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Merck
모든 사진(3)

문서

125318

Sigma-Aldrich

Citraconic anhydride

98%

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C5H4O3
CAS Number:
Molecular Weight:
112.08
Beilstein:
1835
EC Number:
MDL number:
UNSPSC 코드:
12162002
PubChem Substance ID:
NACRES:
NA.23

vapor density

4 (vs air)

분석

98%

형태

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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일반 설명

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.

애플리케이션

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.

픽토그램

Health hazardCorrosion

신호어

Danger

유해 및 위험 성명서

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

개인 보호 장비

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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