217328

Sigma-Aldrich

Trichloroacetyl isocyanate

96%

Linear Formula:
Cl3CCONCO
CAS Number:
Molecular Weight:
188.40
Beilstein/REAXYS Number:
971201
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

96%

refractive index

n20/D 1.480 (lit.)

bp

80-85 °C/20 mmHg (lit.)

density

1.581 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(Cl)(Cl)C(=O)N=C=O

InChI

1S/C3Cl3NO2/c4-3(5,6)2(9)7-1-8

InChI key

GRNOZCCBOFGDCL-UHFFFAOYSA-N

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General description

Conformational stability and vibrational IR and Raman spectra of trichloroacetyl isocyanate has been investigated. Trichloroacetyl isocyanate is commonly employed as in situ derivatizing reagent for the 13C NMR studies of alcohols, phenols and amines. It undergoes 1,5-cycloaddition reaction with anhydro-2-deoxy-D-erythro- and -L-threo-pent-1-enitols and 1,5-anhydro-2-deoxy-D- and -L-arabino-hex-1-enitols to yield [2+2] and [4+2] cycloadducts.

Application

Trichloroacetyl isocyanate was used in catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrate. It was also used as a reagent for the conversion of alcohols to carbamates†.

Packaging

1, 10 g in ampule

Signal Word

Danger

Hazard Statements

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2206PSN1B 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

150.8 °F - closed cup

Flash Point(C)

66 °C - closed cup

NMR spectral studies-XII: Trichloroacetyl isocyanate as an in situ derivatizing reagent for 13C NMR spectroscopy of alcohols, phenols and amines.
Bose AK and Srinivasan PR.
Tetrahedron, 31(24), 3025-3029 (1975)
Hassan M Badawi et al.
Journal of molecular modeling, 8(2), 44-49 (2002-05-29)
The conformational stability and vibrational infrared and Raman spectra of trichloroacetyl isocyanate (CCl3CONCO) were investigated by ab initio MP2 and density functional B3LYP calculations using the 6-311++G** basis set. From the potential energy scans of the internal rotations in both...
Tatsuya Shirahata et al.
Carbohydrate research, 345(6), 740-749 (2010-03-09)
Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5A molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved...
Tetrahedron Letters, 48, 65-65 (2007)
[2+ 2] Cycloaddition of trichloroacetyl isocyanate to glycals.
Chmielewski M and Kaluza Z.
Carbohydrate Research, 167, 143-152 (1987)

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