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140333 Sigma-Aldrich

Benzyl 2,2,2-trichloroacetimidate

99%

Synonym: 2,2,2-Trichloroacetimidic acid benzyl ester

  • CAS Number 81927-55-1

  • Linear Formula CCl3C(=NH)OCH2C6H5

  • Molecular Weight 252.52

  •  Beilstein/REAXYS Number 2525375

  •  MDL number MFCD00000805

  •  PubChem Substance ID 24848466

  •  NACRES NA.22

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Properties

Related Categories Amidates/Imidates, Building Blocks, Chemical Synthesis, Nitrogen Compounds - Organic Building Blocks, Organic Building Blocks More...
Quality Level   200
assay   99%
impurities   <1% benzyl alcohol
refractive index   n20/D 1.545 (lit.)
bp   106-114 °C/0.5 mmHg (lit.)
transition temp   solidification point 3-4 °C
density   1.359 g/mL at 25 °C (lit.)
storage temp.   2-8°C
SMILES string   ClC(Cl)(Cl)C(=N)OCc1ccccc1
InChI   1S/C9H8Cl3NO/c10-9(11,12)8(13)14-6-7-4-2-1-3-5-7/h1-5,13H,6H2
InChI key   HUZCTWYDQIQZPM-UHFFFAOYSA-N

Description

Application

Benzyl 2,2,2-trichloroacetimidate was used as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It was used in the acid-catalyzed benzylation of hydroxy groups.

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

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Protocols & Articles

Articles

Trichloroacetimidate Reagents

As described previously, trichloroacetimidates are also commonly employed as alcohol alkylation reagents, particularly when existing functionality is not acid sensitive.1 Recent applications of allyl...
Aldrich ChemFiles 2007, 7.3, 4.
Keywords: Alkylations, Organic synthesis

Peer-Reviewed Papers
15

References

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