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Cyanuric Fluoride Synthesis Essay

IUPAC name


Other names

cyanuryl fluoride embox


CAS Number

3D model (JSmol)

ECHA InfoCard100.010.565



  • InChI=1S/C3F3N3/c4-1-7-2(5)9-3(6)8-1 Y
  • InChI=1/C3F3N3/c4-1-7-2(5)9-3(6)8-1



Chemical formula

Molar mass135.047 g/mol
Appearancecolourless liquid
Density1.574 g/cm3
Melting point−38 °C (−36 °F; 235 K)
Boiling point74 °C (165 °F; 347 K)
R-phrases(outdated)R24, R26, R35
S-phrases(outdated)S26, S28, S36/37/39, S45
Related compounds

Related compounds

cyanuric acid, cyanuric chloride, cyanuric bromide

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Cyanuric fluoride or 2,4,6-trifluoro-1,3,5-triazine is a chemical compound with the formula (CNF)3. It is a colourless, pungent liquid. It has been used as a precursor for fibre-reactive dyes, as a specific reagent for tyrosine residues in enzymes, and as a fluorinating agent.[1]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[2]

Preparation and reactions[edit]

Cyanuric fluoride is prepared by fluorinating cyanuric chloride. The fluorinating agent may be SbF3Cl2,[3] KSO2F,[4] or NaF.[5][6]

Cyanuric fluoride is used for the mild and direct conversion of carboxylic acids to acyl fluorides:[7]

Other fluorinating methods are less direct and may be incompatible with some functional groups.[8]

Cyanuric fluoride hydrolyses easily to cyanuric acid and it reacts more readily with nucleophiles than cyanuric chloride.[4]Pyrolysis of cyanuric fluoride at 1300 °C is a way to prepare cyanogen fluoride:[9]

(CNF)3 → 3 CNF.


  1. ^"Fluorinated aromatic compounds". Kirk-Othmer Encyclopedia of Chemical Technology. 11. Wiley-Interscience. 1994. p. 608. 
  2. ^"40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities"(PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011. 
  3. ^Abe F. Maxwell; John S. Fry; Lucius A. Bigelow (1958). "The Indirect Fluorination of Cyanuric Chloride". Journal of the American Chemical Society. 80 (3): 548–549. doi:10.1021/ja01536a010. 
  4. ^ abDaniel W. Grisley, Jr; E. W. Gluesenkamp; S. Allen Heininger (1958). "Reactions of Nucleophilic Reagents with Cyanuric Fluoride and Cyanuric Chloride". Journal of Organic Chemistry. 23 (11): 1802–1804. doi:10.1021/jo01105a620. 
  5. ^C. W. Tullock; D. D. Coffman (1960). "Synthesis of Fluorides by Metathesis with Sodium Fluoride". Journal of Organic Chemistry. 25 (11): 2016–2019. doi:10.1021/jo01081a050. 
  6. ^Steffen Groß; Stephan Laabs; Andreas Scherrmann; Alexander Sudau; Nong Zhang; Udo Nubbemeyer (2000). "Improved Syntheses of Cyanuric Fluoride and Carboxylic Acid Fluorides". Journal für Praktische Chemie. 342 (7): 711–714. doi:10.1002/1521-3897(200009)342:7<711::AID-PRAC711>3.0.CO;2-M. 
  7. ^George A. Olah; Masatomo Nojima; Istvan Kerekes (1973). "Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride". Synthesis. 1973 (08): 487–488. doi:10.1055/s-1973-22238. 
  8. ^Barda, David A. (2005). "Cyanuric Fluoride". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. p. 77. doi:10.1002/047084289X.rn00043. 
  9. ^F. S. Fawcett; R. D. Lipscomb (1964). "Cyanogen Fluoride: Synthesis and Properties". Journal of the American Chemical Society. 86 (13): 2576–2579. doi:10.1021/ja01067a011. 

Cyanuric chloride Chemical Properties,Uses,Production


Cyanuric chloride, white crystals with a strong irritant chlorine odor , is corrosive to the skin, having eye irritation and tearing property. Melting point 145 ℃, boiling point 190 ℃, UVλmax241nm (ethanol).it is Soluble in ethanol, ethyl ether, chloroform, acetic acid and acrylonitrile, insoluble in cold water. cooling of reaction of Cyanuric chloride and water is slow, when it is heated it is rapidly hydrolyzed to cyanuric acid (C3H3O3N3) and hydrochloric acid, the product are relatively soluble in water, so you can use the extraction method of separating. It Reacts With concentrated nitric acid and concentrated sulfuric acid at room temperature to be partial conversion of cyanuric acid, and it reacts with the sodium alkoxide to generate cyanuric acid triester, and it can also react with ammonia, amines, phenols and so on.
In recent years, there is rapid growth in consumption of cyanuric chloride in China, from 1998 to 2004 the average annual growth rate of Apparent consumption was about 32.2% ,in 2005, cyanuric chloride demand reached 50,000 tons, according to forecasts, from 2007 to 2012 cyanuric chloride will continue rapid growth in average rate of 6.0% , the market is very promising. Since cyanuric chloride subsequent products are enormous , the market demand is large, national research institutions and related businesses have continued to develop its downstream products, and open cyanuric chloride applications. Therefore, the new product by the cyanuric chloride derivatives are emerging, the market demand will be further expanded.
Related cyanuric chloride chemical reactions involving:
After 2-amino-4-nitrophenol diazotization, and H acid coupling, and chromium, cobalt complex post-processing,it is first condensed with cyanuric chloride ,then after condensation with ammonia to get Reactive Black K-BR. It is Mainly used for cotton, polyester/cotton printing.
With cyanuric chloride as raw materials, in trichlorethylene solution at 20~30 ℃, with the amine reaction , 2,4-dichloro-6-ethyl-1,3,5-triazine is produced, and then it reacts with ammonia to produce 2-amino-4-chloro-6-ethylamino triazine, and then it reacts with 2-chloro-2-methyl propionitrile , which can generate selective herbicides cyanazine for control annual or perennial narrow leaves or broadleaf weeds in corn field.

Chemical Properties

Crystals Having a pungent odor. Soluble in chloroform, carbon tetrachloride, ethanol, hot ether, acetone, dioxane, slightly soluble in water.


cyanuric chloride is an important fine chemical product, with a wide range of uses, it is the intermediate in pesticide industry, and the manufacture of reactive dyes raw material, it can used as all kinds of organic industrial production additives, such as fluorescent brighteners , textiles shrink-proof agents, surface active agents, it is one of the materials used in the manufacture of defense explosives and rubber accelerator and it is also the material for the synthesis of drugs by the pesticide and pharmaceutical industry.
The above information is edited by the chemicalbook of Tian Ye.

production method

Cyanuric chloride production process usually consists of two steps : chloride cyanogen polymerization and chloride cyanogen preparation . There are many ways to generate chloride cyanogen, such as the synthesis of methyl thiocyanate and chlorine, hydrocyanic acid is dissolved in chloroform and chlorine gas is put in to synthesize , hydrocyanic acid method, sodium cyanide, urea, hydrocyanic acid direct method of chlorine and cyanuric chloride and the like, the current production of industrial cyanuric chloride generally uses sodium cyanide and hydrocyanic acid as raw materials in two ways. 1. Sodium cyanide method : using sodium cyanide as raw materials after the reaction of chlorine and cyanuric chloride, it is polymerized to form cyanuric chloride, it is quenched,then after crystallization ,the product is obtained. Material consumption fixed: sodium cyanide 1073kg/t, chlorine 1700kg/t. 2. The method of hydrocyanic acid :with hydrocyanic acid as raw materials ,chloride cyanogen is produced by the reaction of chlorine, and then use polymerization to generate cyanuric chloride, quench, crystallize , the product is obtained. Material consumption fixed: hydrocyanic acid 500kg/t, chlorine 1200kg/t.


corrosive substances

Toxicity grading

Middle toxic

Acute toxicity

Oral-rat LD50: 485 mg/kg; Oral-Mouse LD50: 350 mg/kg

Irritation data

skin-rabbit 500 mg/24 hours of moderate; Eyes-rabbit 0.05 mg/24 hours of severe

Flammability and hazard characteristics

When it contacts with water ,it emits toxic hydrogen chloride gas;when it is thermal it decomposes toxic hydrogen chloride gas

Storage Characteristics

Ventilated, low-temperature ,dry is stored separately from oxidants,and alkali.

Extinguishing agent

carbon dioxide, dry powder,sandy soil

Chemical Properties

White Powder


Cyanurchloride is an intermediate to manufacture of agrochemicals (triazine herbicides), dyestuffs, optical brighteners, tanning agents, reactive dyes, UV-absorbing agent, softening agents and pharmaceuticals, as well as block-builders for plastics. Product Data Sheet


Cyanurchloride is an intermediate to manufacture of agrochemicals, dyestuffs, optical brighteners, tanning agents, softening agents and pharmaceuticals, as well as block-builders for plastics.


Reagent for the conversion of alcohols to chlorides and for the immobilization of microorganisms and enzymes.1


Cyanuric Chloride is extensively used in the preparation of the triazine-class pesticides and herbicides. Cyanuric chloride is also used as a precursor to dyes and crosslinking agents due to the react ive chlorine atoms towards nucleophilic substitution reactions. Cyanuric chloride derivatives possess a large spectrum of activities as antibacterial and anticancer agents.


ChEBI: A chloro-1,3,5-triazine in which the triazine ring is substituted on each carbon by chlorine. Its main use is in the preparation of the triazine-class pesticides.


Intermediate in the synthesis of active dyes, agricultural products, and drug substances. Reagent in organic synthesis. Coupling agent for nucleic acids and proteins; cyanuric chloride-activated paper is used in capillary and electroblotting applications, dot tests, and hybridization protocols.

General Description

A colorless crystalline solid with a pungent odor. Melting point 146°C. Density 1.32 g / cm3. Very slightly soluble in water. Toxic by ingestion and inhalation of vapors. Irritates skin and eyes. Used to make dyes.

Air & Water Reactions

Reacts exothermically with water, especially if catalyzed or heated, to generate fumes of hydrochloric acid. Very slightly soluble in water.

Reactivity Profile

Cyanuric chloride reacts rapidly and exothermically with water to generate hydrogen chloride. A mixture with water in an industrial reactor with refrigeration turned off developed pressure that blew gaskets and filled the building with flammable vapors. An explosion occurred when the vapors were ignited [MCA Case History 1869(1972)]. Runaway reactions have occurred with acetone/water; methanol/water, ethoxyethanol/water, allyl alcohol/sodium hydroxide/water, 2-butanone/sodium hydroxide/water, and methanol/sodium bicarbonate [Loss Prev. Bull., 1979, (25), 21]. Reacts with methanol to give gaseous methyl chloride. Reacts rapidly with bicarbonates to generate gaseous carbon dioxide. Reacts vigorously with dimethyl formamide (DMF) to form carbon dioxide after a deceptive induction period [BCISC Quart. Safety Summ., 1960, 35, 24]. Can react with reducing agents to generate heat and products that may be gaseous (causing pressurization of closed containers). The products may themselves be capable of further reactions (such as combustion in the air).

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Vapors may accumulate in confined areas (basement, tanks, hopper/tank cars etc.). Substance will react with water (some violently), releasing corrosive and/or toxic gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Cyanuric chloride Preparation Products And Raw materials

Raw materials

ChlorineUreaSodium cyanideHYDROGEN CYANIDEMethyl thiocyanate

Preparation Products

C.I. Reactive Blue 1REACTIVE RED 120Fluorescent Brightener 220trisodium 2-[[6-[(4,6-dichloro-1,3,5-triazin-2-yl)methylamino]-1-hydroxy-3-sulphonato-2-naphthyl]azo]naphthalene-1,5-disulphonate Reactive Disperse Scarlet GReactive Red M-3BEC.I. Reactive yellow 1BladexCIBACRON BRILLIANT YELLOW 3G-Pdisodium 4-[[5-(aminocarbonyl)-1-ethyl-2-hydroxy-4-methyl-6-oxopiperidin-3-yl]azo]-6-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]benzene-1,3-disulphonate Reactive Red Violet X-2RDirect Yellow L-5Rfluorescent whitening agent RADirect Blending Brilliant Red D-5BLSimazineTerbutylazineReactive Yellow 179trisodium 2-[[6-[(4-amino-6-chloro-1,3,5-triazin-2-yl)methylamino]-1-hydroxy-3-sulphonato-2-naphthyl]azo]naphthalene-1,5-disulphonate REACTIVE RED 195Reactive Orange 2Reactive Blue 812-[[4-[[4-[bis(2-hydroxyethyl)amino]-6-chloro-1,3,5-triazin-2-yl]amino]phenyl]azo]-p-cresol Direct Blend Rubine D-BLLReactive Red KD-8BNeutral Brilliant Yellow S-5GLCyanuric fluorideReactive Light Yellow M-5GReactive Brilliant Orange K-RANILAZINEReactivebrilliantredKE-7B Reactive Yellow 18REACTIVE ORANGE 14Reactive Yellow 84Reactive Violet 2tetrasodium 3,3'-[(1,6-dihydro-6-oxo-1,3,5-triazine-2,4-diyl)bis[imino(5-methoxy-2-methyl-4,1-phenylene)azo]]bis(naphthalene-1,5-disulphonate) Reactive Yellow KE-RNAltretaminehexasodium 4-amino-3,6-bis[[5-[[4-chloro-6-[(3-sulphonatophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphonatophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonateSSH-108

Cyanuric chloride Suppliers

Global( 215)Suppliers

Capot Chemical Co.,Ltd.+86 (0)571-855 867 18
+86 (0)571-858 647 95sales@capotchem.comChina1995360
Dalian Richfortune Chemicals Co., Ltd86-411-84820922, 84821539
Shanghai Time Chemicals CO., Ltd.+86-021-57951555
Beijing Tianyukanghong Chemical Technology Co., Ltd.010-57794770
Shanghai Aladdin Bio-Chem Technology Co.,LTD021-20337333/400-620-6333
J & K SCIENTIFIC LTD.400-666-7788 +86-10-82848833;market6@jkchemical.comChina9682076
Meryer (Shanghai) Chemical Technology Co., Ltd.+86-(0)21-61259100(Shanghai) +86-(0)755-86170099(ShenZhen) +86-(0)10-62670440(Beijing)
+86-(0)21-61259102(Shanghai) +86-(0)755-86170066(ShenZhen) +86-(0)10-88580358(Beijing)sh@meryer.comChina4039862
Alfa Aesar400-610-6006; 021-67582000
TCI (Shanghai) Development Co., Ltd.800-988-0390
Beijing dtftchem Technology Co., Ltd.13651141086; 86(10)60275028、60275820
86 (10) 60270825dtftchem@sina.comChina144362

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