ChemicalBook Product Catalog Chemical Reagents Organic reagents Esters Other esters Isobornyl acrylate

Isobornyl acrylate

Product NameIsobornyl acrylate
CAS5888-33-5
MFC13H20O2
MW208.3
EINECS227-561-6
MOL File5888-33-5.mol

Chemical Properties

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
optical activity	0.41° (C=1.00 g/100ml, ETOH)
Water Solubility	Difficult to mix in water.
FreezingPoint	5
Sensitive	Light Sensitive
BRN	2254825
Stability	Light sensitive
Cosmetics Ingredients Functions	NAIL SCULPTING
InChI	1S/C13H20O2/c1-5-11(14)15-10-8-9-6-7-13(10,4)12(9,2)3/h5,9-10H,1,6-8H2,2-4H3/t9-,10-,13+/m0/s1
InChIKey	PSGCQDPCAWOCSH-BREBYQMCSA-N
SMILES	[H][C@]12CC[C@@](C)([C@@H](C1)OC(=O)C=C)C2(C)C
LogP	4.52 at 20℃
CAS DataBase Reference	5888-33-5(CAS DataBase Reference)
EPA Substance Registry System	Isobornyl acrylate (5888-33-5)

Safety Information

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	TSCA listed
HazardClass	9
PackingGroup	III
HS Code	29161290
Storage Class	10 - Combustible liquids
Hazard Classifications	Aquatic Acute 1 Aquatic Chronic 1 Eye Irrit. 2 Skin Irrit. 2 Skin Sens. 1A STOT SE 3
Toxicity	LD50 oral in rat: 4890mg/kg

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

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

https://www.sigmaaldrich.com/catalog/product/aldrich/392103?lang=en&region=US
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