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[ CAS No. 3446-90-0 ]

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2D
Chemical Structure| 3446-90-0
Chemical Structure| 3446-90-0
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Product Details of [ 3446-90-0 ]

CAS No. :3446-90-0MDL No. :MFCD00009706
Formula : C8H10OS Boiling Point : 305.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :154.23Pubchem ID :-
Synonyms :

Computed Properties of [ 3446-90-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 3446-90-0 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 3446-90-0 ]

  • Upstream synthesis route of [ 3446-90-0 ]
  • Downstream synthetic route of [ 3446-90-0 ]

[ 3446-90-0 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
59% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In n-heptane at 80℃; for 24 h; General procedure: A mixture of catalyst PS–PEG-TD2–Cu(OAc)2 (100 mg, 0.05mmol Cu), BnOH (1a, 27.0 mg, 0.25 mmol), and TEMPO (7.8 mg,0.05 mmol) in heptane (2.0 mL) was stirred at 80 °C for 24 hunder air (1 atm). The mixture was then cooled and filtered, andthe resulting solid material was washed with Et2O (3 × 2 mL).The organic phases were combined, concentrated to a volume of2 mL, and the internal standard was added to determine the GCyield. The crude product was purified by column chromatography[silica gel, hexane–Et2O (99:1)]. In the formation of somebenzaldehydes, low isolated yields were observed because ofinstability of the benzaldehydes on silica gel
Reference: [1] Synlett, 2018, vol. 29, # 9, p. 1152 - 1156
[2] Organic Letters, 2006, vol. 8, # 1, p. 167 - 170
[3] Mendeleev Communications, 2010, vol. 20, # 4, p. 185 - 191
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YieldReaction ConditionsOperation in experiment
95% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C110H202N8O47; oxygen; copper(II) bis(trifluoromethanesulfonate); potassium carbonate In water at 20℃; for 12 h; Green chemistry General procedure: To a 48 mL tube, were added Cu(II) or Cu(I) salt (0.05 mmol), PEG-PyTa (0.025 mmol) and H2O (3.0 mL). The mixture was stirred for 30 min at room temperature and a clear dark-blue solution was observed. Then alcohols (1.0 mmol), TEMPO (0.05 mmol), and K2CO3 (0.2 mmol) were sequentially added, followed by connecting a balloon of oxygen. The reaction mixture was stirred at room temperature until the reaction completed based on GC analysis. After that, the reaction mixture was extracted with MTBE (3 mL×3) and the extracts were combined, dried over anhydrous Na2SO4 and concentrated under vacuum. Finally, the residue was purified by flash chromatography on silica to afford the desired aldehydes.
94% With Cu2(ophen)2; oxygen In acetonitrile at 60℃; for 12 h; Green chemistry General procedure: To a 10mL round bottom flask, the mixture of 12 benzylalcohol 1a (1.0mmol, 0.104mL) and Cu2(ophen)2 (0.05mmol, 26mg,) in 60 CH3CN (4mL), was stirred in oil bath at 60°C under oxygen atmosphere (oxygen ball). The reaction was monitored and conversions were determined by GC–MS.
90% With chloroamine-T; zinc dibromide In acetonitrile for 2 h; Reflux General procedure: A CH3CN solution of alcohol (1 mmol), ZnBr2 (45 mg, 0.2 mmol), and chloramine-T (282 mg, 1 mmol) was placed in a three necked flask with a reflux condenser. After the mixture was stirred under reflux for 1.5-5 h. After cooling to room temperature, the solution was quenched by adding water and the resulting mixture was extracted with AcOEt. Removal of the solvent under reduced pressure gave the crude product, which was purified by column chromatography on silica gel to give the corresponding carbonyls.
90% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium carbonate; N-Phenylglycine; copper(ll) bromide In water for 3 h; Reflux; Schlenk technique General procedure: A mixture of p-methylbenzyl alcohol (1.0 mmol), N-phenylglycine(0.0076 g, 0.05 mmol), CuBr2 (0.0112 g, 0.05 mmol),Na2CO3 (0.1060 g, 1.0 mmol), TEMPO (0.0078 g, 0.05 mmol),H2O (3.0 mL) were added to a 100 mL Schlenk tube, which wasvigorously stirred in air under reflux for 0.5 h. After the reaction,the product was extracted with CH2Cl2 (3 × 2.0 mL). Thecombined organic phase was washed with H2O (3.0 mL) anddried over anhydrous MgSO4. After concentration undervacuum, the residue was purified by column chromatography toafford p-methylbenzaldehyde.Isolated yield: 0.1080 g (90percent).
90% at 80℃; for 20 h; General procedure: In a 150 mL thick-walled pressure tube equipped with a magnetic stirrer,In an air atmosphere,To the system was added benzyl alcohol (i.e., R1 in formula (I) H) 1.0 mmol (108.1 mg)Ammonia (1.6 x 10-2 mol / L) 5.0 mL,5 molpercent (9.5 mg) of cuprous iodide,TEMPO 5 molpercent (7.8 mg),100 & lt; 0 & gt; C for 12 h,After the reaction is over,The reaction solution was cooled to room temperature,And extracted with ethyl acetate (3 x 5.0 mL). The organic layers were combined and concentrated in vacuo to remove ethyl acetate to give the crude product. The crude product was purified by column chromatography(Petroleum ether: ethyl acetate = 10: 1) to give the pure desired product.The yield of 97.6 mg was 92percent.
86% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; iodic acid In N,N-dimethyl-formamide at 20℃; for 2 h; Inert atmosphere General procedure: To a solution of 1-(p-bromophenyl)ethanol I-23 (201 mg, 1.0 mmol) in DMF (2.0 mL) was added HIO3 (194 mg, 1.1 mmol) and TEMPO (7.8 mg, 0.05 mmol). The mixture was stirred for 2 h at room temperature under an Ar atmosphere. After the reaction, the reaction mixture was poured into aq Na2S2O3, and extracted with a mixture of Et2O: hexane=1:1 (3*10 mL). Then, the organic layer was poured into satd NaCl (10 mL) and extracted with Et2O (10 mL). The organic layer was dried over Na2SO4. After being filtration and removal of the solvent under reduced pressure, the residue was purified by flash short column chromatography on silica gel (EtOAc-hexane, 1:4) to give p-bromoacetophenone II-23 in 99percent yield.
80% With indium isopropoxide; pivalaldehyde In chloroform at 20℃; for 3 h; Glovebox; Sealed tube; Inert atmosphere General procedure: To a screw tube in a glovebox was added In(Oi-Pr)3 (29.2 mg, 0.1 mmol). The tube was then sealed and removed from the glovebox, and CHCl3 (1 mL), alcohol (0.5 mmol), and pivalaldehyde (280 μL, 2.5 mmol) were added under N2 in this order. After stirring the mixture at r.t. for 3 h, H2O (1.0 mL) was added to the reaction mixture, which was then extracted with EtOAc. The organic phase was dried (Na2SO4), and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (Table 2 and Scheme 2).
78% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C20H36N5(3+)*3Br(1-); oxygen; copper In water at 35℃; for 6 h; Schlenk technique General procedure: A 30-mL Schlenk tube was evacuated and filled with O2, the benzyl alcohol (1 mmol), Cu powder (5percent mol), imidazolium (5percent mol), TEMPO (5percent mol), and H2O (3 mL) was added and stirred at 35 °C under an O2 atmosphere by connecting an O2 balloon. When the reaction was complete, the mixture was extracted with CH2Cl2 (3 × 10 mL). The combined extracts were dried (MgSO4). Then the solvent was removed and the mixture was purified by column chromatography (silica gel) to give the product.
90 %Chromat. With oxygen; potassium carbonate In toluene at 90℃; General procedure: In a 5 ml glass flask, catalyst (10 mg, containing 0.2 molpercent Pd), alcohol(0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and H2O or toluene(2 mL) were added and reaction mixture was stirred continuously at90 °C for the desired time under O2 atmosphere (from a balloon). Then,in the case of water as solvent, products were extracted with ethylacetate and the catalyst was recovered by an external magnet. Yields ofdesired products were determined by gas chromatography.

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YieldReaction ConditionsOperation in experiment
83 %Chromat. With oxygen; potassium carbonate In water at 90℃; General procedure: In a 5 ml glass flask, catalyst (10 mg, containing 0.2 molpercent Pd), alcohol(0.5 mmol), K2CO3 (104 mg, 0.75 mmol) and H2O or toluene(2 mL) were added and reaction mixture was stirred continuously at90 °C for the desired time under O2 atmosphere (from a balloon). Then,in the case of water as solvent, products were extracted with ethylacetate and the catalyst was recovered by an external magnet. Yields ofdesired products were determined by gas chromatography.
Reference: [1] Applied Catalysis A: General, 2018, vol. 563, p. 185 - 195
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1854 - 1858[2] Angew. Chem., 2015, vol. 128, # 5, p. 1886 - 1890,5
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Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 22, p. 8452 - 8458
[2] Journal of Organic Chemistry, 2007, vol. 72, # 21, p. 8149 - 8151
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Reference: [1] Advanced Synthesis and Catalysis, 2007, vol. 349, # 16, p. 2425 - 2430
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Reference: [1] Canadian Journal of Chemistry, 1984, vol. 62, p. 1164 - 1168
[2] Patent: WO2017/136871, 2017, A1,
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