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91095

Sigma-Aldrich

Trichloroacetyl isocyanate

purum, ≥97.0% (GC)

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:
329769998
NACRES:
NA.22

grade

purum

Quality Level

100

Assay

≥97.0% (GC)

form

liquid

refractive index

n20/D 1.480 (lit.)
n20/D 1.480

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

Trichloroacetyl isocyanate (TAI) is a versatile building block in organic synthesis. It is also used as an in situ derivatizing reagent for the characterization of phenols, alcohols, and amines.

Application


  • One-pot synthesis of 2-acylaminobenzimidazoles: A study on the synthesis of 2-acylaminobenzimidazoles via a reaction between trichloroacetyl isocyanate and 1,2-phenylenediamine derivatives (Shajari et al., 2018).

  • Cabamothioate compounds: Research on the synthesis of S-aryl (trichloroacetyl) carbamothioate from a reaction of 2-naphthalenethiol or thiophenol derivatives and trichloroacetyl isocyanate (Shajari et al., 2021).

  • Chiral calyx[4]arenes: Diastereoselective synthesis of inherently chiral calyx[4]arenes via reaction of trichloroacetyl isocyanate with 1,3-dihydroxy calixarene (Boyko et al., 2016).

Other Notes

Derivatizing reagent for the structural assignment to hydroxy compounds by NMR; Used in negative ion chemical ionization mass spectrometry

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
0001048847
1059110V
1048847V
1059110

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In situ reactions with trichloroacetyl isocyanate and their application to structural assignment of hydroxy compounds by 1 H NMR spectroscopy. A general comment
Samek et al.
Collection of Czechoslovak Chemical Communications, 44, 558-588 (1979)
D.R. Taylor
Canadian Journal of Chemistry, 54, 189-189 (1976)
Determination of chain branching in epoxy resins by nuclear magnetic resonance spectrometry.
H D Mak et al.
Analytical chemistry, 44(4), 837-839 (1972-04-01)
H. Fujiwara et al.
Pract. Spectrosc., 3, 329-329 (1980)
M. Budesinsky et al.
Collection of Czechoslovak Chemical Communications, 45, 2784-2784 (1980)
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