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[ CAS No. 830-03-5 ]

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2D
Chemical Structure| 830-03-5
Chemical Structure| 830-03-5
Structure of 830-03-5 *Storage: {[proInfo.prStorage]}

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Product Details of [ 830-03-5 ]

CAS No. :830-03-5MDL No. :MFCD00007326
Formula :C8H7NO4Boiling Point :296.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :181.15Pubchem ID :13243
Synonyms :

Computed Properties of [ 830-03-5 ]

TPSA : 72.1 H-Bond Acceptor Count : 4
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.13 Rotatable Bond Count : 2

Safety of [ 830-03-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 830-03-5 ]

  • Downstream synthetic route of [ 830-03-5 ]

[ 830-03-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 100-02-7 ]
  • [ 75-36-5 ]
  • [ 830-03-5 ]
YieldReaction ConditionsOperation in experiment
85% With hydroxyapatite supported copper(I) oxide; In acetonitrile; at 50℃; for 1h; General procedure: A mixture of alcohol or phenol (1 mmol), acetyl chloride(1 mmol), hydroxyapatite -Cu2O (0.1 g) in acetonitrilewas taken in a round-bottom flask and stirred at 50 C foran appropriate time. On completion (monitored by TLC),the reaction mixture was cooled to room temperature andfiltered. The residue was washed with water followed byEtOAc (3 × 10 mL). The product was obtained after theremoval of solvent under reduced pressure followed bycrystallization from pet ether or EtOAc:pet ether or passingthrough column of silica and elution with EtOAc:pet ether.
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  • 2
  • [ 830-03-5 ]
  • [ 13871-68-6 ]
YieldReaction ConditionsOperation in experiment
32% With iron; ammonium chloride; In methanol; water; at 120℃; for 0.0833333h;Microwave irradiation; Sealed tube; General procedure: To a 10-mL microwave vial were added the nitroarene (0.50 mmol), zinc dust (3.00 mmol), MeOH (1.0 mL), and saturated aqueous NH4Cl (1.0 mL). The vial was sealed and heated at 120 C for 5 min. The reaction mixture was transferred to a separatory funnel containing saturated aqueous Na2CO3 (10 mL) and extracted with CH2Cl2 (3x8 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to provide anilines 2.
21% With 6Hf6O4(OH)4(2+)*6C7H3NO4(2-); isopropyl alcohol; for 20h;Irradiation; General procedure: In a typical catalytic reaction, 20 mg of MOF, 1 mmol of substrate and 20 mL of iPrOH were put into the 25 mL J-Young quartz tube. The nreaction vessel was closed and placed 15 cm from 200W Hg/Xe lamp irradiation for 20 h, while the stirring rate was set to 900 rpm. After 20 h, an aliquot of the reaction was transferred through a short Celite plug to remove the solids, and injected into GC.
In 5-(Oxiran-2-yl-methoxy)-2-[(3-trifluoromethyl)phenyl]benzoxazole; Synthesis of 4-aminophenyl Acetate (55): Compound 55 was prepared in the manner of compound 12 substituting 4-nitrophenyl acetate for compound 11 in part C-1 of Example 1.
In 5-(Oxiran-2-yl-methoxy)-2-[(3-trifluoromethyl)phenyl]benzoxazole; Synthesis of 4-aminophenyl acetate (55): Compound 55 was prepared in the manner of compound 12 substituting 4-nitrophenyl acetate for compound 11 in part C-1 of Example 1.
With hydrazine hydrate; In ethanol; at 50℃; for 1h; General procedure: Nitrobenzene 0.5 mmol, solvent 2.0 mL and 50 L p-xylene asan internal standard were added into a 15 mL pressure bottle withmagnetic stirring. Then the hydrazine hydrate and catalyst wereadded into the reactor, and the reaction time was set as zero. Thesamples were obtained by hot filtration and analyzed by GC-MS(GC: Agilent 7890A, MS: Agilent 5975C) and GC (Agilent 7890A).
137.9 g With iron; ammonium chloride; In ethanol; water; for 2h;Reflux; 3000 mL of water and 3000 mL of ethanol were added to the reaction flask,Reduced iron powder (195.5 g, 3.5 mol) was added with stirring,And ammonium chloride (187.2 g, 3.5 mol),Heating reflux 1h,The [830-03-5]p-nitrophenyl acetate (8) obtained in the previous step was added portionwise,Reaction was continued for 2 h and the reaction was complete by TLC.Stop reaction, while hot suction filtration,To the filtrate was added 2000 mLDichloromethane, extraction,The organic layer was separated and washed with water (3 x 500 mL)The organic layer was dried over anhydrous sodium sulfate.Filtration,The filtrate was evaporated under reduced pressure to remove the solvent to give a pale yellow solid,Then recrystallized from ethyl acetate,Drying gave 137.9 g of compound 7; overall yield 90.7%.

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  • 3
  • [ 100-02-7 ]
  • [ 108-24-7 ]
  • [ 830-03-5 ]
YieldReaction ConditionsOperation in experiment
99.5% 4-N,N-dimethylaminopyridinium saccharinate; at 25℃;Product distribution / selectivity; Various secondary alcohols were esterified according to the following scheme by using the method of Example 2, and the results were listed in Table 1. TABLE 1 Temp. Time No. Sec. Alcohol R ( C.) (hr.) Yield (%) 1 1-cylco- Me 25 2.5 99.5, 99.1, 99.7, 96.6, hexanol 97.4, 96.8, 97.6, 93.5, 92.6, 86.6 2 1-cylco- iPr 25 2 >99.5, >99.5, >99.5, >99.5, hexanol >99.5, >99.5, 99, 99, 98, 98 3 1-phenyl- Me 25 2 >99.5, >99.5, >99.5, >99.5, ethanol >99.5, >99.5, >99.5, >99.5, >99.5, >99.5 4 1-phenyl- iPr 25 2 >99.5, >99.5, >99.5, >99.5, ethanol >99.5, >99.5, >99.5, >99.5, >99.5, >99.5 5 menthol Me 25 8-12 97, 96, 96, 96, 95, 92, 95, 98, 92, 87 6 menthol iPr 25 8-12 98, 98, 96, 96, 97, 95, 97, 99, 95, 92 7 1-cyclo- Me 25 8 99, 98, 99, 97, 97, 97, 96, dodecanol 97, 97 8 1-cyclo- iPr 25 8 95, 95, 95, 95, 94, 94, 95, dodecanol 95 9 4-nitro-phenol Me 25 2-4 >99.5, >99.5, >99.5, >97, >99.5, >99.5, 97.5, 96.4, 96, 96 10 4-nitro-phenol iPr 25 2-4 99.5, 99.5, 99.5, 99.5, 99.5, 99.5, 99.5, 99.5, 99.5, 99.5 From the results of No. 1 and No. 2 in Table 1, it can be known that the catalyst of Example 1 can catalyze the esterification of secondary alcohols. Since it is more difficult for a secondary alcohol to be esterified than a primary alcohol, the catalyst of Example 1 can surely catalyze the esterification of a primary alcohol. In addition, the catalyst of Example 1 can catalyze the reaction of an alcohol not only with acetic anhydride (see No. 1), but also with isobutyric anhydride, which has higher steric hindrance (see No. 2). Furthermore, it can be known from the yields that the effect of the catalyst did not decrease even after the catalyst was reused many times. For example, as shown by the results of No. 2 in Table 1, the yield was still as high as 98% after the catalyst was reused 10 times.From the results of No. 3 to 10, it can be known that the catalyst of Example 1 can also catalyze the reaction of secondary alcohols other than 1-cyclohexanol with various acid anhydrides. 1-phenylethanol (Nos. 3 and 4) can be esterified with high yield under substantially the same conditions as those for esterification of 1-cyclohexanol. For menthol (Nos. 5 and 6), longer reaction time (about 8 hours) was needed since menthol had higher steric hindrance than that of 1-cyclohexanol. For 1-cyclododecanol (Nos. 7 and 8), the reaction time is about 8 hours, and high yield was obtained even after the catalyst had been reused 8 times. In addition, for phenols with lower nucleophilicity, such as 4-nitrophenol (Nos. 9 and 10), the catalyst also showed good catalytic effect on acylation thereof since the reaction can be completed in 4 hours and the average yield was still above 98% even after the catalyst was reused 10 times.
> 99% With 4-(1-pyrrolidinyl)pyridinium saccharinate; In neat (no solvent); at 22℃; for 2h; General procedure: The alcohol (2mmol) and the anhydride (2.2mmol) were mixed in a 10mL test tube and 1mol% of salt A (0.02mmol) was added. The tube was then capped (or under N2 purge) and the reaction mixture was stirred at room temperature (except for 1-methylcyclopentanol at 60C). After a couple of hours the acid effluent was evaporated in vacuum. The residue was then allowed to cool to room temperature and the salt was precipitated by adding 2mL hexane (or toluene). After filtration, salt was recovered, and then evaporating solvent from the filtrate afforded the crude ester product. The recovered salt was charged with the substrates, and the reaction mixture was then proceeded to the next run. The products were quantified with GC analysis by comparison to NMP as an internal standard. The products from the 1st run were further purified by column chromatography, and the isolated yields were compared with the GC/MS yields. They were all in good agreement.
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  • 4
  • [ 830-03-5 ]
  • [ 627-18-9 ]
  • [ 99856-52-7 ]
YieldReaction ConditionsOperation in experiment
81% With caesium carbonate; In N,N-dimethyl-formamide; at 80℃; for 6h;Inert atmosphere; General procedure: Phenyl esters 1a-1c (0.5 mmol) were loaded into a flask (10 mL). DMF (2 mL) and Cs2CO3 (488 mg,1.5 mmol, 3.0 equiv) were then added, which was followed by the addition of 3-bromoethanol (2a,0.525 mmol, 1.05 equiv). Then the reaction mixture was stirred at 80 C for 6 h under an Ar atmosphere. After completion of the reaction, as confirmed by TLC, the reaction mixture was cooled down to roomtemperature and 10 mL of CH2Cl2 (DCM) and 10 mL of water were added. After separation of thedichloromethane layer from the water, the aqueous phase was extracted with CH2Cl2 (2 5 mL) again.The combined organic layers were then dried over anhydrous Na2SO4, filtered, and concentratedunder vacuum to yield the crude product. The crude product was purified by silica gel columnchromatography to obtain the desired pure compound.
  • 5
  • [ 830-03-5 ]
  • [ 1223-31-0 ]
YieldReaction ConditionsOperation in experiment
90% With copper(l) iodide; sulfur; sodium t-butanolate; In N,N-dimethyl-formamide; at 120℃; for 5h;Inert atmosphere; General procedure: A one-necked flask was charged with CuI (10 mg, 0.05 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (16 mg, 0.5 mmol), phenolic ester (1 mmol), anhyd DMF (2 mL) under an inert atmosphere. The mixture was magnetically stirred and heated at 120 C for the appropriate reaction time (Table 6). After completion of the reaction, the mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (n-hexane/EtOAc) gave the desired symmetrical diaryl sulfides in 75-93% yields.
  • 6
  • [ 830-03-5 ]
  • [ 65-85-0 ]
  • [ 959-22-8 ]
YieldReaction ConditionsOperation in experiment
88% With phosphotungstic acid; In 5,5-dimethyl-1,3-cyclohexadiene; at 160 - 170℃; for 2h;Reflux; In the reaction container, adding weighed benzoic acid 1.34g (0.011mol), P-nitro-phenol acetic ester 1.81g (0.01mol), xylene 17.5g (20 ml), a condenser, water separator, drying tube, magnetic stirrer, silicone oil oil bath for heating, control temperature at 160-170C. To be after the backflow, by adding 0.1g phosphotungstic acid catalyst reaction. Reaction 2h completed by adding 5Na 2 CO 3 solution and water washing two times, organic add anhydrous MgSO 4 drying, filtering, the solvent is removed by reduced pressure distillation, solid finally the column separation, to obtain the product 2.14 g, yield 88 , to nuclear magnetic resonance and infrared analysis.
83% With phosphotungstic acid; In 5,5-dimethyl-1,3-cyclohexadiene; at 160 - 170℃; In a 100 mL round-bottomed flask, fitted with a mechanical stirrer and water segregator,and a gas tube in a well-ventilated hood, was placed 1.875 g (10 mmol) of benzoic acid and 0.820 g 3-methylphenyl acetate in 20mL xylene. After the mixture was refluxed under temperature 160-170C, 0.1g silicotungstic acid was added in the solution. The mixture was stirred under the same situation for 12 h.The precipitate of the mixture was collected and dried over vacuum.
  • 7
  • [ 100-02-7 ]
  • [ 155164-63-9 ]
  • [ 830-03-5 ]
YieldReaction ConditionsOperation in experiment
96% In neat (no solvent); at 100℃; for 0.0833333h;Sealed tube; Green chemistry; General procedure: Alcohol(1, 5.31 mmol, 1 equiv.) and 2-acylpyridazin-3(2H)-ones (2,6.37 mmol, 1.2 equiv.) were placed in a culture tube (Pyrexbrand 9825 culture tube with screw cap), sealed, and heatedto 100 C. The resulting mixture was kept at this temperatureuntil 1 disappeared (as determined by TLC analysis). Aftercooling of the tube, dichloromethane (5-6 mL) was added tothe mixture with stirring until the reaction mixture wasdissolved. After removing 4,5-dichloropyridazin-3(2H)-oneby filtration, the resulting filtrate was evaporated underreduced pressure. The resulting residue was further purifiedby silica gel column chromatography to give the correspondingesters 3.
93% In tetrahydrofuran; at 150℃; under 10336.0 Torr; for 0.0833333h;Microwave irradiation; General procedure: Alcohol (2 or 5, 5.31 mmol, 1 equiv) and 2-acylpyridazin-3(2H)-ones (1k or 4, 6.37 mmol, 1.2 equiv) were placed in a capped vial without solvent or in the presence of tetrahydrofuran (5 mL, 6f and 6g) at room temperature. The resulting mixture was irradiated in aMWoven (300Woutput,1378 kPa) at 150 C for 5 min, until 1k or 4 was consumed. The reaction was monitored by TLC. After cooling Phenyl acetate (3) of the reaction vial, the product was extracted with dichloromethane (6 mL). The reaction mixture was filtered, and the resultant filtrate was evaporated under reduced pressure. The resulting residue was purified further by silica gel column chromatography to give the corresponding esters 3 and 64-Nitrophenyl acetate (6c) Yield: 608 mg, 93%. White solid. Mp 77-79 C (lit. 15 mp 78-79 C). IR (KBr, CH2Cl2) 3110, 3084, 2936, 2857, 1762, 1615, 1592, 1524, 1490, 1369, 1348, 1189, 1160, 1108, 1101, 911, 866, 851 cm-1. 1H NMR (300 MHz, CDCl3) delta 2.34 (s, 3H), 7.25-7.30 (m, 2H), 8.22-8.27 (m, 2H). 13C NMR (75 MHz, CDCl3) delta 21.07, 122.52, 125.18, 145.31, 155.45, 168.45. HRMS (m/z): [M]+ calcd for C8H7NO4 181.0375. Found: 181.0377.
70% General procedure: To a solution of alcohol 2 (1 equiv, 2 mmol) in THF (20 mL),AlCl3 (1 equiv) was added followed by stirring for 1 min. 2-Acyl-4,5-pyridazin-3(2H)-one 1 (1 equiv) was then added and the mixture was stirred at room temperature until the alcohol was consumed. The reaction was quenched by the addition of H2O (20 mL), and the mixture was stirred for 10 min at room temperature. After the addition of CH2Cl2 (40mL), the organic layer was separated and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure, and the resulting residue was applied to the top of an open-bed silica gel column. The column was eluted with CH2Cl2 (for 3a-g, 5a and 5b), MeCN-CH2Cl2(1:5 v/v for 3 h), EtOAc-CH2Cl2 (1:1 v/v for 3i), n-hexane-CH2Cl2-EtOAc (4:2:1 v/v for 3j and 3k), or n-hexane-EtOAc (10:1 v/v for 5c and 5d). Fractions containing the product were combined and evaporated under reduced pressure to give the desired esters. Fractions containing 4,5-dichloropyridazin-3(2H)-one were combined and evaporated under reduced pressure to quantitatively give reusable 4,5-dichloropyridazin-3(2H)-one.
  • 8
  • [ 108-05-4 ]
  • [ 100-02-7 ]
  • [ 830-03-5 ]
YieldReaction ConditionsOperation in experiment
91% With pyridine; In ethanol; at 90℃; for 20h;Schlenk technique; Accurately weigh p-nitrophenol (69.5mg, 0.5mmol),Vinyl acetate (43.0 mg, 0.5 mmol) and pyridine (15.8 mg, 0.2 mmol),And added to a 50 mL Schlenk bottle in turn, adding ethanol (25.0 mL),The reaction was carried out in an oil bath at 90 C for 20 h. After the reaction was completed, the solvent was removed under reduced pressure.Separation of silica gel column using petroleum ether/ethyl acetate as eluentThe yield of [830-03-5]p-nitrophenyl acetate was 91%.
81% With sodium carbonate; In acetonitrile; at 120℃; for 24h;Schlenk technique; General procedure: A mixture of phenol 1 (0.50 mmol), Na2CO3 (10.6 mg, 0.10mmol, 20 mol%), and alkenyl carboxylate (2.0 mmol, 4.0 equiv)in MeCN (3 mL) was added to a Schlenk flask (25 mL) and stirredat r.t. The mixture was stirred at 120 C until the reaction wasfinished. Then, the solvent was evaporated under reduced pressureand the residue was purified by column chromatography(petroleum ether/ethyl acetate 20:1 to 10:1) to afford theproduct 3.
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