63225-53-6

Basic information

• Product Name: 2-[[(BUTYLAMINO)CARBONYL]OXY]ETHYL ACRYLATE
• Synonyms: 2-Propenoicacid,2-[[(butylamino)carbonyl]oxy]ethylester;2-[[(BUTYLAMINO)CARBONYL]OXY]ETHYL ACRYLATE;2-(((BUTYLAMINO)CARBONYL)OXY)ETHYL ACRYL;2-ACRYLOYLOXYETHYL BUTYLCARBAMATE;Acrylic acid 2-(butylcarbamoyloxy)ethyl ester;Acrylic acid 2-[(butylcarbamoyl)oxy]ethyl ester;Butylcarbamic acid 2-(acryloyloxy)ethyl ester;Propenoic acid 2-[[(butylamino)carbonyl]oxy]ethyl ester
• CAS NO: 63225-53-6
• Molecular Formula: C₁₀H₁₇NO₄
• Molecular Weight: 215.25
• EINECS: 264-036-0
• Product Categories: Acrylate;Acrylic Monomers;Monomers
• Mol File: 63225-53-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 327.9°C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000196mmHg at 25°C
• Refractive Index: n20/D 1.46(lit.)
• Storage Temp.: 2-8°C
• PKA: 12.49±0.46(Predicted)
• Water Solubility: 4.99g/L at 21℃
• CAS DataBase Reference: 2-[[(BUTYLAMINO)CARBONYL]OXY]ETHYL ACRYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[[(BUTYLAMINO)CARBONYL]OXY]ETHYL ACRYLATE(63225-53-6)
• EPA Substance Registry System: 2-[[(BUTYLAMINO)CARBONYL]OXY]ETHYL ACRYLATE(63225-53-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 63225-53-6(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pale yellow oily liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H17NO4/c1-3-5-6-11-10(13)15-8-7-14-9(12)4-2/h4H,2-3,5-8H2,1H3,(H,11,13)

Synthetic route

n-butyl isocyanide (111-36-4) + 2-hydroxyethyl acrylate (818-61-1) → acrylic acid 2-butylcarbamoyloxy-ethyl ester (63225-53-6)

2-hydroxyethyl N-butylcarbamate (13105-54-9) + acrylic acid (79-10-7) → acrylic acid 2-butylcarbamoyloxy-ethyl ester (63225-53-6)

Conditions	Yield
With hypophosphorous acid; 4-methoxy-phenol; toluene-4-sulfonic acid In toluene at 70℃; for 6h; Reduced pressure;

2-hydroxyethyl N-butylcarbamate (13105-54-9) + acrylic acid methyl ester (292638-85-8) → acrylic acid 2-butylcarbamoyloxy-ethyl ester (63225-53-6)

Conditions	Yield
With phenothiazine; 2,6-di-tert-butyl-4-methyl-phenol; titanium(IV) isopropylate; tetrabutoxytitanium at 65℃; for 10.5h;

[1,3]-dioxolan-2-one (96-49-1) + N-butylamine (109-73-9) + acrylic acid methyl ester (292638-85-8) → acrylic acid 2-butylcarbamoyloxy-ethyl ester (63225-53-6)

Conditions	Yield
novozyme 435 at 60℃; for 24h; Enzymatic reaction;

acrylic acid 2-butylcarbamoyloxy-ethyl ester (63225-53-6) → polymer; monomer(s): acrylic acid 2-butylcarbamoyloxy-ethyl ester

Conditions	Yield
With (2-hydroxycyclohexyl)(phenyl)methanone at 25℃; Kinetics; UV-irradiation;

acrylic acid 2-butylcarbamoyloxy-ethyl ester (63225-53-6) → poly(2-[[(butylamino)carbonyl]oxy]ethyl acrylate); monomer(s): 2-[[(butylamino)carbonyl]oxy]ethyl acrylate

Conditions	Yield
With 2-isopropythioxanthone; tris-(trimethylsilyl)silane In benzene at 25℃; Product distribution; Further Variations:; Reagents; Photolysis;

Upstream product

• 96-49-1 [1,3]-dioxolan-2-one 
• 109-73-9 N-butylamine 
• 292638-85-8 acrylic acid methyl ester 
• 13105-54-9 2-hydroxyethyl N-butylcarbamate 
• 79-10-7 acrylic acid 
• 111-36-4 n-butyl isocyanide 
• 818-61-1 2-hydroxyethyl acrylate 

Relevant articles and documents

Enzymatic production of (meth)acrylic esters that contain urethane groups

Enzymatic preparation of (meth)acrylic esters containing urethane groups, and their use in radiation-curable compositions.

Fast monomers: Factors affecting the inherent reactivity of acrylate monomers in photoinitiated acrylate polymerization

A systematic study on the effect of molecular structure on the photoinitiated polymerization of acrylates was undertaken. Initially, the research was focused on the effect of hydrogen bonding, and it was found that preorganization via hydrogen bonding enhances the maximum rate of polymerization (Rp). This hydrogen bonding facilitated preorganization also affected the tacticity of the resultant polymer. Next, the effect of polarity as represented by the calculated dipole moment (μcalc) of a given monomer was investigated. A direct linear correlation between Rp and the calculated Boltzmann-averaged dipole moment (μcalc) was observed. The Rp-μcalc correlation holds for pure monomers, mixtures of monomers, and even mixtures of monomers with inert solvents. This correlation enables the rational design of monomers with a required reactivity. In addition, these studies suggest that the propagation step of polymerization is influenced by hydrogen bonding while the dipole moment influences the termination rate constant. These two mechanistic explanations can be regarded as complementary factors that influence the speed of acrylate polymerization.