula : C12H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :GJCOKGHYIMLMPB-UHFFFAOYSA-N
M.W : 200.24 Pubchem ID :2754750
Synonyms :
Chemical Name :(4'-Methyl-[2,2'-bipyridin]-4-yl)methanol

Safety of [ 81998-04-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 81998-04-1 ]

* 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 [ 81998-04-1 ]

[ 81998-04-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 81998-04-1 ]
  • [ 81998-05-2 ]
YieldReaction ConditionsOperation in experiment
91.3% With sulfuric acid; hydrogen bromide; In water; for 40h;Reflux; A solution of 15(301 mg, 1.50 mmol) in 48% aqueous HBr solution (15 mL) andconcentrated H2SO4 (0.6 mL) was refluxed for 40 h. Aftercooling to room temperature, water (4 mL) was added to thereaction mixture and basified with sat. aqueous Na2CO3 solutionto pH 8. The aqueous solution was extracted with CH2Cl2 until the organic layer wascolorless. The combined organic layer was dried over anhydrous Na2SO4 andconcentrated. The residue was purified by silica gel column chromatography withchloroform / triethylamine (v/v, 40/1) to give 16 (361 mg, 1.37 mmol, 91.3%) as lightbrown . 1H NMR (CDCl3): = 8.66 (d, J = 5.1 Hz, 1H), 8.55 (d, J = 4.8 Hz, 1H), 8.41 (s, 1H),8.24 (s, 1H), 7.34 (dd, J1 = 5.1 Hz, J2 = 1.8 Hz, 1H), 7.16 (d, J = 4.8 Hz, 1H), 4.48 (s,2H), 2.45 (s, 3H). IR (NaCl): = 2918, 1632, 1597, 1567, 1517, 1444, 1379, 1038, 994,827, 749 cm-1
In dichloromethane; (c) 4-bromomethyl-4'-methyl-2,2'-bipyridine To a solution of crude 4-hydroxymethyl-4'-methyl-2,2'-bipyridine in methylene chloride at 0 C. were added a slight excess of both PPh3 and N-bromosuccinimide to immediately give a brown-orange solution. The mixture was stirred for 1 h, warmed to room temperature, and concentrated to a thick brown oil. Chromatography on silica with 1:1 hexanes:diethyl ether as eluent gave the product as a white powder. Yields 50%. 1H NMR spectra are consistent with structure.
(d) Preparation of 4-methyl-4'-bromomethyl-2,2'-bipyridine 1.5 g of 4-methyl-4'-hydroxymethyl-2,2'-bipyridine are reacted analogously to Example 2(e). This gives 1.74 g (88% of theory) of 4-methyl-4'-bromomethyl-2,2'-bipyridine as an unstable oil which is used immediately for the further reaction.
In dichloromethane; (c) 4-bromomethyl-4'-methyl-2,2'-bipyridine To a solution of crude 4-hydroxymethyl-4'-methyl-2,2'-bipyridine in methylene chloride at 0 C. were added a slight excess of both PPh3 and N-bromosuccinimide to immediately give a brown-orange solution. The mixture was stirred for 1 h, warmed to room temperature, and concentrated to a thick brown oil. Chromatography on silica with 1:1 hexanes:diethyl ether as eluent gave the product as a white powder. Yields 50%. 1H NMR spectra are consistent with structure.

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