Trichloroacetyl isocyanate

Trichloroacetyl isocyanate Basic information
Product Name:Trichloroacetyl isocyanate
Synonyms:Trichloroacetyl isocyate;TRICHLOROACETYL ISOCYANATE;Acetyl isocyanate, trichloro-;trichloro-acetylisocyanat;2,2,2-TRICHLOROACETYL ISOCYANATE;Trichloroacetyl isocyanate, NMR grade;Isocyanic Acid Trichloroacetyl Ester;Trichloroacetyl isocyanate, GC 97%
CAS:3019-71-4
MF:C3Cl3NO2
MW:188.4
EINECS:221-165-7
Product Categories:Organics;Isocyanates;Nitrogen Compounds;Organic Building Blocks;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
Mol File:3019-71-4.mol
Trichloroacetyl isocyanate Structure
Trichloroacetyl isocyanate Chemical Properties
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
Stability:Hygroscopic, Moisture Sensitive
InChIKeyGRNOZCCBOFGDCL-UHFFFAOYSA-N
CAS DataBase Reference3019-71-4(CAS DataBase Reference)
NIST Chemistry ReferenceTrichloroacetyl isocyanate(3019-71-4)
EPA Substance Registry SystemAcetyl isocyanate, trichloro- (3019-71-4)
Safety Information
Hazard Codes T
Risk Statements 14-23/24-34-42-23/24/25-36/37/38
Safety Statements 23-26-36/37/39-45-8-7/9
RIDADR UN 2206 6.1/PG 3
WGK Germany 3
10-19
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29291090
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Trichloroacetyl isocyanate Usage And Synthesis
Chemical Propertiesclear colorless to slightly yellow liquid
UsesTrichloroacetyl 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.
ApplicationTrichloroacetyl 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.
PreparationTrichloroacetyl 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 DescriptionConformational 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.
Chloral Trichloroacetyl isocyanate Dichloroacetamide Propyl isocyanate 2-Chloroethyl isocyanate Ethyl isocyanate 1,1,1-Trichloroethane dichloroacetyl isocyanate Ethylamine hydrochloride METHYLISOCYANATE 1 X 500MG NEAT ISOCYANIC ACID Chloroacetamide ISOCYANATE DICHLOROACETALDEHYDE HYDRATE CHLOROACETYL ISOCYANATE 2,2,2-Trichloroacetamide Trichloroacetyl chloride Isocyanatocyclohexane

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