959-52-4

Usage

Uses

Used in Polymer and Adhesive Production:
1,3,5-Triacryloylhexahydro-1,3,5-triazine is used as a crosslinking agent in the production of polymers and adhesives for its ability to chemically bond with other compounds, enhancing the strength and durability of the final products.
Used in Coatings and Adhesives as a UV-Absorber:
In the coatings and adhesives industry, 1,3,5-Triacryloylhexahydro-1,3,5-triazine is used as a UV-absorbing component to protect materials from the damaging effects of ultraviolet radiation, thereby extending their service life and maintaining their aesthetic qualities.
Used in the Synthesis of New Materials:
1,3,5-Triacryloylhexahydro-1,3,5-triazine is utilized as a monomer in the synthesis of new materials with unique properties, contributing to the development of innovative products across various industries that require specialized characteristics such as enhanced stability or reactivity.

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

Synthetic route

1,3,5-Trioxan (110-88-3) + acrylonitrile (107-13-1) → 1,3,5-triacryloylhexahydro-s-triazine (959-52-4)

Conditions	Yield
Stage #1: 1,3,5-Trioxan; acrylonitrile With sulfuric acid In chlorobenzene at 80℃; for 5h; Stage #2: With sodium hydroxide In chlorobenzene at 5 - 20℃; for 2h;	95.1%
With sulfuric acid; hydroquinone In tetrachloromethane; water at 80℃; for 1h; effect of the ratio between the catalyst and water present in the system;	91%
With sulfuric acid; hydroquinone In tetrachloromethane at 80℃; for 1h;	91%

formaldehyd (50-00-0) + acrylonitrile (107-13-1) → 1,3,5-triacryloylhexahydro-s-triazine (959-52-4)

Conditions	Yield
Amberlyst 15 resin In chlorobenzene at 80℃; for 4h;	95%
With sulfuric acid In chlorobenzene at 70℃; for 3h; Temperature; Solvent;	88.2%
With sulfuric acid
With sulfuric acid; acetic anhydride

rac-3-sulfanylpropane-1,2-diol (96-27-5) + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → 1,1′,1″-(1,3,5-triazinane-1,3,5-triyl)tris(3-(2,3-dihydroxypropylthio)propan-1-one) (1123041-92-8)

Conditions	Yield
With propylamine In methanol for 0.166667h; Michael type addition;	96%
In methanol at 30℃; for 0.25h;	79.7%
Stage #1: rac-3-sulfanylpropane-1,2-diol; 1,3,5-triacryloylhexahydro-s-triazine In methanol at 20℃; for 0.25h; Stage #2: With hexan-1-amine In methanol at 20℃;	68%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 2-hydroxyethanethiol (60-24-2) → 1,1',1''-(1,3,5-triazinane-1,3,5-triyl)tris(3-(2-hydroxyethylthio)propan-1-one) (40549-57-3)

Conditions	Yield
With propylamine In methanol	96%
With propylamine In methanol for 0.166667h; Michael type addition;	92%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + Cysteamine (60-23-1) → 1,1',1"-(1,3,5-triazinane-1,3,5-triyl)tris(3-(2-aminoethylthio)propan-1-one) (1123041-98-4)

Conditions	Yield
In methanol for 0.166667h; Michael type addition;	95%
In methanol at 23℃; for 0.166667h;

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + Methyl thioglycolate (2365-48-2) → trimethyl 2,2',2''-(3,3',3''-(1,3,5-triazinane-1,3,5-triyl)tris(3-oxopropane-3,1-diyl))tris(sulfanediyl)triacetate (1123041-93-9)

Conditions	Yield
With propylamine In methanol; chloroform for 0.166667h; Michael type addition;	94%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + Thiosalicylic acid (147-93-3) → 2,2',2''-(3,3',3''-(1,3,5-triazinane-1,3,5-triyl)tris(3-oxopropane-3,1-diyl))tris(sulfanediyl)tribenzoic acid (1123042-01-2)

Conditions	Yield
Stage #1: Thiosalicylic acid With potassium hydrogencarbonate In methanol at 60℃; for 1h; Stage #2: 1,3,5-triacryloylhexahydro-s-triazine In methanol at 20℃; for 0.166667h; Michael type addition;	90%

rac-cysteine (921-01-7, 3374-22-9, 4371-52-2, 40143-64-4, 40143-66-6, 40143-69-9, 52-90-4) + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → 3,3',3''-(3,3',3''-(1,3,5-triazinane-1,3,5-triyl)tris(3-oxopropane-3,1-diyl))tris(sulfanediyl)tris(2-aminopropanoic acid) (1123042-03-4)

Conditions	Yield
In methanol; water for 0.416667h; Michael type addition;	88%

1-aza-18-crown-6 (33941-15-0) + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → 1-[3,5-bis-(3-1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl-propionyl)-[1,3,5]triazinan-1-yl]-3-(1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-yl)-propan-1-one

Conditions	Yield
In methanol at 50℃; for 24h;	85.7%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1-[3,5-bis-(3-1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl-propionyl)-[1,3,5]triazinan-1-yl]-3-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-propan-1-one

Conditions	Yield
In methanol at 50℃; for 24h;	84.9%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 4-aminotiophenol (1193-02-8) → 3-(4-aminophenyl)sulfanyl-1-[3,5-bis[3-(4-aminophenyl)sulfanylpropanoyl]-1,3,5-triazinan-1-yl]propan-1-one

Conditions	Yield
With Dimethyl(phenyl)phosphine In methanol for 16h; Reflux;	84%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 2-amino-benzenethiol (137-07-5) → 1,1',1''-(1,3,5-triazinane-1,3,5-triyl)tris(3-(2-aminophenylthio)propan-1-one) (1123041-99-5)

Conditions	Yield
In methanol; chloroform for 0.166667h; Michael type addition;	82%

4'-aminobenzo-15-crown-5-ether (60835-71-4) + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → C54H78N6O18

Conditions	Yield
With triethylamine In methanol at 50℃; for 144h;	76.5%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 4-aminobenzo-18-crown-6 (68941-06-0) → C60H90N6O21

Conditions	Yield
With triethylamine In methanol at 50℃; for 144h;	76.4%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 2-aminomethyl-15-crown-5 (83585-56-2) → 1-(3,5-Bis-{3-[(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethyl)-amino]-propionyl}-[1,3,5]triazinan-1-yl)-3-[(1,4,7,10,13-pentaoxa-cyclopentadec-2-ylmethyl)-amino]-propan-1-one

Conditions	Yield
In methanol at 50℃; for 24h;	72.2%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 2-(aminomethyl)-18-crown-6 (83585-61-9) → 1-(3,5-Bis-{3-[(1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethyl)-amino]-propionyl}-[1,3,5]triazinan-1-yl)-3-[(1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethyl)-amino]-propan-1-one

Conditions	Yield
In methanol at 50℃; for 24h;	71.8%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + diphenylphosphane (829-85-6) → C48H48N3O3P3

Conditions	Yield
In 2-methyltetrahydrofuran at 90℃; for 12h; Inert atmosphere; Sealed tube; Green chemistry; regioselective reaction;	68%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane (23978-55-4) → 1-[3-acryloyl-5-(3-{16-[3-(3,5-diacryloyl-[1,3,5]triazinan-1-yl)-3-oxo-propyl]-1,4,10,13-tetraoxa-7,16-diaza-cyclooctadec-7-yl}-propionyl)-[1,3,5]triazinan-1-yl]-propenone (868852-74-8)

Conditions	Yield
In methanol at 50℃; for 30h; Michael addition;	65.3%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 3-mercaptopropionic acid (107-96-0) → 3,3',3''-(3,3',3''-(1,3,5-triazinane-1,3,5-triyl)tris(3-oxopropane-3,1-diyl))tris(sulfanediyl)tripropanoic acid (63074-18-0)

Conditions	Yield
Stage #1: 3-mercaptopropionic acid With potassium hydrogencarbonate In methanol at 60℃; for 1h; Stage #2: 1,3,5-triacryloylhexahydro-s-triazine In methanol at 20℃; for 0.166667h; Michael type addition;	63%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 2-(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)phenoxy)-N-(2-mercaptoethyl)acetamide → C48H54N10O5S + C84H93N17O7S2

Conditions	Yield
With potassium carbonate In water; acetonitrile for 1h; pH=8; Inert atmosphere;	A 59% B 28%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + 2-(3,5-bis((bis(pyridin-2-ylmethyl)amino)methyl)phenoxy)-N-(2-mercaptoethyl)acetamide → C120H132N24O9S3

Conditions	Yield
With potassium carbonate In [D3]acetonitrile; water-d2 for 1h; pH=8; Inert atmosphere;	58%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + mercaptoacetic acid (68-11-1) → C14H19N3O5S

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	40.1%
With triethylamine In dichloromethane for 24h; Cooling with ice;
With triethylamine In dichloromethane at 20℃;	1.87 g

mercapto acetic acid + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → C14H19N3O5S

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	36.87%

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + RCFRLPCRQLRCR → TATA-FXII618

Conditions	Yield
In acetonitrile for 0.25h;	27%
With ammonium bicarbonate In water; acetonitrile at 30℃; for 1h; pH=8;
In acetonitrile at 30℃; for 1h; pH=8;

(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)hexanoic acid (1159680-21-3) + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + N-Fmoc-β-alanine (35737-10-1) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7) + N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartic acid (71989-14-5, 112883-39-3) + N-(9-fluorenylmethoxycarbonyl)sarcosine (77128-70-2) + (2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid + (pg)NH-Trp(*)-OH + (pg)NH-Pro-OH + (pg)NH-His(*)-OH + (pg)NH-Leu-OH + (pg)NH-Asn(*)-OH + (pg)NH-Val-OH + (pg)NH-Asp(*)-OH + (pg)NH-Ala-OH → C138H217N43O38S3

Conditions

Yield

Stage #1: N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine With 1-hydroxy-7-aza-benzotriazole; diisopropyl-carbodiimide In N,N-dimethyl-formamide for 1h; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)hexanoic acid; 1,3,5-triacryloylhexahydro-s-triazine; N-Fmoc-β-alanine; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartic acid; N-(9-fluorenylmethoxycarbonyl)sarcosine; (2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid; (pg)NH-Trp(*)-OH; (pg)NH-Pro-OH; (pg)NH-His(*)-OH; (pg)NH-Leu-OH; (pg)NH-Asn(*)-OH; (pg)NH-Val-OH; (pg)NH-Asp(*)-OH; (pg)NH-Ala-OH Further stages;

16.3%

...Expand

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) + diethylamine (109-89-7) → 1,3-diacryloyl-5-(N,N-diethyl-β-alanyl)-hexahydro-[1,3,5]triazine (32112-69-9)

Conditions	Yield
With chloroform

1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → 1,3,5-tripropionylperhydro-1,3,5-triazine (30805-19-7)

propene (187737-37-7) + 1,3,5-triacryloylhexahydro-s-triazine (959-52-4) → 6-methyl-2-vinyl-5,6-dihydro-4H-[1,3]oxazine (31401-10-2)

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 107-13-1 acrylonitrile 
• 50-00-0 formaldehyd 

Downstream Products

• 30805-19-7 1,3,5-tripropionylperhydro-1,3,5-triazine 
• 1123042-01-2 2,2',2''-(3,3',3''-(1,3,5-triazinane-1,3,5-triyl)tris(3-oxopropane-3,1-diyl))tris(sulfanediyl)tribenzoic acid 
• 1123041-99-5 1,1',1''-(1,3,5-triazinane-1,3,5-triyl)tris(3-(2-aminophenylthio)propan-1-one) 
• 1372138-34-5 C₃₉H₄₈N₁₂O₉S₆ 

Relevant academic research and scientific papers

Synthetic method of 1,3,5-triacryloylhexahydro-1,3,5-triazine

The invention discloses a synthetic method of 1,3,5-triacryloylhexahydro-1,3,5-triazine. The method comprises the following steps of a cyclization reaction, a neutralization reaction, cooling crystallization and filtration and drying. The synthetic method of the 1,3,5-triacryloylhexahydro-1,3,5-triazine has the advantages of being few in synthetic step, simple in method, safe in operation process, less in three waste discharge and high in yield and which can reach 85%-95%.

Synthesis of Hexahydro-1,3,5-triacryloyltriazine

The yield of hexahydro-1,3,5-triacryloyltriazine in the reaction of acrylonitrile with trioxane is determined by the ratio between the catalyst (sulfuric acid) and water present in the system. The reaction product is formed only with an excess of acid over water, but a large proportion of acid results in polymerization. Deactivation of the catalyst in the presence of water and side polymerization can be explained by the formation of N-hydroxymethylamide derivatives.

Synthesis of 1,3,5-Triacylperhydro-1,3,5-triazines Catalyzed by Ion-Exchange Resins

1,3,5-Triacylperhydro-1,3,5-triazines can be obtained in high yields by reaction of 1,3,5-trioxan with nitriles in solvents such as chlorobenzene using as catalyst an ion-exchange resin such as Amberlyst 15 with precise control of the hydration rate of the resin.