trichloro-1,3,5-triazine

• ChemBase ID: 103146
• Molecular Formular: C3Cl3N3
• Molecular Mass: 184.4112
• Monoisotopic Mass: 182.91578006
• SMILES: Clc1nc(Cl)nc(Cl)n1
• Canonical SMILES: Clc1nc(Cl)nc(n1)Cl
• InChI: InChI=1S/C3Cl3N3/c4-1-7-2(5)9-3(6)8-1
• InChIKey: MGNCLNQXLYJVJD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trichloro-1,3,5-triazine
• IUPAC Traditional name: cyanuric chloride
• Synonyms: 2,4,6-trichloro-1,3,5-triazine; Trichlorotriazine; s-Triazine trichloride; Cyanuryl chloride; Cyanuric chloride; 2,4,6-Trichloro-1,3,5-triazine; CYANURIC CHLORIDE; TCT; 2,4,6-三氯-1,3,5-三嗪; 三聚氯氰

Database IDs

• CAS Number: 108-77-0
• EC Number: 203-614-9
• MDL Number: MFCD00006046
• Beilstein Number: 124246
• PubChem SID: 162090622; 24857235; 24893171
• PubChem CID: 7954
• CHEBI ID: 58964
• Chemspider ID: 7666
• Wikipedia Title: Cyanuric_chloride

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.581383
• LogD (pH = 7.4): 2.581383
• Log P: 2.581383
• Molar Refractivity: 39.0174 cm^3
• Polarizability: 13.9906645 Å^3
• Polar Surface Area: 38.67 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: hydrolyzes in water; soluble in organic solvents
• Apperance: White powder
• Melting Point: 145 - 146 °C; 145.0-147.0 °C; 145-147 °C; 145-147 °C(lit.); 145-149°C; 154°C
• Boiling Point: 190 °C(lit.); 192°C; 192-194°C; 193 °C at 1013 hPa
• Flash Point: >190°C(374°F); Non-flammable
• Density: 1.32 g/cm^3; 1.92 g/cm^3 at 20 °C; 1.920
• Vapor Pressure: 0.06 mm Hg at 20 °C, 2.25 mm Hg at 70 °C; 0.8 mmHg ( 62.2 °C)
• Vapor Density: 6.3 (air = 1); 6.36 (vs air)
• Odor: pungent

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive
• RTECS: XZ1400000
• European Hazard Symbols: Corrosive (C); Harmful (Xn); Highly toxic (T+); Very toxic (T+); Irritant (Xi)
• UN Number: 2670; UN2670
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 14-22-26-34-43; R:36/37/38; R14, R22, R26, R34, R43
• Safety Statements: 1/2-26-28-36/37/39-45-46-63; 26-28-36/37/39-45-46-63; S:28; S1/2, S26, S28, S36/37/39, S45, S46, S63
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 157
• TSCA Listed: 是
• EU Index: 613-009-00-5
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• NFPA704:
  

  0

  3

  1

  W
• LD50: 485 mg/kg (rat, oral)
• GHS Hazard statements: H302-H314-H317-H330; H330-H302-H317-H314
• GHS Precautionary statements: P260-P280-P284-P305 + P351 + P338-P310; P260-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-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 2670 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); ≥99.5% (w/w); 95+%; 98%; 99%
• Grade: Lonza quality; purum
• Empirical Formula (Hill Notation): C3Cl3N3

DETAILS

MP Biomedicals - 02150742

Reagent for detection of glycine in the presence of other amino acids. Also reacts with cellulose to immobilize DNA.

Sigma Aldrich - 690740

Packaging
1 kg in glass bottle
25 kg in steel drum

Sigma Aldrich - C95501

Packaging
1 kg in glass bottle
5, 250 g in glass bottle
Application
Reagent for the conversion of alcohols to chlorides and for the immobilization of microorganisms and enzymes.1

Sigma Aldrich - 28620

Other Notes
Coupling agent in the immobilization of microorganisms and enzymes1,2

REFERENCES

• Biagioni, S., et al., Anal. Biochem. , 89 : 616 (1978).
• Effects deoxygenation of diaryl sulfoxides. Alkyl sulfoxides undergo ɑ-chlorination, which can be avoided by using cyanuric fluoride: Synthesis, 221 (1980).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 2156 (2006).
• In the presence of triethylamine, carboxylic acids are converted to their acid chlorides, allowing in situ formation of esters, amides and peptides: Tetrahedron Lett., 20, 3037 (1979). Similarly, sulfonic acids are converted to sulfonyl chlorides: Tetrahedron Lett., 44, 1499 (2003). ω-Hydroxy acids are converted to their lactones: Tetrahedron Lett., 21, 1893 (1980). Mild reagent in ?-lactam synthesis: Synthesis, 209 (1981). Carboxylic acids, including N-Boc, -Fmoc and -Cbz amino acids have been converted to alcohols in good yield by activation with cyanuric chloride and N-methylmorpholine (NMM), followed by reduction with aqueous NaBH₄: Tetrahedron Lett., 40, 4395 (1999). Hydroxamic acids can also be prepared in a simple one-flask method using hydroxylamine hydrochloride in the presennce of NMM and DMAP: Org. Lett., 5, 2715 (2003).
• For use, in combination with DMSO, in a mild and efficient alternative to the Swern oxidation of alcohols to aldehydes or ketones, see: J. Org. Chem., 66,7907 (2001).
• Reagent for dehydration of aldoximes: J. Chem. Soc., Chem. Commun., 1226 (1972), and primary carboxamides: Synthesis, 657 (1980) to nitriles. The Vilsmeier-type complex with DMF also converts aldoximes cleanly to nitriles; ketoximes undergo the Beckmann rearrangement at room temperature in high yield: J. Org. Chem., 67, 6272 (2002). The complex converts primary and secondary alcohols to alkyl chlorides in high yield; addition of NaBr affords mainly the alkyl bromide: Org. Lett., 4, 553 (2002); whereas with 4 eq. of LiF, primary alcohols are selectively formylated, providing a mild and convenient method for their protection: J. Org. Chem., 67, 5152 (2002).