| 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℃） | [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. | [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 | [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. | [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 | [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) |
| Hazard Information | Back Directory | [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
|
|
| Company Name: |
NORANA GROUP Gold
|
| Telephone: |
027-59209883 17386138556 |
| Website: |
www.nornachem.com |
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Jia Xing Isenchem Co.,Ltd
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
|