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125318

Citraconic anhydride

Name: Citraconic anhydride
Brand: ALDRICH

98%

Sinónimos:

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

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Fórmula empírica (notación de Hill):

C₅H₄O₃

Número CAS:

616-02-4

Peso molecular:

112.08

UNSPSC Code:

12162002

NACRES:

NA.23

PubChem Substance ID:

24847660

EC Number:

210-459-0

Beilstein/REAXYS Number:

1835

MDL number:

MFCD00005522

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Propiedades

vapor density

4 (vs air)

Quality Level

200

assay

98%

form

liquid

refractive index

n20/D 1.471 (lit.)

bp

213-214 °C (lit.)

mp

6-10 °C (lit.)

density

1.247 g/mL at 25 °C (lit.)

SMILES string

CC1=CC(=O)OC1=O

InChI

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

InChI key

AYKYXWQEBUNJCN-UHFFFAOYSA-N

Descripción

General description

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.