Chloramine-T trihydrate

• Catalog No.: A12044
• CAS Number: 7080-50-4
• M. F.: C7H13ClNNaO5S
• M. W.: 281.68959
• Purity: 98%

SYNONYMS

• Title: 氯胺T三水合物
• IUPAC name: sodium chloro(4-methylbenzenesulfonyl)azanide trihydrate
• IUPAC Traditional name: sodium chloramine T anion trihydrate
• Synonyms: N-Chloro-p-toluenesulfonamide sodium salt trihydrate; Tosylchloramide sodium trihydrate

DATABASE IDS

• EC Number: 204-854-7
• MDL Number: MFCD00149066
• Merck Index: 142075
• Beilstein Number: 3924168
• CAS Number: 7080-50-4

PROPERTIES

• Purity: 98%
• Flash Point: 192°C(377°F)
• Melting Point: 167-170°C
• GHS Hazard statements: H301-H334-H314-H318
• European Hazard Symbols: X
• European Hazard Symbols: Corrosive (C)
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A
• Risk Statements: 22-31-34-42
• RTECS: XT5616800
• Safety Statements: 7-22-26-36/37/39-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN3263
• Packing Group: III

REFERENCES

• Source of positive chlorine. For example, converts alkenes to their chlorohydrins: Synthesis, 362 (1981). Similarly, protonated chloramine-T has been used for the chlorolactonization of unsaturated acids: J. Org. Chem., 46, 3552 (1981). Converts aldoximes, via the chloroximes, to nitrile oxides, which undergo dipolar cycloaddition to alkenes to give 2-isoxazolines: Synthesis, 57 (1989); see also Acetaldoxime, A10640.
• In the presence of NaBr, provides a source of BrCl, which converts alkyl boranes to bromoalkanes: J. Org. Chem., 46, 3113 (1981), or, in combination with NaI, converts both alkyl and aryl boranes to the iodides: J. Org. Chem., 46, 2582 (1981). Vinyl and alkynyl iodides have also been produced in high yield from the corresponding potassium organotrifluorborates: Tetrahedron Lett., 45, 1417 (2004). The same system has also been used for the iodination of phenols: Tetrahedron Lett., 26, 2043 (1985).
• The anhydrous reagent has been used, in combination with Phenyltrimethylammonium tribromide, A15326: J. Am. Chem. Soc., 120, 6844 (1998), or Pyridine hydrobromide perbromide, A15684: Org. Lett., 1, 705 (1999), for the aziridination of alkenes:
  
• Widely used for cleavage of thioacetal protecting groups in oxathiolanes, thiolanes and 1,3-dithianes (compare 1,3-Dithiane, A10505): Tetrahedron Lett., 3445, 3449 (1971); Synth. Commun., 2, 7 (1972).
• For use, in combination with Osmium(VIII) oxide, 12103, in the vicinal oxyamination of olefins, see: Org. Synth. Coll., 7, 375 (1990).
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 2857 (2005).
• Alternatively, the reaction can be carried out in the presence of I₂, under phase-transfer conditions: J. Chem. Soc., Perkin 1, 3186 (2001).