Consentement d'utilisation des Cookies

J'accepte. Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

81927-55-1 - Benzyl 2,2,2-trichloroacetimidate, 98% - 2,2,2-Trichloroacetimidic acid benzyl ester - A12387 - Alfa Aesar

A12387 Benzyl 2,2,2-trichloroacetimidate, 98%

Numéro de CAS
81927-55-1
Synonymes
2,2,2-Trichloroacetimidic acid benzyl ester

Conditionnement Prix ($) Quantité Disponibilité
5g 27,30
25g 88,00
50g 164,00
250g 684,00
Ajouter au panier Ajouter au devis en vrac Afficher l'article

Benzyl 2,2,2-trichloroacetimidate, 98%

MDL
MFCD00000805
EINECS
617-271-1

Propriétés chimiques

Formule
C9H8Cl3NO
Poids moleculaire
252.53
Point d'ébullition
110-114°/0.5mm
Point d'éclair
>110°(230°F)
Densité
1.356
Indice de réfraction
1.5450
Sensibilité
Moisture Sensitive
Solubilité
Miscible with cyclohexane/dichloromethane.

Applications

Benzyl 2,2,2-trichloroacetimidate is used for the acid-catalyzed benzylation of hydroxy groups. It acts as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate.

Notes

Moisture and light sensitive. Incompatible with strong oxidizing agents and strong acids.

Références bibliographiques

Mild, selective benzylating agent. Formation of benzyl ethers from alcohols at room temperature is catalyzed by triflic acid; isopropylidene and benzylidene protecting groups are unaffected: J. Chem. Soc., Perkin 1., 2247 (1985). TMS triflate has also been recommended as a catalyst, avoiding racemization of sensitive substrates: Tetrahedron, 43, 1619 (1993). For use in the preparation of benzyl ethers of ß-hydroxy esters, see: Synthesis, 568 (1987).

The reagent can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF3 etherate: Synthesis, 168 (1997). For conversion of N-Boc groups to N-Cbz, catalyzed by triflic acid, see: J. Org. Chem., 55, 5170 (1990). See also Appendix 6.

Chen, T.; Altmann, K. H. Directed Hydrogenations and an Ireland-Claisen Rearrangement Linked to Evans-Tishchenko Chemistry: The Highly Efficient Total Synthesis of the Marine Cyclodepsipeptide Doliculide. Chem. Eur. J 2015, 21 (23), 8403-8407.

Miller, D. C.; Carbain, B.; Beale, G. S.; Alhasan, S. F.; Reeves, H. L.; Baisch, U.; Newell, D. R.; Golding, B. T.; Griffin, R. J. Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases. Org. Biomol. Chem. 2015, 13 (18), 5279-5284 .

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
2525375
Code tarifaire harmonisé
2925.29
TSCA
No

Recommandé

  • A10173

    Trifluoromethanesulfonic acid, 98+%
  • A10322

    n-Hexadecane, 99%
  • L00313

    1,8-Bis(dimethylamino)naphthalene, 98+%
  • L11464

    Benzoyl fluoride, 97%
  • 42967

    Borane-dimethyl sulfide complex, packaged under Argon in resealable ChemSeal™ bottles

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire