87-90-1

Basic information

• Product Name: Trichloroisocyanuric acid
• Synonyms: CDB 90;LABOTEST-BB LT00138113;BLEACH;BLEACH CLEANING SOLUTION;BLEACH SOLUTION;1,3,5-TRICHLOROHEXAHYDRO-1,3,5-TRIAZINE-2,4,6-TRIONE;1,3,5-Trichloroisocyanuric acid;1,3,5-TRICHLORO-1,3,5-TRIAZINE-2,4,6-TRIONE
• CAS NO: 87-90-1
• Molecular Formula: C₃Cl₃N₃O₃
• Molecular Weight: 232.41
• EINECS: 201-782-8
• Product Categories: INORGANIC & ORGANIC CHEMICALS;Water Treatment;Organics;Chlorination;Halogenation;Synthetic Organic Chemistry;Biocide;Water Ttreatment Chemicals;NAPA
• Mol File: 87-90-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 249-251 °C(lit.)
• Boiling Point: 272.3 °C at 760 mmHg
• Flash Point: 121°C
• Appearance: White to almost white/Powder or Granules
• Density: 2.07
• Vapor Pressure: 0.001-0.002Pa at 20-25℃
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform (Sparingly, Heated), DMSO (Sparingly)
• PKA: -4.49±0.20(Predicted)
• Water Solubility: 1.2 g/100mL (25 ºC)
• Sensitive: Hygroscopic
• Stability: Stable. Hygroscopic, and may decompose in contact with moisture. Contact with combustible material may lead to fire. Incompatibl
• Merck: 14,9641
• BRN: 202022
• CAS DataBase Reference: Trichloroisocyanuric acid(CAS DataBase Reference)
• NIST Chemistry Reference: Trichloroisocyanuric acid(87-90-1)
• EPA Substance Registry System: Trichloroisocyanuric acid(87-90-1)

Safety Data

• Hazard Codes: O,Xn,N
• Statements: 8-22-31-36/37-50/53-36/37/38
• Safety Statements: 8-26-41-60-61
• RIDADR: UN 2468 5.1/PG 2
• WGK Germany: 2
• RTECS: XZ1925000
• TSCA: Yes
• HazardClass: 5.1
• PackingGroup: II
• Hazardous Substances Data: 87-90-1(Hazardous Substances Data)

Usage

Chemical Description

Trichloroisocyanuric acid is a chlorinated derivative of isocyanuric acid.

Chemical Description

Trichloroisocyanuric acid is a white crystalline powder that is commonly used as a disinfectant and bleaching agent.

InChI:InChI=1/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11

Synthetic route

cyanuric acid (108-80-5) → trichloroisocyanuric acid (87-90-1)

Conditions	Yield
With chlorine; calcium carbonate In water	100%
With hypochlorous anhydride In water at 25℃; for 6h; pH=3.5; pH-value; Temperature; Large scale;	98%
With sodium hydroxide; chlorine unter der Einwirkung von UV-Licht;
With potassium hydroxide; chlorine unter der Einwirkung von UV-LIcht;

sodium cyanurate (3047-33-4) → trichloroisocyanuric acid (87-90-1)

Conditions	Yield
With chlorine In toluene at 30 - 40℃; pH=3 - 3.5; Solvent; pH-value; Temperature; Large scale;	93.65%
With chlorine at 10 - 23℃; Temperature; Flow reactor; Large scale;
With chlorine; sodium hydroxide In methanol; water at 5 - 65℃; for 0.166667h; pH=2.5 - 3; Solvent; Temperature; Reagent/catalyst;	12.98 g

N'-carbonyl-N,N-dichloro-urea (26231-96-9) → trichloroisocyanuric acid (87-90-1)

isocyanuric acid (108-80-5) → trichloroisocyanuric acid (87-90-1)

Conditions	Yield
With potassium hydroxide; chlorine
With chlorine; calcium hydroxide In water at 40 - 50℃; pH=4;

cyanuric acid (108-80-5) → trichloroisocyanuric acid (87-90-1) + 1,3-dichloro-[1,3,5]triazinane-2,4,6-trione (2782-57-2) + chloro-isocyanuric acid

Conditions	Yield
In water reactn. with single positive charged Cl;
In water reactn. with single positive charged Cl;

1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione (17497-85-7) → trichloroisocyanuric acid (87-90-1) + bromine chloride (13863-41-7)

Conditions	Yield
90°C;	A >99 B n/a

chlorine isocyanate (13858-09-8) + sodium fluoride → Carbonyl fluoride (353-50-4) + carbon monoxide (201230-82-2) + trichloroisocyanuric acid (87-90-1)

Conditions	Yield
byproducts: NaCl, SiF4; with dry NaF, 300°C;

chlorine isocyanate (13858-09-8) → nitrogen trichloride (10025-85-1) + carbon dioxide (124-38-9) + trichloroisocyanuric acid (87-90-1) + 1,3-dichloro-[1,3,5]triazinane-2,4,6-trione (2782-57-2) + 1,3-dichloro-1,3-diazetidine-2,4-dione (24604-62-4)

Conditions	Yield
slow react. above the melting point, fast at room temp., dichlorouretidindione formed by vac. sublimation (50.degrre.C, 0.1 Torr), di- and trichlocyanuric acid yielded by 48h sublimation of the residue at 95-160°C;

chlorine isocyanate (13858-09-8) → N'-carbonyl-N,N-dichloro-urea (26231-96-9) + trichloroisocyanuric acid (87-90-1)

Conditions	Yield
With alkali fluorides in presence of anhyd. alkali fluorides, 50 Torr, room temp.;

cyanuric acid (108-80-5) + chlorine (7782-50-5) → trichloroisocyanuric acid (87-90-1)

Conditions	Yield
vigorous stirring, 0°C; filtering, drying, sublimated in vac. at 170°C;
vigorous stirring, 0°C; filtering, drying, sublimated in vac. at 170°C;

triiodoisocyanuric acid (27694-85-5) + chlorine (7782-50-5) → trichloroisocyanuric acid (87-90-1) + iodine (7553-56-2)

Conditions	Yield
room temp.;

1,3-dichloro-1,3-diazetidine-2,4-dione (24604-62-4) → trichloroisocyanuric acid (87-90-1)

Conditions	Yield
above the melting point at atmospheric pressure;
In acetonitrile

trichloroisocyanuric acid (87-90-1) + 6-bromo-7-fluoro-4-{[(1S)-1-(tetrahydro-2H-pyran-4-yl)ethyl]amino}-3-quinolinecarboxamide → (S)-8-bromo-7-fluoro-1-(1-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-c]quinolin-2(3H)-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0 - 20℃; for 0.333333h; Inert atmosphere;	100%

trichloroisocyanuric acid (87-90-1) + Benzyl 4-hydroxybenzoate (94-18-8) → benzyl 4-formylbenzoate (78767-55-2)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate In dichloromethane for 0.0833333h;	99%

trichloroisocyanuric acid (87-90-1) + 6-bromo-4-[(cis-3-methoxycyclobutyl)amino]quinoline-3-carboxamide → 8-bromo-1-(cis-3-methoxycyclobutyl)-3H-imidazo[4,5-c]quinolin-2-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0 - 20℃; for 18h; Inert atmosphere;	99%

trichloroisocyanuric acid (87-90-1) + 2-(2-((trifluoromethyl)thio)phenyl)pyridine (1584705-57-6) → 2-(2-((trifluoromethyl)sulfinyl)phenyl)pyridine

Conditions	Yield
Stage #1: 2-(2-((trifluoromethyl)thio)phenyl)pyridine In dichloromethane; acetonitrile at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: trichloroisocyanuric acid In dichloromethane; acetonitrile at 20℃; for 1h; Schlenk technique; Inert atmosphere;	99%

trichloroisocyanuric acid (87-90-1) + 6-bromo-7-fluoro-4-(tetrahydro-2H-pyran-4-ylamino)quinoline-3-carboxamide → 8-bromo-7-fluoro-1-(oxan-4-yl)-3H-imidazo[4,5-c]quinolin-2-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0 - 20℃; for 0.25h; Inert atmosphere;	98%

trichloroisocyanuric acid (87-90-1) + 1-(4-bromophenyl)-1H-imidazole (10040-96-7) → 2-hydroxy-4,6-bis(4-bromophenylimidazolium)-1,3,5-triazinide dichloride

Conditions	Yield
In acetonitrile at 0 - 110℃; for 20.5h;	96%

2,3,5-trimethyl-pyridine (695-98-7) + trichloroisocyanuric acid (87-90-1) + benzamide (55-21-0) → 2-chloromethyl-3,5-dimethyl-4-nitro-pyridine N-oxide (142885-89-0)

Conditions	Yield
With sodium hydroxide In water	93%

trichloroisocyanuric acid (87-90-1) → dicloroiodoisocyanuric acid (1376143-54-2)

Conditions	Yield
Stage #1: trichloroisocyanuric acid With iodine at 170℃; for 18h; Stage #2: at 220℃; for 24h;	93%

trichloroisocyanuric acid (87-90-1) + thiophenol (108-98-5) → isocyanuric acid (108-80-5) + diphenyldisulfane (882-33-7)

Conditions	Yield
With pyridine; water; benzoic acid In dichloromethane; acetonitrile at 40℃;	A n/a B 91%

1-(Trimethylsilyloxy)cyclohexene (6651-36-1) + trichloroisocyanuric acid (87-90-1) → silyl enol ether + 2-Chlorocyclohexanone (822-87-7)

Conditions	Yield
With hydrogenchloride In diethyl ether; ethyl acetate	A n/a B 91%
With hydrogenchloride In diethyl ether; ethyl acetate	A n/a B 91%

trichloroisocyanuric acid (87-90-1) → triiodoisocyanuric acid (27694-85-5)

Conditions	Yield
With iodine at 180 - 230℃; for 72h;	90%
With iodine at 180 - 230℃; for 72h; Sealed tube;	90%
With iodine Sealed tube; Heating;

trichloroisocyanuric acid (87-90-1) + para-thiocresol (106-45-6) → di(p-tolyl) disulfide (103-19-5) + isocyanuric acid (108-80-5)

Conditions	Yield
With pyridine; water; benzoic acid In dichloromethane; acetonitrile at 40℃;	A 89% B n/a

trichloroisocyanuric acid (87-90-1) + 2-(3-hydroxypropoxy)ethyl nitrate (1321459-27-1) → 3-(2-(nitrooxy)ethoxy)propanoic acid (1321459-22-6)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium bromide In acetone at 0 - 20℃; for 3h;	89%

trichloroisocyanuric acid (87-90-1) + potassium-2-phenyl-3-(trifluoro-l4-boraneyl)-1,2-dihydrobenzo[e][1,2]-azaborinine → 3-chloro-2-phenyl-1,2-dihydrobenzo[e][1,2]azaborinine

Conditions	Yield
In diethyl ether; water at 20℃; Inert atmosphere;	89%

trichloroisocyanuric acid (87-90-1) + diphenylgermane (1675-58-7) → diphenylchlorogermane (7366-23-6)

Conditions	Yield
In tetrahydrofuran at -80 - 20℃; Inert atmosphere; Schlenk technique;	89%

2-(4-nitro-phenyl)-4,4-dimethyl-5-methylene-4,5-dihydrooxazole (214420-92-5) + trichloroisocyanuric acid (87-90-1) → N-(1-chloro-3-methyl-2-oxobut-3-yl)-4-nitrobenzamide

Conditions	Yield
With hydrogenchloride In hexane; water; ethyl acetate	88%
With hydrogenchloride In hexane; water; ethyl acetate	88%

trichloroisocyanuric acid (87-90-1) + (1-naphthyl)2GeH2 → 1-naphthylGe(Cl)H2

Conditions	Yield
In tetrahydrofuran at -80 - 20℃; Inert atmosphere; Schlenk technique;	88%

2-(3,5-dichloro-4-methylphenyl)-4-ethyl-4-methyl-5-methyleneoxazoline (209809-70-1) + trichloroisocyanuric acid (87-90-1) → zoxamide (156052-68-5)

Conditions	Yield
With hydrogenchloride In water; ethyl acetate	87%

trichloroisocyanuric acid (87-90-1) + 6-(pyridin-3-yl)-4-(tetrahydro-2H-pyran-4-ylamino)quinoline-3-carboxamide → 8-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-4-yl)-1H-imidazo[4,5-c]quinolin-2(3H)-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0 - 20℃; for 0.5h; Inert atmosphere;	87%

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3) + trichloroisocyanuric acid (87-90-1) → cyanuric acid (108-80-5) + 6-chloro-3,7-dimethyl-2,7-octadiene-1-acetate

Conditions	Yield
In hexane	A n/a B 86%
In hexane	A n/a B 86%

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3) + trichloroisocyanuric acid (87-90-1) → cyanuric acid (108-80-5) + 6-chloro-3,7-dimethyl-2,7-octadien-1-acetate

Conditions	Yield
In hexane	A n/a B 86%

trichloroisocyanuric acid (87-90-1) + tert-butyl (2R,4R)-2-(5-fluoropyridin-3-yl)-4-hydroxypyrrolidine-1-carboxylate → tert-butyl (R)-2-(5-fluoropyridin-3-yl)-4-oxopyrrolidine-1-carboxylate

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical at -10 - 25℃; for 1.25h;	85.32%

trichloroisocyanuric acid (87-90-1) + 7-fluoro-4-((trans-3-methoxycyclobutyl)amino)-6-(6-(methoxymethyl)pyridin-3-yl)quinoline-3-carboxamide → 7-fluoro-1-(trans-3-methoxycyclobutyl)-8-(6-(methoxymethyl)pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-2(3H)-one

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 0 - 20℃; Inert atmosphere;	85%

trichloroisocyanuric acid (87-90-1) + dibutylgermane (29823-30-1) → di-n-butylchlorogermane (14275-42-4)

Conditions	Yield
In tetrahydrofuran at -80 - 20℃; Inert atmosphere; Schlenk technique;	85%

4-Methoxybenzenethiol (696-63-9) + trichloroisocyanuric acid (87-90-1) → 4,4'-dimethoxyphenyl disulfide (5335-87-5) + isocyanuric acid (108-80-5)

Conditions	Yield
With pyridine; water; benzoic acid In dichloromethane; acetonitrile at 40℃;	A 83% B n/a

trichloroisocyanuric acid (87-90-1) + benzamide (55-21-0) + 4-chloro-2,3,5-trimethylpyridine 1-oxide (109371-20-2) → 4-chloro-2-chloromethyl-3,5-dimethylpyridine N-oxide

Conditions	Yield
In dichloromethane; chloroform; water	83%

trichloroisocyanuric acid (87-90-1) + triethyl phosphite (122-52-1) → hexahydro-1,3,5-tris(diethoxyphosphoryl)-1,3,5-triazine-2,4,6-trione

Conditions	Yield
at 100 - 110℃; for 12h;	82%
at 90℃;	78%
In benzene	72%

trichloroisocyanuric acid (87-90-1) + ((2S,3R)-2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolan-4-yl)methanol (42927-35-5) → (2S,3R)-2,2-dimethyl-5-((4'R,5'S)-2',2',5'-trimethyl-1',3'-dioxolan-4'-yl)-1,3-dioxolane-4-carbaldehyde (212065-83-3)

Conditions	Yield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In dichloromethane at 0 - 20℃;	82%

Upstream product

• 108-80-5 cyanuric acid 
• 26231-96-9 N'-carbonyl-N,N-dichloro-urea 
• 108-80-5 isocyanuric acid 
• 13858-09-8 chlorine isocyanate 
• 7681-49-4 sodium fluoride 
• 7782-50-5 chlorine 
• 27694-85-5 triiodoisocyanuric acid 
• 3047-33-4 sodium cyanurate 
• 17497-85-7 1,3,5-tribromo-1,3,5-triazinane-2,4,6-trione 
• 24604-62-4 1,3-dichloro-1,3-diazetidine-2,4-dione 

Downstream Products

• 7664-93-9 sulfuric acid 
• 13898-47-0 hypochloric acid 
• 108-80-5 isocyanuric acid 
• 2782-57-2 1,3-dichloro-[1,3,5]triazinane-2,4,6-trione 
• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 2757-37-1 didodecyl disulfide 
• 17172-27-9 N-monochlorosulfamic acid 
• 791750-27-1 N-bromosulfamic acid 
• 7647-14-5 sodium chloride 
• 177785-14-7 2-chloromethyl-pyridine-3-carboxylic acid methyl ester 
• 108-80-5 cyanuric acid 
• 121-44-8 triethylamine 
• 153582-38-8 5-chloro-6-(2-bromophenyl)-2,3-dihydrofuro[2,3-b]pyridine 
• 146650-65-9 2-ethyl-4-chloro-5-(hydroxymethyl)-imidazole 

Relevant articles and documents

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The invention relates to a preparation method of 2-chloromethyl-3,5-dimethyl-4-methoxypyridine shown in a chemical structural formula I. The method is characterized by comprising the steps of a catalytic hydrogenation reaction, wherein Raney nickel or Pd/C is selected as a catalyst; a chlorination reaction, wherein YCln is selected from N-chloroacetamides or N-chlorosuccinimide or 1,3-dichloro-5,5-dimethylhydantoin or dichlord isocyanurice acid or symclosene; n is selected from 3 or 2 or 1; m is selected from 0 or 1 or 2.

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The invention relates to the field of chemical synthesis, particularly a preparation method of 2-chloro-5-chloromethylpyridine. The preparation method comprises the following step: carrying out cyclization reaction on 2-chloro-2-chloromethyl-4-cyanobutyraldehyde and cyanuric chloride to obtain the 2-chloro-5-chloromethylpyridine. The preparation method provided by the invention has the advantages of low production cost, high product quality, high yield and the like. Besides, the byproduct sodium cyanurate of the preparation method can be treated to prepare thetrichloroisocyanuric acid superior product, thereby further enhancing the economic benefits.

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