2-Propenoic acid,2-(hydroxymethyl)-, methyl ester

Base Information

• Chemical Name: 2-Propenoic acid,2-(hydroxymethyl)-, methyl ester
• CAS No.: 15484-46-5
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: 2918199090
• ChEMBL ID: CHEMBL1256639
• DSSTox Substance ID: DTXSID20473358
• Nikkaji Number: J910.588C
• Wikidata: Q27452691
• Mol file: 15484-46-5.mol

Synonyms:Acrylicacid, 2-(hydroxymethyl)-, methyl ester (8CI);Hydracrylic acid, 2-methylene-,methyl ester (7CI);Methyl 2-hydroxymethyl-2-propenoate;Methyl a-(hydroxymethyl)acrylate;

Chemical Property of 2-Propenoic acid,2-(hydroxymethyl)-, methyl ester

Chemical Property:

• Vapor Pressure: 0.205mmHg at 25°C
• Refractive Index: 1.438
• Boiling Point: 184.807 °C at 760 mmHg
• PKA: 13.66±0.10(Predicted)
• Flash Point: 75.041 °C
• PSA: 46.53000
• Density: 1.086 g/cm³
• LogP: -0.29210
• Storage Temp.: 2-8°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 106

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=C)CO
• Use Description: 2-Propenoic acid, 2-(hydroxymethyl)-, methyl ester, known as methyl methacrylate, is a versatile compound with applications in various fields. In the field of polymer chemistry, it serves as a vital monomer in the production of polymethyl methacrylate (PMMA), a transparent and impact-resistant plastic known for its use in optical lenses, acrylic glass, and various medical devices. In the construction and automotive industries, PMMA is employed as a lightweight alternative to glass for windows and facades, contributing to energy efficiency and design flexibility. Additionally, in dentistry, methyl methacrylate-based materials are used for dental prosthetics and restorative procedures. Furthermore, it plays a role in the production of adhesives and coatings, finding applications in various manufacturing processes. Its versatility and adaptability make methyl methacrylate a key component in enhancing materials, design, and functionality across these diverse fields.

Technology Process of 2-Propenoic acid,2-(hydroxymethyl)-, methyl ester

There total 16 articles about 2-Propenoic acid,2-(hydroxymethyl)-, methyl ester 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: 90.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 2-hydroxymethylacrylate (15484-46-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; water; at 20 ℃; for 9h;

DOI:10.1021/jo015628m

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (methyloxycarbonylmethyl)triphenylphosphonium bromide (1779-58-4) → methyl 2-hydroxymethylacrylate (15484-46-5)

Guidance literature:

With potassium carbonate; In water; at 10 - 20 ℃; for 6h;

Reference yield: 77.0%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9,88935-43-7) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 2-hydroxymethylacrylate (15484-46-5)

Guidance literature:

With formaldehyd; paraformaldehyde; In diethyl ether; nitrogen;

upstream raw materials:

2-acetoxymethyl-acrylic acid

methanol

propargyl alcohol

tetracarbonyl nickel

Downstream raw materials:

methyl (2S)-4-[(2R,S)-3-hydroxy-2-(methoxycarbonyl)propylthio]-2-[N-[(4-nitrobenzyloxy)carbonyl]amino]butanoate

methyl 2-benzyl-3-oxo-propionate

cyclohexanone

3-hydroxy-(2S)-methylpropionate

Refernces

• 1、 Scrivanti,Beghetto,Bertoldini. "New insights into the alkoxycarbonylation of propargyl alcohol". . p. 38 - 42. Retrieved 2017.
• 2、 Hotoda, Koki,Ohnuma, Asami,Kusakabe, Kosuke,Tanaka, Aki,Sasaki, Ikuo,Sugimura, Hideyuki. "Stereoselective synthesis of the (?)-dysiherbaine furopyran core via BF3-promoted formal [3+2] annulation of aldehydo-aldoses with allylsilanes". . p. 5359 - 5362. Retrieved 2016.
• 3、 He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng. "Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines". supporting information. . Retrieved 2021/05/31.
• 4、 -. "Reaction type ultraviolet light absorber and preparation method and application thereof". Paragraph 0047-0049. . Retrieved 2020/07/03.