133098-05-2

Basic information

• Product Name: S-(+)-Isoflurane
• Synonyms: (S)-Isoflurane;Ethane, 2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-, (2S)- (9CI);Ethane, 2-chloro-2-(difluoromethoxy)-1,1,1-trifluoro-, (S)-;S-(+)-Isoflurane
• CAS NO: 133098-05-2
• Molecular Formula: C3H2ClF5O
• Molecular Weight: 184.49
• Mol File: 133098-05-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: S-(+)-Isoflurane(CAS DataBase Reference)
• NIST Chemistry Reference: S-(+)-Isoflurane(133098-05-2)
• EPA Substance Registry System: S-(+)-Isoflurane(133098-05-2)

Safety Data

• Hazardous Substances Data: 133098-05-2(Hazardous Substances Data)

Upstream product

• 1885-48-9 1,1,1-trifluoro-2-difluoromethoxypropane 
• 26644-88-2 1-Chlor-2,2,2-trifluorethyl-dichlormethylether 
• 32778-07-7 1,1-Dichloro-2,2,2-trifluoroethyl difluoromethyl ether 
• 306-83-2 1,1,1-trifluoro-2,2-dichloroethane 
• 1426-06-8 difluoromethyl alcohol 

Relevant articles and documents

The fluoromethyl ether sevoflurane as a fluoride source in halogen-exchange reactions 1

Fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether (sevoflurane), fluoromethyl 1,1,2,3,3,3-hexafluoropropyl ether, and fluoromethyl 1,2,2,2-tetrafluoroethyl ether are found to be selective fluoride donors in some halogen-exchange reactions. For example, treatment of a mixture of a polychlorinated substrate and one equivalent of sevoflurane with a catalytic amount of antimony pentachloride gives a monofluorinated product and one equivalent of chloromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether as by-product.

Diisopropylethylamine mono(hydrogen fluoride) for nucleophilic fluorination of sensitive substrates: Synthesis of sevoflurane

Diisopropylethylamine mono(hydrogen fluoride) (8), which can be prepared by addition of two equivalents of diisopropylethylamine to the complex diisopropylethylamine tris(hydrogen fluoride) (7), is shown to be an effective and selective nucleophilic fluorinating reagent when applied to halogen-exchange reactions of chloromethyl ethers, in particular the conversion of 1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether (3) to the volatile anesthetic sevoflurane (1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether). The amine portion of the reagent does not react with the starting material to give a troublesome quaternary ammonium salt, as is the case for the species formed by addition of two equivalents of triethylamine to triethylamine tris(hydrogen fluoride). These particular chloromethyl ether substrates require a 1:1 stoichiometry of diisopropylethylamine to hydrogen fluoride to give useful rates of reaction and yields when solventless conditions are desired. Two other complexes, diisopropylethylamine bis(hydrogen fluoride) and 7, are ineffective for conversion of 3 to sevoflurane.

Selective free-radical dechlorination of 1,1-dichloro-2,2,2-trifluoroethyl difluoromethyl ether initiated thermally or by UV light: A practical and 'green' method for isoflurane synthesis

Treatment of 1,1-dichloro-2,2,2-trifluoroethyl difluoromethyl ether (3) with 2-propanol followed by either irradiation with UV light or heating with radical initiators gives the inhalational anesthetic isoflurane. Unlike most other common dechlorination methods, monoreduction is the exclusive process and the by-products acetone and HC1 are relatively benign. Some comments about the mechanism of the reduction will be presented, along with solutions to problems encountered during scale-up.

METHOD FOR PRODUCING HALOGENATED ETHER

PROBLEM TO BE SOLVED: To provide a method for producing 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (isoflurane) or 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) useful as an inhaled anesthetic, on an industrial scale with high efficie

Preparation method of isoflurane

The invention belongs to the field of organic chemical synthesis, and particularly relates to a preparation method of isoflurane. The method for preparing the isoflurane comprises the following steps:taking Freon 22 as a raw material to obtain difluoromet

Improvements in or relating to contrast agents

Combined preparations comprising an injectable gas dispersion and a coadministrable diffusible component which is capable of inward diffusion into the dispersed gas so as to promote temporary growth of the gas in vivo, the preparations being for use as contrast agents in ultrasound cardiac studies of patients who have undergone physical exercise-induced stress in order to promote vasodilatation.

Process for the manufacture of halo esters of carboxylic or dicarboxylic acids

A compound (Ia) or (Ib) is prepared by reacting, in a polar aprotic solvent, a compound (III) with a salt of a carboxylic or dicarboxylic acid (IIa) or (IIb). The reaction may be carried out under pressure, but also at normal atmospheric pressure or in the region of normal atmospheric pressure (especially between 0.10 bar and 2 bars). The product (Ia) or (Ib) formed is, in this latter case, recovered continuously as it is formed. STR1 R1, R2 =optionally substituted saturated or unsaturated acyclic or cyclic hydrocarbon radicals; R3 =C1 -C10 perhaloalkyl; 0n≤4; X=halogen. The applications of the fluoroalkyl (meth)acrylates obtained are especially: anti-dust or anti-soiling paints for various supports such as exterior coatings and metal furniture; optical fibers; contact lenses; lithography; electrophotography; heat-resistant materials; dental resins.

Preparation of the Isoflurane Enantiomers

The enantiomers of the inhalation anesthetic agent, isoflurane (1-chloro-2,2,2-trifluoroethyl difluoromethyl ether), are prepared by a synthesis starting from 2,2,2-trifluoroethanol. (R)-(+)-Dehydroabietylamine is used as the resolving agent for the racemic acid intermediate 1.The optical purities of both (S)-(+)- and (R)-(-)-isofluranes are determined to be >99percent ee (enantiomeric excess) by chiral capillary gas chromatography.

Process for adjusting the halogen content of halogenated aliphatic ethers

Process for adjusting the halogen content of halogenated aliphatic ethers, by selective replacement of a halide substituent on the ether with a hydrogen. The process is particularly useful for the production of certain inhalant anesthetics.

Deuterated isoflurane as an anesthetic agent

Deuterated Isoflurane and anesthetic compositions thereof useful as inhalation anesthetics show reduced levels of inorganic fluoride in urine of anesthetized animals.