Ethyl 2-(hydroxymethyl)acrylate

Base Information

• Chemical Name: Ethyl 2-(hydroxymethyl)acrylate
• CAS No.: 10029-04-6
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 2918199090
• European Community (EC) Number: 680-008-4
• DSSTox Substance ID: DTXSID00143108
• Nikkaji Number: J55.134A
• Wikidata: Q72475241
• Mol file: 10029-04-6.mol

Synonyms:Ethyl 2-(hydroxymethyl)acrylate;10029-04-6;ethyl 2-(hydroxymethyl)prop-2-enoate;2-Propenoic acid, 2-(hydroxymethyl)-, ethyl ester;2-(Hydroxymethyl)acrylic Acid Ethyl Ester;Ethyl 2-(hydroxymethyl)-2-propenoate;Ethyl alpha-(hydroxymethyl) acrylate;BRN 1753938;ACRYLIC ACID, 2-(HYDROXYMETHYL)-, ETHYL ESTER;MFCD01673859;4-03-00-00997 (Beilstein Handbook Reference);ethyl (hydroxymethyl)acrylate;SCHEMBL36653;Ethyl-2(hydroxymethyl)acrylate;Ethyl2-(hydroxymethyl)acrylate;ethyl alpha-hydroxymethylacrylate;ethyl--2--hydroxymethylacrylate;Hydroxymethylacrylicacidethylester;DTXSID00143108;2-(Hydroxymethyl)acrylic acid ethyl;AKOS009157706;CS-W005253;Ethyl 2-(hydroxymethyl)acrylate, 97%;GS-3963;2-Hydroxymethyl-acrylic acid ethyl ester;2-hydroxylmethyl acrylic acid ethyl ester;SY053134;2-(hydroxymethyl)-acrylic acid ethyl ester;FT-0649247;H0916;2-(hydroxymethyl)-2-propenoic acid ethyl ester;EN300-128521;A800087;J-000086;Ethyl 2-(hydroxymethyl)acrylate (stabilized with HQ)

Chemical Property of Ethyl 2-(hydroxymethyl)acrylate

Chemical Property:

• Appearance/Colour: colourless oil
• Vapor Pressure: 1.76mmHg at 25°C
• Refractive Index: n20/D 1.450
• Boiling Point: 198.6°Cat760mmHg
• PKA: 13.69±0.10(Predicted)
• Flash Point: 78.9°C
• PSA: 46.53000
• Density: 1.054g/cm³
• LogP: 0.09800
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 118

Purity/Quality:

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

Ethyl 2-(hydroxymethyl)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 36/37/38-41-38-24-22
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=C)CO
• Uses: Ethyl 2-(hydroxymethyl)acrylate is used for the synthesis of aza inhibitors and some potential antitumor agents. Intermediate used for the synthesis of aza inhibitors and some potential antitumor agents.

Technology Process of Ethyl 2-(hydroxymethyl)acrylate

There total 20 articles about Ethyl 2-(hydroxymethyl)acrylate 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: 93.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + ethyl acrylate (140-88-5,9003-32-1) → ethyl 2-(hydroxymethyl)acrylate (10029-04-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1021/ol802577z

Reference yield: 88.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl 2-(hydroxymethyl)acrylate (10029-04-6)

Guidance literature:

With potassium carbonate; In water; at 20 ℃; for 0.75h;

DOI:10.1021/acs.orglett.9b01497

Reference yield: 73.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-ethoxy-buta-1,3-diene (4747-05-1) → ethyl 2-(hydroxymethyl)acrylate (10029-04-6)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1002/adsc.200800504

upstream raw materials:

diethyl bis(hydroxymethyl)malonate

chloroformic acid ethyl ester

epichlorohydrin

ethanol

Downstream raw materials:

(E)-3-methylene-5-styryldihydrofuran-2(3H)-one

ethyl 2-(chloromethyl)acrylate

ethyl 2-bromomethyl-2-propenoate

3-methylene-1-oxa-spiro[4.5]decan-2-one

Refernces

• 1、 Villieras, Jean,Rambaud, Monique. "Wittig-Horner Reactions in Heterogeneous Media; 2. A Convenient Synthesis of α,β-Unsaturated Esters and Ketones using Weak Bases in Water". . p. 300 - 303. Retrieved 1983.
• 2、 Che, Wen,Wen, Danyang C.,Zhu, Shou-Fei,Zhou, Qi-Lin. "Iterative Synthesis of Polydeoxypropionates Based on Iridium-Catalyzed Asymmetric Hydrogenation of α-Substituted Acrylic Acids". . p. 3305 - 3309. Retrieved 2018.
• 3、 Villieras, Jean,Rambaud, Monique. "Wittig-Horner Reaction in Heterogeneous Media; 1. An Easy Synthesis of Ethyl α-Hydroxymethylacrylate and Ethyl α-Halomethylacrylates using Formaldehyde in Water". . p. 924 - 926. Retrieved 1982.
• 4、 Suizu, Hiroshi,Shigeoka, Daisuke,Aoyama, Hiroshi,Yoshimitsu, Takehiko. "Total Synthesis of Clavilactone B: A Radical Cyclization-Fragmentation Strategy". . p. 126 - 129. Retrieved 2014.
• 5、 Gintner, Manuel,Denner, Christian,Schm?lzer, Christoph,Fischer, Michael,Frühauf, Peter,K?hlig, Hanspeter,Schmid, Walther. "Synthesis of 3-deoxy-2-uloses via the indium-mediated allylation reaction". . . Retrieved 2019.
• 6、 Xia, Qing,Tian, Hao,Dong, Jianyang,Qu, Yi,Li, Lili,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin. "N-Arylamines Coupled with Aldehydes, Ketones, and Imines by Means of Photocatalytic Proton-Coupled Electron Transfer". . p. 9269 - 9273. Retrieved 2018.
• 7、 Li, Yang,Zhang, Jing,Li, Defang,Chen, Yiyun. "Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex". . p. 3296 - 3299. Retrieved 2018.
• 8、 Del Pozo, Sandra,Vera, Silvia,Oiarbide, Mikel,Palomo, Claudio. "Catalytic Asymmetric Synthesis of Quaternary Barbituric Acids". . p. 15308 - 15311. Retrieved 2017.
• 9、 Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi. "An efficient and simple strategy toward the synthesis of highly functionalized compounds". . p. 978 - 995. Retrieved 2021/08/06.
• 10、 Guo, Hongchao,Li, Hongxiang,Liu, Hao,Shi, Wangyu,Wang, Chang,Wang, Wei,Wu, Yongjun. "Phosphine-Catalyzed Cascade Annulation of MBH Carbonates and Diazenes: Synthesis of Hexahydrocyclopenta[c]pyrazole Derivatives". supporting information. p. 5571 - 5575. Retrieved 2021/07/31.