| Identification | More | [Name]
2,3-Dimethylmaleic anhydride | [CAS]
766-39-2 | [Synonyms]
2,3-DIMETHYLMALEIC ANHYDRIDE
3,4-DIMETHYL-2,5-DIHYDROFURAN-2,5-DIONE
DIMETHYLMALEIC ANHYDRIDE
2,2’-Dimethylmaleinsαureanhydrid
2,5-Furandione,3,4-dimethyl-
3,4-Dimethyl-2,5-furandione
3,4-dimethyl-2,5-furanedione
3,4-dimethyl-5-furandione
alpha,beta-Dimethylmaleic anhydride
alpha,beta-dimethylmaleicanhydride
Anhydride of dimethylmaleic acid
Dimethylmaleic acid anhydride
dimethylmaleicacidanhydride
dimethyl-maleicanhydrid
Maleic anhydride, dimethyl-
Pyrocinchonic anhydride
pyrocinchonicanhydride
DIMETHYLMALEIC ANHYDRIDE CRYSTALLINE
4,5-DIMETHYL-1,3-DIOXA-2-OXO-CYCLOPENTENE
2,5-Dihydro-3,4-dimethylfuran-2,5-dione | [EINECS(EC#)]
212-165-8 | [Molecular Formula]
C6H6O3 | [MDL Number]
MFCD00005523 | [Molecular Weight]
126.11 | [MOL File]
766-39-2.mol |
| Questions And Answer | Back Directory | [Synthesis]
A boiling solution of maleic anhydride (128) (196.2 g, 2.0 mol) in AcOH (200 mL) was added dropwise over 1 hour to a boiling solution of 2-aminopyridine (129) (94.1 g, 1.0 mol) in AcOH (200 mL). A strong CO2 evolution was observed. The mixture was heated under reflux for 2.5 hours, and then acetic acid was distilled off through a Claisen bridge. After adding 2 M H2SO4 (600 mL), the mixture was stirred under reflux for 2 hours. After cooling, the precipitated crystals were filtered off and washed with 2 M H2SO4 (3 x 50 mL) and H2O (2 x 50 mL). Light brown flakes (obtained after 24 hours in a desiccator (P2O5)) were sublimated at 60 °C and 0.02 mbar. Yield: 68.0 g (0.54 mmol, 54%) colorless crystals of 2,3-dimethylmaleic anhydride, Rf(SiO2) = 0.46 (c-hexane/EA 1:1). mp 91-92°C (95°C).
 Figure 2,3-Dimethylmaleic Anhydride Synthetic Route |
| Chemical Properties | Back Directory | [Appearance]
white to beige crystals or cryst. powder | [Melting point ]
93-96 °C (lit.) | [Boiling point ]
223 °C (lit.) | [density ]
1.107 g/cm3 (100℃) | [refractive index ]
1.5627 (estimate) | [Fp ]
222-223°C | [storage temp. ]
0-6°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Water Solubility ]
Soluble in ethanol, ether and chloroform. Slightly soluble in water. | [Sensitive ]
Moisture Sensitive | [BRN ]
112044 | [InChI]
1S/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3 | [InChIKey]
MFGALGYVFGDXIX-UHFFFAOYSA-N | [SMILES]
CC1=C(C)C(=O)OC1=O | [LogP]
0.183 (est) | [CAS DataBase Reference]
766-39-2(CAS DataBase Reference) | [NIST Chemistry Reference]
2,5-Furandione, 3,4-dimethyl-(766-39-2) | [EPA Substance Registry System]
766-39-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P264-P270-P301+P312-P501 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
ON4025000
| [F ]
9-21 | [TSCA ]
Yes | [HS Code ]
29171900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Safety Profile]
Questionable
carcinogen with experimental tumorigenic
data. When heated to decomposition it
emits acrid smoke and irritating fumes. See
also ANHYDRIDES.
| [Hazardous Substances Data]
766-39-2(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Chemical Properties]
white to beige crystals or cryst. powder | [Uses]
2,3-Dimethylmaleic anhydride can be usually used in the synthesis of maleimides and as an amino group protecting agent for superoxide dismutase. It is also used in the preparation of dimethylmaleic acid dimethyl ester. Further, it serves as a reactant in the dissociation of ribosomal proteins. In addition to this, The isolated molecule 2, 3-dimethylmaleic anhydride showed potent insecticidal activity in fumigation bioassay against several insect species, viz., adults of houseflies, cockroaches and stored-product insects. | [Definition]
ChEBI: 2,3-Dimethylmaleic anhydride is a butenolide. It is a 5-membered cyclic anhydride with a double bond between carbon atoms C2 and C3. The double bond locks the molecule in a planar conformation and stabilizes the acid anhydride against hydration. It was used as linker to a cell penetrating peptidebased nanoparticle. | [Purification Methods]
Distil the anhydride from *benzene/ligroin and sublime in a vacuum. [Beilstein 17/11 V 69.] |
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J & K SCIENTIFIC LTD.
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Alfa Aesar
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Energy Chemical
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Shanghai Ennopharm Co., Ltd.
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