trichloro-1,3,5-triazinane-2,4,6-trione

• ChemBase ID: 90300
• Molecular Formular: C3Cl3N3O3
• Molecular Mass: 232.4094
• Monoisotopic Mass: 230.90052392
• SMILES: n1(c(=O)n(c(=O)n(c1=O)Cl)Cl)Cl
• Canonical SMILES: O=c1n(Cl)c(=O)n(c(=O)n1Cl)Cl
• InChI: InChI=1S/C3Cl3N3O3/c4-7-1(10)8(5)3(12)9(6)2(7)11
• InChIKey: YRIZYWQGELRKNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trichloro-1,3,5-triazinane-2,4,6-trione
• IUPAC Traditional name: trichloroisocyanuric acid
• Synonyms: TCICA; 1,3,5-Trichloro-2,4,6-triazinetrione; Symclosene; Trichlorocyanuric acid; Trichloroisocyanuric acid; trichloro-1,3,5-triazinane-2,4,6-trione; Isocyanuric chloride; 1,3,5-Trichloro-1,3,5-triazine-2,4,6-trione; 1,3,5-Trichloro-1,3,5-triazinane-2,4,6-trione; TCICA, 1,3,5-trichloro-1,3,5-triazine; -2,4,6(1H,3H,5H)-trione, Symclosene, trichloro-s-triazinetrione, TCCCA, trichlor; Trichloroisocyanuric acid; 三氯三嗪三酮; 三氯氰尿酸; 强氯精; 三氯异氰尿酸; 三氯异三聚氰酸

Database IDs

• CAS Number: 87-90-1
• EC Number: 201-782-8
• MDL Number: MFCD00006553
• Beilstein Number: 202022
• Merck Index: 149641
• PubChem SID: 24889457; 162077121; 24850553
• PubChem CID: 6909
• CHEBI ID: 33015
• Chemspider ID: 6643
• Unique Ingredient Identifier: RL3HK1I66B
• Wikipedia Title: Trichloroisocyanuric_acid

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.2518321
• LogD (pH = 7.4): 1.2518321
• Log P: 1.2518321
• Molar Refractivity: 40.7367 cm^3
• Polarizability: 15.511293 Å^3
• Polar Surface Area: 60.93 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.2% in water; chlorocarbons; acetone; acetonitrile
• Apperance: colourless solid
• Melting Point: 245-251°C; 246–47 °C; 249 - 251°C; 249-251 °C(lit.); ca 245°C dec.
• Boiling Point: decomp.
• Flash Point: >250°C(482°F); NA
• Density: 2.07; 2.19 ± 0.1 g/cm3
• Hydrophobicity(logP): -2.603

Safety Information

• Storage Warning: Harmful/Hygroscopic; Moisture Sensitive
• RTECS: XZ1925000
• European Hazard Symbols: Nature polluting (N); Oxidising (O); X; Harmful (Xn)
• UN Number: 2468; UN2468
• German water hazard class: 3
• Hazard Class: 5.1
• Packing Group: 2; II
• Risk Statements: 8-22-31-36/37-50/53; R8, R22, R31, R36/37, R50/53
• Safety Statements: 8-26-41-60-61; S8, S26, S41, S60, S61
• TSCA Listed: 是
• GHS Pictograms: GHS03; GHS07; GHS09
• GHS Signal Word: Danger
• Main Hazard: lung irritant
• GHS Hazard statements: H272-H302-H319-H335-H410; H272-H400-H410-H302-H319-H335
• GHS Precautionary statements: P220-P261-P273-P305 + P351 + P338-P501; P221-P210-P220-P305+P351+P338-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2468 5.1/PG 2
• Supplemental Hazard Statements: Contact with acids liberates toxic gas.

Product Information

• Purity: ≥95% (CHN); 95%; 95+%; 97%
• Grade: technical
• Empirical Formula (Hill Notation): C3Cl3N3O3

DETAILS

Sigma Aldrich - 176125

Packaging
1 kg in glass bottle
50, 250 g in glass bottle

REFERENCES

• Note: Confusion with Cyanuric chloride, L03442, exists in some earlier Fieser references.
• For a brief feature on uses in synthesis, see: Synlett, 2265 (2005).
• Low-cost chlorinating and oxidizing agent; review: Org. Process Res. Dev., 6, 384 (2002). Aromatic compounds can be chlorinated either on the ring (ionic conditions) or on the side chain (free-radical conditions): J. Org. Chem., 35, 719 (1970). In the presence of BF₃ etherate, ketones are ɑ-chlorinated at the more substituted position: Synth. Commun., 15, 385 (1985). In combination with pyridine, sulfides are selectively oxidized to sulfoxides: Synth. Commun., 31, 245 (2001), thiols to disulfides: Synth. Commun, 31, 1825 (2001), and secondary alcohols to ketones: Synth. Commun., 22, 1589 (1992). In the presence of methanol in acetonitrile, acetone or dichloromethane, the same reagent system converts aldehydes directly to methyl esters: Synth. Commun., 26, 2633 (1996). Effective co-oxidant for the TEMPO-catalyzed chemoselective oxidation of alcohols to aldehydes and ketones: Org. Lett., 3, 3041 (2001). In acetic acid, pyridines are converted to their N-oxides: Synth. Commun., 34, 247 (2004).
• With NaNO₂ and wet silica selective mononitration of phenols is accomplished under mild conditions: Synlett, 191 (2003). Effectively catalyzes both the protection and deprotection of alcohols as their tetrahydropyranyl ethers: Synth. Commun., 34, 3623 (2004).