Citraconic anhydride Chemical Properties

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)

vapor pressure 

1.3 hPa ( 47 °C)

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℃）

InChI

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

InChIKey

AYKYXWQEBUNJCN-UHFFFAOYSA-N

SMILES

CC1=CC(=O)OC1=O

LogP

-0.232 (est)

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

Hazard Codes 

T

Risk Statements 

23/24/25-36/37/38-42/43-34-24

Safety Statements 

26-36/37/39-45-28A-23-36/37

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

RTECS 

GE6825000

F 

10-21

TSCA 

TSCA listed

HazardClass 

6.1

PackingGroup 

III

HS Code 

29171990

Storage Class

8A - Combustible corrosive hazardous materials

Hazard Classifications

Eye Dam. 1
Resp. Sens. 1
Skin Corr. 1B
Skin Sens. 1

Hazardous Substances Data

616-02-4(Hazardous Substances Data)

MSDS

• Language:English Provider:2-Methylmaleic anhydride
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Citraconic anhydride Usage And Synthesis

Chemical Properties

clear colorless to very slightly yellow liquid

Uses

Reagent for alkalies, alcohols, and amines.

Uses

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.

Uses

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.

Flammability and Explosibility

Non flammable

Reactions

Citraconic anhydride is highly reactive due to the presence of anhydride groups and can undergo hydrolysis, esterification, amidation, and addition reactions.

Chemical Reactivity

Citraconic anhydride (CA) is defined as a derivative of maleic anhydride that reacts with amines to form amide linkages at alkaline pH and can be hydrolyzed at acidic pH to release citraconic acid and free the amine, making it useful for temporarily blocking amine groups during molecular modifications.

Synthesis

Citraconic anhydride was prepared by using alkaline earth metal oxides or alkaline earth metal sulfates as catalysts, and reacting for 1.0-10.0h at a mass ratio of itaconic acid and catalyst of 50:1 to 500:1, a mass ratio of itaconic acid and solvent of 1:1 to 1:10, and a reaction temperature of 130-210??C, and recovering and reusing solvents;

Said alkaline earth metal oxide or alkaline earth metal sulfate catalyst is one of magnesium oxide, calcium oxide, barium oxide, strontium oxide, magnesium sulfate, calcium sulfate, barium sulfate, and strontium sulfate; and said solvent is one of xylene, o-dichlorobenzene, and tetrahydronaphthalene.

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.]

Citraconic anhydride(616-02-4)Related Product Information

• Erythromycin Estolate
• Chitosan
• Isatoic Anhydride
• 2,3-Dimethylmaleic anhydride
• ISOVALERIC ANHYDRIDE
• Trimellitic Anhydride
• POLY(MALEIC ANHYDRIDE)
• Succinic anhydride
• Propionic anhydride
• Chromium(VI) oxide
• Polymaleic acid
• Trifluoromethanesulfonic anhydride
• Maleic anhydride
• Phthalic anhydride
• Tartrazine
• Citric acid monohydrate
• AMMONIUM BISMUTH CITRATE
• Citral