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Merck
CN

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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About This Item

Empirical Formula (Hill Notation):
C5H4O3
CAS Number:
Molecular Weight:
112.08
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
210-459-0
Beilstein/REAXYS Number:
1835
MDL number:
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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

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.


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pictograms

Health hazardCorrosion

signalword

Danger

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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



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Global Trade Item Number

SKUGTIN
125318-100G04061838723420
125318-25G04061838723437
125318-500G04061838723444