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Chemical Structure| 6665-98-1 Chemical Structure| 6665-98-1

Structure of 6665-98-1

Chemical Structure| 6665-98-1

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Product Details of [ 6665-98-1 ]

CAS No. :6665-98-1
Formula : C6H5NO4
M.W : 155.11
SMILES Code : OC1=CC=CC([N+]([O-])=O)=C1O
MDL No. :MFCD00463758

Safety of [ 6665-98-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 6665-98-1 ]

* 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 [ 6665-98-1 ]

[ 6665-98-1 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 6665-98-1 ]
  • [ 75-11-6 ]
  • [ 72744-45-7 ]
YieldReaction ConditionsOperation in experiment
79% To a suspension of sodium hydride (60 %, 1 .0 g, 25 mmo.) in hexamethylphosphorous triamide (100 mL) was added a solution of 3-nitrobenzene-1 ,2-dioi (from Intermediate B3, 1.55 g, 10 mmol) in hexamethylphosphorous triamide (20 mL) during 10 minutes. Then diiodomethane (0.94 mL, 1 1.6 mmol) was added and the solution was stirred for another 30 minutes, quenched by ice-water and extracted with ether. The combined organic extracts were dried over anhydrous sodium suifate, concentrated to afford the product 4-nitrobenzo[rfj[1 ,3]dioxole (1.32 g, yield 79 %). 1H NMR (400 MHz, CDC.3) delta ppm 7.59-7.62 (dd, 1 H, J = 1.2 Hz, 8.8 Hz), 7.06-7.09 (dd, 1 H, J = 0.8 Hz, 8.0 Hz), 6.91-6.96 (dt, 1 H, J = 0.8 Hz, 8.4 Hz), 6.219-6.221 (d, 2H, J = 0.8 Hz).
  • 3
  • [ 6665-98-1 ]
  • [ 20734-66-1 ]
YieldReaction ConditionsOperation in experiment
palladium; In methanol; (1) To a solution of <strong>[6665-98-1]3-nitrobenzene-1,2-diol</strong> (600 mg) in methanol (6 ml) was added 10% palladium on carbon (60 mg), and the mixture was stirred for 3 hours at ambient temperature under hydrogen atmosphere. Insoluble material was filtered off, and the filtrate was concentrated in vacuo. The residue was crystallized with diisopropyl ether to give 3-aminobenzene-1,2,-diol (470 mg). mp: 163-166 C. NMR (DMSO-d6, delta): 4.30 (2H, br s), 6.01-6.13 (2H, m), 6.34 (1H, t, J=8 Hz)
  • 7
  • 2-Acetoxy-6-nitro-phenol [ No CAS ]
  • [ 6665-98-1 ]
  • 8
  • [ 116668-84-9 ]
  • [ 6665-98-1 ]
  • 9
  • [ 60-29-7 ]
  • [ 120-80-9 ]
  • [ 110-46-3 ]
  • [ 6665-98-1 ]
  • [ 3316-09-4 ]
  • 10
  • [ 120-80-9 ]
  • [ 110-46-3 ]
  • [ 6665-98-1 ]
  • [ 3316-09-4 ]
  • 11
  • [ 120-80-9 ]
  • [ 6665-98-1 ]
YieldReaction ConditionsOperation in experiment
75% With uronium nitrate; In water; acetonitrile; at 80℃; for 0.5h;Microwave irradiation; General procedure: Phenol (10 mmol) and urea nitrate (10 mmol)were mixed together in acetonitrile-water (95:5, 5 ml) in a 25 ml round bottomed flask and placed in a Milestone?s Start SYNTH microwave reactor. The reaction mixture was heated at 80C for 40-50 min. At the end of the reaction, the reaction mixture was allowed to cool at room temperature,treated with water, and extracted with dichloromethane. After removing the solvent under reduced pressure, the residue was purified by column chromatography on silica gel to give the corresponding nitrophenol. In allcases ortho-nitrophenols were obtained selectively without any evidence forthe formation of the para-substituted nitrophenols. All the compoundsobtained were characterized by 1H NMR, 13C NMR, mp (for solids), GC-MSand in comparison with authentic samples.
31.2% With nitric acid; In diethyl ether; at 0 - 20℃; catechol (22 g, 0.2 mol) was dissolved in 824 mL of diethyl ether,Cooled to 0 C,Dropping smoke nitric acid 8.8mL,After dripping,Allow to stir at room temperature overnight.The system was poured into 250 mL of ice water,After stirring for 20 minutes,The aqueous phase was extracted six times with 150 mL of ether,Combined organic phase,After neutralizing the organic phase with saturated sodium carbonate,Dispensing,Dried over anhydrous sodium sulfate,filter,The filtrate was dried to obtain 38.2 g of crude product,Silica gel column chromatography of nitrated products 9.6g,Yield 31.2%.
30% With nitric acid; In diethyl ether; at 0 - 20℃; for 0.333333h; -nitrobenzene-1 ,2-diol To a solution of pyrocatechol (60 g, 0.54 mol) in ether (2000 mL) at 0 C was added fuming nitric acid (24 mL) dropwise. After the addition was over, the reaction was allowed to stand at room temperature for 20 minutes, decanted into ice-water and the resulting solution was extracted with ether. The combined organic extracts were neutralized with aqueous sodium carbonate (10%), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was purified by silica gel column chromatography (petroleum ether/ethyl acetate 5/1 ) to afford the product 3-nitroberizene-1 ,2-diol (25 g, yield 30 %). 1H NMR (400 MHz, CDCI3) delta ppm 10.62 (s, 1 H), 7.64-7.67 (dd, 1 H, J = 1 .6 Hz, 8.8 Hz), 7.23-7.26 (m, 1 H), 6.89-6.93 (t, 1 H, J = 8.4 Hz), 5.79 (br, 1 H).
With conc. nitric acid; In Petroleum ether; EXAMPLE 109 3-Nitrocatechol To a solution containing 2.5 g of catechol in 125 ml of ether 1.0 ml of conc. nitric acid (d=1.52) was gradually added. The solution was stirred over night at room temperature and washed with water. The solvent was evaporated and the residue was treated with boiling petroleum ether (b.p. 60-80 C.). The insoluble 4-nitrocatechol was filtered and the filtrate concentrated in vacuo. After cooling the 3-nitrocatechol was filtered. Yield 0.85 g (24%), m.p. 82-85 C.
With nitric acid; EXAMPLE 10; Compound No 35 Step 1: Step carried out in accordance with the operating protocol described in J. Organometall. Chem. 1996, 507, 1-21.
With nitric acid; In diethyl ether; 8A. 3-Nitrocatechol To a solution of catechol (5 g, 45 mmol) in Et2O (187 mL) cooled to 0 C. was added dropwise fuming HNO3 (2 mL). After addition, the reaction was allowed to stand at rt overnight, and the Et2O was removed by evaporation under reduced pressure. The residue was triturated with pentane (3*), and the combined organics were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluding with 10%-20% EtOAc/hexane to give the title compound (2.94 g).
With nitric acid; In diethyl ether; at 20℃; for 0.333333h; Catechol (2.2 g, 20.0 mmol) was dissolved in ether (100 ml_) and to the resulting solution was added fuming nitric acid (1.0 mL) dropwise. The reaction was stirred at room temperature for 20 minutes, decanted into ice-water and the resulting solution was extracted with ether(3 x 50 mL). The combined organic extracts were neutralized with 10% sodium carbonate solution, dried over Na2SO4, filtered and concentrated in vacuo. The residue obtained was purified using flash column chromatography on silica gel (40% ethyl acetate-hexanes) to provide compound 16A.

  • 13
  • [ 6665-98-1 ]
  • [ 67-64-1 ]
  • 2,2-dimethyl-4-nitro-benzo[1,3]dioxole [ No CAS ]
YieldReaction ConditionsOperation in experiment
23.8% Nitrocatechol (0.5 g, 3.23 mmol)And phosphorus pentoxide (0.053 g)Was dissolved in toluene (2 mL)Heating to 75 C,After stirring for 10 min,Add acetone (0.275 mL).Phosphorus pentoxide (0.053 g) was added every 30 min,A total of 4 times,2 hours plus finished.After the addition, the reaction was continued for 1 hour.The reaction solution was lowered to room temperature,The solution was poured out of NaOH (20 mL, 1 mol / l)Dispensing,The organic phase was dried over anhydrous sodium sulfate,filter,Spin dry,A solid 0.15 g (yield: 23.8%) was obtained.
  • 14
  • [ 6665-98-1 ]
  • [ 77-78-1 ]
  • [ 116668-84-9 ]
  • 16
  • [ 6665-98-1 ]
  • [ 74-88-4 ]
  • [ 116668-84-9 ]
  • 17
  • [ 111-24-0 ]
  • [ 6665-98-1 ]
  • [ 135399-40-5 ]
  • 19
  • [ 6665-98-1 ]
  • [ 116-54-1 ]
  • [ 110683-67-5 ]
YieldReaction ConditionsOperation in experiment
Step 2: Step carried out in accordance with J. Med. Chem. 1988, 31, 84-91.
  • 20
  • [ 6665-98-1 ]
  • [ 106-93-4 ]
  • [ 57356-28-2 ]
YieldReaction ConditionsOperation in experiment
62% With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 2h; Ste B: 5-nitro-2,3-dihydrobenzo[b][1 ,4]dioxineTo a solution of 3-nitrobenzene-1 ,2-diol (11 g , 0.071 mol) in Lambda/,Nu -dimethylformamide (500 mL) was added potassium carbonate (29 g ,0.0.213 mol) followed by 1 ,2-dibromoethane (14.7 g, 0.078 mol). The mixture was heated at 110 C for 2 hours. After cooled to room temperature, the mixture was poured into water and then extracted with ether. The organic phases were combined and dried over anhydrous sodium sulfate, filtrated and concentrated to give a crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 20/1 ) to afford the product 5-nitro-2,3-dihydrobenzo[to][1 ,4]dioxine (8 g, yield 62 %). 1 H NMR (400 MHz, CDCI3) delta ppm 7.48-7.50 (dd, 1 H, J = 1 .6 Hz, 8.4 Hz), 7.09-7.12 (dd, 1 H, J = 1.6 Hz, 8.4 Hz), 6.88-6.92 (t, 1 H, J = 8.4 Hz), 4.40-4.42 (m, 2H), 4.34-4.36 (m, 2H).
With potassium carbonate; In i-Amyl alcohol; for 15h;Heating / reflux; A mixture of compound 16A (1.10 g, 7.1 mol), 1 ,2-dibromoethane (9.33 g, 49.7 mmol) and anhydrous potassium carbonate (2.94 g, 21.3 mmol) in isoamyl alcohol (100 mL) was heated to reflux and allowed to stir at this temperature for 7 hours. Additional 1 ,2-dibromoethane (6.57 g, 35.0 mmol) and anhydrous potassium carbonate (4.84 g, 35.0 mmol) were added to the reaction mixture and reaction was stirred at reflux for 8 additional hours, then cooled to room temperature. The isoamyl alcohol was removed in vacuo and the liquid residue obtained was decanted into water, extracted with dichlorometha?e and the dichloromethane solution was concentrated in vacuo. The resulting residue was purified using flash column chromatography on silica gel (20% ethyl acetate-hexanes) to provide compound 16B as pale-yellow solid. HPLC-MS tR = 1.57 min (UV254 nm); mass calculated for formula C8H7NO4 181.0. observed LCMS m/z 182.1 (M+H).
  • 21
  • [ 6665-98-1 ]
  • [ 109-64-8 ]
  • [ 115464-84-1 ]
  • 22
  • [ 6665-98-1 ]
  • [ 106-89-8 ]
  • [ 2271-71-8 ]
  • (5-Nitro-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol [ No CAS ]
  • 23
  • [ 88-75-5 ]
  • [ 6665-98-1 ]
  • 24
  • [ 6665-98-1 ]
  • [ 108-24-7 ]
  • 3-nitro-1,2-benzenediol diacetate [ No CAS ]
  • 25
  • [ 6665-98-1 ]
  • [ 155728-88-4 ]
  • (8-Nitro-3-phenyl-2,3-dihydro-benzo[1,4]dioxin-2-yl)-methanol [ No CAS ]
  • 26
  • [ 6665-98-1 ]
  • [ 5332-81-0 ]
  • 8-nitro-2-vinyl-2,3-dihydro-benzo[1,4]dioxine [ No CAS ]
  • 5-nitro-2-vinyl-2,3-dihydro-benzo[1,4]dioxine [ No CAS ]
  • 27
  • [ 60-29-7 ]
  • [ 7697-37-2 ]
  • [ 120-80-9 ]
  • [ 6665-98-1 ]
  • [ 3316-09-4 ]
  • 28
  • [ 591-27-5 ]
  • sulfomonoperoxoic acid [ No CAS ]
  • [ 6665-98-1 ]
  • [ 17540-51-1 ]
  • [ 3316-09-4 ]
  • [ 554-84-7 ]
  • 32
  • 2-oxy-3-nitro-benzaldehyde [ No CAS ]
  • [ 6665-98-1 ]
  • 33
  • [ 6665-98-1 ]
  • [ 7726-95-6 ]
  • [ 64-19-7 ]
  • [ 2435-54-3 ]
  • [ 488-47-1 ]
  • 34
  • [ 6665-98-1 ]
  • [ 7697-37-2 ]
  • [ 144-62-7 ]
  • [ 15719-64-9 ]
 

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