Isopropyl 2-methylisocrotonate

Base Information

• Chemical Name: Isopropyl 2-methylisocrotonate
• CAS No.: 61692-76-0
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.445
• Hs Code.: 2916190090
• European Community (EC) Number: 262-899-8,217-067-9
• DSSTox Substance ID: DTXSID401017420
• Nikkaji Number: J213.408J
• Wikidata: Q99242413
• Metabolomics Workbench ID: 47843
• Mol file: 61692-76-0.mol

Synonyms:Isopropyl 2-methylisocrotonate;61692-76-0;propan-2-yl (Z)-2-methylbut-2-enoate;EINECS 262-899-8;2-Butenoic acid, 2-methyl-, 1-methylethyl ester, (Z)-;propan-2-yl (2Z)-2-methylbut-2-enoate;Isopropyl 2-methylcrotonate;Isopropyl alpha-methylcrotonate;Isopropyl 2-methyl-2-butenoate;Isopropyl alpha-methyl crotonate;Isopropyl angelate;(E)-1-Methylethyl 2-methyl-2-butenoate;SCHEMBL13613127;FEMA 3229;Isopropyl alpha -methyl crotonate;DTXSID401017420;LMFA07010924;Isopropyl (2E)-2-methyl-2-butenoate;2-Methyl-propyl ester(E)-2-Butenoicacid;3-Methyl-2-butenoic acid, isopropyl ester;2-Methylisocrotonic acid 1-methylethyl ester;2-Methyl-1-isopropyl ester(E)-2-Butenoic acid;2-Methyl1-isopropyl ester (E)-2-Butenoic acid;2-Methyl-1-methylethyl ester(E)-2-Butenoic acid;2-Methyl-1-methylethyl ester(2E)-2-Butenoic acid;2-Butenoic acid, 2-methyl-, 1-methylethyl ester, (E)- (9CI)

Chemical Property of Isopropyl 2-methylisocrotonate

Chemical Property:

• Vapor Pressure: 1.88mmHg at 25°C
• Boiling Point: 165.4°C at 760 mmHg
• Flash Point: 54.9°C
• PSA: 26.30000
• Density: 0.9g/cm³
• LogP: 1.90420
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC(C)C
• Isomeric SMILES: C/C=C(/C)\C(=O)OC(C)C

Technology Process of Isopropyl 2-methylisocrotonate

There total 7 articles about Isopropyl 2-methylisocrotonate 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%

1-piperidinoethanol (3040-44-6) + methanol (67-56-1) + 2-(4-bromobenzoyl)benzoic acid (2159-40-2) → 2-methoxycarbonyl-4'-(2-piperidinoethyloxy)benzophenone (54063-52-4)

Guidance literature:

1-piperidinoethanol; With sodium hydride; In tetrahydrofuran; for 0.5h; Reflux;

methanol; 2-(4-bromobenzoyl)benzoic acid; With sodium hydride; In tetrahydrofuran; at 20 ℃;

With thionyl chloride; at 0 - 20 ℃;

DOI:10.1021/ol400919u

Reference yield: 88.0%

2-(4-hydroxybenzoyl)benzoic acid methyl ester (21147-23-9) + N-chloroethylpiperidine hydrochloride (2008-75-5) → 2-methoxycarbonyl-4'-(2-piperidinoethyloxy)benzophenone (54063-52-4)

Guidance literature:

With potassium carbonate; In ethyl acetate; at 60 ℃; for 15h;

DOI:10.1021/jacs.6b13113

Reference yield: 85.0%

piperidine (110-89-4) + methyl 2-(4-(2-bromoethoxy)benzoyl)benzoate → 2-methoxycarbonyl-4'-(2-piperidinoethyloxy)benzophenone (54063-52-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 1h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.6b01064

upstream raw materials:

2-(piperidin-4-yl)ethyl chloride

2-(4-hydroxybenzoyl)benzoic acid methyl ester

1-piperidinoethanol

methanol

Refernces

• 1、 Sagadevan, Arunachalam,Charpe, Vaibhav Pramod,Ragupathi, Ayyakkannu,Hwang, Kuo Chu. "Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C C Triple Bond Cleavage". . p. 2896 - 2899. Retrieved 2017/03/11.
• 2、 Miao, Jinmin,Ge, Haibo. "Palladium-catalyzed chemoselective decarboxylative ortho acylation of benzoic acids with α-oxocarboxylic acids". supporting information. p. 2930 - 2933. Retrieved 2013/07/26.