3-Methyl-2-phenylbut-2-enoic acid

Base Information

• Chemical Name: 3-Methyl-2-phenylbut-2-enoic acid
• CAS No.: 4412-08-2
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• DSSTox Substance ID: DTXSID50196043
• Nikkaji Number: J608.022G
• Mol file: 4412-08-2.mol

Synonyms:3-methyl-2-phenylbut-2-enoic acid;beta,beta-Dimethylatropic acid;4412-08-2;3-Methyl-2-phenyl-crotonic acid;BRN 1937711;CROTONIC ACID, 3-METHYL-2-PHENYL-;Benzeneacetic acid, alpha-(1-methylethylidene)-;SCHEMBL2555176;DTXSID50196043;2-Phenyl-3-methyl-2-butenoic acid;LS-55609;4-09-00-02086 (Beilstein Handbook Reference);EN300-24209515;Benzeneacetic acid, alpha-(1-methylethylidene)- (9CI);Z1262510971

Chemical Property of 3-Methyl-2-phenylbut-2-enoic acid

Chemical Property:

• Vapor Pressure: 0.00182mmHg at 25°C
• Boiling Point: 280.3°C at 760 mmHg
• Flash Point: 186.6°C
• Density: 1.093g/cm³
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 176.083729621
• Heavy Atom Count: 13
• Complexity: 218

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C(C1=CC=CC=C1)C(=O)O)C

Technology Process of 3-Methyl-2-phenylbut-2-enoic acid

There total 23 articles about 3-Methyl-2-phenylbut-2-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: 91.0%

3-Hydroxy-3-methyl-2-phenylbutanoic acid (6343-61-9) → 3-methyl-2-phenylbut-2-enoic acid (4412-08-2)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja807129e

Reference yield: 88.0%

phenylacetic acid (103-82-2) + acetone (67-64-1) → 3-methyl-2-phenylbut-2-enoic acid (4412-08-2)

Guidance literature:

phenylacetic acid; acetone; With isopropylmagnesium chloride; In tetrahydrofuran; at 25 - 40 ℃; for 1.5h; Inert atmosphere; Schlenk technique;

With sulfuric acid; In tetrahydrofuran; water; Cooling with ice;

DOI:10.1021/ol401593a

Reference yield: 49.0%

1-Phenylprop-1-yne (673-32-5) + carbon dioxide (124-38-9,18923-20-1) + methylmagnesium bromide (75-16-1) → 3-methyl-2-phenylbut-2-enoic acid (4412-08-2) + (Z)-3,5-dimethyl-2,4-diphenylhexa-2,4-dienoic acid

Guidance literature:

1-Phenylprop-1-yne; methylmagnesium bromide; With nickel(II) bromide diethylene glycol dimethyl ether; triphenylphosphine; In tetrahydrofuran; 2-methyltetrahydrofuran; at 60 ℃; for 1h; Schlenk technique; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; 2-methyltetrahydrofuran; at 25 ℃; for 0.5h; regioselective reaction; Schlenk technique;

DOI:10.1002/ejoc.201801364

upstream raw materials:

methyl 3-methyl-2-phenylbut-2-enoate

β,β-dimethyl-α-phenylacrylonitrile

1-bromo-2-methyl-1-phenyl-1-propene

carbon dioxide

Downstream raw materials:

ethyl isopropylidenephenylacetic carboxylate

(S)-2-phenyl-3-methylbutyric acid

C₁₁H₁₁O⁽¹⁺⁾

(R)-2-isopropyl-2-phenylacetic acid

Refernces

• 1、 Coles, Simon J.,Hareram, Mishra Deepak,Harnedy, James,Morrill, Louis C.,Tizzard, Graham J.. "Electrochemical oxidative: Z -selective C(sp2)-H chlorination of acrylamides". supporting information. p. 12643 - 12646. Retrieved 2021/12/07.
• 2、 Hung, Chen-Hsun,Santhoshkumar, Rajagopal,Chang, Yu-Che,Cheng, Chien-Hong. "Synthesis of Trisubstituted Acrylic Acids through Nickel-Catalyzed Carbomagnesiation of Alkynes and Carbon Dioxide Fixation". supporting information. p. 6924 - 6928. Retrieved 2018/11/23.