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[ CAS No. 766-47-2 ] {[proInfo.proName]}

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Chemical Structure| 766-47-2
Chemical Structure| 766-47-2
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Product Citations

Product Citations

Krzysztof Kuciński ; Grzegorz Hreczycho ; DOI:

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C?H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

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Product Details of [ 766-47-2 ]

CAS No. :766-47-2 MDL No. :MFCD03427202
Formula : C9H8 Boiling Point : -
Linear Structure Formula :- InChI Key :MYBSUWNEMXUTAX-UHFFFAOYSA-N
M.W : 116.16 Pubchem ID :136598
Synonyms :

Safety of [ 766-47-2 ]

Signal Word:Danger Class:3
Precautionary Statements:P261-P305+P351+P338 UN#:3295
Hazard Statements:H225-H315-H319-H335 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 766-47-2 ]

* 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 [ 766-47-2 ]

[ 766-47-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 766-47-2 ]
  • [ 122394-38-1 ]
  • methyl 2-(2-methylphenyl)-ethynylphenylglyoxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With nitrogen; triphenylphosphine;palladium diacetate; copper(I) iodide; In dichloromethane; triethylamine; a) Preparation of methyl 2-(2-methylphenyl)-ethynylphenylglyoxylate O-methyloxime (European Patent 253,213, No. 136) 300 mg of palladium(II) acetate, 1.5 g of triphenylphosphine and 100 mg of copper(I) iodide and 11 g (0.095 mol) of 2-methylphenylacetylene are added to a solution of 10 g (0.041 mol) of <strong>[122394-38-1]methyl 2-bromophenylglyoxylate</strong> in 50 ml of triethylamine. Nitrogen is passed through the solution for 30 minutes, after which the solution is heated for 3 hours at 80 C. After cooling, methylene chloride is added and the solution is washed with water. The organic phase is dried and evaporated down. 16.5 g of methyl 2-(2-methylphenyl)-ethynylphenylglyoxylate remain as a black oil. 1 H-NMR (CDCl3 /TMS): delta=2.53 (s, 3H, CH3); 3.81 (s, 3H, OCH3); 7.13-7.88 ppm (m, 8H, aryl).
  • 2
  • [ 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.
  • 3
  • [ 766-47-2 ]
  • [ 32024-15-0 ]
  • C18H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With C22H20Cl4N4O2PdS; 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.
  • 4
  • [ 766-47-2 ]
  • [ 611-14-3 ]
  • [ 611-15-4 ]
  • 5
  • [ 201230-82-2 ]
  • [ 766-47-2 ]
  • [ 939-57-1 ]
  • [ 109548-76-7 ]
  • 6
  • [ 766-47-2 ]
  • [ 412947-54-7 ]
  • methyl 3-amino-4-(o-tolylethynyl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; triphenylphosphine; at 60℃;Inert atmosphere; To a solution of <strong>[412947-54-7]methyl 3-amino-4-iodobenzoate</strong> (Int 24a) (1.10 g, 4.03 mmol) in Et3N (15 ml_) was added Pd(PPh3)4 (185 mg, 0.16 mmol), Cul (46 mg, 0.24 mmol), PPh3 (63 mg, 0.24 mmol) and 1 -ethynyl-2-methylbenzene (604 mg, 5.21 mmol). The mixture was stirred at 60 C under N2 overnight. The mixture was filtered and concentrated to dryness. The residue was purified by silica gel column chromatography (PE/EtOAc = 5:1 ) to give the title compound as yellow solid.
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