3019-71-4 Usage
Description
Trichloroacetyl isocyanate is a clear colorless to slightly yellow liquid that is commonly employed as an in situ derivatizing reagent for the 13C NMR studies of alcohols, phenols, and amines. It is known for its conformational stability and has been investigated for its vibrational IR and Raman spectra. It also undergoes 1,5-cycloaddition reactions with certain anhydro-deoxy sugars to yield [2+2] and [4+2] cycloadducts.
Uses
Used in Pharmaceutical Industry:
Trichloroacetyl isocyanate is used as a reagent for the conversion of alcohols to carbamates, which is an important step in the synthesis of various pharmaceutical compounds.
Used in Chemical Research:
Trichloroacetyl isocyanate is used as an in situ derivatizing reagent for the characterization of alcohols, glycols, phenols, and amines by nuclear magnetic resonance (NMR). This application is crucial for understanding the structure and properties of these compounds.
Used in Catalytic One-Pot Dehydrative Glycosylation:
Trichloroacetyl isocyanate is used in the catalytic one-pot dehydrative glycosylation of 1-hydroxy carbohydrates, which is a significant process in the synthesis of complex carbohydrate structures.
Used in the Preparation of Cefuroxime Axetil:
Trichloroacetyl isocyanate has been reported in the literature for the preparation of cefuroxime axetil, which is an antibiotic prodrug. This application highlights its importance in the development of pharmaceuticals.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 3019-71-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,0,1 and 9 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3019-71:
(6*3)+(5*0)+(4*1)+(3*9)+(2*7)+(1*1)=64
64 % 10 = 4
So 3019-71-4 is a valid CAS Registry Number.
InChI:InChI=1/C3Cl3NO2/c4-3(5,6)2(9)7-1-8
3019-71-4Relevant articles and documents
KRAS G12C INHIBITORS
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Paragraph 0313, (2020/07/25)
The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.
CONDENSATION OF ACYL CHLORIDE ON SODIUM CYANATE : PREPARATION OF ACYL ISOCYANATES
Deng, M. Z.,Caubere, P.,Senet, J. P.,Lecolier, S.
, p. 6079 - 6086 (2007/10/02)
The catalytic effects of various metal halides and solvents on the reaction of benzoyl chloride with sodium cyanate were studied.It has been found that SnCl4, and ZnCl2 catalyze the reaction to give the corresponding acyl isocyanates in good yields.The scope of the reaction was studied and a number of aroyl isocyanates and their derivatives were prepared.A few non aromatic isocyanates and their derivatives were also prepared.
REACTIVITY OF N,N-DICHLOROURETHANES. X. ADDITION OF N,N-DICHLOROURETHANES TO VINYL ETHERS
Bal'on, Ya. G.,Paranyuk, V. E.
, p. 1910 - 1914 (2007/10/02)
N,N-Dichlorourethanes add readily to vinyl ethers to form alkyl N-chloro-N-(2-chloro-1-alkoxyethyl)carbamates, which are used for the production of alkyl N-(2-chloro-1-alkoxyethyl)carbamates, 2-alkoxyaziridines, 1-chloro-2-di(alkoxycarbonylamino)ethanes, 1-alkoxyperchloroethyl and 1,2,2-trichloro-1-alkoxyethyl isocyanates.