125318

Citraconic anhydride

98%

• Synonym(s): 2-Methylmaleic anhydride, 3-Methyl-2,5-furandione, Citraconic acid anhydride, Methylmaleic anhydride, Monomethylmaleic anhydride
• Empirical Formula (Hill Notation): C₅H₄O₃
• CAS Number: 616-02-4
• Molecular Weight: 112.08
• Beilstein/REAXYS Number: 1835
• EC Number: 210-459-0
• MDL number: MFCD00005522
• UNSPSC Code: 12162002
• PubChem Substance ID: 24847660
• NACRES: NA.23

Properties

• vapor density: 4 (vs air)
• 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

Description

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.

Safety Information

• pictograms: GHS08,GHS05
• signalword: Danger
• hcodes: H314,H317,H334
• pcodes: P261 - P272 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1
• Storage Class: 8A - Combustible corrosive hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 231.8 °F - closed cup
• flash_point_c: 111 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter