Alternatived Products of [ 5320-91-2 ]
Product Details of [ 5320-91-2 ]
CAS No. : | 5320-91-2 |
MDL No. : | MFCD00496622 |
Formula : |
C16H14N2O4
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
298.29
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 5320-91-2 ]
Signal Word: | |
Class: | |
Precautionary Statements: | |
UN#: | |
Hazard Statements: | |
Packing Group: | |
Application In Synthesis of [ 5320-91-2 ]
* 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 [ 5320-91-2 ]
- 1
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[ 619-50-1 ]
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[ 5320-91-2 ]
Yield | Reaction Conditions | Operation in experiment |
85% |
|
General procedure: To a 5 mL screw vial under N2 containing a freshly distilled DMF (0.6 mL) were successively added aromatic nitro compound (0.60 mmol), In(OTf)3 (0.030 mmol, 17 mg), and Et3SiH (1.80 mmol, 287 muL). The resulting mixture was stirred at 60 C (bath temperature), and monitored by TLC analysis. After completion of the reaction, the resultant mixture was further stirred under either an ambient or an O2 atmosphere during the corresponding reaction time. The reaction was quenched with H2O (6 mL). The aqueous layer was extracted with AcOEt (6 mL×3), the combined organic phases were dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure. The crude product was purified by recrystallization from the solvent (hexane/chloroform) or silica gel column chromatography (hexane/AcOEt) to afford the corresponding azobenzene derivatives. |
Reference:
[1]Chemical Communications,2010,vol. 46,p. 3173 - 3175
[2]Catalysis science and technology,2013,vol. 3,p. 3200 - 3206
[3]Green Chemistry,2020,vol. 22,p. 1301 - 1307
[4]Tetrahedron,2014,vol. 70,p. 2027 - 2033
[5]Angewandte Chemie - International Edition,2014,vol. 53,p. 7624 - 7628
Angew. Chem.,2014,vol. 126,p. 7754 - 7758,5
[6]ACS Catalysis,2017,vol. 7,p. 8480 - 8486
[7]Organic Letters,2011,vol. 13,p. 5640 - 5643
[8]Journal of Organic Chemistry,1968,vol. 33,p. 851 - 855
[9]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 407 - 410
[10]Chemical Communications,2012,vol. 48,p. 3445 - 3447
- 2
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4-(methoxycarbonyl)benzenediazonium tetrafluoroborate
[ No CAS ]
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[ 792-74-5 ]
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[ 17104-81-3 ]
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[ 5320-91-2 ]
- 3
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[ 586-91-4 ]
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[ 5320-91-2 ]
Yield | Reaction Conditions | Operation in experiment |
|
Multi-step reaction with 2 steps
1: thionyl chloride / 5 h / Reflux
2: triethylamine / tetrahydrofuran / 12 h / 20 °C |
|
- 4
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[ 5320-91-2 ]
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[ 586-91-4 ]
Yield | Reaction Conditions | Operation in experiment |
|
With sodium hydroxide In ethanol; water at 20℃; Darkness; |
General Procedure A - hydrolysis of the methyl esters of templates 1-3
General procedure: To a vigorously stirred and protected from light solution of the corresponding methyl ester template in a EtOH-H2O mixture (10 mL per 1 mmol of template, 3:1 v/v) 2M NaOH (2equiv per methyl ester group) was added. After stirring overnight at rt, 10% NaHSO4 was added until pH =/~2 was reached. Acid was extracted with ethyl acetate two times, combined organic phases were washed with brine and dried over anhydrous Na2SO4. The solution was then concentrated and thoroughly dried under high vacuum (p ~2 mBar) for 24 h. |
- 5
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[ 5320-91-2 ]
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[ 37797-30-1 ]
Yield | Reaction Conditions | Operation in experiment |
100% |
With lithium aluminium hydride In tetrahydrofuran; dichloromethane at 0℃; for 5h; Inert atmosphere; |
|
438.2 mg |
With diisobutylaluminium hydride In tetrahydrofuran at 0℃; Inert atmosphere; Cooling; |
2 Synthesis of Compound (10)
Compound (9) (797.5 mg, 2.95 mmol) was weighed into a 100 ml eggplant flask, vacuum-dried, and then placed in an argon atmosphere. Dehydrated THF (29.5 ml) was added thereto, and the mixture was cooled to -78°C. Then, diisobutylaluminum hydride (1.0M THF solution, 14.8 ml) was added dropwise thereto. The temperature was raised from -78°C. to 0°C., and the mixture was stirred at 0°C. for 3 hours. Thereafter, 1 N hydrochloric acid was added to adjust the pH to 3.0. The mixture was left to stand until normal temperature was reached. After extraction with THF, the organic layer was dried over sodium sulfate. Sodium sulfate was removed by filtration, and the solvent was distilled off. The resultant solid was washed with dichloromethane to obtain Compound (10) (orange, solid, 438.2 mg) at a yield of 61%. |