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Sevoflurane
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  • Name Sevoflurane
  • EINECS-0
  • CAS No. 28523-86-6
  • Density1.505 g/cm3
  • PSA9.23000
  • LogP2.42320
  • Solubilityinsoluble in water
  • Melting Point58 °C
  • FormulaC4H3F7O
  • Boiling Point49.5 °C at 760 mmHg
  • Molecular Weight200.056
  • Flash Point58 °C
  • Transport InformationN/A
  • Appearancecolorless liquid
  • Safety26-36/37/39
  • Risk Codes36/37/38
  • Molecular Structure
    Molecular Structure of 28523-86-6 (Sevoflurane)
  • Hazard SymbolsIrritantXi
  • SynonymsIrritantXi
  • Article Data29

Sevoflurane Synthetic route

26103-07-1

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether

28523-86-6

sevoflurane

Conditions
ConditionsYield
With diisopropylethylamine hydrofluoride for 16h; Heating;95%
With potassium fluoride; potassium hydrogenfluoride; water; Aliquat HTA-1 at 100℃; for 3h; Product distribution / selectivity;90%
With potassium fluoride; tetraethylammonium chloride In water at 100℃; for 3h; Product distribution / selectivity;86%
26103-07-1

1,1,1,3,3,3-hexafluoroisopropyl chloromethyl ether

A

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

B

28523-86-6

sevoflurane

Conditions
ConditionsYield
With hydrogenchloride; potassium fluoride; water; Aliquat HTA-1 at 100℃; for 3h; Product distribution / selectivity;A 1.05 %Chromat.
B 93%
With potassium fluoride; potassium hydrogenfluoride; water; Aliquat 175 at 100℃; for 3h; Product distribution / selectivity;A 3.8 %Chromat.
B 89%
With potassium fluoride; potassium hydrogenfluoride; water; benzyl triethyl ammonium dichloride at 100℃; for 3h; Product distribution / selectivity;A 4 %Chromat.
B 88%
373-53-5

fluoroiodomethane

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

28523-86-6

sevoflurane

Conditions
ConditionsYield
With triethylamine In acetonitrile at 60℃; for 8h; Product distribution / selectivity; Inert atmosphere; Sealed vesselaturated gas;91.43%
With triethylamine; potassium hydroxide In acetonitrile at 60℃; for 8h; Product distribution / selectivity; Inert atmosphere;91.43%
110-88-3

1,3,5-Trioxan

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

28523-86-6

sevoflurane

Conditions
ConditionsYield
boron trifluoride diethyl etherate for 5h; Product distribution / selectivity; Heating / reflux;84%
aluminum(III) fluoride In chloroform for 5h; Product distribution / selectivity; Heating / reflux;72%
With hydrogen fluoride at -30 - 67℃; under 2257.73 - 3862.89 Torr; Pressure; Temperature;

S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulphonium tetrafluoroborate

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

28523-86-6

sevoflurane

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃;83%
373-52-4

bromofluoromethane

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

28523-86-6

sevoflurane

Conditions
ConditionsYield
With triethylamine In acetonitrile at 60℃; for 8h; Product distribution / selectivity; Inert atmosphere; Sealed vessel;81.8%
With triethylamine; potassium hydroxide In acetonitrile at 60℃; for 8h; Product distribution / selectivity; Inert atmosphere;81.8%
593-70-4

R32

920-66-1

1,1,1,3',3',3'-hexafluoro-propanol

28523-86-6

sevoflurane

Conditions
ConditionsYield
With sodium carbonate In 1-methyl-pyrrolidin-2-one; water at 50℃; for 6h; Product distribution / selectivity; Sealed vessel;71.57%
With 1-methyl-pyrrolidin-2-one; sodium carbonate In water at 50℃; for 6h;71.57%
97614-43-2

1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose

28523-86-6

sevoflurane

Conditions
ConditionsYield
With potassium fluoride In various solvent(s) at 95℃; for 1h; Substitution;71%
194039-83-3

bis {[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]methyl} ether

28523-86-6

sevoflurane

Conditions
ConditionsYield
With hydrogen fluoride at -30 - 70℃; for 1.5h;53%
1152045-94-7

methyl 3,3,3-trifluoro-2-trifluoromethyl-2-chloromethoxypropionate

28523-86-6

sevoflurane

Conditions
ConditionsYield
With potassium fluoride In polyethyleneglycol at 90 - 95℃; for 5h; Product distribution / selectivity; Autoclave;51.7%

Sevoflurane History

First reports of sevoflurane appeared in the literature in 1971. The agent was developed by scientists at Baxter Laboratories. It was introduced into clinical practice initially in Japan in 1990. The rights for sevoflurane in the US and other countries are held by Abbott Laboratories.

Sevoflurane Consensus Reports

Sevoflurane is reported in EPA TSCA Inventory. Glycol ether compounds are on the Community Right-To-Know List.The U.S. Environmental Protection Agency(EPA) has classified sevoflurane as a greenhouse gas, with a global warming potential of 345. One tonne of sevoflurane emitted is equivalent to 345 tonnes of carbon dioxide in the atmosphere.

Sevoflurane Specification

The Sevoflurane with CAS registry number of 28523-86-6 is also known as Ether,fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl (8CI). The IUPAC name is 1,1,1,3,3,3-Hexafluoro-2-(fluoromethoxy)propane. It belongs to product categories of Fluoro Series. In addition, the formula is C4H3F7O and the molecular weight is 200.05. This chemical is a colorless liquid and should be stored in refrigerated place away from oxidizing agents. It is used as inhalation anesthetic.

Physical properties about Sevoflurane are: (1)ACD/LogP: 2.48; (2)ACD/LogD (pH 5.5): 2.48; (3)ACD/LogD (pH 7.4): 2.48; (4)ACD/BCF (pH 5.5): 45.27; (5)ACD/BCF (pH 7.4): 45.27; (6)ACD/KOC (pH 5.5): 533.13; (7)ACD/KOC (pH 7.4): 533.13; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.266; (11)Molar Refractivity: 23.36 cm3; (12)Molar Volume: 139.5 cm3; (13)Surface Tension: 13 dyne/cm; (14)Density: 1.433 g/cm3; (15)Enthalpy of Vaporization: 28.08 kJ/mol; (16)Boiling Point: 49.5 °C at 760 mmHg; (17)Vapour Pressure: 311 mmHg at 25 °C.

Preparation of Sevoflurane: it is prepared by reaction of hexafluoroacetone with catalyst Pd-carbon. After hexafluoro isopropanol is obtained, add formaldehyde, hydrogen fluoride and sulfuric acid to the reaction product to generate product.

Sevoflurane is prepared by reaction of hexafluoroacetone with catalyst Pd-carbon.

When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C(OC(C(F)(F)F)C(F)(F)F)F
2. InChI: InChI=1S/C4H3F7O/c5-1-12-2(3(6,7)8)4(9,10)11/h2H,1H2
3. InChIKey: DFEYYRMXOJXZRJ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation 28300ppm/3H (28300ppm) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 5497, 1987.
mouse LD50 intraperitoneal 10500mg/kg (10500mg/kg)   Drugs in Japan Vol. -, Pg. 591, 1990.
mouse LD50 oral 18200mg/kg (18200mg/kg)   Drugs in Japan Vol. -, Pg. 591, 1990.
rat LC50 inhalation 28800ppm/3H (28800ppm) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Kiso to Rinsho. Clinical Report. Vol. 21, Pg. 5497, 1987.
rat LD50 intraperitoneal 6300mg/kg (6300mg/kg)   Drugs in Japan Vol. -, Pg. 591, 1990.
rat LD50 oral 10800mg/kg (10800mg/kg)   Drugs in Japan Vol. -, Pg. 591, 1990.

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