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Chemical Structure| 2402-78-0 Chemical Structure| 2402-78-0
Chemical Structure| 2402-78-0

2,6-Dichloropyridine

CAS No.: 2402-78-0

4.5 *For Research Use Only !

Cat. No.: A623095 Purity: 98%

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Product Details of [ 2402-78-0 ]

CAS No. :2402-78-0
Formula : C5H3Cl2N
M.W : 147.99
SMILES Code : ClC1=CC=CC(Cl)=N1
MDL No. :MFCD00006244
InChI Key :FILKGCRCWDMBKA-UHFFFAOYSA-N
Pubchem ID :16989

Safety of [ 2402-78-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H315-H319
Precautionary Statements:P264-P270-P280-P301+P310+P330-P302+P352-P305+P351+P338-P332+P313-P337+P313-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis [ 2402-78-0 ]

* 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.

  • Upstream synthesis route of [ 2402-78-0 ]
  • Downstream synthetic route of [ 2402-78-0 ]

[ 2402-78-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 2402-78-0 ]
  • [ 925-90-6 ]
  • [ 935-28-4 ]
YieldReaction ConditionsOperation in experiment
89% at 0 - 20℃; Heating / reflux A mixture of NaOH (14.7 g, 0.37 mol), hydrazine monohydrate (15 ml) and 2,6-diacetylpyridine (6g, 36.8 mmol) suspended in diethylene glycol (27 ml_) was cautiously heated to 120 °C for 16 hours. The mixture was cooled to room temperature and partitioned between H2O and ether. The ether extracts were washed with 1 N NaOH, dried over MgSO4 and concentrated to a clear oil. Flash column chromatography (0percent to 15percent EtOAc in hexanes) gave the product as a clear oil (2.9 g, 58percent). 1H NMR (400 MHz, CDCI3): 5 1.29 (t, J=7.8 Hz, 3 H), 2.80 (d, J=7.8 Hz, 2 H), 6.97 (d, J=2.0 Hz, 2 H), 7.51 (t, J=7.6 Hz, 1 H). 2,6-Diethyl-pyridine has also been prepared as follows:A solution of ethylmagnesium bromide in ethyl ether [prepared from Mg (16.5 g, 0.68 mol) and ethyl bromide (50 mL, 0.68 mol) in 500 ml_ of ether] was added dropwise to a mixture of 2,6-dichloropyridine (50 g, 0.34 mol) and NiCI2(dppp) (1.0 g, 2 mol) in anhydrous ethyl ether(500 mL).at 0 °C unde(r N3 atmosphere. After addition, the resulting mixture was stirred,. , ' >.,"?, '['A V ' "' > 'ambient temperature oveifngh'tj was then heated to reflux for about 3 hours. The suspensiatonwas poured into cushed ice (200 g) and the mixture was saturated with NH4CI. The organic layer was separated and the aqueous phase was extracted with ether (200 mL x 3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give the product (41 .1 g, 89percent).
References: [1] Synlett, 2010, # 5, p. 796 - 800.
[2] Patent: WO2006/18725, 2006, A1, . Location in patent: Page/Page column 119.
[3] Journal of the American Chemical Society, 2017, vol. 139, # 37, p. 13126 - 13140.
[4] Journal of Organic Chemistry, 1994, vol. 59, # 18, p. 5125 - 5127.
[5] Chemistry - A European Journal, 2017, vol. 23, # 7, p. 1521 - 1525.
  • 2
  • [ 2402-78-0 ]
  • [ 52764-11-1 ]
References: [1] Tetrahedron, 2005, vol. 61, # 6, p. 1417 - 1421.
 

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