3-Methyl-3-butenoic acid

Base Information

• Chemical Name: 3-Methyl-3-butenoic acid
• CAS No.: 1617-31-8
• Molecular Formula: C5H8 O2
• Molecular Weight: 100.117
• European Community (EC) Number: 838-020-4
• UNII: R0Z725B1UA
• DSSTox Substance ID: DTXSID001313242
• Nikkaji Number: J496.585J
• Metabolomics Workbench ID: 180
• Mol file: 1617-31-8.mol

Synonyms:3-methylbut-3-enoic acid;3-Methyl-3-butenoic acid;1617-31-8;3-Butenoic acid, 3-methyl-;Isopropenylacetic acid;3-Methylvinylacetic acid;Butanoic acid, 3-methylene-;R0Z725B1UA;3-methylbut-3-enoicacid;3-methyl-but-3-enoic acid;UNII-R0Z725B1UA;SCHEMBL75359;CH2=C(CH3)CH2COOH;CHEBI:178220;DTXSID001313242;LMFA01020110;MFCD09038392;AKOS000192127;CS-0222727;EN300-112366;F87165;Z295890066

Chemical Property of 3-Methyl-3-butenoic acid

Chemical Property:

• Melting Point: 21°C
• Refractive Index: 1.4191 (estimate)
• Boiling Point: 194.4°C (estimate)
• PKA: 4.39±0.10(Predicted)
• PSA: 37.30000
• Density: 0.9776 (rough estimate)
• LogP: 1.03720
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 94.3

Purity/Quality:

99%, ^*data from raw suppliers

3-Methylbut-3-enoicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C)CC(=O)O

Technology Process of 3-Methyl-3-butenoic acid

There total 36 articles about 3-Methyl-3-butenoic 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: 95.0%

2-Hydroxy-2-(2-methyl-allyl)-indan-1,3-dione (145046-36-2) → 3-methylbut-3-enoic acid (1617-31-8)

Guidance literature:

With periodic acid; In diethyl ether; for 2h; Ambient temperature;

Reference yield: 89.0%

carbon dioxide (124-38-9,18923-20-1) + 3-Chloro-2-methylpropene (563-47-3) → 3-methylbut-3-enoic acid (1617-31-8)

Guidance literature:

With tetraethylammonium chloride; silver; magnesium; In acetonitrile; at 0 ℃; under 760.051 Torr; Electrolysis;

DOI:10.1016/j.tet.2008.08.093

Reference yield: 86.0%

2-methyl-1-buten-4-ol (763-32-6) → 3-methylbut-3-enoic acid (1617-31-8)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 1h;

DOI:10.1021/ja00398a021

upstream raw materials:

2-methylallylmagnesium chloride

methylammonium carbonate

Ketene

trifluoroborane diethyl ether

Downstream raw materials:

2-methyl-1-buten-4-ol

formaldehyd

3-Methylbutenoic acid

3-Methyl-but-3-enoic acid benzylamide

Refernces

• 1、 Oppolzer, Wolfgang,Kuendig, Ernest Peter,Bishop, Paul M.,Perret, Celia. "EFFICIENT PREPARATION OF ALLYLIC GRIGNARD REAGENTS USING SLURRIES OF PRECONDENSED MAGNESIUM". . p. 3901 - 3904. Retrieved 1982.
• 2、 Fujisawa, Tamotsu,Sato, Toshio,Gotoh, Yoshihiko,Kawashima, Masatoshi,Kawara, Tatsuo. "Reaction of Diketene with Grignard Reagents in the Presence of Cobalt Catalyst. A Convenient Method for the Synthesis of 3-Methylenealkanoic Acids Leading to Terpenoids". . p. 3555 - 3559. Retrieved 1982.
• 3、 Kiji, Jitsuo,Okano, Tamon,Nishiumi, Wataru,Konishi, Hisatoshi. "Palladium-Catalyzed, Atmospheric Pressure Carbonylation of Allylic Chlorides in Two-Phase Aqueous Sodium Hydroxide-Organic Solvent Media". . p. 957 - 960. Retrieved 1988.
• 4、 Wu, La-Xia,Zhao, Ying-Guo,Guan, Ye-Bin,Wang, Hui,Lan, Yang-Chun,Wang, Huan,Lu, Jia-Xing. "Silver encapsulated copper salen complex: Efficient catalyst for electrocarboxylation of cinnamyl chloride with CO2". . p. 32628 - 32633. Retrieved 2019.
• 5、 Manick, Anne-Doriane,Tanaka, Hirotaka,Oisaki, Kounosuke,Kanai, Motomu. "Organophotoredox/Copper Hybrid Catalysis for Regioselective Allylic Aminodecarboxylation of β,γ-Unsaturated Carboxylic Acids". . p. 2936 - 2947. Retrieved 2018.
• 6、 Occhialini, Gino,Palani, Vignesh,Wendlandt, Alison E.. "Catalytic, contra-Thermodynamic Positional Alkene Isomerization". supporting information. p. 145 - 152. Retrieved 2022/01/19.
• 7、 Walker, Paul D.,Williams, Christopher,Weir, Angus N. M.,Wang, Luoyi,Crosby, John,Race, Paul R.,Simpson, Thomas J.,Willis, Christine L.,Crump, Matthew P.. "Control of β-Branching in Kalimantacin Biosynthesis: Application of 13C NMR to Polyketide Programming". supporting information. p. 12446 - 12450. Retrieved 2019/08/16.