959-52-4

Basic information

• Product Name: 1,3,5-Triacryloylhexahydro-1,3,5-triazine
• Synonyms: hexahydro-1,3,5-tris(1-oxoallyl)-1,3,5-triazine;1,3,5-Triazine, hexahydro-1,3,5-tris(1-oxo-2-propenyl)-;1,3,5-TRIACRYLOYLTRIHYDRO-S-TRIAZINE;Hexahydro-1,3,5-tris(1-oxallyl)-1,3,5-triazin;1,3,5-Triacryloyl-sym-hexahydrotriazine;1,3,5-trisacroylhexahydro-S-triazine TAHT;1,1',1''-(Hexahydro-1,3,5-triazine-1,3,5-triyl)tris(2-propene-1-one);1,1',1''-(Hexahydro-s-triazine-1,3,5-triyl)tris(2-propene-1-one)
• CAS NO: 959-52-4
• Molecular Formula: C₁₂H₁₅N₃O₃
• Molecular Weight: 249.27
• EINECS: 213-501-6
• Product Categories: Acrylic Monomers;Monomers;Polyfunctional Acrylics
• Mol File: 959-52-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 156 °C (dec.)(lit.)
• Boiling Point: 392.37°C (rough estimate)
• Flash Point: 301 °C
• Appearance: /
• Density: 1.1998 (rough estimate)
• Vapor Pressure: 1.98E-13mmHg at 25°C
• Refractive Index: 1.5290 (estimate)
• PKA: -1.00±0.20(Predicted)
• Water Solubility: Slightly soluble in water
• CAS DataBase Reference: 1,3,5-Triacryloylhexahydro-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Triacryloylhexahydro-1,3,5-triazine(959-52-4)
• EPA Substance Registry System: 1,3,5-Triacryloylhexahydro-1,3,5-triazine(959-52-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 23/24/25-34-42/43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2928 6.1/PG 2
• WGK Germany: 3
• RTECS: XY9260000
• HazardClass: 4.2
• PackingGroup: II
• Hazardous Substances Data: 959-52-4(Hazardous Substances Data)

Usage

General Description

1,3,5-Triacryloylhexahydro-1,3,5-triazine is a chemical compound with the molecular formula C15H17N3O3. It is a triacrylate derivative of hexahydro-1,3,5-triazine and is used in various industrial applications. This chemical is known for its ability to crosslink with other compounds, making it useful in the production of polymers and adhesives. It is also used as a UV-absorber in coatings and adhesives, providing protection against UV radiation. Additionally, 1,3,5-Triacryloylhexahydro-1,3,5-triazine is utilized as a monomer in the synthesis of new materials with unique properties. However, it is important to handle this chemical with care as it may cause irritation and should be used in accordance with safety guidelines.

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 

Relevant articles and documents

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 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.