10276-09-2

Basic information

• Product Name: 2,2-dimethylbut-3-enoic acid
• Synonyms: 2,2-dimethylbut-3-enoic acid;2,2-Dimethyl-3-butenoic acid;3-Butenoic acid, 2,2-diMethyl-
• CAS NO: 10276-09-2
• Molecular Formula: C₆H₁₀O₂
• Molecular Weight: 114.15
• Mol File: 10276-09-2.mol
• Article Data: 24

Chemical Properties

• Melting Point: -6℃
• Boiling Point: 185℃
• Flash Point: 84.257 °C
• Appearance: Colorless/Liquid
• Density: 0.957
• Vapor Pressure: 0.294mmHg at 25°C
• Refractive Index: 1.4305 (589.3 nm 18℃)
• Storage Temp.: 2-8°C
• PKA: 4.42±0.10(Predicted)
• CAS DataBase Reference: 2,2-dimethylbut-3-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethylbut-3-enoic acid(10276-09-2)
• EPA Substance Registry System: 2,2-dimethylbut-3-enoic acid(10276-09-2)

Safety Data

• HazardClass: 8
• Hazardous Substances Data: 10276-09-2(Hazardous Substances Data)

Usage

Description

2,2-Dimethylbut-3-enoic acid, also known as 2,2-dimethylacrylic acid, is an organic compound characterized by a carboxylic acid functional group and a double bond in its structure. It is a key intermediate in the synthesis of various chemical compounds and pharmaceuticals.
Used in Pharmaceutical Industry:
2,2-Dimethylbut-3-enoic acid is used as a key intermediate in the synthesis of metabolites of Simvastatin (S485000), a synthetic derivative of a fermentation product of Aspergillus terreus. 2,2-dimethylbut-3-enoic acid plays a crucial role in the production of Simvastatin, which is a widely used cholesterol-lowering drug, highlighting its importance in the pharmaceutical industry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 34, p. 1717, 1969 DOI: 10.1021/jo01258a041

InChI:InChI=1/C6H10O2/c1-4-6(2,3)5(7)8/h4H,1H2,2-3H3,(H,7,8)

Upstream product

• 625-38-7 but-3-enoic acid 
• 74-88-4 methyl iodide 
• 124-38-9 carbon dioxide 
• 78-79-5 isoprene 
• 14660-45-8 potassium monomethylcarbonate 
• 141550-13-2 4,4,5,5-tetramethyl-2-(3-methylbut-2-enyl)-1,3,2-dioxaborolane 
• 129813-21-4 2-(1,1-dimethyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 598-25-4 Dimethylallene 
• 80-59-1 Tiglic acid 
• 77-78-1 dimethyl sulfate 
• 19757-86-9 methyl 2,2-dimethyl-3-pentenoate 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 58544-20-0 ethyl 2,2-dimethyl-3-butenoate 

Downstream Products

• 109069-32-1 2,2-dimethyl-but-3-enoic acid anilide 
• 1369430-89-6 C₅₀H₆₉N₃O₁₃ 
• 1369430-80-7 C₄₇H₆₅N₃O₁₃ 
• 1369430-91-0 C₄₇H₆₅N₃O₁₃ 
• 1369430-76-1 C₄₃H₅₅NO₁₄ 
• 1369430-92-1 C₃₇H₅₅N₃O₈ 
• 1369430-81-8 C₃₇H₅₅N₃O₈ 
• 351325-37-6 3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione 
• 507485-39-4 3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione 
• 1531585-26-8 benzyl 2-cyclopropyl-2-methylpropanoate 
• 1369430-77-2 C₄₂H₅₅NO₁₃ 
• 1240305-17-2 (E)-N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-isopropyl-4-methoxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-2,2-dimethylbut-3-enamide 
• 1369431-11-7 C₄₅H₆₃N₃O₁₂ 

Relevant articles and documents

An oxidative approach to a hydroxypiperidinone utilizing a Rh-catalyzed C-H activation process

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Preferential Photoreaction in a Porous Crystal, Metal-Macrocycle Framework: PdII-Mediated Olefin Migration over [2+2] Cycloaddition

A nanosized confined space with well-defined functional surfaces has great potential to control the efficiency and selectivity of catalytic reactions. Herein we report that a 1,6-diene, which normally forms an intramolecular [2+2] cycloadduct under photoirradiation, preferentially undergoes a photoinduced olefin migration in a porous crystal, metal-macrocycle framework (MMF), and alternatively [2+2] cycloaddition is completely inhibited in the confined space. A plausible reaction mechanism for olefin migration triggered by the photoinduced dissociation of the Pd-Cl bond is suggested based on UV-vis diffuse reflectance spectroscopy, single-crystal XRD, and MS-CASPT2 calculation. The substrate scope of the photoinduced olefin migration in MMF was also examined using substituted allylbenzene derivatives.