| Identification | More | [Name]
Citraconic anhydride | [CAS]
616-02-4 | [Synonyms]
2-METHYLMALEIC ANHYDRIDE
CITRACONIC ANHYDRIDE
CTA
METHYLMALEIC ANHYDRIDE
2,5-Furanedione, 3-methyl
3-Methyl-2,5-furandione
3-methyl-5-furandione
3-methyl-furan-2,5-dione
3-Methylmaleic anhydride
3-methylmaleicanhydride
alpha-Methylmaleic anhydride
alpha-methylmaleicanhydride
Anhydrid kyseliny citrakonove
anhydridkyselinycitrakonove
Citraconic acid anhydride
citraconicacidanhydride
Maleic anhydride, methyl-
methyl-maleicacidanhydride
methyl-maleicanhydrid
Monomethylmaleic anhydride | [EINECS(EC#)]
210-459-0 | [Molecular Formula]
C5H4O3 | [MDL Number]
MFCD00005522 | [Molecular Weight]
112.08 | [MOL File]
616-02-4.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to very slightly yellow liquid | [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.)
| [Fp ]
215 °F
| [storage temp. ]
Store at RT. | [solubility ]
Decomposes in contact with water,Insoluble[in water] | [form ]
Liquid | [color ]
Clear colorless to very slightly yellow | [Water Solubility ]
decomposes | [Sensitive ]
Moisture Sensitive | [BRN ]
1835 | [Dielectric constant]
40.3（20℃） | [LogP]
-0.232 (est) | [Uses]
Reagent for alkalies, alcohols, and amines. | [CAS DataBase Reference]
616-02-4(CAS DataBase Reference) | [NIST Chemistry Reference]
2,5-Furandione, 3-methyl-(616-02-4) | [EPA Substance Registry System]
616-02-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R42/43:May cause sensitization by inhalation and skin contact .
R34:Causes burns.
R24:Toxic in contact with skin. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 2810 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
GE6825000
| [F ]
10-21 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29171990 | [Hazardous Substances Data]
616-02-4(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to very slightly yellow liquid | [Flammability and Explosibility]
Nonflammable(100%) | [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.
| [Reactions]
Citraconic anhydride is highly reactive due to the presence of anhydride groups and can undergo hydrolysis, esterification, amidation, and addition reactions.
| [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.] |
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