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Chemical Structure| 97-65-4 Chemical Structure| 97-65-4
Chemical Structure| 97-65-4

Itaconic acid

CAS No.: 97-65-4

Itaconic acid is an endogenous metabolite.

Synonyms: Methylenesuccinic acid

4.5 *For Research Use Only !

Cat. No.: A697659 Purity: 99% +(stabilized with TBC)

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Product Details of [ 97-65-4 ]

CAS No. :97-65-4
Formula : C5H6O4
M.W : 130.10
SMILES Code : O=C(O)C(CC(O)=O)=C
Synonyms :
Methylenesuccinic acid
MDL No. :MFCD00004260
InChI Key :LVHBHZANLOWSRM-UHFFFAOYSA-N
Pubchem ID :811

Safety of [ 97-65-4 ]

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

Application In Synthesis [ 97-65-4 ]

* 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 [ 97-65-4 ]

[ 97-65-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 151-50-8 ]
  • [ 6127-92-0 ]
  • [ 97-65-4 ]
  • [ 99-14-9 ]
  • 2
  • [ 97-65-4 ]
  • sulfuric acid containing alcohol [ No CAS ]
  • [ 99-14-9 ]
  • 4
  • [ 97-65-4 ]
  • [ 2848-01-3 ]
  • 3-[(2,3-dicarboxypropyl)diphenylphosphonio]propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.2% In ethyl acetate; A solution of itaconic acid (2c) (0.15 g, 0.0012 mol) in ethylacetate (3 mL) was added dropwise to a solution of acid 1 (0.3 g,0.0012 mol) in ethyl acetate (5 mL) with continuous stirring.The reaction reached completion within several minutes to forma white precipitate of 3b. The precipitate was filtered on a Shottfunnel, washed with diethyl ether, and dried in vacuo. The product 3b is well soluble in water and ethanol, poorly soluble inacetonitrile, m.p. 122 C (from acetonitrile). The yield was 0.379g (84.2%). IR (Nujol), ν/cm-1: 1550 (COO-); 1700 (COOH).1H NMR (D2O), δ: 2.43-2.57 (m, 2 H, PCH2CH2; 1 H,CHCH2); 2.58-2.78 (m, 2 H, CHCH2); 2.43-2.57 (m, 2 H,PCH2); 7.53-7.80 (m, 10 H, Ar). 13C NMR, δ: 17.18 (d,PCH2CH2, 1JP,C = 54.3 Hz); 22.7 (d, PCH2CH, 1JP,C = 52.3 Hz);26.7 (d, PCH2CH2, 2JP,C = 1.3 Hz); 37.07 (s, PCH2CHCH2);37.98 (d, PCH2CH, 2JP,C = 12.8 Hz); 116.23 (d, Cipso, 1JP,C == 84.7 Hz); 130.05 (d, Co, 2JP,C = 12.4 Hz); 133.57 (d, Cm,3JP,C = 9.6 Hz); 135.30 (d, Cp, 4JP,C = 2.5 Hz); 175.05-175.35(m, 2 C(O)O); 176.78 (d, C(O)O, 4JP,C = 3.1 Hz). 31P NMR,δ: 27.0. Found (%): C, 60.99; H, 5.70; P, 7.98. C20H21O6P. Calculated (%): C, 61.86; H, 5.41; P, 7.99.
  • 5
  • [ 77-92-9 ]
  • [ 97-65-4 ]
  • [ 99-14-9 ]
  • 6
  • [ 97-65-4 ]
  • [ 486460-21-3 ]
  • C11H11F3N4O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.1% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 8h; The compound of formula 7 (1.3 g, 0.01 mol) was reacted withCompound 9 (1.9 g, 0.01 mol) was added to a 50 ml two-necked flask,Join20 ml of methylene chloride,Added HOBt at -10-10 (1.49,0.011mol) andEDC.HCl (2.9 g, 0.015 mol) The reaction mixture was stirred at room temperature for 8 hours,After completion of the reaction, 15 mL of aqueous NaHCO3 solution was added and the organic phase was saturatedWashed with brine, dried over anhydrous sodium sulfate, concentrated, purified by column chromatography,To give 2.67 g of the compound of formula b,The yield was 89.1%.
  • 7
  • [ 97-65-4 ]
  • [ 23156-27-6 ]
  • 1-(2,6-difluoro-4-nitrophenyl)-5-oxopyrrolidine-3-carboxylic acid [ No CAS ]
  • 8
  • [ 97-65-4 ]
  • [ 23156-27-6 ]
  • methyl 1-(2,6-difluoro-4-nitrophenyl)-5-oxopyrrolidine-3-carboxylate [ No CAS ]
 

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