ChemicalBook CAS DataBase List 616-02-4

616-02-4

Name	Citraconic anhydride
CAS	616-02-4
EINECS(EC#)	210-459-0
Molecular Formula	C5H4O3
MDL Number	MFCD00005522
Molecular Weight	112.08
MOL File	616-02-4.mol

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

Chemical Properties

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℃）
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)
Uses	Reagent for alkalies, alcohols, and amines. less more
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

Symbol(GHS)	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	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. less more
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) . less more
RIDADR	UN 2810 6.1/PG 3
WGK Germany	3
RTECS	GE6825000
F	10-21
TSCA	Yes
REACH Registrations	Active
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)

Raw materials And Preparation Products

Hazard Information

Chemical Properties

clear colorless to very slightly yellow liquid

Application

Citraconic anhydride(methylmaleic anhydride) is a versatile compound. It may be used in the synthesis of antireversion agents used in the rubber industry or in the copolymerisation, e.g. with styrene. On a smaller scale, it is studied as a building block for the synthesis of strigol-type germination stimulants or of chemotherapy drugs^[2].

General Description

Citraconic anhydride is a reversible blocking agent for the lysine side chain. A major advantage of the citraconic anhydride reaction is that the blocking group can be readily removed without causing protein denaturation^[1].

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.

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

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.]

References

[1] Simpson, R. J. (2006). Modification of lysyl side chains using citraconic anhydride. CSH Protocols, 2006 5. https://doi.org/10.1101/pdb.prot4552
[2] R Philipps,  M. A. L.,  St Walter. (2002). Selective oxidation of isoprene to citraconic anhydride. Chemical Engineering Journal, 90 1, Pages 107-116. https://doi.org/10.1016/S1385-8947(02)00072-4

Material Safety Data Sheet(MSDS)

Spectrum Detail

Well-known Reagent Company Product Information

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