Methyl crotonate

Base Information

• Chemical Name: Methyl crotonate
• CAS No.: 623-43-8
• Molecular Formula: C5H8O2
• Molecular Weight: 100.117
• Hs Code.: 29161980
• European Community (EC) Number: 210-793-7,242-517-6
• UNII: 3T02JIH93S
• DSSTox Substance ID: DTXSID10878813
• Nikkaji Number: J183.087B,J43.555D
• Wikidata: Q1141622
• ChEMBL ID: CHEMBL3273387
• Mol file: 623-43-8.mol

Synonyms:Methyl crotonate;623-43-8;trans-Methyl crotonate;(E)-Methyl but-2-enoate;methyl (E)-but-2-enoate;18707-60-3;Methyl E-crotonate;Methyl trans-crotonate;(E)-Crotonic acid methyl ester;Methyl trans-2-butenoate;trans-2-Butenoic acid methyl ester;2-Butenoic acid, methyl ester, (2E)-;Methyl 2-butenoate;Methyl (E)-2-butenoate;2-Butenoic acid, methyl ester, (E)-;Crotonic acid, methyl ester;Methyl E-Propene-1-carboxylate;(E)-2-Butenoic acid methyl ester;CROTONIC ACID, METHYL ESTER, (E)-;2-Butenoic acid, methyl ester;1-(Methoxycarbonyl)propene;methyl (2E)-but-2-enoate;EINECS 210-793-7;METHYL-2-CROTONATE;BRN 1720292;UNII-3T02JIH93S;3T02JIH93S;EINECS 242-517-6;NSC 18745;AI3-06008;methylcrotonate;MFCD00009287;Crotonic Acid Methyl Ester;NSC-18745;crotonic acid methyl;Methyl T2 Butenoate;Methyl crotonate, 98%;Methyl crotonate, (E)-;Methyl 2-butenoate, (E)-;SCHEMBL37099;2-butenoic acid methyl ester;Methyl (2E)-2-butenoate #;CHEMBL3273387;SCHEMBL15460624;(E)-CH3CH=CHC(O)OCH3;DTXSID10878813;Methyl .alpha.-crotonate, trans-;(E)-2-Butenoic acid-methyl ester;AMY15442;(E)-but-2-enoic acid methyl ester;Methyl crotonate, analytical standard;Methyl crotonate, 96%, trans-isomer;AKOS000121298;CS-W020591;CROTONIC ACID METHYL ESTER [MI];LS-55600;(2E)-2-BUTENOIC ACID METHYL ESTER;EN300-15459;A833724;J-502052;Q1141622;F0001-1670

Chemical Property of Methyl crotonate

Chemical Property:

• Appearance/Colour: colorless Liquid
• Vapor Pressure: 0.152mmHg at 25°C
• Melting Point: -42°C
• Refractive Index: n20/D 1.423(lit.)
• Boiling Point: 121 °C at 760 mmHg
• Flash Point: 4.4 °C
• PSA: 26.30000
• Density: 0.925 g/cm³
• LogP: 0.73550
• Storage Temp.: Flammables area
• Water Solubility.: IMMISCIBLE
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 100.052429494
• Heavy Atom Count: 7
• Complexity: 84.1

Purity/Quality:

99% ^*data from raw suppliers

trans-Methyl crotonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36-9-33

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CC=CC(=O)OC
• Isomeric SMILES: C/C=C/C(=O)OC
• Uses: Methyl crotonate was used to investigate chemo selectivity in the reaction between methyl crotonate and benzyl amine catalyzed by lipase B from Candida Antarctica using solvent engineering. It was used as starting reagent during the total synthesis of phytotoxins solanapyrones D(1) and E(2).

Technology Process of Methyl crotonate

There total 98 articles about Methyl crotonate 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: 94.0%

methanol (67-56-1) + (E)-but-2-enoic acid (107-93-7) → crotonic acid methyl ester (623-43-8)

Guidance literature:

With sulfuric acid; for 0.25h; Irradiation;

Reference yield: 90.0%

2-(diethylamino)ethyl crotonate (84115-05-9) → crotonic acid methyl ester (623-43-8) + 2-(Diethylamino)ethanol (100-37-8)

Guidance literature:

With methanol; toluene-4-sulfonic acid; for 4h; Heating;

Reference yield: 90.0%

wt.-% NaOH + wt.-% sodium methylate + water (7732-18-5) + 3-chloroprop-1-ene (107-05-1) → crotonic acid methyl ester (623-43-8)

Guidance literature:

Ni(CO)4; In methanol; aqueous KCl;

upstream raw materials:

3,5-dimethyl-4-thia-heptanedioic acid dimethyl ester

4-methyloxetan-2-one

potassium methanolate

ethyl iodide

Downstream raw materials:

3-aziridin-1-yl-butyric acid methyl ester

(+/-)-3-(1-pyrrolidinyl)butyric acid methyl ester

4-methyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester

4,5-dimethyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester

Refernces

• 1、 Wang, Jingjing,Jiang, Feng,Tao, Chaofu,Yu, Han,Ruhlmann, Laurent,Wei, Yongge. "Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst". supporting information. p. 2652 - 2657. Retrieved 2021/04/21.
• 2、 Hu, Hao,Ota, Hajime,Baek, Heeyoel,Shinohara, Kenta,Mase, Toshiaki,Uozumi, Yasuhiro,Yamada, Yoichi M. A.. "Second-Generation meta-Phenolsulfonic Acid-Formaldehyde Resin as a Catalyst for Continuous-Flow Esterification". supporting information. p. 160 - 163. Retrieved 2020/01/02.