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HomeProduct name listCitraconic anhydride

Citraconic anhydride

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

  • CAS NO.:616-02-4
  • Empirical Formula: C5H4O3
  • Molecular Weight: 112.08
  • MDL number: MFCD00005522
  • EINECS: 210-459-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-04 13:44:46
Citraconic anhydride Structural

What is Citraconic anhydride?

Chemical properties

clear colorless to very slightly yellow liquid

The Uses of Citraconic anhydride

Citraconic anhydride is used as a monomer for specialty unsaturated polyester resins. It is used to prepare bicyclic pyrrolidines, maleimides and co- and terpolymers. It is also used for the protection of N-terminal amino acids. Further, it is involved in the preparation of clothing ping acid and its amide. In addition to this, it is selectively used for the isolation of histidyl peptides.

The Uses of Citraconic anhydride

Reagent for alkalies, alcohols, and amines.

The Uses of Citraconic anhydride

Versatile reagent used for the synthesis of maleimides, bicyclic pyrrolidines, and co- and terpolymers, as well as for the protection of N-terminal amino acids.

What are the applications of Application

Citraconic anhydride is a versatile reagent

Flammability and Explosibility

Non flammable

Purification Methods

Possible contamination is from the acid formed by hydrolysis. If the IR has OH bands, then reflux with Ac2O for 30minutes, evaporate, then distil the residue in a vacuum, otherwise distil in a vacuum. Store in a dry atmosphere. [Vaughan & Andersen J Am Chem Soc 77 6702 1955, Vaughan & Andersen J Org Chem 21 680 1956, Beilstein 17 H 440, 17 I 234, 17 II 448, 17 III/IV 5912, 17/11 V 65.]

Properties of Citraconic anhydride

Melting point: 6-10 °C (lit.)
Boiling point: 213-214 °C (lit.)
Density  1.247 g/mL at 25 °C (lit.)
vapor density  4 (vs air)
refractive index  n20/D 1.471(lit.)
Flash point: 215 °F
storage temp.  Inert atmosphere,2-8°C
solubility  Chloroform (Slightly), Methanol (Slightly)
form  Liquid
color  Clear colorless to very slightly yellow
Water Solubility  decomposes
Sensitive  Moisture Sensitive
BRN  1835
Dielectric constant 40.3(20℃)
CAS DataBase Reference 616-02-4(CAS DataBase Reference)
NIST Chemistry Reference 2,5-Furandione, 3-methyl-(616-02-4)
EPA Substance Registry System 2,5-Furandione, 3-methyl- (616-02-4)

Safety information for Citraconic anhydride

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Health Hazard
GHS08
GHS Hazard Statements H314:Skin corrosion/irritation
H317:Sensitisation, Skin
H334:Sensitisation, respiratory
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P272:Contaminated work clothing should not be allowed out of the workplace.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Citraconic anhydride

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