2-Isocyanatoethyl Acrylate Chemical Properties

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

Flash point:

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 Information

RIDADR 

UN 2206 6.1/PG III

HazardClass 

6.1

PackingGroup 

III

HS Code 

2929100090

2-Isocyanatoethyl Acrylate Usage And Synthesis

Uses

2-Isocyanatoethyl Acrylate is an important compound intermediate commonly used in chemical research and development as an API for organic synthesis.

Synthesis

2-Isocyanatoethyl Acrylate 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(13641-96-8)Related Product Information

• TERT-BUTYL ISOCYANIDE
• m-Tolyl isocyanate
• ISOCYANIC ACID
• Isothiazolinones
• 2-Isocyanatoethyl methacrylate
• 2-(THIEN-2-YL)ETHYL ISOCYANATE
• Isopropylsulfonamide
• METHYL ISOCYANOACETATE
• 2-FLUORO-5-METHYLPHENYL ISOCYANATE
• 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 2-METHOXYPHENYL ISOTHIOCYANATE
• METHYL ISOINDOLINE-5-CARBOXYLATE
• ETHYL 2-CYANOACRYLATE
• Toluene diisocyanate
• Ethyl isobutyrylacetate
• ISOPROPYLHYDRAZINE HYDROCHLORIDE
• Ethyl isocyanoacetate
• ISONICOTINOYL CHLORIDE HYDROCHLORIDE