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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%

Numéro de CAS
108-77-0
Synonymes
TCT
2,4,6-Trichloro-1,3,5-triazine

Conditionnement Prix ($) Quantité Disponibilité
50g 17,10
250g 20,30
1000g 82,80
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Cyanuric chloride, 98%

MDL
MFCD00006046
EINECS
203-614-9

Propriétés chimiques

Formule
C3Cl3N3
Poids moleculaire
184.41
Point de fusion
145-149°
Point d'ébullition
192-194°
Point d'éclair
>190°(374°F)
Densité
1.920
Sensibilité
Moisture Sensitive
Solubilité
Soluble in acetone, diethyl ether, dioxane, chloroform, carbon tetrachloride and ketones. Slightly soluble in methanol. Insoluble in cold water.

Applications

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.

Notes

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

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H330-H314-H317

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

Mentions de prudence: P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501a

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). Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
124246
Classe de danger
8
Groupe d'emballage
II
Code tarifaire harmonisé
2933.69
TSCA
Yes
RTECS
XZ1400000

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