101-37-1

Basic information

• Product Name: 2,4,6-Triallyloxy-1,3,5-triazi
• Synonyms: 1,3,5-Triazine, 2,4,6-tris(2-propenyloxy)-;1,3,5-Triazine,2,4,6-tris(2-propenyloxy)-;2-(2’-Thiazolylazo)-4-cresol;2,4,6-Tri(allyloxy)-s-triazine;2,4,6-triprop-2-ynyloxy-s-triazine;2,4,6-tris(allyloxy)-s-triazin;3,5-Triazine,2,4,6-tris(2-propenyloxy)-1;5-triazine,2,4,6-tris(2-propenyloxy)-3
• CAS NO: 101-37-1
• Molecular Formula: C₁₂H₁₅N₃O₃
• Molecular Weight: 249.27
• EINECS: 202-936-7
• Product Categories: Chemical
• Mol File: 101-37-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 26-28 °C
• Boiling Point: 156 °C
• Flash Point: >230 °F
• Appearance: colourless solid
• Density: 1.11 g/mL at 30 °C
• Vapor Pressure: 4.63E-05mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• Storage Temp.: Store at
• Solubility: 0.3g/l
• PKA: 2.04±0.10(Predicted)
• Water Solubility: 6g/L(20 oC)
• Stability: Stable, but moisture-sensitive. Incompatible with acids, peroxides, strong oxidizing agents, copper, iron and its salts.
• BRN: 235560
• CAS DataBase Reference: 2,4,6-Triallyloxy-1,3,5-triazi(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Triallyloxy-1,3,5-triazi(101-37-1)
• EPA Substance Registry System: 2,4,6-Triallyloxy-1,3,5-triazi(101-37-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 36-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: XZ2080000
• F: 21
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 101-37-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid or solid. Miscible with acetone, benzene, chloroform, dioxane, ethyl acetate, ethanol, and xylene. Combustible.

Uses

Polymers as monomer and modifier, organic intermediate.

Hazard

Toxic by ingestion and inhalation.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intravenous route. Flammable when exposed to heat, flame, or oxidizers. To fight fire, use spray, foam, dry chemical. When heated to decomposition or on contact with acid or acid fumes it emits hghly toxic fumes of CNand NOx. See also ESTERS and ALLYL, COMPOUNDS.

InChI:InChI=1/C12H15N3O3/c1-4-7-16-10-13-11(17-8-5-2)15-12(14-10)18-9-6-3/h4-6H,1-3,7-9H2

Synthetic route

1,3,5-trichloro-2,4,6-triazine (108-77-0) + allyl alcohol (107-18-6) → triallyl cyanurate (101-37-1)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; allyl alcohol With sodium hydroxide In water at -5 - 40℃; for 1.25 - 1.5h; Stage #2: With 4-methoxy-phenol Product distribution / selectivity;	93%
Stage #1: 1,3,5-trichloro-2,4,6-triazine; allyl alcohol With sodium hydroxide In water at 8 - 35℃; for 1.25 - 1.5h; Industry scale; Stage #2: With 4-methoxy-phenol Product distribution / selectivity;	93.8%
With sodium hydroxide In water at -5 - 40℃; for 1.25 - 1.5h; Product distribution / selectivity;	93%

1,3,5-trichloro-2,4,6-triazine (108-77-0) + sodium allyloxide (20907-32-8) → triallyl cyanurate (101-37-1)

Conditions	Yield
With benzene

1,3,5-trichloro-2,4,6-triazine (108-77-0) + allyl alcohol (107-18-6) → 4,6-bis-allyloxy-1H-[1,3,5]triazin-2-one (1081-69-2) + triallyl cyanurate (101-37-1)

Conditions	Yield
With sodium hydroxide; water

1,3,5-trichloro-2,4,6-triazine (108-77-0) → 4,6-bis-allyloxy-1H-[1,3,5]triazin-2-one (1081-69-2) + triallyl cyanurate (101-37-1)

Conditions	Yield
With sodium carbonate; allyl alcohol

carbonimidic acid diallyl ester → triallyl cyanurate (101-37-1)

Conditions	Yield
With iron(III) chloride at 150℃;

rac-3-sulfanylpropane-1,2-diol (96-27-5) + triallyl cyanurate (101-37-1) → C21H39N3O9S3 (1020540-40-2)

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone at 20℃; for 0.5h; UV-irradiation;	95%

1-Hexadecanol (36653-82-4) + triallyl cyanurate (101-37-1) → allyl-1-hexadecyl ether (26459-58-5)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 31h; Catalytic behavior; Concentration; Molecular sieve;	95%

triallyl cyanurate (101-37-1) + 2-hydroxyethanethiol (60-24-2) → C18H33N3O6S3

Conditions	Yield
With phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide at 20℃; for 0.833333h; Temperature; Reagent/catalyst; UV-irradiation;	94%
With 2,2-dimethoxy-2-phenylacetophenone for 0.666667h; UV-irradiation;	84%

triallyl cyanurate (101-37-1) → 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7)

Conditions	Yield
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; Inert atmosphere;	92%
With boron trifluoride; acetic acid; xylene unter Zusatz von Bleicherde;
With Isopropylbenzene; boron trifluoride; acetic acid unter Zusatz von Bleicherde;

(-)-menthol (2216-51-5) + triallyl cyanurate (101-37-1) → (1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane (40940-58-7, 144266-44-4, 67528-21-6)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 50℃; for 5.5h; Catalytic behavior; Temperature; Molecular sieve;	92%

triallyl cyanurate (101-37-1) → allyl chloroacetate (2916-14-5) + 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With chloroacetic acid In toluene for 2h; Heating; Yields of byproduct given;	A n/a B 91.5% C n/a
With chloroacetic acid In toluene for 2h; Heating; Yield given. Yields of byproduct given;

triallyl cyanurate (101-37-1) + silver perchlorate → [Ag(triallyl cyanurate)(ClO4)]n

Conditions	Yield
In acetone	91.1%

triallyl cyanurate (101-37-1) → triallyl isocyanurate (1025-15-6)

Conditions	Yield
copper(II) chloride hydrate In xylene at 120℃; for 2h;	90%
With copper(II) choride dihydrate In 5,5-dimethyl-1,3-cyclohexadiene at 65 - 75℃; Inert atmosphere;	90%
copper dichloride In toluene at 113 - 140℃; under 1.50015 - 2.25023 Torr; Product distribution / selectivity;

1-adamanthanol (768-95-6) + triallyl cyanurate (101-37-1) → 1-(2-propenyloxy)tricyclo<3.3.1.13,7>decane (135394-83-1)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 29h; Molecular sieve;	87%

triallyl cyanurate (101-37-1) → propenyl-1,3,5-triazine-2,4,6-(1H,3H,5H)trione (3030-60-2)

Conditions	Yield
With acetic acid In 5,5-dimethyl-1,3-cyclohexadiene at 65 - 75℃; Inert atmosphere;	85%
With phenol unter Zusatz von Bleicherde;

triallyl cyanurate (101-37-1) → Allyl acetate (591-87-7) + 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With acetic acid In toluene for 2h; Heating; Yields of byproduct given;	A n/a B 85% C n/a
With acetic acid In toluene for 2h; Heating; Yield given. Yields of byproduct given;

triallyl cyanurate (101-37-1) + silver perchlorate → [Ag(triallyl cyanurate)(ClO4)]n + [Ag2(triallyl cyanurate)(ClO4)2]n

Conditions	Yield
In nitromethane	A n/a B 84%

triallyl cyanurate (101-37-1) + 3-Phenylpropionic acid (501-52-0) → allyl 3-phenylpropionate (15814-45-6)

Conditions	Yield
In 1,2-dichloro-benzene at 180℃; for 24h; Temperature; Solvent; Molecular sieve;	83%

3-Phenyl-1-propanol (122-97-4) + triallyl cyanurate (101-37-1) → 3-phenylpropyl alcohol allyl ether (93981-51-2)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 43h; Molecular sieve;	82%

triallyl cyanurate (101-37-1) → Allyl ether (557-40-4) + 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione (6294-79-7) + triallyl isocyanurate (1025-15-6)

Conditions	Yield
With allyl alcohol In toluene for 2h; Heating; Yields of byproduct given;	A n/a B 81.5% C n/a
With allyl alcohol In toluene for 2h; Heating; Yield given. Yields of byproduct given;

1-bromo-6-hexanol (4286-55-9) + triallyl cyanurate (101-37-1) → allyl 6-bromohexyl ether (128133-87-9)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 31h; Molecular sieve;	79%

rac-3-sulfanylpropane-1,2-diol (96-27-5) + triallyl cyanurate (101-37-1) → C15H23N3O5S

Conditions	Yield
With 2,2-dimethoxy-2-phenylacetophenone In methanol at 20℃; for 0.5h; UV-irradiation;	60.3%

triallyl cyanurate (101-37-1) + methyl-alpha-D-glucopyranoside (97-30-3) → 1-methyl-2,3,4,6-tetra-O-(2-propynyl)-α-D-glucopyranoside (13035-25-1)

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20℃; for 23h; Molecular sieve;	57%

triallyl cyanurate (101-37-1) + 2,4,6-tris(methallyloxy)-1,3,5-triazine (16715-84-7) → triallyl isocyanurate (1025-15-6) + 1-(allyl)-3,5-bis(2-methylprop2-en-1-yl)isocyanurate (118361-38-9) + 1-(2-methylprop-2-en-1-yl)-3,5-bis(3-propenyl)isocyanurate (73669-73-5) + tris-2-methylprop-2-en-1-ylisocyanurate (6291-95-8)

Conditions	Yield
With CuCl2.2H2O In toluene for 4h; Heating;	A 18.5% B 31.7% C 40.4% D 9.4%
at 190 - 200℃; for 5h;	A 23.3% B 31.6% C 24% D 21.1%
at 190 - 200℃; for 5h;	A 23.3% B 31.6% C 24% D 21.1%

3-Phenyl-1-propanol (122-97-4) + triallyl cyanurate (101-37-1) → 1-[3-(2-propynyloxy)propyl]benzene

Conditions	Yield
With trifluorormethanesulfonic acid In 1,4-dioxane at 20 - 60℃; for 24h; Inert atmosphere;	39%

triallyl cyanurate (101-37-1) + mercury(II) diacetate (1600-27-7) → tris-(3-mercurio(1+)-2-methoxy-propoxy)-[1,3,5]triazine; trihydroxide

Conditions	Yield
With methanol anschliessendes Behandeln mit methanol.NaOH;
With methanol anschliessendes Behandeln mit methanol.NaOH;

triallyl cyanurate (101-37-1) + mercury(II) diacetate (1600-27-7) → tris-(2-ethoxy-3-mercurio(1+)-propoxy)-[1,3,5]triazine; trihydroxide

Conditions	Yield
With ethanol anschliessendes Behandeln mit aethanol.NaOH;
With ethanol anschliessendes Behandeln mit aethanol.NaOH;

triallyl cyanurate (101-37-1) → 2,4,6-Tris-[((E)-propenyl)oxy]-[1,3,5]triazine

Conditions	Yield
tris(triphenylphosphine)ruthenium(II) chloride at 160℃; for 6h; Yield given;

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 107-18-6 allyl alcohol 
• 20907-32-8 sodium allyloxide 

Downstream Products

• 52434-59-0 tris(2,3-dibromopropyl)isocyanurate 
• 2916-14-5 allyl chloroacetate 
• 6294-79-7 1,3-diallyl-[1,3,5]triazinane-2,4,6-trione 
• 1025-15-6 triallyl isocyanurate 
• 591-87-7 Allyl acetate 
• 557-40-4 Allyl ether 
• 118361-38-9 1-(allyl)-3,5-bis(2-methylprop2-en-1-yl)isocyanurate 
• 73669-73-5 1-(2-methylprop-2-en-1-yl)-3,5-bis(3-propenyl)isocyanurate 
• 6291-95-8 tris-2-methylprop-2-en-1-ylisocyanurate 
• 93981-51-2 3-phenylpropyl alcohol allyl ether 
• 40940-58-7 (1S,2R,4R)-2-(allyloxy)-1-isopropyl-4-methylcyclohexane 
• 15814-45-6 allyl 3-phenylpropionate 

Relevant articles and documents

Method for preparing triallyl cyanurate

The invention discloses a method for preparing triallyl cyanurate. The method includes the steps that cyanuric chloride and allyl alcohol are dispersed in organic solvent in the first place, acid-binding agent alkali metal hydroxide is dropwise added at the temperature controlled to be proper, the cyanuric chloride and the allyl alcohol are made to react, after the reaction is completed, water is added, generated salt is separated and removed, finally decompression and distillation are conducted to recycle solvent, and a triallyl cyanurate product with the content larger than 99% is obtained. The method has the advantages of being high in product yield, good in product quality and low in cost.

PROCESS FOR PREPARING TRIALLYL CYANURATE

The invention relates to an improved process for preparing triallyl cyanurate (TAC) by reacting cyanuric chloride with allyl alcohol in the presence of an alkali metal acid acceptor and in the absence of an organic solvent other than allyl alcohol. According to the invention, TAC is obtained in over 99% purity with an APHA colour number below 10 in a yield of over 90% when 3.9 to 6.0 mol of allyl alcohol and 3.0 to 3.2 equivalents of acid acceptor are used per mole of cyanuric chloride, cyanuric chloride and acid acceptor are added simultaneously or successively to anhydrous or at least 50% by weight aqueous allyl alcohol, and the reaction is performed in one or more stages at a temperature in the range of ?5 to +50° C.