839-90-7

Basic information

• Product Name: 1,3,5-Tris(2-hydroxyethyl)cyanuric acid
• Synonyms: 1,3,5-tris(2-hydroxyethyl)triazine-2,4,6-trione;3,5-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris(2-hydroxyethyl)-1;5-triazine-2,4,6(1h,3h,5h)-trione,1,3,5-tris(2-hydroxyethyl)-3;6(1h,3h,5h)-trione,1,3,5-tris(2-hydroxyethyl)-s-triazine-4;n,n’,n’’-tris(2-hydroxyethyl)isocyanurate;tris(2-hydroxyethyl)-s-triazine-2,4,6-trione;1,3,5-TRIS(2-HYDROXYETHYL)-1,3,5-TRIAZINE-2,4,6(1H,3H,5H)-TRIONE;1,3,5-TRIS(2-HYDROXYETHYL) 1,3,5-TRIAZINE-2,4,6(1H,3H,6H)TRIONE
• CAS NO: 839-90-7
• Molecular Formula: C₉H₁₅N₃O₆
• Molecular Weight: 261.23
• EINECS: 212-660-9
• Product Categories: Intermediates;Organics
• Mol File: 839-90-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 136-140 °C(lit.)
• Boiling Point: 526.7 °C at 760 mmHg
• Flash Point: 241℃
• Appearance: white powder
• Density: 1.498 g/cm³
• Vapor Pressure: 0.001Pa at 50℃
• Storage Temp.: Store below +30°C.
• Solubility: 1150g/l
• PKA: 14.03±0.10(Predicted)
• Water Solubility: 572g/L at 20℃
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 1,3,5-Tris(2-hydroxyethyl)cyanuric acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Tris(2-hydroxyethyl)cyanuric acid(839-90-7)
• EPA Substance Registry System: 1,3,5-Tris(2-hydroxyethyl)cyanuric acid(839-90-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 839-90-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 839-90-7 differently. You can refer to the following data:
1. Additive to plastics, especially to impart thermal stability.
2. 1,3,5-Tris(2-hydroxyethyl)cyanuric Acid, is a building block that can be used in polymer science. It has also shown to have synergistic flame retardancy properties.

Synthesis Reference(s)

The Journal of Organic Chemistry, 28, p. 85, 1963 DOI: 10.1021/jo01036a019

General Description

White powder.

Air & Water Reactions

Water soluble.

Reactivity Profile

An organo-isocyanate. Isocyanates and thioisocyanates 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.

Fire Hazard

Flash point data for 1,3,5-Tris(2-hydroxyethyl)cyanuric acid are not available, but 1,3,5-Tris(2-hydroxyethyl)cyanuric acid is probably combustible.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H16N3O6/c13-4-1-7-8(16)10(2-5-14)12(18)11(3-6-15)9(7)17/h7,13-15H,1-6H2

Synthetic route

cyanuric acid (108-80-5) + 2-chloro-ethanol (107-07-3) → 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7)

Conditions	Yield
With sodium hydride 1.) HMPA, 100 deg C, 3 h, 2.) HMPA, 100 deg C, 7 h; Yield given. Multistep reaction;

isocyanuric acid (108-80-5) + 2-chloro-ethanol (107-07-3) → 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 80 - 85℃; Reagent/catalyst; Temperature; Solvent;	271.6 g

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tri(2-chloroethyl)-1,3,5-triazine-2,4,6-trione (6299-37-2)

Conditions	Yield
With thionyl chloride In 1,4-dioxane	100%

dimethyldibromosilane (4095-10-7) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + epichlorohydrin (106-89-8) → C27H51Cl6N3O9Si3

Conditions	Yield
Stage #1: dimethyldibromosilane; 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With hydrogen bromide In 1,4-dioxane at 70℃; for 5h; Inert atmosphere; Stage #2: epichlorohydrin In 1,4-dioxane at 60 - 100℃; for 6h; Reagent/catalyst; Solvent; Temperature;	98.7%

dimethyldibromosilane (4095-10-7) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C15H30Br3N3O6Si3

Conditions	Yield
In 1,4-dioxane at 50℃; for 5h;	98.4%
In 1,4-dioxane at 50℃; for 9h; Solvent; Temperature; Inert atmosphere;
In acetonitrile at 40℃; for 7h; Solvent; Temperature;
In diethylene glycol dimethyl ether at 70℃; for 4h; Temperature; Solvent;
In 1,2-dimethoxyethane at 70℃; for 4h; Temperature; Solvent; Inert atmosphere;

triethyl phosphate (78-40-0) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C15H27N3O11P2

Conditions	Yield
With sodium carbonate at 78 - 200℃; Temperature;	98.07%

C14H20N2O3 + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C42H63N3O15

Conditions	Yield
With cesium fluoride at 50℃;	98%

p-toluenesulfonyl chloride (98-59-9) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tris(2-tosylethyl)-1,3,5-triazine-2,4,6-trione (951016-94-7)

Conditions	Yield
With pyridine at -30 - 0℃; for 17h;	97%

methyl 2-hydroxy-5-nitrobenzoate (17302-46-4) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C33H30N6O18 (130839-94-0)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In 1,4-dioxane	95%

octadec-1-ene (112-88-9) + dilauryl peroxide (105-74-8) + toluene-4-sulfonic acid (104-15-4) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + 3-mercaptopropionic acid (107-96-0) → tris(2-hydroxyethyl)isocyanurate tris(3-stearylthiopropionate)

Conditions	Yield
In water; toluene	94.6%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + 1-chloro-3-hydroxypropane (627-30-5) → tris[2-tris(3-chloropropoxy)silanyloxyethyl]isocyanurate

Conditions	Yield
Stage #1: 1-chloro-3-hydroxypropane With hydrogenchloride; tetrachlorosilane In 1,4-dioxane; water at 85℃; for 8h; Inert atmosphere; Stage #2: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With hydrogenchloride In 1,4-dioxane; water at 85℃; for 6h; Inert atmosphere;	93.4%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tris(2-bromoethyl)-1,3,5-triazacyclohexane-2,4,6-trione

Conditions	Yield
With carbon tetrabromide; triphenylphosphine In acetonitrile at 20℃; for 12h; Inert atmosphere;	90%
With carbon tetrabromide; triphenylphosphine In acetonitrile at 20℃; for 12h; Cooling with ice;	70%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tris-(2-azidoethyl)-[1,3,5]triazinane-2,4,6-trione (522614-81-9)

Conditions	Yield
Stage #1: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With methanesulfonyl chloride; triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; Stage #2: With sodium azide In N,N-dimethyl-formamide at 70℃; for 120h; Further stages.;	89%
Stage #1: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With methanesulfonyl chloride; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Stage #2: With sodium azide In N,N-dimethyl-formamide at 70℃; for 120h; Further stages.;	88%
Stage #1: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With methanesulfonyl chloride; triethylamine In N,N-dimethyl-formamide at 0℃; for 3h; Inert atmosphere; Stage #2: With sodium azide In N,N-dimethyl-formamide at 75℃; for 48h; Inert atmosphere;	76%

3-((benzylsulfanylthiocarbonyl)sufanyl)propionic acid chloride (497931-77-8) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C20H25N3O7S3

Conditions	Yield
With pyridine In dichloromethane at 40℃; for 3h;	88.1%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + 3-mercaptopropionic acid (107-96-0) → tris[2-(3-mercaptopropionyloxy)ethyl] isocyanurate (36196-44-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 125℃;	88%

3-((benzylsulfanylthiocarbonyl)sufanyl)propionic acid chloride (497931-77-8) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C31H35N3O8S6

Conditions	Yield
With pyridine In dichloromethane at 40℃; for 3h;	82.4%

3-((benzylsulfanylthiocarbonyl)sufanyl)propionic acid chloride (497931-77-8) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C42H45N3O9S9

Conditions	Yield
With pyridine In dichloromethane at 40℃; for 3h;	79.3%

isonicotinoyl chloride hydrochloride (39178-35-3) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tris(2-(isonicotinoyloxy)ethyl)cyanurate (1263078-42-7)

Conditions	Yield
With triethylamine In toluene for 48h; Reflux;	74%

pyridine-3-carbonyl chloride hydrochloride (20260-53-1) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tris(nicotinoyloxyethyl)cyanurate

Conditions	Yield
With triethylamine In toluene at 20℃; for 48h; Reflux;	74%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + bis(tri-n-butyltin)oxide (56-35-9) → tris[2-(tributylstannyloxy)ethyl] isocyanurate (84838-99-3)

Conditions	Yield
byproducts: Bu3SnI; molar ratio org. compd.:Sn-compd.=2:1;	73%

p-toluenesulfonyl chloride (98-59-9) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1,3,5-tris(2-tosylethyl)-1,3,5-triazine-2,4,6-trione (951016-94-7) + C23H27N3O10S2

Conditions	Yield
Stage #1: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With triethylamine In tetrahydrofuran at 0℃; for 0.5h; Cooling with ice; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	A 66% B n/a

4,4'-dimethoxytrityl chloride (40615-36-9) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C51H51N3O10 (210563-95-4)

Conditions	Yield
With dmap In pyridine at 0 - 20℃; Inert atmosphere;	52%

2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid (55750-53-3) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C39H48N6O15

Conditions	Yield
Stage #1: 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid; 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With sulfuric acid In toluene at 115℃; Heating / reflux; Stage #2: With triethylamine for 1h;	50%

propargyl bromide (106-96-7) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 3-(prop-2-yn-1-yl)oxazolidin-2-one (823-53-0)

Conditions	Yield
Stage #1: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With sodium hydride In dimethyl sulfoxide at 35 - 40℃; Stage #2: propargyl bromide In dimethyl sulfoxide	31%

propargyl bromide (106-96-7) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 3-(prop-2-yn-1-yl)oxazolidin-2-one (823-53-0) + 1,3,5-tris(3-oxahexa-5-ynyl)-1,3,5-triazinane-2,4,6-trione (1234387-26-8)

Conditions	Yield
Stage #1: 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione With sodium hydride In dimethyl sulfoxide at 20℃; Inert atmosphere; Cooling with ice; Stage #2: propargyl bromide In dimethyl sulfoxide; toluene at 35 - 40℃; Inert atmosphere;	A 31% B 20%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → C30H33N3O8

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 20 - 60℃; for 16h;	30%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + N-[(3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl]-acetamide → 1-(2-acetamido-2-deoxy-β-D-glucopyranosylethyl)-3,5-bis(hydroxyethyl)cyanuric acid

Conditions	Yield
β-N-acetylhexosaminidase In various solvent(s) pH=5; Substitution; Enzymatic reaction;	29%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + p-nitrophenyl galactose → 1-(β-D-galactopyranosylethyl)-3,5-bis(hydroxyethyl)cyanuric acid

Conditions	Yield
β-galactosidase In phosphate buffer pH=5; Substitution; Enzymatic reaction;	20%

D-Mannose (530-26-7) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 1-(α-D-mannopyranosylethyl)-3,5-bis(hydroxyethyl)cyanuric acid

Conditions	Yield
α-mannosidase In various solvent(s) at 37℃; for 96h; pH=5; Etherification; Enzymatic reaction;	4%

1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) + C75H93Cl3O9 (157336-53-3) → C84H105N3O15

Conditions	Yield
With pyridine In tetrahydrofuran Heating;	2.5%

levulinic anhydride (40608-06-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) + 1,3,5-tris(2-hydroxyethyl)-S-triazine-2,4,6-trione (839-90-7) → 4-Oxo-pentanoic acid 2-[3-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-5-(2-hydroxy-ethyl)-2,4,6-trioxo-[1,3,5]triazinan-1-yl]-ethyl ester

Conditions	Yield
Multistep reaction;

Upstream product

• 108-80-5 isocyanuric acid 
• 107-07-3 2-chloro-ethanol 
• 108-80-5 cyanuric acid 

Downstream Products

• 36196-44-8 tris[2-(3-mercaptopropionyloxy)ethyl] isocyanurate 
• 34137-09-2 1,3,5-tris(3,5-di-tert-butyl-4-hydroxyphenylpropionyloxyethyl)isocyanurate 
• 4171-10-2 C₁₂H₂₁N₃O₁₂S₃ 
• 1410808-22-8 N,N',N''-((2,4,6-trioxo-1,3,5-triazinan-1,3,5-triyl)tris(ethane-2,1-diyl))tris(2,3,4,5,6-pentafluorobenzamide) 

Relevant articles and documents

Preparation method of theic

The invention relates to the field of organic chemical industry, in particular to a preparation method of tris (2-hydroxyethyl) isocyanurate. According to the method, a chloroethanol route is used, iodide ions are used as a catalyst, a proper feeding mode and a purification method are adopted, and the defects that the method is complex in process, long in reaction period and inconvenient in excessive recovery of chloroethanol are overcome. Iodine ions are used as a catalyst so that the temperature during the reaction of chloroethanol and cyanuric acid is reduced. Meanwhile, the equivalent chloroethanol is added in a dropwise adding manner so that the self reaction of the chloroethanol and the generation of impurities generated by the reaction of the theic and the chloroethanol are reduced,the operation is simple, the purification is convenient, and the industrial prospect is better.

Application of the study of reactivity of alkaline salts of isocyanuric acid to the synthesis of mono and trisubstituted isocyanurates

Reactivity of alkaline salts of isocyanuric acid has been studied. It has been established that the nucleophilic substitution is not selective because of the protonic exchanges between salts and substituted derivatives. The synthesis of mono or trisubstituted derivative is due to secondary reactions and to solvent effects. With this study, it has been possible to settle a method to prepare mono and trisubstituted derivatives of isocyanuric acid.