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Merck

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:

Product Name

Citraconic anhydride, 98%

InChI key

AYKYXWQEBUNJCN-UHFFFAOYSA-N

InChI

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

SMILES string

CC1=CC(=O)OC1=O

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.)

Quality Level

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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.

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.

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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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)
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
Synthetic Communications, 23, 1321-1321 (1993)
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
Macromolecules, 25, 102-102 (1992)

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