Isobornyl acrylate Property

Melting point:

<-35°C

Boiling point:

119-121 °C15 mm Hg(lit.)

Density 

0.986 g/mL at 25 °C(lit.)

vapor pressure 

1.3Pa at 20℃

refractive index 

n20/D 1.476(lit.)

Flash point:

207 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

clear liquid

color 

Colorless to Almost colorless

Water Solubility 

Difficult to mix in water.

FreezingPoint 

5

Sensitive 

Light Sensitive

BRN 

2254825

Stability:

Light sensitive

InChIKey

PSGCQDPCAWOCSH-BREBYQMCSA-N

LogP

4.52 at 20℃

CAS DataBase Reference

5888-33-5(CAS DataBase Reference)

EPA Substance Registry System

Isobornyl acrylate (5888-33-5)

Safety

Hazard Codes 

Xn,N,Xi

Risk Statements 

20/22-36/37/38-51/53

Safety Statements 

26-36-61-28

RIDADR 

UN 3082 9 / PGIII

WGK Germany 

2

RTECS 

UD3940000

TSCA 

Yes

HazardClass 

9

PackingGroup 

III

HS Code 

29161290

Toxicity

LD50 oral in rat: 4890mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Isobornyl acrylate Chemical Properties,Usage,Production

Description

Isobornyl acrylate can be used to prepare block copolymers with n-butyl acrylate by atom transfer radical polymerization (ATRP)¹. It is a photo-polymerizable monomer that is employed in micro-fluidic devices because of desirable properties, such as inertness, transparency, and resolution².

Sources

1. https://www.sigmaaldrich.com/catalog/product/aldrich/392103?lang=en&region=US
2. López-García, M. D. C., D. J. Beebe, and W. C. Crone. Characterization of poly(isobornyl acrylate) as a construction material for microfluidic applications. Journal of Applied Polymer Science. 2007:1894–1902.

Uses

Isobornyl acrylate (IBA) is used as UVcuring EBcuring adhesive, it can also be used to prepare block copolymers with n-butyl acrylate by atom transfer radical polymerization (ATRP).

Application

Isobornyl acrylate can be used as a co-monomer with other acrylic monomers in the preparation of pressure-sensitive adhesives (PSAs) for optical applications. It is also used in the development of high-performance and stable polymer gate dielectrics for organic thin-film transistors (OTFTs). Furthermore, it can also used in the preparation of UV-curable waterborne polyurethane (WPU) by copolymerization.

Hazard

Moderately toxic by ingestion. Low toxicity by skin contact. A moderate skin and mild eye irritant.

Flammability and Explosibility

Non flammable

Synthesis

Isobornyl acrylate is prepared by reacting (-)- borneol,triethylamine with acryloyl chloride in anhydrous THF.Dissolve (-)- borneol (1.00 g, 6.48 mmol, 1 equiv) and triethylamine (0.98 g, 9.72 mmol, 1.5 equiv) in anhydrous THF (20 mL) in a 100 mL round-bottom flask. Add acryloyl chloride (0.88 g, 9.72 mmol, 1.5 equiv) dropwise to the reaction mixture at 0 °C. Allow the reaction to stir at room temperature overnight. Filter the reaction solution. Concentrate the reaction solution on the rotary evaporator. Wash the mixture with water (20 mL). Extract the mixture with dichloromethane (3x20 mL). Dry the combined organic phases over anhydrous sodium sulfate. Filter and concentrate the residue. Purify the crude product further by silica gel column chromatography (petroleum ether/ethyl acetate = 4:1) to obtain isobornyl acrylate.
Fig Synthetic method of Isobornyl acrylate