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Chemical Structure| 20299-79-0 Chemical Structure| 20299-79-0

Structure of 20299-79-0

Chemical Structure| 20299-79-0

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Product Details of [ 20299-79-0 ]

CAS No. :20299-79-0
Formula : C11H9NO2
M.W : 187.19
SMILES Code : O=C(C=C1)N(C2=CC=CC(C)=C2)C1=O
English Name :1-(m-Tolyl)-1H-pyrrole-2,5-dione
MDL No. :MFCD00047117
InChI Key :PRZFFHNZHXGTRC-UHFFFAOYSA-N
Pubchem ID :247652

Safety of [ 20299-79-0 ]

Application In Synthesis of [ 20299-79-0 ]

* 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 [ 20299-79-0 ]

[ 20299-79-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 54012-55-4 ]
  • [ 20299-79-0 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; acetic anhydride
With sodium acetate; acetic anhydride Reflux;
With sodium acetate In acetic anhydride at 120℃; for 0.5h; Microwave irradiation; Preparation of substrate compound 19v-19γ General procedure: Primary amine (1.0 eq.) were dissolved in THF. Maleimide (1.1 eq.) dissolved in THF was slowly added to amine solution. The reaction mixture was stirred for 30 min atroom temperature. A lot of precipitation appeared. The precipitation was collected by filtration. The filtrate was dissolved in acetic anhydride and sodium acetic acid (1.2 eq.) was added. The mixture was heated at 120°C by microwave irradiation for 30 mins and then poured into water. Saturated NaHCO3 solution was added to neutralize the mixture. Precipitation appeared and the solid was collected by filtration. The precipitate was purified by column chromatography to afford maleimide 19a-19γ.
at 135℃;
With manganese(II) acetate; acetic anhydride; triethylamine In acetone at 55 - 65℃;

  • 2
  • [ 4506-71-2 ]
  • [ 20299-79-0 ]
  • [ 374778-17-3 ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate With sulfuric acid; sodium nitrite In acetic acid; propionic acid at 0 - 5℃; for 2h; Stage #2: 1-(3-methylphenyl)-1H-pyrrole-2,5-dione In acetic acid at 0 - 5℃;
  • 3
  • [ 42537-50-8 ]
  • [ 20299-79-0 ]
YieldReaction ConditionsOperation in experiment
41% With sodium acetate; acetic anhydride at 100℃; for 6h; 2.4 N-(3-Methylphenyl)maleimide (3MPMI) N-(3-Methylphenyl)maleimide was synthesized from a two-step reaction (Scheme 2 ). The second step of the reaction used a modified literature method [31]. To synthesize N-(3-methylphenyl)maleamic acid, maleic anhydride (10.0g, 102mmol) and toluene (8ml) were stirring in a 100ml flask. m-Toluidine (11.1g, 102mmol) was added drop wise. During the addition, 15ml toluene was added to maintain a good slurry consistency, after which the mixture was refluxed for 15min. The product precipitated from solution was filtered warm and vacuum dried for 24h to afford a light yellow solid (19.63g, 94%). 1H NMR (DMSO-d6, 400MHz) δ ppm: 10.27 (s, 1H), 7.43-6.87 (m, 4H), 6.42 (d, 1H), 6.26 (d, 1H), 2.23 (s, 3H). A mixture of N-(3-methylphenyl)maleamic acid (17.6g, 85.9mmol), acetic anhydride (43.8g, 429mmol) and anhydrous sodium acetate (3.52g, 42.9mmol) was heated at 100°C for 6h. The reaction mixture was cooled and poured in ice water. The crude product was then washed with ice water and vacuum distilled (62°C, 0.2mmHg) to afford N-(3-methylphenyl)maleimide (yellow liquid, 15.1g, 94%). The crude product was purified by column chromatography (silica gel, hexane-ethyl acetate=5:1). The first band afforded pure product as a yellow liquid (6.19, 41%) (lit [32] 78%) 1H NMR (CDCl3, 500MHz) δ ppm: 7.36 (m, 1H), 7.22-7.10 (m, 5H), 2.34 (t, 3H) (FigureS2).
With sodium acetate; acetic anhydride at 90 - 100℃; for 0.5h;
With sodium acetate; acetic anhydride for 0.5h; Heating;
With acetic anhydride

  • 4
  • [ 20299-79-0 ]
  • [ 4815-30-9 ]
  • [ 344451-24-7 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: diethyl 5-amino-3-methyl-2,4-thiophenedicarboxylate With sulfuric acid; sodium nitrite In acetic acid; propionic acid at 0℃; for 2h; Stage #2: 1-(3-methylphenyl)-1H-pyrrole-2,5-dione In acetic acid; propionic acid at 0 - 30℃;
  • 5
  • [ 108-31-6 ]
  • [ 108-44-1 ]
  • [ 20299-79-0 ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid at 130℃; for 6h;
48% With acetic acid for 18h; Reflux; 8 Maleic anhydride (25 g, 250 mmol) and 380 ml of acetic acid were added to a 500 mL single-necked bottle, and then m-toluidine (26.75 g, 250 mmol) was slowly added dropwise to the reaction solution with stirring at room temperature. After the dropwise addition, the reaction solution was placed in an oil bath and refluxed for 18 hours. After the reaction was completed, the reaction solution was cooled to room temperature, spin-dried the solvent, 100-200 mesh silica gel column chromatography, and a mixed solvent (3: 1) of petroleum ether and ethyl acetate was rinsed. 22.54 g of the compound represented by the structure of formula IVb was isolated with a yield of 48%.
Stage #1: maleic anhydride; 1-amino-3-methylbenzene In diethyl ether at 20℃; Stage #2: With sodium acetate; acetic anhydride at 120℃;
Stage #1: maleic anhydride; 1-amino-3-methylbenzene With acetic acid at 125℃; for 6h; Stage #2: With sodium hydrogencarbonate In water at 20℃;
With acetic acid at 130℃; for 8h;
With acetic acid at 125℃;
With acetic acid Reflux;
With acetic acid Reflux;
With acetic acid at 130℃;
With acetic acid Reflux;
With acetic acid at 125℃; Schlenk technique;
Stage #1: maleic anhydride; 1-amino-3-methylbenzene In dichloromethane at 20℃; for 0.75h; Stage #2: With sodium acetate; acetic anhydride In dichloromethane at 100℃; for 4h;

References: [1]Maharana, Prabhat Kumar; Muthuraja, Perumal; Kar, Subhradeep; Veerappan, Tamilthendral; Punniyamurthy, Tharmalingam [Chemical Communications, 2025, vol. 61, # 71, p. 13449 - 13452].
[2]Current Patent Assignee: INSTITUTE OF CHEMISTRY OF CHINESE ACADEMY OF SCIENCES - CN111018866, 2020, A Location in patent: Paragraph 0145; 0152; 0153.
[3]Location in patent: scheme or table Chen, Hai-Jun; Liu, Yong; Wang, Li-Na; Shen, Qiang; Li, Jia; Nan, Fa-Jun [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2876 - 2879].
[4]Ghosh, Asim Kumar; Samanta, Sadhanendu; Ghosh, Payel; Neogi, Sukanya; Hajra, Alakananda [Organic and Biomolecular Chemistry, 2020, vol. 18, # 16, p. 3093 - 3097].
[5]Li, Xiaolan; Zhang, Xiuqi; Zhang, Fukuan; Luo, Xuzhong; Luo, Haiqing [Advanced Synthesis and Catalysis, 2022, vol. 364, # 10, p. 1683 - 1688] Yin, Qi; Zhou, Xinlin; Tan, Bin; Wang, Xueao; Liu, Jiao; Deng, Guo-Jun; Chen, Shanping [Advanced Synthesis and Catalysis, 2025, vol. 367, # 23].
[6]Zheng, Jing; He, Yuan; Dong, Lin [European Journal of Organic Chemistry, 2023, vol. 26, # 3].
[7]Hota, Sudhir Kumar; Panda, Satya Prakash; Das, Sanju; Mahapatra, Sanat Kumar; Roy, Lisa; De Sarkar, Suman; Murarka, Sandip [Journal of Organic Chemistry, 2023, vol. 88, # 4, p. 2543 - 2549] Jiang, Bo; Wang, Hui; Sun, Xiaobin; Qiao, Yiyang; Xu, Xiufang; Miao, Zhiwei [Advanced Synthesis and Catalysis, 2025, vol. 367, # 9].
[8]Liu, Hao; Gong, Zi-Rong; Lin, Meng-Ling; Luo, Wen; Xu, Yan-Jun; Dong, Lin [Journal of Organic Chemistry, 2023, vol. 88, # 6, p. 3916 - 3926].
[9]Wang, Shuowen; Chen, Zhuohao; Chen, Shanping; Shao, Wen; Chen, Ya; Deng, Guo-Jun [Organic Letters, 2023, vol. 25, # 39, p. 7142 - 7147].
[10]Mandal, Tanumoy; Das, Sanju; Maji, Rohan; De Sarkar, Suman [Organic Letters, 2023, vol. 25, # 42, p. 7727 - 7732].
[11]Hao, Jun-Jie; Jiang, Tao; Wu, FuJunyang; Luo, Hejiang; Li, Rong-Tao [Organic Letters, 2025, vol. 27, # 18, p. 4817 - 4822].
[12]Guo, Ting-Ting; Zhao, Qing-Sheng; Yang, Shu; Chen, Tian-Tian; Liu, Jin; Yan, Sheng-Jiao [Chemical Communications, 2025, vol. 61, # 86, p. 16846 - 16849].
  • 6
  • [ 20299-79-0 ]
  • [ 67-64-1 ]
  • [ 1233703-80-4 ]
YieldReaction ConditionsOperation in experiment
97% With N-((1R,2R)-2-amino-1,2-diphenylethyl)-2,6-dichlorobenzenesulfonamide; benzoic acid In toluene at 20℃; for 48h; optical yield given as %ee; enantioselective reaction;
  • 7
  • [ 20299-79-0 ]
  • [ CAS Unavailable ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
97% With 1-((1R,2R)-2-aminocyclohexyl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; benzoic acid In dichloromethane at 20℃; for 5h; optical yield given as %ee; enantioselective reaction;
  • 8
  • [ 20299-79-0 ]
  • [ 88014-09-9 ]
  • [ 1264932-10-6 ]
YieldReaction ConditionsOperation in experiment
85% With N-hydroxyphthalimide; oxygen; copper(I) bromide In acetonitrile at 60℃; Inert atmosphere; Green chemistry;
77% With tert.-butylhydroperoxide; copper(ll) bromide In toluene at 50℃; for 48h;
 

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