Isobornyl acrylate
Basic information
- CAS
5888-33-5- Standard SMILES
C=CC(=O)O[C@@H]1C[C@H]2CC[C@]1(C)C2(C)C- InChIKey
PSGCQDPCAWOCSH-BREBYQMCSA-N- Molecular formula
- C13H20O2
- Average molar mass
- 208.3 g/mol
- Monoisotopic mass
- 208.14632988
Overview
causes contact dermatitis in some individuals; structure in first source
Names & identifiers
- Preferred name
- Isobornyl acrylate
- IUPAC
- [(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] prop-2-enoate
- English name
- Isobornyl acrylate
- Molecular formula
- C13H20O2
- Molecular weight
- 208.3
Names & synonyms
Isobornyl acrylate5888-33-5Sartomer 506Acrylic acid, isobornyl ester2-Propenoic acid, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-IX0PRH184P2-Propenoic acid, 1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, exo-2-Propenoic acid, (1R,2R,4R)-1,7,7-trimethylbicyclo(2.2.1)hept-2-yl ester, rel-DTXCID701475251RefChem:149053227-561-6DTXSID5052250
Show more names
iboaIBXAsr506exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acrylateebecryliboaqm589EM70DNsartomer506
(1R,2R,4R)-rel-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl acrylateLight Acrylate IB-XASR 506 (acrylate)MFCD00080424EINECS 227-561-6QM 589Isobornyl acrylate (stabilized with MEHQ)(1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acrylate
Database identifiers
- CAS
5888-33-5- PubChem CID
- 639970
- UNII
- IX0PRH184P
- EC Number
- 227-561-6
- Nikkaji
- J215.747K
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 306
Experimental & physicochemical properties
Physical DescriptionCBI; Liquid
Physicochemical properties
- Melting point
- -35 °C · <-35°C
- Boiling point
- 121 °C/15 · 121 °C/15 mmHg
- Density
- 0.99 · 0.99
- vapor pressure
- 1.3 Pa · 1.3Pa at 20℃
- refractive index
- 1.48 · 1.48
- Flash point
- 109 °C · 109 °C
- 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 ° · 0.41° (C=1.00 g/100ml, ETOH)
- Viscosity
- 9 cp · 9cp (25C)
- Water Solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 3.7% (35 of 950) of reports.
Warning
H315 (84.7%): Causes skin irritation [Warning Skin corrosion/irritation]
Hazard information
Regulatory Information
Chemical: 2-Propenoic acid, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-
2-Propenoic acid, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propenoic acid, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
REACH registered substance: Exo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl acrylate (EC: 227-561-6)
exo-Isobornyl acrylate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Skin Irrit. 2 (84.7%)
Skin sensitization - Category 1A
Skin Sens. 1A
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- UD3940000
- ridadr
- UN 3082 9 / PGIII
Chemistry & industry
Uses & manufacturing
UsesGlucose monitoring systems and insulin pumps were noted in 2020 as newer uses (as of 2020, there are glucose monitoring systems that are free of Isobornl Acrylate).
U.S. Production2023: 2,500,000 - <4,000,000 lb
Consumer UsesPhotosensitive agent
Industry UsesOther
General Manufacturing Information
Printing and Related Support Activities
2-Propenoic acid, (1R,2R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl ester, rel-: ACTIVE
Applications
DescriptionIsobornyl 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.
UsesIsobornyl 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).
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…