7098-80-8

Basic information

• Product Name: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methacrylate
• Synonyms: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methacrylate;Glycerine-1-Methacrylate Acetone Ketal;(2,2-Dimethyl-1,3-dioxolan-4-yl)methylmethacrylat;2,3-Isopropylideneglycol methacrylate;2,2-Dimethyl-1,3-dioxolane-4-methanol methacrylate;2-Methylpropenoic acid (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester;Methacrylic acid 2,2-dimethyl-1,3-dioxolane-4-ylmethyl ester;Methacrylic acid (2,2-dimethyl-1,3-dioxolan-4-yl)methyl ester
• CAS NO: 7098-80-8
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23164
• EINECS: 230-408-6
• Mol File: 7098-80-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 275℃
• Flash Point: 116℃
• Appearance: /
• Density: 1.028
• Vapor Pressure: 0.00537mmHg at 25°C
• Refractive Index: n20/D1.438
• Storage Temp.: ?20°C
• CAS DataBase Reference: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methacrylate(7098-80-8)
• EPA Substance Registry System: (2,2-dimethyl-1,3-dioxolan-4-yl)methyl methacrylate(7098-80-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-37/38-40-41
• Safety Statements: 26-36/37/39
• RIDADR: UN 1992 6.1(3) / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 7098-80-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C10H16O4/c1-7(2)9(11)12-5-8-6-13-10(3,4)14-8/h8H,1,5-6H2,2-4H3

Synthetic route

methacrylic acid methyl ester (80-62-6) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With titanium(IV) isopropylate; 1,4-phenylenediamine In cyclohexane for 15h; Heating;	67%
With methanol; sodium methylate; 1,1'-bi-2-naphthol
With titanium(IV) isopropylate transesterification;
Industry scale;
With dibutyltin dilaurate; hydroquinone at 110℃; for 8h;

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) + Methacryloyl chloride (920-46-7) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 48h;	64%

10H-phenothiazine (92-84-2) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With sodium carbonate	64%

2,3-Epoxypropyl methacrylate (106-91-2) + acetone (67-64-1) → 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8)

Conditions	Yield
With phosphoric acid at 60℃; Product distribution; Further Variations:; Catalysts; Cyclization;
With iron(III) chloride In hexane at 40℃; for 0.666667h; Ring cleavage; cyclization;

2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → 2,3-dihydroxypropyl methacrylate (5919-74-4)

Conditions	Yield
With acetic acid; 4-methoxy-phenol at 80℃; for 0.166667h;	80%
Hydrolysis; Acid hydrolysis;
With hydrogenchloride; water at 20℃; for 48h; Industry scale; Air stream;
With methanol; TEMPOL; 4-methoxy-phenol at 65℃; for 20h; Reagent/catalyst; Temperature;	73.1 %Chromat.

2-bromo-2-methyl propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → polymer, Mn=34500, Mw/Mn=1.15; monomer(s): glycerol-1-(methacrylate)-2,3-acetonide; 2-bromo-2-methylpropionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester

Conditions	Yield
With N-propyl 2-pyridylmethanimine; copper(I) bromide In toluene at 40℃;

2-bromo-2-methyl propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → polymer, Mn=6600, Mw/Mn=1.28; monomer(s): glycerol-1-(methacrylate)-2,3-acetonide; 2-bromo-2-methylpropionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)ethyl ester

Conditions	Yield
With N-propyl 2-pyridylmethanimine; copper(I) bromide In toluene at 40℃;

2-methyl-acrylic acid 3-trimethylsilanyl-propyn-2-ynyl ester (214268-06-1) + hostasol methacrylate (767357-31-3) + 2-bromo-2-methyl-propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl ester (1069117-44-7) + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → polymer, Mn = 11.5 kDa, PDi = 1.15

Conditions

Yield

Stage #1: hostasol methacrylate; 2-bromo-2-methyl-propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl ester; 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester With N-propyl 2-pyridylmethanimine; copper(I) bromide In methoxybenzene at 20℃; Stage #2: 2-methyl-acrylic acid 3-trimethylsilanyl-propyn-2-ynyl ester With N-propyl 2-pyridylmethanimine; copper(I) bromide In methoxybenzene at 20℃; Further stages.;

2-bromo-2-methyl-propionic acid 2-(3,5-dioxo-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl ester (1069117-44-7) + 2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → α-oxanorbornenyl poly(solketal) methacrylate

Conditions	Yield
With N-propyl 2-pyridylmethanimine; copper(I) bromide In methoxybenzene at 20℃;

2-methyl-acrylic acid 2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (7098-80-8) → 2-methyl-acrylic acid 7,7,9,9-tetrachloro-1,4-dioxa-6,8,10-triaza-5λ5,7λ5,9λ5-triphospha-spiro[4.5]deca-5,7,9-trien-2-ylmethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: Acid hydrolysis 2: hexachlorocyclotriphosphazene View Scheme

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 920-46-7 Methacryloyl chloride 
• 92-84-2 10H-phenothiazine 
• 106-91-2 2,3-Epoxypropyl methacrylate 
• 67-64-1 acetone 

Downstream Products

• 5919-74-4 2,3-dihydroxypropyl methacrylate 

Relevant articles and documents

Dimethyl dioxin pentane ethanol methyl acrylate monomer and application (by machine translation)

The invention discloses a with ultraviolet cured role of dimethyl dioxin pentane ethanol methyl acrylate monomer and its application, dimethyl dioxin pentane ethanol methyl acrylate monomer is of the structural formula: the dimethyl dioxin pentane ethanol methyl acrylate monomer is a good light curing agent, can make use of the ultraviolet-curable modified epoxy acrylic resin oligomer, so as to form a cured film. (by machine translation)

Formation of giant amphiphiles by post-functionalization of hydrophilic protein-polymer conjugates

A novel, generic method for the synthesis of families of tri-block protein-polymer giant amphiphiles was designed and developed. We have synthesized a hydrophilic α-maleimido poly-1-alkyne with Mn = 9.5 kDa (1H-NMR) and narrow PDi (1.15 as measured by SEC) via ATRP (Atom Transfer Radical Polymerization). This polymer was succesfully coupled to BSA to afford a hydrophilic multifunctional bioconjugate which was isolated using protein purification techniques and fully characterized. Following the post-functionalization approach, we introduced hydrophobicity to the resulting hydrophilic biohybrid by a straightforward, high yield "click"- chemistry cycloaddition step. The resulting tri-block protein-polymer amphiphiles were isolated and showed interesting aggregation patterns (TEM, confocal microscopy). The Royal Society of Chemistry 2007.

Isolation and purification of dioxolanylmethyl methacrylates

A process was developed for isolation and purification of dioxolanylmethyl methacrylates prepared from glycidyl methacrylate and carbonyl compounds, with (2-methyl-1,3-dioxolan-4-yl)methyl methacrylate prepared from glycidyl methacrylate and paraldehyde as example.