Citraconic anhydride

ALDRICH/125318 - 98%

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

CAS Number: 616-02-4
Empirical Formula (Hill Notation): C₅H₄O₃
Molecular Weight: 112.08
EC Number: 210-459-0
MDL Number: MFCD00005522
Linear Formula: C₅H₄O₃
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-125318-25G	25 g	$45.80 1/EAAdd To Favorites	Add To Favorites
45-125318-100G	100 g	$115.00 1/EAAdd To Favorites	Add To Favorites
45-125318-500G	500 g	$369.00 1/EAAdd To Favorites	Add To Favorites

assay	98%
bp	213-214 °C (lit.)
density	1.247 g/mL at 25 °C (lit.)
form	liquid
InChI	1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3
InChI key	AYKYXWQEBUNJCN-UHFFFAOYSA-N
mp	6-10 °C (lit.)
Quality Level	200
refractive index	n20/D 1.471 (lit.)
SMILES string	CC1=CC(=O)OC1=O
vapor density	4 (vs air)

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.
Packaging:	25, 100, 500 g in glass bottle

Symbol	GHS05,GHS08
Signal word	Danger
Hazard statements	H314 - H317 - H334
Precautionary statements	P261 - P272 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
Hazard Codes	T
Risk Statements	24-34-42/43
Safety Statements	23-26-36/37/39-45
RIDADR	UN 2810 6.1 / PGIII
WGK Germany	WGK 3
Flash Point(F)	231.8 °F
Flash Point(C)	111 °C

Purity	98%
bp	213-214 °C (lit.)
mp	6-10 °C (lit.)
Density	1.247 g/mL at 25 °C (lit.)
Refractive Index	n20/D 1.471 (lit.)
UNSPSC	12162002