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1,2-Dimethoxybenzene is an aromatic ether commonly found in secondary metabolites of plants, showing some antioxidant and antimicrobial activities. It protects cells from oxidative stress by inhibiting ROS production and enhancing cellular antioxidant enzyme activity.

Synonyms: Veratrole

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Product Citations

Product Citations

Canan Sener ; Vitaliy I. Timokhin ; Jan Hellinger ; John Ralph ; Steven D. Karlen ;

Abstract: Hydrogenolysis of lignin generates a portfolio of products, the yields of which are generally calculated using a subset of phenolic monomers that are dependent on the lignin composition, product distribution, and analytical technique. Some lignins are naturally γ-acylated; poplar lignins, for example, have p-hydroxybenzoate groups on 1–15% of their syringyl subunits. Upon hydrogenolysis, it is generally assumed that the p-hydroxybenzoate is cleaved before the deacylated lignin is depolymerized. Hydrogenolysis of model γ-p-hydroxybenzoylated β-aryl ethers do not, however, produce the deacylated β-aryl ether intermediates, as was previously conjectured; products instead derive from palladium-assisted reactions on the cinnamyl p-hydroxybenzoates resulting in initial β-ether cleavage. The p-hydroxybenzoate moiety itself also undergoes carboxylate-assisted palladium-catalyzed C–H bond activation to form the 2,4-dihydroxybenzoate, that subsequently converts to the 2,4-dihydroxycyclohex-1-enoate. These details underscore previously unrec_x0002_ognized pathways and products that are key to understanding the different hydrogenolysis product distributions from naturally acylated lignins that are prevalent biomass-conversion feedstocks.

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Product Details of 1,2-Dimethoxybenzene

CAS No. :91-16-7
Formula : C8H10O2
M.W : 138.16
SMILES Code : COC1=CC=CC=C1OC
Synonyms :
Veratrole
MDL No. :MFCD00008357
InChI Key :ABDKAPXRBAPSQN-UHFFFAOYSA-N
Pubchem ID :7043

Safety of 1,2-Dimethoxybenzene

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of 1,2-Dimethoxybenzene

* 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.

  • Upstream synthesis route of [ 91-16-7 ]
  • Downstream synthetic route of [ 91-16-7 ]

[ 91-16-7 ] Synthesis Path-Upstream   1~17

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References: [1] Patent: WO2013/39854, 2013, A1, .
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 934 - 946.
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References: [1] European Journal of Organic Chemistry, 2003, # 19, p. 3735 - 3743.
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  • [ 37637-88-0 ]
  • [ 4136-26-9 ]
References: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 339 - 341.
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References: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 12, p. 1801 - 1805.
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YieldReaction ConditionsOperation in experiment
90.1% at 25℃; for 24 h; A type B crystal of 2,3,6,7,10,11-hexahydroxytriphenylene monohydrate was synthesized according to the process described in Synthesis, 477, 1994 and JP-A-8-119894. Namely, 1,2-dimethoxybenzene (31.78 g, 0.23 moles) and anhydrous ferric chloride (120 g, 0.74 moles) were dissolved in 70percent sulfuric acid, and the solution was reacted at 25°C for 24 hours with stirring. After completion of the reaction, the solution was poured into ice water (500 g), and the precipitated crystal was collected by filtration. After the resultant crystal was washed with water (1 L), and then dried to give pale purple colored 2,3,6,7,10,11-hexamethoxytriphenylene (28.2 g, theoretical yield from 1,2-dimethoxybenzene: 90.1percent) (the method of Synthesis, 477, 1994).
85.4% at 10 - 15℃; for 6 h; 600 ml of ethyl acetate was added into a 1000ml four-necked flask, sodium peroxydisulfate 102.4g (0.43 mol) and o-xylene 45.7 g (0.43 mol) were added, stirred and cooled at internal temperature of 10 degrees C. Anhydrous iron(III) chloride 345.4g (2.10 mol) was added little by little, reacted at an internal temperature of 10-15 degrees C for 6 hours. After completion of the reaction, reaction mixture was cooled, 2000 ml of water was added and stirred for 10minutes. The aqueous layer of the solution was separated, and the organic layer was washed with 800 ml of salt solution. 600 ml of methanol was added to the organic layer and crystallized at 15-25 degrees C for 1 hour, the crystals were filtered, and dried to obtain 19.5 g (43.6percent of yield) of objects as gray crystal.
82% With trifluorormethanesulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 10 h; Inert atmosphere General procedure: An oven-dried 20 mL scintillation vial, equipped with a magnetic stir-bar, was charged with the starting material (1.0 equiv), DDQ (1.0 equiv), trifluoromethanesulfonic acid (1.4percent v/v, 3.0 equiv), and 1,2-dichloroethane (0.05 M). The reaction mixture was then allowed to stir at ambient temperature for 10 h. After this time, methanol (0.05M) was added, and the solution was then allowed to stir at ambient temperature for an additional hour. Upon addition of the methanol, some solids precipitated out of the solution. Then, the solvent was removed from the heterogeneous mixture under reduced pressure. The crude material was purified by either recrystallization (methanol/DCM) or silica-gel column chromatography (hexanes/DCM) to give the title compounds.
80% With iron(III) chloride; sulfuric acid In dichloromethane at 20℃; for 3 h; A solution of 1,2-dimethoxybenzene (10 g, 72.4 mmol) in dichloromethane(50 ml) was added dropwise to a suspension of anhydrous FeCl3 (35.22 g, 217.2 mmol) in dichloromethane (100 ml) and concentrated sulphuric acid (0.5 ml). After complete addition (15 min), the reaction mixture was further stirred for 3 h at room temperature. 200 ml of methanol were then slowly added under vigorous stirring. The obtained mixture was further stirred for additional 30 min. And the precipitate was filtered off, washed with methanol (5 × 100 ml) and dried under reduced pressure to give a purple solid. Yield: 80percent, 1HNMR (CDCl3) δ/ppm: 4.10 (s, 18H, OCH3), 7.80 (s, 6H, ArH).

References: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 44, p. 8209 - 8213.
[2] Synthesis, 1994, vol. 1, # 5, p. 477 - 478.
[3] Patent: EP2177495, 2010, A1, . Location in patent: Page/Page column 12.
[4] Synthetic Communications, 1999, vol. 29, # 10, p. 1767 - 1771.
[5] Journal of the American Chemical Society, 2017, vol. 139, # 46, p. 16759 - 16767.
[6] Patent: JP5731346, 2015, B2, . Location in patent: Paragraph 0086; 0087; 0095.
[7] Journal of Materials Chemistry, 2002, vol. 12, # 8, p. 2208 - 2213.
[8] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3458 - 3462.
[9] Journal of Molecular Liquids, 2016, vol. 223, p. 734 - 740.
[10] Journal of the American Chemical Society, 2009, vol. 131, p. 7662 - 7677.
[11] Chemical Communications, 1997, # 17, p. 1615 - 1616.
[12] Journal of the American Chemical Society, 1980, vol. 102, # 21, p. 6504 - 6512.
[13] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1975, p. 2185 - 2189.
[14] Tetrahedron, 1965, vol. 21, p. 3229 - 3236.
[15] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
[16] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 125, p. 279 - 288.
[17] Journal of Structural Chemistry, 2001, vol. 42, # 1, p. 38 - 42.
[18] Chemistry Letters, 1994, # 6, p. 981 - 984.
[19] Journal of Physical Chemistry, 1995, vol. 99, # 3, p. 1005 - 1017.
[20] Synthesis, 1997, # 11, p. 1285 - 1290.
[21] Russian Chemical Bulletin, 2004, vol. 53, # 8, p. 1743 - 1748.
[22] Chemical Communications, 2015, vol. 51, # 21, p. 4368 - 4371.
[23] Chimia, 2015, vol. 69, # 9, p. 520 - 523.
[24] Patent: JP2017/31106, 2017, A, . Location in patent: Paragraph 0052-0055.
[25] Journal of Materials Chemistry A, 2017, vol. 5, # 24, p. 12080 - 12085.
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References: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326.
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References: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 4, p. 465 - 466.
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References: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326.
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References: [1] Journal of the Chemical Society, Chemical Communications, 1994, # 4, p. 465 - 466.
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References: [1] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 5, p. 317 - 326.
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References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
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References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
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References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
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References: [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408.
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References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
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References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
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References: [1] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
[2] Tetrahedron, 1991, vol. 47, # 4/5, p. 791 - 798.
 

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