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125318

Sigma-Aldrich

Citraconic anhydride

98%

Synonyme(s) :

2-Methylmaleic anhydride, 3-Methyl-2,5-furandione, Citraconic acid anhydride, Methylmaleic anhydride, Monomethylmaleic anhydride

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About This Item

Formule empirique (notation de Hill):
C5H4O3
Numéro CAS:
616-02-4
Poids moléculaire :
112.08
Numéro Beilstein :
1835
Numéro CE :
210-459-0
Numéro MDL:
MFCD00005522
Code UNSPSC :
12162002
ID de substance PubChem :
24847660
Nomenclature NACRES :
NA.23

Densité de vapeur

4 (vs air)

Pureté

98%

Forme

liquid

Indice de réfraction

n20/D 1.471 (lit.)

Point d'ébullition

213-214 °C (lit.)

Pf

6-10 °C (lit.)

Densité

1.247 g/mL at 25 °C (lit.)

Chaîne SMILES 

CC1=CC(=O)OC1=O

InChI

1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3

Clé InChI

AYKYXWQEBUNJCN-UHFFFAOYSA-N

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Catégories apparentées

Description générale

Citraconic anhydride is a derivative of maleic anhydride and is also known as 2-methylmaleic anhydride. It is highly reactive due to the presence of anhydride groups and can undergo hydrolysis, esterification, amidation, and addition reactions. It can be used as a crosslinking agent to create covalent bonds between polymer chains, enhancing the mechanical strength and thermal stability of the polymer network. They arepotential tools for bioconjugation and immobilization of bioactive molecules.

Application

Citraconic anhydride can be used:

  • As an electrolyte additive for high-temperature pouch lithium-ion batteries. Citraconic anhydride reduces the interfacial impedance of pouch cells during high-temperature storage and enhances their stability.
  • As a pH-sensitive linker to surface functionalization of biomolecules used in drug delivery systems. The high pH sensitivity of citraconic anhydride conjugates is attributed to the presence of a double bond that restricts the separation between the amide and carboxylic acid groups.
  • As a reagent to synthesize new thiopyrano[2,3-d][1,3]thiazole derivatives via hetero-Diels–Alder reactions. These thiopyrano derivatives exhibit diverse biological activities such as anticancer, antiviral, and antitrypanosomal.
  • As a co-monomer in the ring-opening polymerization with d-xylose 3,5-anhydrosugar derivative to form novel sugar-derived polyesters, with up to 100% renewable content. This can serve as a sustainable feedstock for polymer synthesis.

Pictogrammes

Health hazardCorrosion
GHS08,GHS05

Mention d'avertissement

Danger

Mentions de danger

H314,H317,H334

Classification des risques

Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

231.8 °F - closed cup

Point d'éclair (°C)

111 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Citraconic anhydride as an electrolyte additive to improve the high temperature performance of LiNi0?6Co0?2Mn0?2O2/graphite pouch batteries
Chengyun Wang, et al.
Journal of alloys and compounds, 805, 757-766 (2019)
Synthetic Communications, 23, 1321-1321 (1993)
A Fischer et al.
Biomedica biochimica acta, 50(10-11), S169-S174 (1991-01-01)
Several amino acid derivatives with the negatively charged N alpha-protecting groups Maleyl (Mal) and Citraconyl (Cit) were synthesized and used in enzyme-catalyzed peptide synthesis. Compared to commonly used alpha-amino protecting groups in chemical peptide synthesis (Z, Fmoc, Boc, etc.), these
Anh H Cao-Pham et al.
Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology, 189(6), 693-706 (2019-10-06)
In light, giant clams can increase rates of shell formation and growth due to their symbiotic relationship with phototrophic zooxanthellae residing extracellularly in a tubular system. Light-enhanced shell formation necessitates increase in the uptake of Ca2+ from the ambient seawater
Raphael Haase et al.
PloS one, 12(6), e0179217-e0179217 (2017-06-13)
Injury of the glomerular filter causes proteinuria by disrupting the sensitive interplay of the glomerular protein network. To date, studies of the expression and trafficking of glomerular proteins have been mostly limited to in vitro or histologic studies. Here, we
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