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ChemicalBook--->CAS DataBase List--->13641-96-8

13641-96-8

13641-96-8 Structure

13641-96-8 Structure
IdentificationBack 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 PropertiesBack 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
[EPA Substance Registry System]

2-Propenoic acid, 2-isocyanatoethyl ester (13641-96-8)
Safety DataBack Directory
[RIDADR ]

UN 2206 6.1/PG III
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

2929100090
Hazard InformationBack Directory
[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.
2-Isocyanatoethyl Acrylate synthesis
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