2,2-dimethylbut-3-enoic acid

Base Information

• Chemical Name: 2,2-dimethylbut-3-enoic acid
• CAS No.: 10276-09-2
• Molecular Formula: C6H10O2
• Molecular Weight: 114.144
• Hs Code.: 2916190090
• Mol file: 10276-09-2.mol

Synonyms:3-Butenoic acid,2,2-dimethyl-;

Chemical Property of 2,2-dimethylbut-3-enoic acid

Chemical Property:

• Vapor Pressure: 0.294mmHg at 25°C
• Melting Point: -6 °C
• Refractive Index: 1.4305 (589.3 nm 18℃)
• Boiling Point: 186.773 °C at 760 mmHg
• PKA: 4.42±0.10(Predicted)
• Flash Point: 84.257 °C
• PSA: 37.30000
• Density: 0.973 g/cm³
• LogP: 1.28320
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,2-Dimethyl-3-butenoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,2-Dimethyl-3-butenoic Acid is an constituent in the synthesis of metabolites of Simvastatin (S485000), a synthetic derivative of a fermentation product of Aspergillus terreus.

Technology Process of 2,2-dimethylbut-3-enoic acid

There total 14 articles about 2,2-dimethylbut-3-enoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ethyl 2,2-dimethyl-3-butenoate (58544-20-0) → 2,2-dimethyl-but-3-enoic acid (10276-09-2)

Guidance literature:

With sodium hydroxide; In ethanol; at 20 ℃; for 16h;

DOI:10.1021/jo0012905

Reference yield: 95.0%

Dimethylallene (598-25-4) + carbon dioxide (124-38-9,18923-20-1) → 2,2-dimethyl-but-3-enoic acid (10276-09-2)

Guidance literature:

Dimethylallene; carbon dioxide; With [Pd(OSO₂CF₃)(CH₃Si(C₆H₄P(C₆H₅)2)2)]; triethylaluminum; In N,N-dimethyl-formamide; toluene; at 20 ℃; for 48h;

With hydrogenchloride; In water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja806677w

Reference yield: 88.0%

methyl 2,2-dimethyl-3-pentenoate (19757-86-9) → 2,2-dimethyl-but-3-enoic acid (10276-09-2)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

ethyl 2,2-dimethyl-3-butenoate

carbon dioxide

3,3-dimethyl-allyl chloride

but-3-enoic acid

Downstream raw materials:

4-bromo-2,2-dimethyl-butyric acid

C₄₂H₅₅NO₁₃

3Z-benzylidene-6Z-[[5-(1,1-dimethyl-2-propenyl)-1H-imidazol-4-yl]methylene]-2,5-piperazinedione

3-E-benzylidene-6-[5-(1,1-dimethylallyl)-1H-imidazol-4-Z-ylmethylene]-piperazine-2,5-dione

Refernces

• 1、 Wang, Liping,Hale, Karl J.. "Total Synthesis of the Potent HIF-1 Inhibitory Antitumor Natural Product, (8R)-Mycothiazole, via Baldwin-Lee CsF/CuI sp3-sp2-Stille Cross-Coupling. Confirmation of the Crews Reassignment". . p. 4200 - 4203. Retrieved 2015.
• 2、 Yonezawa, Hirotaka,Tashiro, Shohei,Shiraogawa, Takafumi,Ehara, Masahiro,Shimada, Rintaro,Ozawa, Takeaki,Shionoya, Mitsuhiko. "Preferential Photoreaction in a Porous Crystal, Metal-Macrocycle Framework: PdII-Mediated Olefin Migration over [2+2] Cycloaddition". supporting information. p. 16610 - 16614. Retrieved 2018/12/11.
• 3、 -. "MACROCYCLIC INHIBITORS OF FLAVIVIRIDAE VIRUSES". Paragraph 0269. . Retrieved 2017/08/01.