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Chemical Structure| 590-17-0 Chemical Structure| 590-17-0
Chemical Structure| 590-17-0

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Product Details of Bromoacetonitrile

CAS No. :590-17-0
Formula : C2H2BrN
M.W : 119.95
SMILES Code : N#CCBr
MDL No. :MFCD00001884
InChI Key :REXUYBKPWIPONM-UHFFFAOYSA-N
Pubchem ID :11534

Safety of Bromoacetonitrile

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H301+H311+H331-H315-H319-H335
Precautionary Statements:P210-P233-P240-P241-P242-P243-P261-P264-P270-P271-P280-P301+P310+P330-P303+P361+P353-P304+P340+P311-P305+P351+P338-P332+P313-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Class:6.1(3)
UN#:3275
Packing Group:

Application In Synthesis of Bromoacetonitrile

* 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 [ 590-17-0 ]
  • Downstream synthetic route of [ 590-17-0 ]

[ 590-17-0 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 186581-53-3 ]
  • [ 60-29-7 ]
  • [ 506-68-3 ]
  • [ 13273-53-5 ]
  • [ 16681-67-7 ]
  • [ 16681-82-6 ]
  • [ 590-17-0 ]
References: [1] Acta Chemica Scandinavica (1947-1973), 1959, vol. 13, p. 888,890.
  • 2
  • [ 142851-03-4 ]
  • [ 590-17-0 ]
  • [ 495414-81-8 ]
YieldReaction ConditionsOperation in experiment
2.6 g With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane for 12 h; Cooling with ice A)
1-tert-butyl 4-ethyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate
To a mixture of diisopropylamine (4.7 g) and THF (75 mL) was added n-butyllithium hexane solution (1.6 M, 29 mL) under ice-cooling, and the mixture was stirred for 30 min.
To the mixture was added a mixture of 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate (6.0 g) and THF (10 mL) under ice-cooling, the mixture was stirred under ice-cooling for 3 hr, and 2-bromoacetonitrile (5.6 g) was added thereto under ice-cooling.
The mixture was stirred for 12 hr, and the solvent was evaporated under reduced pressure.
Water was added thereto, and the mixture was extracted with ethyl acetate.
The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure.
The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.6 g).
1H NMR (300 MHz, DMSO-d6) δ 1.21 (3H, t, J = 7.0 Hz), 1.39 (9H, s), 1.43-1.54 (2H, m), 1.90-2.00 (2H, m), 2.87 (2H, s), 2.96-3.12 (2H, m), 3.57-3.67 (2H, m), 4.11-4.22 (2H, m).
References: [1] Patent: EP2933247, 2015, A1, . Location in patent: Paragraph 0333.
[2] Patent: WO2010/130665, 2010, A1, . Location in patent: Page/Page column 136-137.
 

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