52434-90-9

Basic information

• Product Name: Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione
• Synonyms: 3,5-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris(2,3-dibromopropyl)-1;5-triazine-2,4,6(1h,3h,5h)-trione,1,3,5-tris(2,3-dibromopropyl)-3;TRIS(2,3-DIBROMOPROPYL) ISOCYANURATE;ISOCYANURIC ACID TRIS(2,3-DIBROMOPROPYL) ESTER;HEXAHYDRO-1,3,5-TRIS(2,3-DIBROMOPROPYL)-1,3,5-TRIAZINE-2,4,6-TRIONE;1,3,5-tris(2,3-dibromoisopropyl) isocyanurate;1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione;TRIS(2,3-DIBROMOPROPYL) ISOCYANURATE, 97 %
• CAS NO: 52434-90-9
• Molecular Formula: C₁₂H₁₅Br₆N₃O₃
• Molecular Weight: 728.69
• EINECS: 257-913-4
• Product Categories: Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Triazines
• Mol File: 52434-90-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 110 °C
• Boiling Point: 618.8 °C at 760 mmHg
• Flash Point: 328 °C
• Appearance: White powder
• Density: 2.338 g/cm³
• Vapor Pressure: 3.07E-15mmHg at 25°C
• Refractive Index: 1.645
• Solubility: Soluble in chloroform.
• PKA: -2.72±0.20(Predicted)
• Water Solubility: 5.07mg/L at 20℃
• CAS DataBase Reference: Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione(CAS DataBase Reference)
• NIST Chemistry Reference: Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione(52434-90-9)
• EPA Substance Registry System: Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione(52434-90-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 2
• Hazardous Substances Data: 52434-90-9(Hazardous Substances Data)

Usage

Description

Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione, also known as tris(2,3-dibromopropyl) isocyanurate (TBC), is a novel, efficient, and additive brominated flame retardant. It is characterized by its flame retardant effect, low volatility, good compatibility, durability, and being lightweight with water and non-toxic properties. TBC is a non-degradable heterocyclic hexabrominated flame retardant that has been found to inhibit the expression of certain genes, leading to a decrease in the growth biomass of certain organisms.

Uses

Used in Flame Retardancy:
Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione is used as an additive flame retardant for its flame retardant effect, low volatility, and good compatibility with various materials.
Used in Environmental and Health Assessments:
In the Environmental Science industry, Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione is used as a subject for assessing potential bioaccumulation and impact on endocrine activity. It is particularly relevant in studies focusing on the effects of flame retardants on human health and the environment.
Used in Biomedical Research:
In the Biomedical Research industry, Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione has been employed in flow-cytometric proliferation assays to determine the potential estrogen-disruptive effects of flame retardants in MCF-7 cells, contributing to the understanding of their impact on human health.
Used in Material Science:
In the Material Science industry, Hexahydro-1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazine-2,4,6-trione is used as a component in the development of durable and lightweight materials with enhanced flame retardant properties, contributing to improved safety standards in various applications.

InChI:InChI=1/C12H15Br6N3O3/c13-1-7(16)4-19-10(22)20(5-8(17)2-14)12(24)21(11(19)23)6-9(18)3-15/h7-9H,1-6H2

Synthetic route

triallyl isocyanurate (1025-15-6) → 1,3,5-tris(β,γ-dibromopropyl)-2,4,6-trioxo-1,3,5-triazine (52434-90-9)

Conditions	Yield
With tetraethylammonium bromide; bromine In dichloromethane at 60℃; for 20h; Reagent/catalyst; Solvent; Temperature;	99.5%

1,3,5-tris(β,γ-dibromopropyl)-2,4,6-trioxo-1,3,5-triazine (52434-90-9) + vanadocene → bis(η5-cyclopentadienyl)vanadium(IV) dibromide

Conditions	Yield
In toluene byproducts: trially isocyanurate; V-compd. to triazine 3:1, evacuated ampule, keeping at room temperature (50-100 h) or at 120 to 130°C (15-20 h); vacuum filtration; elem. anal., ESR;	80%

1,3,5-tris(β,γ-dibromopropyl)-2,4,6-trioxo-1,3,5-triazine (52434-90-9) + vanadocene → vanadocene monobromide

Conditions	Yield
In toluene byproducts: triallyl isocyanurate; V-compd. to triazine 6:1, evacuated ampule, keeping at room temperature (50-100 h) or at 120 to 130°C (15-20 h); vacuum filtration; elem. anal., ESR;	60%

Upstream product

• 1025-15-6 triallyl isocyanurate 

Relevant articles and documents

Synthesis method of thermal-stability TBC fire retardant

The invention relates to a synthesis method of a thermal-stability TBC fire retardant. The technical problem that a TBC fire retardant synthesized in the prior art is high in bromine impurity content,prone to corrosion, color changing, electrical property degradation and the like during processing, poor in thermal stability, complicated in product postprocessing method and not convenient to use is solved. The method includes the following steps of firstly, adding triallyl isocyanurate and an organic solvent to a reaction still to prepare a TAIC organic solvent reaction system, adding the organic solvent and quaternary ammonium salt to a reactor, and dropwise adding bromine Br2 to prepare a brominating agent; secondly, dropwise adding the brominating agent prepared in the first step into the TAIC organic solvent reaction system, and keeping the temperature until the reaction is completed; thirdly, conducting washing, standing and liquid separating to obtain an organic layer; fourthly,adding a seed crystal into a solvent separating kettle, and conducting suction filtration and drying under the vacuum condition of 60-65 DEG C to obtain the TBC fire retardant product. The method is widely applied in the technical field of fire retardant synthesis.