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Benzyl 2,2,2-trichloroacetimidate, 98%, Thermo Scientific Chemicals
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Catalog number A12387.06
also known as A12387-06
Price (USD)/ Each
37.00
-
Quantity:
5 g
Price (USD)/ Each
37.00
Benzyl 2,2,2-trichloroacetimidate, 98%, Thermo Scientific Chemicals
Catalog numberA12387.06
Price (USD)/ Each
37.00
-
Chemical Identifiers
CAS81927-55-1
IUPAC Namebenzyl 2,2,2-trichloroethanimidate
Molecular FormulaC9H8Cl3NO
InChI KeyHUZCTWYDQIQZPM-UHFFFAOYSA-N
SMILESClC(Cl)(Cl)C(=N)OCC1=CC=CC=C1
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless to pale yellow
Refractive Index1.5425-1.5465 @ 20?C
Assay (GC)≥97.5%
FormLiquid
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Miscible with cyclohexane/dichloromethane.
Notes
Moisture and light sensitive. Incompatible with strong oxidizing agents and strong acids.
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.
Solubility
Miscible with cyclohexane/dichloromethane.
Notes
Moisture and light sensitive. Incompatible with strong oxidizing agents and strong acids.
RUO – Research Use Only
General References:
- 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 .