125318
Citraconic anhydride
98%
Synonym(s):
2-Methylmaleic anhydride, 3-Methyl-2,5-furandione, Citraconic acid anhydride, Methylmaleic anhydride, Monomethylmaleic anhydride
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All Photos(3)
About This Item
Empirical Formula (Hill Notation):
C5H4O3
CAS Number:
Molecular Weight:
112.08
Beilstein:
1835
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23
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vapor density
4 (vs air)
Quality Level
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
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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1
Storage Class Code
8A - Combustible corrosive hazardous materials
WGK
WGK 3
Flash Point(F)
231.8 °F - closed cup
Flash Point(C)
111 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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