766-39-2

Basic information

• Product Name: 2,3-Dimethylmaleic anhydride
• Synonyms: 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
• CAS NO: 766-39-2
• Molecular Formula: C₆H₆O₃
• Molecular Weight: 126.11
• EINECS: 212-165-8
• Product Categories: Heterocycles series;Carbonyl Compounds;Carboxylic Acid Anhydrides;Organic Building Blocks
• Mol File: 766-39-2.mol
• Article Data: 17

Chemical Properties

• Melting Point: 93-96 °C(lit.)
• Boiling Point: 223 °C(lit.)
• Flash Point: 222-223°C
• Appearance: white to beige crystals or cryst. powder
• Density: 1.107 g/cm3 (100℃)
• Vapor Pressure: 0.0986mmHg at 25°C
• Refractive Index: 1.5627 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: Soluble in ethanol, ether and chloroform. Slightly soluble in water.
• Sensitive: Moisture Sensitive
• BRN: 112044
• CAS DataBase Reference: 2,3-Dimethylmaleic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethylmaleic anhydride(766-39-2)
• EPA Substance Registry System: 2,3-Dimethylmaleic anhydride(766-39-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 45-36/37/39-28A-26
• WGK Germany: 3
• RTECS: ON4025000
• F: 9-21
• TSCA: Yes
• Hazardous Substances Data: 766-39-2(Hazardous Substances Data)

Usage

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.

Safety Profile

Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits acrid smoke and irritating fumes. See also ANHYDRIDES.

Purification Methods

Distil the anhydride from *benzene/ligroin and sublime in a vacuum. [Beilstein 17/11 V 69.]

InChI:InChI=1/C6H6O3/c1-3-4(2)6(8)9-5(3)7/h1-2H3

Upstream product

• 123-91-1 1,4-dioxane 
• 488-21-1 2,3-dimethylmaleic acid 
• 71-43-2 benzene 
• 89533-85-7 α-methyl-γ-butyrolactone-β-carboxylic acid 
• 60-29-7 diethyl ether 
• 111829-46-0 dimethyl-fumaric acid monomethyl ester 
• 64-17-5 ethanol 
• 141-52-6 sodium ethanolate 
• 35612-17-0 dimethyl (E)-2,3-dimethyl-2-butenedioate 
• 4363-44-4 2,3-Dicarboxy-but-2-enedioic acid 
• 110-15-6 succinic acid 
• 108-24-7 acetic anhydride 
• 127-17-3 2-oxo-propionic acid 
• 150-90-3 sodium succinate 

Downstream Products

• 58349-91-0 (Z)-2,3-Dimethyl-4-oxo-4-benzylaminobut-2-enoic acid 
• 98453-81-7 2-(bromomethyl)-3-methyl maleic anhydrate 
• 479035-70-6 bis(bromomethyl)maleic anhydride 
• 608-40-2 rac-2,3-dimethylsuccinic acid 
• 608-40-2 meso 2,3-dimethylsuccinic acid 
• 608528-09-2 cis-3,4-bis(benzyloxymethyl)-3,4-dimethylcyclobutene 
• 608527-93-1 (3S,4R)-3,4-Bis-benzyloxymethyl-3,4-dimethyl-cyclobutane-1,2-diol 

Relevant articles and documents

Mechanism of the decarboxylative dimerization of maleic anhydride under the influence of 2-aminopyridine

-

-

-

Preparation method of 2-methyl-3-ethyl maleic amide

The invention relates to a preparation method of 2-methyl-3-ethyl maleic amide. The method comprises the following steps: preparing dimethyl maleic anhydride; preparing 2-methyl-3-ethyl maleic anhydride; and preparing 2-methyl-3-ethyl maleic amide. A process route develops a synthetic method of a series of maleimide and maleic anhydride, and meanwhile, a flavoring application experiment is performed on the series of precursor-aroma compounds, thereby providing an important support for developing novel perfume materials.

Preparation of the maleic anhydride nucleus from dichloro γ-lactams: Focus on the role of the N-substituent in the functional rearrangement and in the hydrolytic steps

The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro γ-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide. Georg Thieme Verlag Stuttgart.