27746-99-2

Basic information

• Product Name: 2,2,2-TRIFLUOROETHYL CHLOROFORMATE
• Synonyms: 2,2,2-Trifluoroethyl chloroformate;Carbonochloridic acid, 2,2,2-trifluoroethyl ester
• CAS NO: 27746-99-2
• Molecular Formula: C₃H₂ClF₃O₂
• Molecular Weight: 162.4949896
• Mol File: 27746-99-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 40 °C(Press: 165 Torr)
• Appearance: /
• Density: 1.4896 g/cm3
• CAS DataBase Reference: 2,2,2-TRIFLUOROETHYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUOROETHYL CHLOROFORMATE(27746-99-2)
• EPA Substance Registry System: 2,2,2-TRIFLUOROETHYL CHLOROFORMATE(27746-99-2)

Safety Data

• Statements: 23/24/25-34
• Safety Statements: 26-36/37/39
• RIDADR: 3277
• Hazardous Substances Data: 27746-99-2(Hazardous Substances Data)

Usage

Uses

2,2,2-Trifluoroethyl chloroformate is a derivatization reagent used to produce primary and secondary aliphatic amines (e.g. N-Methylhexadecylamine [M311995]).

Upstream product

• 75-44-5 phosgene 
• 75-89-8 2,2,2-trifluoroethanol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 71674-19-6 Thiocarbonic acid S-ethyl ester O-(2,2,2-trifluoro-ethyl) ester 
• 27746-95-8 hypochlorous acid 2,2,2-trifluoro-ethyl ester 
• 201230-82-2 carbon monoxide 

Downstream Products

• 37888-15-6 Trifluorethoxy-carbonyl-glycin 
• 152898-95-8 (4-Methoxy-benzyl)-carbamic acid 2,2,2-trifluoro-ethyl ester 
• 243143-24-0 (3S)-1-(2,2,2-trifluoroethyloxycarbonyl)-3-(tert-butyloxycarbonyl)aminoazetidin-2-one 
• 951242-60-7 N-(2,2,2-trifluoroethoxycarbonyl)-L-valinamide 
• 951242-82-3 N-(2,2,2-trifluoroethoxycarbonyl)-L-alaninamide 
• 951242-93-6 N-methyl-N-(2,2,2-trifluoroethoxycarbonyl)-L-valinamide 
• 1197808-29-9 (2-(morpholin-4-yl)ethyl)carbamic acid 2,2,2-trifluoroethyl ester 
• 874594-92-0 pyridin-3-ylcarbamic acid 2,2,2-trifluoroethyl ester 
• 1197741-10-8 thiazol-2-ylcarbamic acid 2,2,2-trifluoroethyl ester 
• 1211199-35-7 [1,3,4]thiadiazol-2-ylcarbamic acid 2,2,2-trifluoroethyl ester 
• 1197480-43-5 (2,5-dimethyl-2H-pyrazol-3-yl)carbamic acid 2,2,2-trifluoroethyl ester 
• 929975-42-8 3-methoxyphenylcarbamic acid 2,2,2-trifluoroethyl ester 
• 782-94-5 4-chlorophenylcarbamic acid 2,2,2-trifluoroethyl ester 
• 370-32-1 phenylcarbamic acid 2,2,2-trifluoroethyl ester 

Relevant articles and documents

Catalytic synthesis of polyfluoroalkyl chloroformates

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Cu(II)-promoted methanolysis of N, N -bis(2-picolyl)carbamates: Rate-limiting metal ion delivery of coordinated alcoholate nucleophile followed by fast partitioning of a tetrahedral intermediate

Five O-aryl/alkyl N,N-bis(2-picolyl)carbamates were prepared with the O-aryl/alkyl portions being p-nitrophenoxy, m-nitrophenoxy, trifluoroethoxy, methoxy, and isopropoxy (4a,b,c,d,e, respectively) and the kinetics and reaction products of their methanolysis reactions in the presence of Cu(O3SCF3)2 determined. The catalyzed reactions have maximal rates for each substrate at a 1:1 ratio of [4]:[Cu2+] at sspH 7.9, where the active forms are Cu(II):4:(-OCH3). The reactions are fast, that for the complex of 4a having a t1/2 of 30 s. The products of the reaction with 4a and 4b arise exclusively from C-OAr cleavage: those with 4d and 4e arise exclusively from C-N cleavage. With 4c, products from both C-O and C-N cleavage are observed in a 2.17:1 ratio. The common mechanism involves rate-limiting delivery of a Cu(II)-coordinated methoxide to the C=O unit to form a tetrahedral intermediate followed by fast partitioning to products by two pathways with relative barriers dependent on the sspKaHOAr/HOR. The data allow one to predict an effective sspKa of ～15.6 for the sspKaNH of Cu(II):bis(2-picolyl)amine.

Synthesis and properties of di(polyfluoroalkyl) peroxydicarbonates

Synthesis of di(polyfluoroalkyl)peroxydicarbonates [X(CF2) nCH2OC(O)O]2, where X = H, F; n = 1, 2, 4, 6 (yield 80%) involves the step of the chloroformate formation (yield up to 93%) via the phosgenation of polyfluorinated alcohols followed by the reaction with sodium peroxide. The rate constant of monomolecular decomposition k term was found to decrease as the polyfluoroalkyl groups were incorporated into the peroxide: it equaled 3.30 and 3.10 s-1 for X = H, n = 2 and 4, respectively, and 7.36 s-1 for di-n- butylperoxydicarbonate. The new peroxides are a source of the polyfluoroalkoxy radicals and nano-modifiers of the polymers to improve their heat resistance and light stability. Pleiades Publishing, Ltd., 2011.