1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione Chemical Properties

Melting point:

20.5°C

Boiling point:

149-152 °C4 mm Hg(lit.)

Density 

1.159 g/mL at 25 °C(lit.)

vapor pressure 

3.5 hPa (143 °C)

refractive index 

n20/D 1.513(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

3.7g/l

pka

-2.33±0.20(Predicted)

form 

Liquid After Melting

color 

Clear colorless to yellow

Water Solubility 

> 1 g/L (20 ºC)

BRN 

225482

Stability:

May be prone to spontaneous polymerization. Commercial product is generally supllied with added stabilizer such as t-butylhydroquinone. Incompatible with peroxides, strong oxidizing agents, strong acids, strong bases.

InChIKey

KOMNUTZXSVSERR-UHFFFAOYSA-N

LogP

1.92 at 25℃

CAS DataBase Reference

1025-15-6(CAS DataBase Reference)

NIST Chemistry Reference

1,3,5-Triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tri-2-propenyl-(1025-15-6)

EPA Substance Registry System

Triallyl isocyanurate (1025-15-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36/37/39

WGK Germany 

1

RTECS 

XZ1915000

F 

10

HS Code 

2929109000

Toxicity

LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rat 2480 mg/kg

MSDS

• Language:English Provider:1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione Usage And Synthesis

Chemical Properties

colourless viscous liquid or white powder

Uses

crosslinking accelerator agent for peroxide

Uses

The Progress in Development of Dental Restorative Materials

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 4931, 1994 DOI: 10.1021/jo00096a041

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Isocyanates and thioisocyanates, such as 1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, are incompatible with many classes of compounds, reacting exothermically to release toxic gases. Reactions with amines, aldehydes, alcohols, alkali metals, ketones, mercaptans, strong oxidizers, hydrides, phenols, and peroxides can cause vigorous releases of heat. Acids and bases initiate polymerization reactions in these materials. Some isocyanates react with water to form amines and liberate carbon dioxide. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence, [Wischmeyer(1969)].

Fire Hazard

1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione is probably combustible.

Flammability and Explosibility

Non flammable

Synthesis

6.45 g (50 mmol) of cyanuric acid, 670 mg (2.5 mmol) of triphenylphosphine (as an organophosphorus compound) and 25.8 g of xylene (as a solvent) were added to the reaction vessel. Under nitrogen protection, 266 mg of palladium-loaded activated carbon catalyst (trade name E101 NE/W, manufactured by Evonik Degussa Co., Ltd. which is a mixture of zero-valent metallic palladium and divalent palladium compounds with activated carbon in terms of palladium atoms) was added. The mixture was stirred at 95°C for 1 hour. Subsequently, 13.1 g (225 mmol) of propenol (as an allyl-type alcohol) was added slowly and dropwise over 1 h. The reaction lasted for 20 h, during which xylene, propenol, and generated water were removed by azeotropic distillation through a Dean-Stark apparatus. Upon completion of the reaction, the insoluble material was removed by filtration. Analysis of the filtrate showed 98.6% triallyl isocyanurate and 1.4% diallyl isocyanurate in the product based on the conversion of cyanuric acid, and no monoallyl isocyanurate generation was detected.

References

[1] Patent: JP6288459, 2018, B2. Location in patent: Paragraph 0018; 0022; 0026-0029; 0031-0032; 0034-0035; 0037

1,3,5-Tri-2-propenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione(1025-15-6)Related Product Information

• Benzyl isocyanate
• 2-Methoxyphenyl isocyanate
• Ethyl isocyanoacetate
• 2-BROMOPHENYL ISOCYANATE
• METHYL ISOCYANOACETATE
• ISOCYANOBENZENE
• Ethyl Isocyanatoacetate
• 1,3,5-TRIMETHYLHEXAHYDRO-1,3,5-TRIAZINE
• METHYLENEDIFORMAMIDE
• Cyanuric acid
• 1,1,3,3-Tetramethylurea
• HEXAHYDRO-1,3,5-TRIETHYL-S-TRIAZINE
• 1,3,5-Triazine
• CYANOGEN
• Uric acid
• N,N,N',N'-TETRAMETHYLDIAMINOMETHANE
• Biuret
• TRIMETHALLYL ISOCYANURATE