638-16-4

Basic information

• Product Name: Trithiocyanuric acid
• Synonyms: 1,3,5-Triazine-2,4,6(1H,3H,5H)-trithione;1,3,5-triazine-2,4,6-trimercaptan;1,3,5-trimercaptotriazine;2,4,6-triazinetrithiol;2,4,6-trimercapto-s-triazine;trithio-cyanuricaci;usafth-3;S-TRIAZINE-2,4,6-TRITHIOL
• CAS NO: 638-16-4
• Molecular Formula: C₃H₃N₃S₃
• Molecular Weight: 177.27
• EINECS: 211-322-8
• Product Categories: rubber additive;rubber auxiliary;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;Triazines;crosslinking agnt forAR.ECO.CR;Rubber Auxiliary Agents;fine chemicals
• Mol File: 638-16-4.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 242.5 °C at 760 mmHg
• Flash Point: 100.5 °C
• Appearance: Yellow/Amorphous Powder
• Density: 1.589 (estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 6.35±0.20(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Trithiocyanuric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Trithiocyanuric acid(638-16-4)
• EPA Substance Registry System: Trithiocyanuric acid(638-16-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 2
• RTECS: XZ2830000
• TSCA: Yes
• Hazardous Substances Data: 638-16-4(Hazardous Substances Data)

Usage

Uses

Used in Crosslinking Agents for Eco-Friendly and Cost-Effective Crosslinking:
Trithiocyanuric acid is used as a crosslinking agent for eco-friendly and cost-effective crosslinking in various industries. It helps to improve the stability, durability, and performance of materials by forming covalent bonds between polymer chains. This results in enhanced mechanical properties, thermal stability, and resistance to degradation.
Used in Chemical Reactions for the Synthesis of Metal Complexes:
Trithiocyanuric acid is used in chemical reactions for the synthesis of metal complexes. For example, the reaction of BunLi (butyllithium) with trithiocyanuric acid in toluene/HMPA (hexamethylphosphoramide) yields a mono-lithiated species, [(LH2Li)·HMPA2]. This reaction is crucial for the formation of metal complexes with trithiocyanuric acid, which have potential applications in various fields.
Used in Analytical Chemistry for the Elucidation of Coordination Polymer Stoichiometry:
Trithiocyanuric acid is used in analytical chemistry for the elucidation of coordination polymer stoichiometry via thermometric titrimetry. This technique involves the measurement of temperature changes during the titration process, which provides valuable information about the stoichiometry and stability of coordination polymers. The use of trithiocyanuric acid in this process allows for a more accurate determination of the composition and structure of these materials.

InChI:InChI=1/C3H3N3S3/c7-1-2(8)4-6-5-3(1)9/h(H,6,7)(H2,4,5,8,9)

Synthetic route

2,4,6-trimereaptotriazine, trisodium salt, nonahydrate → Thiocyanuric acid (638-16-4)

Conditions	Yield
With Praestol 2500; sulfuric acid In water at 60℃; for 3 - 3.5h; pH=1.7 - 2.0; Product distribution / selectivity;	99.8%
With hydrogenchloride; Praestol 2500 In water at 40 - 60℃; for 2h; pH=1.8 - 2.0; Product distribution / selectivity;	98.4%
With sulfuric acid In water at 20 - 45℃; for 2h; pH=1.9; Product distribution / selectivity;	92.5%

disodium salt of trimercapto-s-triazine → Thiocyanuric acid (638-16-4)

Conditions	Yield
With hydrogenchloride In water for 1h; pH=1.89;	95.4%

1,3,5-trichloro-2,4,6-triazine (108-77-0) → Thiocyanuric acid (638-16-4)

Conditions	Yield
With sodium hydroxide; tiolacetic acid In ethanol at 20℃; for 4h;	90%

pyridine thiocyanate (30248-54-5) → Thiocyanuric acid (638-16-4)

Conditions	Yield
With sulfuric acid In 1,4-dioxane	29%

C21H39N3O3S3 → Thiocyanuric acid (638-16-4)

Conditions	Yield
at 180℃; for 0.0833333h; Conversion of starting material; Neat (no solvent);

C21H39N3O3S3 → Thiocyanuric acid (638-16-4)

Conditions	Yield
at 180℃; for 0.0833333h; Conversion of starting material; Neat (no solvent);
at 23℃; for 1680h; Neat (no solvent);

titanium(IV) trithiocyanurate → Thiocyanuric acid (638-16-4)

Conditions	Yield
In diethyl ether
In ethanol
In water

Thiocyanuric acid (638-16-4) + 2-[4-Amino-6-(3,3-dimethyl-butylamino)-[1,3,5]triazin-2-ylamino]-5-bromo-N-(3-bromomethyl-phenyl)-N-(4-tert-butyl-benzyl)-benzamide (174355-83-0) → N,N',N''-[1,3,5-triazine-2,4,6-triyltris(thiomethylene-3,1-phenylene)]tris[2-{4-amino-6-[(3,3-dimethylbutyl)amino]-1,3,5-triazin-2-yl}amino]-5-bromo-N-{[4-(1,1-dimethylethyl)phenyl]methyl}benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran 1.) room temperature, 6 h, 2.) reflux, 10 h;	97%

Thiocyanuric acid (638-16-4) + propargyl bromide (106-96-7) → 2,4,6-tris(prop-2-yn-1-ylthio)-1,3,5-triazine

Conditions	Yield
Stage #1: Thiocyanuric acid With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: propargyl bromide In N,N-dimethyl-formamide for 24h;	97%
With sodium hydroxide In water at 20℃; for 3h;	75%

Thiocyanuric acid (638-16-4) → C42H69N3O12S3

Conditions	Yield
With sodium carbonate In 1,4-dioxane at 100℃; for 12h; Temperature; Reagent/catalyst; Inert atmosphere;	96%

Thiocyanuric acid (638-16-4) + dimethyl sulfate (77-78-1) → 2,4,6-tris(methylthio)-1,3,5-triazine (5759-58-0)

Conditions	Yield
With sodium hydroxide In water	95%

Thiocyanuric acid (638-16-4) + copper(l) chloride → CuCl(trithiocyanuric acid) (854588-92-4)

Conditions	Yield
In acetonitrile at 60 - 80℃; for 48h; High pressure;	95%
In dichloromethane; acetonitrile placing solid copper salt and ligand in opposite sides of a beaker filled with a mixt. of CH2Cl2 and acetonitrile, standing at room temp. for 2 d; elem. anal.;	15%

(3R,5S)-6-<(p-tolylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester (136006-37-6) + Thiocyanuric acid (638-16-4) → C42H69N3O12S3

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 90℃; for 12h; Temperature; Inert atmosphere;	94.5%

Upstream product

• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 30248-54-5 pyridine thiocyanate 
• 5759-58-0 2,4,6-tris(methylthio)-1,3,5-triazine 

Downstream Products

• 75-15-0 carbon disulfide 
• 463-56-9 thiocyanic acid 
• 1502-47-2 melem 
• 13320-09-7 1,3,5-Triazine-2,4,6-trisulfenyltrichloride 
• 108-80-5 isocyanuric acid 
• 7783-06-4 hydrogen sulfide 
• 744202-16-2 Ni[bis(2-diphenylphosphinoethyl)phenylphosphine](2,4,6-trimercaptotriazine dianion)*DMF 
• 744202-15-1 Ni[bis(2-diphenylphosphinoethyl)phenylphosphine](2,4,6-trimercaptotriazine dianion) 
• 868170-35-8 [silver(I)(PPh₃)2(H₂-trimercaptotriazine)] 
• 108-80-5 cyanuric acid 
• 255901-24-7 C₃N₃(SAuP(C₆H₅)3)3 
• 947261-88-3 (η5-C5H4SiMe3)2Nb(CNC6H3-2,6-Me2)(κ1-1,3,5-triazine-2,4,6-trithiol(3-)) 
• 13270-05-8 2,4,6-tris(p-tolylthio)-1,3,5-triazine 
• 1609653-62-4 2,4,6-tris(3-methoxyphenylthio)-1,3,5-triazine 

Relevant articles and documents

CYCLOTRIMERIZATION OF THIOCYANIC ACID IN ORGANIC SOLVENTS

Thiocyanic acid in organic solvents (i-PrOH Bu2O, AcOH, dioxane) trimerizes to form 1,3,5-trimercapto-sym-triazine.

Preparation method and application of 2,4,6-trisulfydryl s-triazine disodium salt aqueous solution

The invention relates to the field of environmental protection, in particular to a preparation method and application of a 2,4,6-trisulfydryl s-triazine disodium salt aqueous solution. The preparationmethod of the 2,4,6-trisulfydryl s-triazine disodium salt aqueous solution comprises the following steps: adding cyanuric chloride and a sodium sulfide aqueous solution into a sodium hydrosulfide aqueous solution, wherein the adding speed of the cyanuric chloride and the sodium sulfide aqueous solution are controlled to obtain a mixed solution with the pH value of 10-12, the temperature of the mixed solution being controlled to be 0-20 DEG C; heating the mixed solution to initiate the reaction between sodium hydrosulfide and sodium sulfide react with cyanuric chloride, conducting cooling treatment and suction filtration in sequence after the reaction is completed, thus preparing the 2,4,6-trimercapto-s-triazine disodium salt aqueous solution. According to the method, the molar ratio of sodium hydrosulfide to sodium sulfide is changed, so that alkali is prevented from being used for controlling the pH value of a reaction system, hydrolysis reaction is inhibited to the maximum extent, and therefore, the purity and the yield of the 2,4,6-trimercaptos-triazine disodium salt are guaranteed.

METHOD FOR THE PRODUCTION OF 2, 4, 6-TRIMERCAPTO-1, 3, 5-TRIAZINE

The present invention is directed towards a method for the production of 2, 4, 6-trimercapto-1, 3, 5-triazine (TMT-H3). In particular, the method of the subject matter relates to the operation of acidifying the salts of 2, 4, 6-trimercapto-1, 3, 5-triazine in aqueous solution and in a defined pH range.

THIOL COMPOUND DERIVATIVES, HARDENING COMPOSITIONS CONTAINING THESE DERIVATIVES AND MOLDED ARTICLES THEREOF

The present invention relates to a thiol compound derivative represented by the following formula (1), a curable composition containing the derivative, and a molded product made of the composition. More particularly, the invention relates to a thiol compound derivative which is added to a polymer having reactivity to a thiol derivative substituent to provide a curable composition, a curable composition containing the derivative and a crosslinkable halogen-containing crosslinking polymer, and a crosslinked molded product of the composition. wherein X1, X2 and X3 are each a group represented by the following formula (2).