trichloroethanecarbonyl isocyanate

• ChemBase ID: 149032
• Molecular Formular: C3Cl3NO2
• Molecular Mass: 188.3966
• Monoisotopic Mass: 186.89946129
• SMILES: C(=NC(=O)C(Cl)(Cl)Cl)=O
• Canonical SMILES: O=C=NC(=O)C(Cl)(Cl)Cl
• InChI: InChI=1S/C3Cl3NO2/c4-3(5,6)2(9)7-1-8
• InChIKey: GRNOZCCBOFGDCL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trichloroethanecarbonyl isocyanate
• IUPAC Traditional name: trichloroethanecarbonyl isocyanate
• Synonyms: Trichloroacetyl isocyanate; 三氯乙酰异氰酸酯; 三氯乙酰基异氰酸酯

Database IDs

• CAS Number: 3019-71-4
• EC Number: 221-165-7
• MDL Number: MFCD00002033
• Beilstein Number: 971201
• PubChem SID: 24853009; 162243201; 24889445
• PubChem CID: 76400

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.0225978
• LogD (pH = 7.4): 1.0225978
• Log P: 1.0225978
• Molar Refractivity: 33.322 cm^3
• Polarizability: 12.901277 Å^3
• Polar Surface Area: 46.5 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 58-60°C/20mm; 80-85 °C/20 mmHg(lit.)
• Flash Point: 150.8 °F; 65°C(149°F); 66 °C
• Density: 1.581 g/mL at 25 °C(lit.); 1.585
• Refractive Index: 1.4800; n20/D 1.480; n20/D 1.480(lit.)

Safety Information

• Storage Warning: Moisture Sensitive
• European Hazard Symbols: Toxic (T)
• UN Number: 2206; UN2927
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; II
• Risk Statements: 14-23/24-34-42; 14-23-34-42
• Safety Statements: 23-26-30-36/37/39-45; 23-26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H311-H314-H331-H334; H330-H334-H314-H318-H227
• GHS Precautionary statements: P210-P303+P361+P353-P304+P340-P305+P351+P338-P320-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2206 6.1/PG 3
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 96%; 97%
• Grade: purum
• Linear Formula: Cl3CCONCO

DETAILS

Sigma Aldrich - 217328

Application
Reagent for the conversion of alcohols to carbamates.1
Packaging
1, 10 g in ampule

Sigma Aldrich - 91095

Other Notes
Derivatizing reagent for the structural assignment to hydroxy compounds by NMR1,2,3; Used in negative ion chemical ionization mass spectrometry4

REFERENCES

• [2+2]-Cycloaddition with cyclic enol ethers gives fused azetidinones: Tetrahedron, 45, 227 (1989).
• Causes characteristic chemical shifts in the ɑ-protons of alcohols by in situ conversion to the carbamates: Anal. Chem., 431 (1965).
• Reacts with nucleophiles to give ureas, carbamates, etc., from which the trichloroacetyl group can readily be removed. For reaction of acyl isocyanates with Grignard reagents to give primary carboxamides, see: Tetrahedron Lett., 981 (1975).
• Reviews: Chemistry of ɑ-haloisocyanates: Synthesis, 85 (1980). General isocyanate chemistry: Appendix 3.