Citraconic anhydride
ALDRICH/125318 - 98%
Synonym: 2-Methylmaleic anhydride; 3-
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
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 125318-100G.
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: 125318-500G.
| 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( |
| InChI key | AYKYXWQEBUNJCN-UHFFFAOYSA |
| mp | 6-10 °C (lit.) |
| Quality Level | 200  |
| refractive index | n |
| 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]thi • 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 | n |
| UNSPSC | 12162002 |