Isoflurane

Base Information

• Chemical Name: Isoflurane
• CAS No.: 26675-46-7
• Molecular Formula: C3H2ClF5O
• Molecular Weight: 184.493
• Hs Code.: 2909191800
• European Community (EC) Number: 247-897-7
• ICSC Number: 1435
• UNII: CYS9AKD70P
• DSSTox Substance ID: DTXSID3020752
• Nikkaji Number: J2.770G
• Wikipedia: Isoflurane
• Wikidata: Q413918
• NCI Thesaurus Code: C65978
• RXCUI: 6026
• Pharos Ligand ID: XUMC5VNDWJVP
• Metabolomics Workbench ID: 53234
• ChEMBL ID: CHEMBL1256
• Mol file: 26675-46-7.mol

Synonyms:Ether,1-chloro-2,2,2-trifluoroethyl difluoromethyl (8CI);1-Chloro-2,2,2-trifluoroethyl difluoromethyl ether;Aerrane;Attane;Compound469;Difluoromethyl 1-chloro-2,2,2-trifluoroethyl ether;Forane;Forene;HCFE235da2;IsoFlo;IsoFlo (anesthetic);Isoforine;R-E 235da1;

Chemical Property of Isoflurane

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.00167mmHg at 25°C
• Melting Point: 48.5°C
• Refractive Index: 1.3002
• Boiling Point: 48.5 °C at 760 mmHg
• Flash Point: 48-49°C
• PSA: 9.23000
• Density: 1.489 g/cm³
• LogP: 2.35280
• Storage Temp.: 2-8°C
• Solubility.: Practically insoluble in water, miscible with ethanol and trichloroethylene.
• Water Solubility.: Soluble in chloroform and ethyl acetate. Not miscible or difficult to mix in water.
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 183.9714332
• Heavy Atom Count: 10
• Complexity: 102

Purity/Quality:

99% ^*data from raw suppliers

Isoflurane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T,Xn
• Statements: 36/37/38-67-48/20
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Waste Anesthetic Gases
• Drug Classes: Anesthetics, Halogenated
• Canonical SMILES: C(C(F)(F)F)(OC(F)F)Cl
• Recent ClinicalTrials: Remote Ischemic Preconditioning in Coronary Artery Bypass Grafting With Cold Crystalloid Cardioplegic Arrest
• Recent EU Clinical Trials: A Randomised Active-controlled Study to Compare Efficacy and Safety of Inhaled Isoflurane Delivered by the AnaConDa-S (Anaesthetic Conserving Device) to Intravenous Midazolam for Sedation in Mechanically Ventilated Paediatric Patients 3 to 17 (Less than 18) Years Old
• Recent NIPH Clinical Trials: Age-associated differences in the minimum alveolar concentration of volatile anesthetics
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes and skin. The vapour is irritating to the respiratory tract. The substance may cause effects on the central nervous system and cardiovascular system. Exposure at high levels could cause unconsciousness.
• Uses: Isoflurane is a volatile anesthetic agent mainly used to study its interaction with the biological system. Isoflurane is a halogenated ether used for inhalational anesthesia. Recent studies suggest that there might be a relationship between administration of isoflurane and postoperative cognitive dysfunct ion (POCD). Solvent and dispersant for fluorinated materials.
• Therapeutic Function: Inhalation anesthetic
• Biological Functions: Isoflurane (Forane) is a structural isomer of enflurane and produces similar pharmacological properties: some analgesia, some neuromuscular blockade, and depressed respiration. In contrast, however, isoflurane is considered a particularly safe anesthetic in patients with ischemic heart disease, since cardiac output is maintained, the coronary arteries are dilated, and the myocardium does not appear to be sensitized to the effects of catecholamines. Also, blood pressure falls as a result of vasodilation, which preserves tissue blood flow. Isoflurane causes transient and mild tachycardia by direct sympathetic stimulation; this is particularly important in the management of patients with myocardial ischemia. Unlike enflurane, isoflurane does not produce a seizurelike EEG pattern. Furthermore, the metabolic transformation of isoflurane is only one-tenth that of enflurane, so fluoride production is quite low. Among the halogenated hydrocarbons, isoflurane is one of the most popular, since it preserves cardiovascular stability and causes a low incidence of untoward effects.
• Clinical Use: Isoflurane was introduced in the United States in 1981 and is a potent anesthetic agent with many similarities to its isomer enflurane (potent, nonflammable, and intermediate blood solubility). It does produce significantly fewer cardiovascular effects than enflurane, however, and it can be used safely with epinephrine without as great a concern for arrhythmia production. Isoflurane has a more pungent odor than halothane and, thus, can cause irritation to the throat and respiratory tract, triggering coughing and laryngospasm. To overcome this problem, it often is supplemented with intravenous agents. Less than 0.2% of an administered dose is metabolized, mostly to fluoride and trifluoroacetic acid. Some minimal potential for hepatotoxicity is associated with a trifluoroacetyl halide metabolite.

Technology Process of Isoflurane

There total 6 articles about Isoflurane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,1-Dichloro-2,2,2-trifluoroethyl difluoromethyl ether (32778-07-7) → isoflurane (26675-46-7,133098-05-2)

Guidance literature:

In water; acetone; for 20h; Irradiation;

DOI:10.1016/S0022-1139(96)03504-X

Reference yield: 88.3%

1,1,1-trifluoro-2,2-dichloroethane (306-83-2) + difluoromethyl alcohol (1426-06-8) → isoflurane (26675-46-7,133098-05-2)

Guidance literature:

at 30 - 35 ℃; for 3h; Temperature; Autoclave; Inert atmosphere;

Reference yield: 67.0%

1-chloro-2,2,2-trifluoroethyl chlorofluoromethyl ether → isoflurane (26675-46-7,133098-05-2)

Guidance literature:

With diisopropylethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; for 21h; Heating;

DOI:10.1016/S0022-1139(01)00396-7

upstream raw materials:

1,1,1-trifluoro-2-difluoromethoxypropane

1-Chlor-2,2,2-trifluorethyl-dichlormethylether

1,1-Dichloro-2,2,2-trifluoroethyl difluoromethyl ether

1,1,1-trifluoro-2,2-dichloroethane

Downstream raw materials:

1,1,1,2-tetrafluoro-2-chloroethane

desflurane

Refernces

• 1、 -. "Preparation method of isoflurane". Paragraph 0021; 0034; 0036-0037; 0039-0040; 0042-0043; 0045. . Retrieved 2020/12/15.
• 2、 Kudzma,Huang,Lessor,Rozov,Afrin,Kallashi,McCutcheon,Ramig. "Diisopropylethylamine mono(hydrogen fluoride) for nucleophilic fluorination of sensitive substrates: Synthesis of sevoflurane". . p. 11 - 16. Retrieved 2007/10/03.