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217328

Sigma-Aldrich

Trichloroacetyl isocyanate

96%

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Synonym(s):
2,2,2-Trichloroacetyl isocyanate, alpha,alpha,alpha-Trichloroacetyl isocyanate
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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1 of 4

This Item
189278220574188204
vibrant-m

217328

Trichloroacetyl isocyanate

vibrant-m

189278

p-Toluenesulfonyl isocyanate

vibrant-m

220574

(R)-(+)-α-Methylbenzyl isocyanate

vibrant-m

188204

p-Toluenesulfonylmethyl isocyanide

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

density

1.581 g/mL at 25 °C (lit.)

density

1.291 g/mL at 25 °C (lit.)

density

1.045 g/mL at 20 °C (lit.)

density

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

bp

80-85 °C/20 mmHg (lit.)

bp

144 °C/10 mmHg (lit.), 275-278 °C (lit.)

bp

55-56 °C/2.5 mmHg (lit.)

bp

-

refractive index

n20/D 1.480 (lit.)

refractive index

n20/D 1.534 (lit.)

refractive index

n20/D 1.513 (lit.)

refractive index

-

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†.

signalword

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

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

wgk_germany

WGK 3

flash_point_f

150.8 °F - closed cup

flash_point_c

66 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Customers Also Viewed

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

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