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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%

CAS Number
81927-55-1
Synonyms
2,2,2-Trichloroacetimidic acid benzyl ester

Size Price ($) Quantity Availability
5g 27.19
25g 87.55
50g 157.42
250g 683.92
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Benzyl 2,2,2-trichloroacetimidate, 98%

MDL
MFCD00000805
EINECS
617-271-1

Chemical Properties

Formula
C9H8Cl3NO
Formula Weight
252.53
Boiling Point
110-114°/0.5mm
Flash Point
>110°(230°F)
Density
1.356
Refractive Index
1.5450
Sensitivity
Moisture Sensitive
Solubility
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 BF<sub>3</sub> etherate.

Notes

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

Literature 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 .

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H335

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

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P301+P312-P312-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. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. 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

Beilstein
2525375
Harmonized Tariff Code
2925.29
TSCA
No

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