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36982-84-0 - 2,4,6-Triisopropylbenzenesulfonyl azide, 98%, stab. with ca 10% water - Trisyl azide - L19383 - Alfa Aesar

L19383 2,4,6-Triisopropylbenzenesulfonyl azide, 98%, stab. with ca 10% water

CAS Number
36982-84-0
Synonyms
Trisyl azide

Size Price ($) Quantity Availability
1g 50.70
5g 148.00
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2,4,6-Triisopropylbenzenesulfonyl azide, 98%, stab. with ca 10% water

MDL
MFCD00859286

Chemical Properties

Formula
C15H23N3O2S
Formula Weight
309.43
Melting point
40-44°
Solubility
Insoluble in water.

Applications

2,4,6-Triisopropylbenzenesulfonyl azide is used as a reagent for diazo transfer to ketones, e.g. under phase-transfer conditions, giving better yields of sterically-hindered ?-diazo ketones than other methods. It is also used for azide transfer to potassium enolates (KHMDS) to form the ?-azido derivatives.

Notes

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature is 2 - 8°C.

Literature References

Joshua V. Ruppel.; Rajesh M. Kamble.; X. Peter Zhang. Cobalt-Catalyzed Intramolecular C-H Amination with Arylsulfonyl Azides. Org. Lett. 2007, 9 (23), 4889-4892.

David A. Evans.; Thomas C. Britton. Electrophilic azide transfer to chiral enolates. A general approach to the asymmetric synthesis of .alpha.-amino acids. J. Am. Chem. Soc. 1987, 109 (22), 6881-6883.

Reagent for diazo transfer to ketones, e.g. under phase-transfer conditions, giving better yields of sterically-hindered ɑ-diazo ketones than other methods: Synthesis, 368 (1980); J. Am. Chem. Soc., 102, 6626 (1980); 113, 2598 (1991); Tetrahedron, 43, 5677 (1987).

Also used for azide transfer to potassium enolates (KHMDS) to form the ɑ-azido derivatives: J. Am. Chem. Soc., 109, 6881 (1987); 112, 4011 (1990); Tetrahedron Lett., 28, 6141 (1987). Other bases tend to favor diazo transfer. For further discussion and examples, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 5174.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Harmonized Tariff Code
2927.00
TSCA
No

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