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[ CAS No. 5294-03-1 ] 1,2-Di-o-tolylethyne

Cat. No.: A1353554
Chemical Structure| 5294-03-1
Chemical Structure| 5294-03-1
Structure of 5294-03-1 * Storage: Sealed in dry,Room Temperature
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
98% 100mg $89.00 Inquiry Inquiry
98% 250mg $151.00 Inquiry Inquiry
98% 1g $406.00 Inquiry Inquiry

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* Storage: Sealed in dry,Room Temperature

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Product Details of [ 5294-03-1 ]

CAS No. :5294-03-1 MDL No. :MFCD28452932
Formula : C16H14 Boiling Point : -
Linear Structure Formula :C2(C6H4CH3)2 InChI Key :SVIUEMOZHFTFEZ-UHFFFAOYSA-N
M.W : 206.28 Pubchem ID :10242091
Synonyms :

Safety of [ 5294-03-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5294-03-1 ]

* 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 [ 5294-03-1 ]

[ 5294-03-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 615-37-2 ]
  • [ 766-47-2 ]
  • [ 5294-03-1 ]
YieldReaction ConditionsOperation in experiment
75% With C17H32Cl2N4OPd; potassium carbonate; In ethanol; at 80℃; for 1h; General procedure: K2CO3 (2.5 × 10-4 mol, 2.5 equiv), aryl iodide (1.0 × 10-4 mol, 1.0 equiv), and alkyne (1.5 × 10-4 mol, 1.5 equiv) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1 × 10-8 mol) in EtOH (1 mL). The vial was placed in a preheated oil bath at 80 C and stirred for 1 h. After cooling to 20-25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equiv of 1,2-dimethoxyethane as NMR internal standard, and extraction of the reaction mixture with three 0.20-mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on the authentic samples or on published dat, whereas quantifications were performed upon integration of the selected peak of the product relatively to the peak of the standard.
With C23H20Cl4N4OPd; potassium carbonate; In ethanol; at 80℃; for 4h; General procedure: Selected base (1.5×10-4 mol, 1.5 equivs), aryl iodide (1.0×10-4 mol, 1.0 equiv) and terminal alkyne (1.0×10-4 mol, 1.0 equivs) were mixed in a 10-mL vial, followed by addition of a solution of the selected catalyst (1×10-8 mol) in EtOH (1 mL). The vial was placed in a pre heated oil bath at 80 C and stirred for 4 h. After cooling to ca. 25 C, the reaction mixture was evaporated to dryness under a stream of dinitrogen followed by addition of 1.0 equivof 1,2-dimethoxyethane (NMR internal standard), and extraction of the reaction mixture with three 0.20 mL portions of CDCl3. All fractions were joined and analyzed by 1H NMR spectroscopy. The product peak assignments were based on authentic samplesor on published data [56,62-68] (several sources were used for published compounds), while the structure of two new products,i.e. 3,4-dimethoxy-5-(phenylethynyl)benzaldehyde (derived from the coupling of 3-iodo-4,5-dimethoxybenzaldehyde with phenylacetylene) and 1-fluoro-2-[(2-methylphenyl)ethynyl]benzene (prepared from 2-fluorophenylacetylene and 2-iodotoluene were undoubtedly established using NMR spectroscopy, MS and elemental analyses (see Supplementary data). Quantifications were performed upon integration of the selected peak of the product in the 1H NMR relatively to the peak of the standard.
  • 2
  • [ 615-37-2 ]
  • [ 1066-54-2 ]
  • [ 5294-03-1 ]
YieldReaction ConditionsOperation in experiment
91% General procedure: 4-Iodoanisole (1mmol), TMSA (1.1mmol) and K2CO3 (2mmol) were added to a freshly prepared solution of PdNPs (5mL) in a 25mL round bottomed flask fitted with stopper. Then, the reaction mixture was stirred at 40C. The reaction progress was monitored by TLC, until complete consumption of aryl iodide. To the reaction mixture containing in situ formed 4-ethynylanisole the next batch of aryliodide (1mmol) was added and the reaction mixture was further allowed to stir until complete consumption of the arylacetylene. In this manner the targeted unsymmetrical diarylacetylene was formed. The detailed procedure is provided in the Supp. Info. Detailed procedure for synthesis of symmetrical diarylacetylenes is also mentioned in SI.
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