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56602-33-6 - 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 98% - BOP Reagent - Castro's Reagent - A16140 - Alfa Aesar

A16140 1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 98%

Numéro CAS
56602-33-6
Synonymes
BOP Reagent
Castro's Reagent

Dimensions Prix ($) Quantité Disponibilité
1g 18,30
5g 56,80
25g 248,00
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1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, 98%

MDL
MFCD00011948
EINECS
260-279-1

Propriétés chimiques

Formule
C12H22F6N6OP2
Poids formulaire
442.29
Point de fusion
ca 138° dec.
Sensibilité
Moisture & Light Sensitive
Solubilité
Soluble in methanol, acetone and dichloromethane. Insoluble in water.

Applications

1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate is used as a reagent for peptide coupling, lactonization, selective esterification, amidation of alfa amino acids without racemization and synthesis of magnolamide for antioxidative activity and catalyst for 9-acridinecaroboxamide derivative. It is also used as a precursor for the synthesis of phenyl esters of amino acids. It acts as a substitute for (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) reagent.

Notes

Moisture and light sensitive. Incompatible with strong oxidizing agents. Store in a cool place. Keep the container tightly closed.

Références bibliographiques

Reagent for high yield, low racemization peptide coupling: Tetrahedron Lett., 1219 (1975). See Appendix 6.

Mild and efficient reagent for the preparation of esters from carboxylic acids and alcohols: Tetrahedron Lett., 36, 4253 (1995); for esterification of amino acids at low temperatures, see: Tetrahedron Lett., 35, 5603 (1994); for use in formation of mixed phosphonate diesters, see: J. Org. Chem., 60, 5214 (1995).

The carboxyphosphonium salts formed by reaction with carboxylic acids can be reduced with NaBH4, providng a mild method for reduction of acids to alcohols: Tetrahedron lett., 39, 3319 (1998).

Promotes the reaction of aliphatic primary amines with CS2 to give isothiocyanates which can be isolated in high yield or reacted in situ with nucleophiles: J. Chem. Soc., Chem. Commun., 1995 (1995).

Hu, J.; Zhao, R.; Wang, D.; Xu, X.; Chen, X.; Shen, D. Phase Transition Regulated by Photo-Controlled Molecular Recognition of Alpha- Cyclodextrin. Curr. Org. Chem. 2015, 19 (3), 282-288.

Hu, J.; Wang, X.; Zheng, S. Photo-regulated phase transition of poly(ethylene glycol) derivative containing azobenzene group. Polym. Adv. Technol. 2012, 23 (12), 1590-1595.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H228-H315-H319-H335

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

Mentions de prudence: P210-P261-P280-P240-P241-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
4287025
Classe de danger
4.1
Groupe d'emballage
II
Code tarifaire harmonisé
2933.99
TSCA
No

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