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[ CAS No. 24973-50-0 ]

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Chemical Structure| 24973-50-0
Chemical Structure| 24973-50-0
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CAS No. :24973-50-0 MDL No. :MFCD00236364
Formula : C13H9N Boiling Point : 326.3°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :179.22 g/mol Pubchem ID :-
Synonyms :

Safety of [ 24973-50-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P302+P352 UN#:3439
Hazard Statements:H302+H312-H331 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24973-50-0 ]

  • Downstream synthetic route of [ 24973-50-0 ]

[ 24973-50-0 ] Synthesis Path-Downstream   1~15

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  • trans-2-(4-cyanophenyl)-1-methoxycyclohexane [ No CAS ]
  • cis-2-(4-cyanophenyl)-1-methoxycyclohexane [ No CAS ]
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YieldReaction ConditionsOperation in experiment
95% With Lindlar's catalyst; at 100℃; for 2h; Add 3-bromobenzonitrile (1mmol), phenylboronic acid (1.1mmol) and palladium calcium carbonate catalyst (0.001mmol), Suwana extract (4ml) to a 10ml round bottom flask, and stir at 100C under air for 2 hours . After the reaction, the mixture was cooled to room temperature. After filtration, the obtained filter residue was mixed with a palladium catalyst to obtain a mixture dissolved in 20 mL of ethyl acetate. The solution was collected after filtration, and the final product was obtained after evaporation to dryness. The structure of the product was identified by nuclear magnetic resonance hydrogen spectroscopy and carbon spectroscopy. The yield was 95%.
88% With potassium phosphate; [bis{2-(3-(2,4,6-trimethylbenzyl)imidazolin-2-yliden-1-yl)-4-methylphenyl}amido]chloronickel; In 1,4-dioxane;Inert atmosphere; Schlenk technique; Reflux; General procedure: In a typical reaction, to a 25-mL Schlenk tube equipped with amagnetic stirring bar were added nickel(II) catalyst 2a (0.005mmol, 1.0mol %), aryl halides (0.5mmol), phenylboronic acids (0.75mmol), and anhydrous K3PO4 (2.0mmol). The tube was then evacuated (3×5min) under vacuum and backfilled with N2. Dried dioxane (4.0mL) was injected via a syringe, and the reaction mixture was stirred at reflux until the aryl halides had disappeared as monitored by TLC. The reaction mixture was treated with H2O (20mL), then extracted with Et2O (3×15mL). The combined organic extracts were washed with sat. aq NaCl (10mL) and dried with anhydrous MgSO4. The solvent was removed under reduced pressure and the crude material was purified by silica gel column chromatography to give the corresponding biaryl. All the coupling products are known and their structures were identified by comparing their 1H NMR and 13C NMR spectral data with those reported in literature.
59% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane;Reflux; Inert atmosphere; General procedure: A benzonitrile derivative was reacted with theboronic acid (1.2 eq) in the presence of Pd(PPh) (5 mol%) and 2M NaCO in DME, and the reactionmixture was refluxed overnight under a nitrogen atmosphere. After completion, the reaction wascooled and ethyl acetate and water were added. After separation, the organic layer was dried over Na2SO4 and the solvent removed under reduced pressure. The mixture was then purified using flashsilica gel column chromatography using 5% ethyl acetate/hexane.
85%Chromat. With C24H22N2O4Pd; potassium hydroxide; In ethanol; at 70℃; for 7h;Inert atmosphere; General procedure: A mixture of aryl halide (1 mmol), phenylboronic acid (1 mmol),KOH (2.4 mmol), and PdL (5 mg including 0.01 mmol Pd(II)) was sustainedin a three-necked round-bottom flask. The mixture was stirred at the desired time and temperature under inert gas. Gas chromatographywas used to track the progression of the reaction.

Reference: [1]Archiv der Pharmazie,1996,vol. 329,p. 73 - 82
[2]Tetrahedron,2007,vol. 63,p. 12277 - 12285
[3]Journal of Organic Chemistry,2014,vol. 79,p. 888 - 900
[4]Journal of Chemical Research,2018,vol. 42,p. 54 - 56
[5]Journal of Organic Chemistry,2003,vol. 68,p. 7733 - 7741
[6]Organic Letters,2002,vol. 4,p. 3371 - 3374
[7]Journal of Chemical Research,2018,vol. 42,p. 320 - 325
[8]Organic Letters,2017,vol. 19,p. 654 - 657
[9]Catalysis science and technology,2016,vol. 6,p. 1764 - 1771
[10]Tetrahedron,2009,vol. 65,p. 2889 - 2897
[11]Advanced Synthesis and Catalysis,2008,vol. 350,p. 2391 - 2400
[12]Patent: CN111253234,2020,A .Location in patent: Paragraph 0027-0028
[13]RSC Advances,2016,vol. 6,p. 92463 - 92472
[14]Tetrahedron Letters,2003,vol. 44,p. 7993 - 7996
[15]Journal of Organic Chemistry,2004,vol. 69,p. 4330 - 4335
[16]Journal of Organic Chemistry,2011,vol. 76,p. 4379 - 4391
[17]Journal of Organometallic Chemistry,2007,vol. 692,p. 3914 - 3921
[18]Advanced Synthesis and Catalysis,2013,vol. 355,p. 957 - 972
[19]Journal of Organometallic Chemistry,2015,vol. 788,p. 27 - 32
[20]Synthesis,2007,p. 2853 - 2861
[21]Inorganic Chemistry,2021,vol. 60,p. 6209 - 6217
[22]Organic Letters,2008,vol. 10,p. 1333 - 1336
[23]Catalysis science and technology,2019,vol. 9,p. 3820 - 3827
[24]Molecules,2020,vol. 25
[25]RSC Advances,2017,vol. 7,p. 21036 - 21044
[26]Synthetic Communications,2000,vol. 30,p. 3501 - 3509
[27]Journal of Organometallic Chemistry,2009,vol. 694,p. 1473 - 1481
[28]European Journal of Inorganic Chemistry,2018,vol. 2018,p. 751 - 758
[29]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3716 - 3731
[30]Applied Organometallic Chemistry,2019,vol. 33
[31]RSC Advances,2021,vol. 11,p. 35311 - 35320
[32]Polyhedron,2022,vol. 213
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YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In water; at 60℃; for 16h;Green chemistry; General procedure: A mixture of Fe3O4(at)SiO2-NHC-Pd(II) (0.006 g, 0.37 mol%), arylboronic acid (1.1 mmol), aryl halide (1.0 mmol), and K2CO3(2 mmol) in H2O (3 mL)was stirred at 60 C for the appropriate timeas indicated in Table 3. The completion of the reaction was monitoredby TLC. After completion of the reaction, the catalyst wasremoved by an external magnetic field and was then washed withH2O (5 mL) and ethyl acetate (10 mL). The organic layer was separated,dried over anhydrous Na2SO4, and filtered. Then, the solventwas evaporated under reduced pressure. The pure product wasobtained via silica gel column chromatography with an eluent of nhexaneand ethylacetate.
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 60℃; for 24h;Inert atmosphere; Sealed vessel; Typical preparative procedures were performed on 10.0 mmol scale using a Mettler-Toledo FlexiWeigh 30 automated solid handling unit to pre-weigh the aryl halide (10.0 mmol, 1.0 equiv), aryl boronic acid (12.0 mmol, 1.2 equiv) and Pd-118 (65.2 mg, 0.1 mmol, 1.0 mol %). Acetonitrile (10.0 mL) was added, followed by K2CO3 added as a stock aqueous solution (10.0 mL water containing 2.07 g, 15.0 mmol, 1.5 equiv). NB. No internal standard was added for preparative reactions. Reaction mixtures were sealed under a N2 atmosphere and heated to 60 C with magnetic stirring. HPLC analysis showed that reactions using aryl bromides were complete within 1 h but that aryl chlorides typically required 24 h.After reaction mixtures had cooled to room temperature, stirring was stopped and the phases were allowed to separate. The lower aqueous phase was removed and discarded (cutting away any interfacial catalyst residues if present) and the acetonitrile phase concentrated to dryness to give typically a light to dark brown solid or dark-coloured gum. Solids were triturated with methanol (20 mL) for 1-2 h, then isolated by filtration, washed once or twice with methanol (4 mL each wash) and dried under vacuum. Oils were purified by flash silica gel chromatography as noted below. All isolated compounds gave 1H NMR data in agreement with published values. Literature data is given for mp values for comparison.
94%Chromat. With [Pd2(μ-1,1′-bis(diphenylphosphino)ferrocene)(4-methoxy-N′-(mesitylidene)benzohydrazide)2]; tetrabutylammomium bromide; potassium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 12h; General procedure: An oven-dried round bottom flask (10 ml) was charged with 0.1ml dimethylformamide solution of complex IV (0.1 mol % for aryl bromides and 0.2 mol % for aryl chlorides), aryl boronic acid (1.2 mmol), aryl halide (1.0 mmol), K2CO3 (1.5 mmol), TBAB (1.0 mmol) and 2 ml water. The reaction mixture was then heated (to 70 C for aryl bromides and 90 C for aryl chlorides) with stirring under aerobic conditions for the required time. At the end of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (2×5 ml). The combined extract was washed with water (2×10 ml), dried over anhydrous sodium sulfate and then subjected to GC-MS analysis for identification and yield determination (from the areas under the peaks) of the products. In the case of reactions with 2-naphthylboronic acid, the combined extract was evaporated to dryness under reduced pressure and the residue was purified by column chromatography (silica gel, ethyl acetate/n-hexane) to afford the coupling products. The products were identified by 1H and 13C NMR and HR-MS analysis.
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