198220-53-0

Basic information

• Product Name: 4-(2,6-DIMETHYLANILINO)-4-OXOBUT-2-ENOIC ACID
• Synonyms: 4-(2,6-DIMETHYLANILINO)-4-OXOBUT-2-ENOIC ACID;TIMTEC-BB SBB000587;2',6'-DIMETHYLMALEANILIC ACID
• CAS NO: 198220-53-0
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Mol File: 198220-53-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 169 °C
• Boiling Point: 436.3°C at 760 mmHg
• Flash Point: 217.6°C
• Appearance: /
• Density: 1.243g/cm³
• Vapor Pressure: 2.21E-08mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 4-(2,6-DIMETHYLANILINO)-4-OXOBUT-2-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,6-DIMETHYLANILINO)-4-OXOBUT-2-ENOIC ACID(198220-53-0)
• EPA Substance Registry System: 4-(2,6-DIMETHYLANILINO)-4-OXOBUT-2-ENOIC ACID(198220-53-0)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 198220-53-0(Hazardous Substances Data)

Usage

General Description

4-(2,6-Dimethylanilino)-4-oxobut-2-enoic acid is a chemical compound that belongs to the class of organic compounds known as quinones. It is a derivative of 2,6-dimethylaniline and has a molecular formula of C14H15NO3. 4-(2,6-DIMETHYLANILINO)-4-OXOBUT-2-ENOIC ACID is a yellowish-brown crystalline powder and is commonly used as a dye, particularly in the textile industry. It is also used in the synthesis of various pharmaceuticals and agrochemicals. Additionally, it has been studied for its potential antioxidant and antimicrobial properties.

InChI:InChI=1/C12H13NO3/c1-8-4-3-5-9(2)12(8)13-10(14)6-7-11(15)16/h3-7H,1-2H3,(H,13,14)(H,15,16)/b7-6+

Upstream product

• 108-31-6 maleic anhydride 
• 87-62-7 2,6-dimethylaniline 

Downstream Products

• 1206-49-1 N-(2,6-dimethylphenyl)maleimide 

Relevant articles and documents

Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives

Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.