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Chemical Structure| 20734-66-1 Chemical Structure| 20734-66-1

Structure of 3-Aminobenzene-1,2-diol
CAS No.: 20734-66-1

Chemical Structure| 20734-66-1

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Product Details of [ 20734-66-1 ]

CAS No. :20734-66-1
Formula : C6H7NO2
M.W : 125.13
SMILES Code : OC1=CC=CC(N)=C1O
MDL No. :MFCD14584779
InChI Key :MGBKJKDRMRAZKC-UHFFFAOYSA-N
Pubchem ID :189460

Safety of [ 20734-66-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 20734-66-1 ]

* 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 [ 20734-66-1 ]

[ 20734-66-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 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)
  • 2
  • [ 6299-67-8 ]
  • [ 20734-66-1 ]
YieldReaction ConditionsOperation in experiment
16% With boron tribromide; In dichloromethane; at -78 - 20℃;Inert atmosphere; 2,3-dimethoxy aniline (438 μl, 3.26 mmol) in dichloromethane (5.0 ml)In solution, 1 mol / l boron tribromide / dichloromethane solution (11.4ml, 11.4 mmol)Under an argon atmosphere, it was dropped slowly from the dropping funnel at -78 .The temperature was raised to room temperature and stirred overnight. The reaction was quenched with saturated sodium hydrogen carbonate aqueous solution was neutralized with saturated ammonium chloride aqueous solution. And extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane / ethyl acetate) to give the title compound (67 mg, 16%).
188 mg (46%) With hydrogen iodide; sodium thiosulfate; In methanol; dichloromethane; water; acetic acid; a) 2,3-Dihydroxyaniline <strong>[6299-67-8]2,3-dimethoxyaniline</strong> (500 mg, 3.26 mmol) was dissolved in acetic acid (10 mL). Hydriodic acid 47% solution in water (10 mL) was added and the reaction stirred under reflux 8 h. The reaction was cooled to room temperature and stirred for 3 days. Solvent was removed in vacuo and the yellow solid dissolved in water and neutralized with sodium bicarbonate saturated aqueous solution. The aqueous layer was extracted with ethyl acetate (4*20 mL). The organic layers were combined, washed with a 10% solution of sodium thiosulfate (30 mL), water (30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated. The crude product was purified by Biotage (cartridge 40S, SiO2) using 1, 2 and 4% methanol in dichloromethane to yield 188 mg (46%) of 2,3-dihydroxyaniline as a beige solid. 1H NMR (CD3OD): 6.47 (t, J=8.0 Hz, 1H), 6.28 (dd, J=8.0, 1.6 Hz, 1H), 6.24 (dd, J=8.0, 1.6 Hz, 1H).
To a stirred solution 2,3-bis(methyloxy)aniline (3.0 g), in dry DCM (30 mL) at -450C under nitrogen was added a solution of boron tribromide (1 M in DCM, 68.5 mL) dropwise over 10 mins. After 0.5 h at -450C the cooling bath was removed and the mixture was allowed to <n="62"/>stand at room temperature overnight. The mixture was then cooled to 50C and water was added dropwise with stirring. The aqueous phase was adjusted to pH 5/6 using saturated sodium bicarbonate solution and the resulting mixture was extracted with DCM (x 2). The aqueous layer was separated using a hydrophobic frit and was passed down a pre- conditioned OASIS HLB cartridge. The cartridge was eluted with methanol to give the title compound.1H NMR Cd6-DMSO) δ 6.35 (1 H, t), 6.10 (1 H, d), 6.06 (1 H, d), amino and hydroxyl protons not seen.
 

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