| Identification | Back Directory | [Name]
2-IsocyanatoethylAcrylate | [CAS]
13641-96-8 | [Synonyms]
AOI-VM
2-IsocyatoethylAcrylate
2-IsocyanatoethylAcrylate
2-isocyanatoethyl prop-2-enoate
2-(Acryloyloxy)ethyl Isocyanate
Acrylic Acid 2-Isocyanatoethyl Ester
2-Propenoic acid 2-isocyanatoethyl ester
2-IsocyanatoethylAcrylate ISO 9001：2015 REACH
2-IsocyanatoethylAcrylate(stabilizedwithBHT)>
2-Isocyanatoethyl Acrylate (stabilized with BHT) | [EINECS(EC#)]
482-140-6 | [Molecular Formula]
C6H7NO3 | [MDL Number]
MFCD11112219 | [MOL File]
13641-96-8.mol | [Molecular Weight]
141.12 |
| Chemical Properties | Back Directory | [Melting point ]
-25 °C | [Boiling point ]
80-95 °C(Press: 15 Torr) | [density ]
1.05 | [vapor pressure ]
21.4Pa at 20℃ | [refractive index ]
1.4470 to 1.4510 | [Fp ]
97°C(lit.) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8C | [form ]
clear liquid | [color ]
Colorless to Almost colorless | [Specific Gravity]
1.10 | [InChI]
InChI=1S/C6H7NO3/c1-2-6(9)10-4-3-7-5-8/h2H,1,3-4H2 | [InChIKey]
DPNXHTDWGGVXID-UHFFFAOYSA-N | [SMILES]
C(OCCN=C=O)(=O)C=C | [EPA Substance Registry System]
2-Propenoic acid, 2-isocyanatoethyl ester (13641-96-8) |
| Hazard Information | Back Directory | [Description]
2-Isocyanatoethyl Acrylate (AOI) is a key photoreactive functional monomer, primarily used in the preparation of high-performance UV-induced peelable acrylic pressure-sensitive adhesives via chemical grafting strategies. It is widely used in the field of semiconductor wafer cutting protection, enabling precise control of adhesion strength and clean peel performance [1]. | [Uses]
2-Isocyanatoethyl Acrylate(13641-96-8) is an important compound intermediate commonly used in chemical research and development as an API for organic synthesis.
| [Synthesis]
2-Isocyanatoethyl Acrylate(13641-96-8) is prepared by the reaction of phosgene, ethanolamine and 2-chloropropionyl chloride. The steps are as follows:
In a 500 mL four-necked flask equipped with a stirrer, condenser, thermometer and inner tube, 250 mL of toluene and 25 g (0.41 mol) of 2-aminoethanol were added, heated to 90° C. and supplied with about 20 g of hydrogen chloride gas. Then 56 g (0.44 mol) of 3-chloropropionic acid chloride was added dropwise over 90 minutes and heated at 90° C. for 1 hour. Thereafter, 80 g (0.81 mol) of phosgene was supplied. Dissolved phosgene was then removed by nitrogen gas bubbling. Subsequently, 0.4 g of phenothiazine and 0.4 g of 2,6-bis-t-butylhydroxytoluene were added, and 50 g of triethylamine (0.49 mol) was supplied, and the mixture was heated and stirred at 50° C. for 6 hours. Thereafter, the mixture was cooled to room temperature, the formed hydrochloride salt was filtered, and toluene was distilled off. By the above process, Mixture 2 containing the main product of 2-acryloyloxyethyl isocyanate (AOI) 55 g (0.35 mol) (87% yield) and the by-product of 2-acryloyloxyethyl acrylate (2547 ppm by mass) was obtained.
| [References]
[1] Wang, R., Niu, T., Chen, S., Li, J., Fu, Q., Wei, D. (2025). Steric and photoreactive control of UV-Induced debonding in acrylic Pressure-Sensitive adhesives for wafer cutting via isocyanate monomer grafting. European Polymer Journal, 236, Article 114128. https://doi.org/10.1016/j.eurpolymj.2025.114128 |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Struchem Co., Ltd.
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| Telephone: |
0512-63009836 18994340901 |
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http://www.beidapharma.com |
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