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108-77-0 - Cyanuric chloride, 98% - TCT - 2,4,6-Trichloro-1,3,5-triazine - L03442 - Alfa Aesar

L03442 Cyanuric chloride, 98%

CAS-Nummer
108-77-0
Synonyme
TCT
2,4,6-Trichloro-1,3,5-triazine

Größe Preis ($) Menge Verfügbarkeit
50g 15,21
250g 18,27
1000g 73,80
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Cyanuric chloride, 98%

MDL
MFCD00006046
EINECS
203-614-9

Chemische Eigenschaften

Formel
C3Cl3N3
Molmasse
184.41
Schmelzpunkt
145-149°
Siedepunkt
192-194°
Flammpunkt
>190°(374°F)
Dichte
1.920
Sensitivität
Moisture Sensitive
Löslichkeit
Soluble in acetone, diethyl ether, dioxane, chloroform, carbon tetrachloride and ketones. Slightly soluble in methanol. Insoluble in cold water.

Anwendungen

Reagent for detection of glycine in presence of other amino acids.Cyanuric chloride is a reagent used for the conversion of alcohols and carboxylic acids to alkyl chlorides and acid chlorides respectively. It acts as an intermediate to prepare dyestuffs, optical brighteners, tanning agents, UV-absorbing agent, softening agents and pharmaceuticals. It is also used as a precursor to dyes and crosslinking agents due to the presence of reactive chlorine atoms. It is used as a dehydrating agent as well as reacting with dimethylformamide to give Gold’s reagent, which is a versatile source of aminoalkylations and a precursor to heterocycles. Further, it is considered as an alternative to oxalyl chloride in the Swern oxidation. In addition to this, it is involved in the synthesis of adenosine receptor ligand.

Bemerkungen

Air and moisture sensitive. Store in a cool place. Incompatible with strong oxidizing agents, strong acids, alcohols, dimethylformamide, amines and dimethyl sulfoxide.

Literaturverweise

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 ß-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).

Effects deoxygenation of diaryl sulfoxides. Alkyl sulfoxides undergo ɑ-chlorination, which can be avoided by using cyanuric fluoride: Synthesis, 221 (1980).

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).

For a brief feature on uses of the reagent in synthesis, see: Synlett, 2156 (2006).

Wang, H.; Li, C.; Wang, W.; Jin, W. J. Strength order and nature of the π-hole bond of cyanuric chloride and 1, 3, 5-triazine with halide. Phys. Chem. Chem. Phys. 2015, 17 (32), 20636-20646.

Anbia, M.; Khoshbooei, S. Functionalized magnetic MCM-48 nanoporous silica by cyanuric chloride for removal of chlorophenol and bromophenol from aqueous media. J. nanostructure chem. 2015, 5 (1), 139-146.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H330-H302-H317-H314

Fatal if inhaled. Harmful if swallowed. May cause an allergic skin reaction. Causes severe skin burns and eye damage.

Sicherheitshinweise: P260-P284-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P301+P330+P331-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear respiratory protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Specific treatment is urgent (see label). Rinse mouth. IF SWALLOWED: Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
124246
Gefahrenklasse
8
Verpackungsgruppe
II
Harmonized Tariff Code
2933.69
TSCA
Yes
RTECS
XZ1400000

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