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217328

Sigma-Aldrich

Trichloroacetyl isocyanate

96%

Synonym(s):

2,2,2-Trichloroacetyl isocyanate, alpha,alpha,alpha-Trichloroacetyl isocyanate

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About This Item

Linear Formula:
Cl3CCONCO
CAS Number:
3019-71-4
Molecular Weight:
188.40
Beilstein:
971201
EC Number:
221-165-7
MDL number:
MFCD00002033
UNSPSC Code:
12352100
PubChem Substance ID:
24853009
NACRES:
NA.22

Quality Level

200

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.)

functional group

amine
chloro
isocyanate

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[1]. Trichloroacetyl isocyanate is commonly employed as in situ derivatizing reagent for the 13C NMR studies of alcohols, phenols and amines[2]. 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[3].

Application

Trichloroacetyl isocyanate was used in catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrate[4]. It was also used as a reagent for the conversion of alcohols to carbamates†.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Eye Dam. 1 - Resp. Sens. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

150.8 °F - closed cup

Flash Point(C)

66 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0001059110
1048847V
1059110
1048847
07114HH

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[2+ 2] Cycloaddition of trichloroacetyl isocyanate to glycals.
Chmielewski M and Kaluza Z.
Carbohydrate Research, 167, 143-152 (1987)
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
Tetrahedron Letters, 48, 65-65 (2007)
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

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