| Identification | More | [Name]
Trichloroacetyl isocyanate | [CAS]
3019-71-4 | [Synonyms]
2,2,2-TRICHLOROACETYL ISOCYANATE
TRICHLOROACETYL ISOCYANATE
Acetyl isocyanate, trichloro-
trichloro-acetylisocyanat
Trichloroacetyl isocyanate, NMR grade
Trichloroacetyl isocyanate, GC 97%
Isocyanic Acid Trichloroacetyl Ester
1-Oxo-2,2,2-trichloroethyl isocyanate | [EINECS(EC#)]
221-165-7 | [Molecular Formula]
C3Cl3NO2 | [MDL Number]
MFCD00002033 | [Molecular Weight]
188.4 | [MOL File]
3019-71-4.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow liquid | [Melting point ]
135-140 °C | [Boiling point ]
80-85 °C/20 mmHg (lit.) | [density ]
1.581 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.480(lit.)
| [Fp ]
150 °F
| [storage temp. ]
2-8°C
| [solubility ]
Miscible with dichloromethane, ether, terahydrofuran and protic solvents. | [form ]
Liquid | [color ]
Clear colorless to slightly yellow | [Water Solubility ]
Decomposition | [Sensitive ]
Moisture Sensitive | [BRN ]
971201 | [InChIKey]
GRNOZCCBOFGDCL-UHFFFAOYSA-N | [CAS DataBase Reference]
3019-71-4(CAS DataBase Reference) | [NIST Chemistry Reference]
Trichloroacetyl isocyanate(3019-71-4) | [EPA Substance Registry System]
3019-71-4(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R14:Reacts violently with water.
R23/24:Toxic by inhalation and in contact with skin .
R34:Causes burns.
R42:May cause sensitization by inhalation.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S8:Keep container dry .
S7/9:Keep container tightly closed and in a well-ventilated place . | [RIDADR ]
UN 2206 6.1/PG 3
| [WGK Germany ]
3
| [F ]
10-19 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29291090 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to slightly yellow liquid | [Uses]
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. | [Application]
Trichloroacetyl Isocyanate is used as an in situ derivatizing reagent for characterization of alcohols, glycols, phenols, and amines by nuclear magnetic resonance (NMR).It has been reported in the literature that it can be used for the preparation of cefuroxime axetil. | [Preparation]
Trichloroacetyl isocyanate can be obtained by reacting 2,2,2-trichloroacetamide with oxalyl chloride.
Procedure: A reaction mixture of 2,2,2-trichloroacetamide (100 g, 616 mmol, 1.0 eq) in (COCl)2 (725 g, 5.71 mol, 500 mL, 9.28 eq) was heated to 70°C for 24 hours. The reaction mixture was concentrated under vacuum. To the mixture was added 1,2,4-trichlorobenzene (500 mL) and (COCl)2 (116 g, 914 mmol, 80 mL, 1.48 eq). The reaction mixture was stirred at 100°C for 5 hours. Heat to 125°C for 15 hours. The mixture was then heated to 140°C for 5 hours. The reaction mixture was distilled under water pump (72°C-76°C fractions) to give trichloroacetyl isocyanate (60 g, 319 mmol, 52% yield) as a colorless oil. | [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. |
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