| Identification | More | [Name]
2-CHLORO-1,1,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER | [CAS]
13838-16-9 | [Synonyms]
2-CHLORO-1,1,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER
2-CHLORO-1-(DIFLUOROMETHOXY)-1,1,2-TRIFLUOROETHANE
ENFLURANE
(2-chloro-1,1,2-trifluoro-ethoxy)-difluoro-methane
2-chloro-1-(difluoromethoxy)-1,1,2-trifluoro-ethan
2-Chloro-1,1,2-difluoroethane, 1-difluoromethoxy-
347
Alyrane
Anesthetic 347
Anesthetic Compound No. 347
anestheticcompoundno.347
C 347
Compound 347
compound347
Efrane
Ethane, 2-chloro-1-(difluoromethoxy)-1,1,2-trifluoro-
ethane,2-chloro-1-(difluoromethoxy)-1,1,2-trifluoro-
Ether, 2-chloro-1,1,2-trifluoroethyl difluoromethyl
ether,2-chloro-1,1,2-trifluoroethyldifluoromethyl
Ethrane | [EINECS(EC#)]
237-553-4 | [Molecular Formula]
C3H2ClF5O | [MDL Number]
MFCD00069095 | [Molecular Weight]
184.49 | [MOL File]
13838-16-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear, colorless liquid; mild, sweet odor.
Soluble in organic solvents;
slightly soluble in water. | [Boiling point ]
56 °C | [density ]
1.517 | [refractive index ]
1.303 | [Fp ]
56-57°C | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Chloroform (Soluble), DMSO (Sparingly), Dichloromethane (Sparingly), Methanol (S | [form ]
Liquid | [color ]
Colorless to light yellow | [Specific Gravity]
1.517 | [Merck ]
14,3581 | [BRN ]
1737129 | [Exposure limits]
TLV-TWA 570 mg/m3 (75 ppm) (ACGIH). | [InChIKey]
JPGQOUSTVILISH-UHFFFAOYSA-N | [Uses]
Clinical anesthetic. | [CAS DataBase Reference]
13838-16-9(CAS DataBase Reference) | [EPA Substance Registry System]
Enflurane (13838-16-9) |
| Safety Data | Back Directory | [Hazard Codes ]
F,T | [Risk Statements ]
R36:Irritating to the eyes. | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [OEL]
Ceiling: 2 ppm (15.1 mg/m3) [60-minute] [*Note: REL for exposure to waste anesthetic gas.] | [RIDADR ]
UN 3334 | [RTECS ]
KN6800000 | [Hazard Note ]
Flammable/Toxic | [HS Code ]
2909191800 | [Safety Profile]
Mildly toxic by
inhalation, ingestion, and subcutaneous
routes. Human systemic effects by
inhalation: decreased urine volume or
anuria. An experimental teratogen.
Experimental reproductive effects. Human
mutation data reported. An eye irritant.
Questionable carcinogen with experimental
carcinogenic data. An anesthetic. When
heated to decomposition it emits very toxic
fumes of Fand Cl-. See also ETHERS. | [Hazardous Substances Data]
13838-16-9(Hazardous Substances Data) | [Toxicity]
LD50 oral in rat: 5450uL/kg |
| Hazard Information | Back Directory | [General Description]
ENFLURANE(13838-16-9) (Ethrane, 2-chloro-1,1,2-trifluoroethyldifluoromethyl ether) is a nonflammable halogenated hydrocarbon that exists as a clear, colorless, odorless to sweet, volatile liquid at ordinary temperature and pressure. Bp: 56.8°C. Density 1.50 g cm-3 at room temperature. Used as an anesthetic. | [Reactivity Profile]
The material ENFLURANE is incompatible with the following oxidizing materials, peroxides, combustible materials. Although nonflammable, a fire may cause enflurane to decompose to toxic compounds including phosgene, hydrogen chloride, and hydrogen fluoride. Decomposes slowly in the light. | [Hazard]
Volatile with anesthetic properties, but nonflammable. Cardiac and central nervous system
impairment. Questionable carcinogen. | [Potential Exposure]
FDA-proprietary drug, used as an
anesthetic (gas). Axphyxiant | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautionsincluding resuscitation mask) if breathing has stopped and
CPR if heart action has stopped. Transfer promptly to a
medical facility. When this chemical has been swallowed,
get medical attention. Give large quantities of water and
induce vomiting. Do not make an unconscious person
vomit. | [Shipping]
UN1851 Medicine, liquid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials. Cylinders must
be transported in a secure upright position, in a wellventilated truck. Protect cylinder and labels from physical
damage. The owner of the compressed gas cylinder is the
only entity allowed by federal law (49CFR) to transport
and refill them. It is a violation of transportation regulations to refill compressed gas cylinders without the express
written permission of the owner. | [Incompatibilities]
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or
explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, and epoxides. Decomposes
on heating, forming toxic and corrosive fumes of hydrogen
chloride, hydrogen fluoride, and phosgene. Decomposes in
strong sunlight | [Description]
Enflurane is a clear, colorless liquid with amild, sweet odor, which easily turns into a nonflammablegas. Molecular weight = 184.50; Specific gravity(H2O:1) = 1.52; Boiling point = 56.7 ℃; Vaporpressure 5 175 mmHg; Relative vapor density (air 5 1)=1.92. Hazard Identification (based on NFPA-704 M RatingSystem): Health 2, Flammability 1, Reactivity 0. Veryslightly soluble in water | [Chemical Properties]
Clear, colorless liquid; mild, sweet odor.
Soluble in organic solvents;
slightly soluble in water. | [Chemical Properties]
Enflurane is a clear, colorless liquid that easily
turns into a nonflammable gas. Mild, sweet odor | [Chemical Properties]
The halogenated methyl ethyl ether enflurane is a geometric isomer of
isoflurane and boasts similar properties. It is no longer in use in modern
clinical practice largely because of some unfavourable adverse effects.
Enflurane has been associated with: tonic–clonic muscle activity;
epileptiform EEG changes; sensitisation of the myocardium to
catecholamines causing dysrhythmias; and hepatotoxicity as a result of its
significant liver metabolism. | [Waste Disposal]
Return refillable compressed
gas cylinders to supplier | [Originator]
Ethrane,Ohio Medical,US,1972 | [Definition]
ChEBI: An ether in which the oxygen atom is connected to 2-chloro-1,1,2-trifluoroethyl and difluoromethyl groups. | [Manufacturing Process]
Preparation of the Intermediate CHCl2OCF2CHFCl: To a 3-necked roundbottomed flask fitted with a Dry Ice condenser, a fritted glass gas inlet tube, a
thermometer and a stirrer, was charged 1,180 grams (8 mols) of
CH3OCF2CHFCl.After flushing the system with nitrogen, chlorine gas was
added via the inlet tube while the reaction was stirred and illuminated with a
300 watt incandescent lamp. The chlorination was rapid and exothermic and
the reactor was cooled to hold the temperature between 30° and 35°C. The
effluent gases were led from the top of the condenser to a water scrubber
which was titrated at intervals with standard base. When a total of 1.45 mols
of HCl per mol of ether was titrated the reaction was stopped. The crude
product obtained weighed 1,566 grams which corresponded to the addition of
1.41 mols of chlorine per mol of the starting ether. The product was flash
distilled to yield 1,480 grams of product which had the following composition
as determined by vapor phase chromatography: 45.3% CH2ClOCF2CHFCl;
50.5% CHCl2OCF2CHFCl, plus a small amount of CH2ClOCF2CFCl2; 1.8%
CHCl2OCF2CFCl2 and 2.1% CCl3OCF2CHFCl.
Fractional distillation of this mixture using a 5 x 120 cm column packed with
?" Penn State packing yielded 670 grams of product containing 95%
CH2ClOCF2CHFCl and 5% CHCl2OCF2CHFCl; BP 55° to 60°C at 100 mm, nD20
= 1.3748 to 1.3795; and 670 grams of CHCl2OCF2CHFCl (95% pure,
containing 5% CH2ClOCF2CFCl2); BP 60°C at 100 mm, nD20 = 1.3870 to
1.3875. The still bottoms were comprised mostly of CCl3OCF2CHFCl and
CHCl2OCF2CFCl2.
Preparation of CHF2OCF2CHFCl: To a mixture of 2,172 grams (10 mols)
CHCl2OCF2CHFCl prepared as described above (containing approximately 5%
CH2ClOCF2CFCl2) and 40 grams (2% by weight) SbCl5 was added anhydrous
hydrogen fluoride while the temperature was maintained at 0-5°C. The
reaction was carried out in a 3-necked stainless steel flask fitted with a
stainless steel stirrer, a thermocouple well and a copper Dry Ice condenser.
The amount of hydrogen fluoride added was measured by titration of the HCl
given off. At the end of the reaction (total HCl evolved: 1.98 mols per mol of
starting ether) the mixture was poured into water and the organic layer
(1,803 grams, nD20 = 1.3080) recovered. The crude product was flash distilled
in a 60 x 2 cm column packed with ?" Penn State packing giving 1,594 grams
of substantially pure CHF2OCF2CHFCl, BP 56° to 57°C. By further distillation
1,450 grams of the pure ether were obtained, BP 56.5°C, nD20 = 1.3030 as
described in each of the patents cited as references. | [Therapeutic Function]
Anesthetic | [Biological Functions]
Enflurane (Ethrane) depresses myocardial contractility
and lowers systemic vascular resistance. In contrast to
halothane, it does not block sympathetic reflexes, and
therefore, its administration results in tachycardia.
However, the increased heart rate is not sufficient to oppose
enflurane’s other cardiovascular actions, so cardiac
output and blood pressure fall. In addition, enflurane
sensitizes the myocardium to catecholamine-induced
arrhythmias, although to a lesser extent than with
halothane. Enflurane depresses respiration through
mechanisms similar to halothane’s and requires that the
patient’s ventilation be assisted.
Neuromuscular transmission is depressed by enflurane,
resulting in some skeletal muscle paralysis.Although
muscle relaxation is inadequate for many surgical procedures,
the anesthetic enhances the action of neuromuscular
blocking agents, thereby lowering the dose of the paralytic
agent needed and minimizing side effects.
Deep anesthesia with enflurane is associated with
the appearance of seizurelike electroencephalographic
(EEG) changes. Occasionally frank tonic–clonic seizures
are observed. Consequently, other inhalational
agents are usually given to patients with preexisting
seizure disorders.
Another concern associated with the use of enflurane
is its biotransformation, which leads to increased
plasma fluoride. Following lengthy procedures in
healthy patients, fluoride may reach levels that result in
a mild reduction in renal concentrating ability.Thus, enflurane
should be used cautiously in patients with clinically
significant renal disease. | [Health Hazard]
The acute toxicity of ethrane by inhalation,ingestion, or intraperitoneal or subcutaneousapplications in rodents was found tobe low to very low at concentrationsof <1000 ppm in air or dosages below1000 mg/kg. In humans it causes anesthesiaat 1.5–2% concentrations (by volume of air).Exposure to concentrations above this levelcan be dangerous. The target organs arethe central nervous system, cardiovascularsystem, kidney, and bladder. The symptomsare anesthesia, respiratory depression, andseizure. Hypotension can occur due toits action on the cardiovascular system.Exposure to a 1% concentration in air for6 hours caused anuria in humans
LC50 value, inhalation (mice): 8100 ppm/3 h
LD50 value, oral (mice): 5000 mg/kg
The pure liquid can cause mild to moder ate irritation of the eyes.
Inhalation of ethrane vapors produced teratogenic effects in mice and rats. Theseeffects pertained to specific developmen tal abnormalities in the urogenital, mus culoskeletal, and central nervous systems.These reproductive effects, however, weremanifested at high exposure levels in therange of LC50 concentrations.
Under the conditions of its use, the con centrations of ethrane in air should be toolow to produce any adverse health effects onhumans. However, it should be borne in mindthat this compound is highly volatile [vaporpressure 175 torr at 20°C (68°F)] and its con centration in air can go up from a spill orimproper handling in confined space.
Inhalation of its vapors resulted in lungand liver tumors in mice. There is no evi dence of its carcinogenic actions in humans. | [Fire Hazard]
Noncombustible liquid; flash point >94°C
(200°F); low reactivity. Pressure buildup in a
closed bottle may occur at elevated temper atures. | [Clinical Use]
Enflurane was introduced into medical practice in the United States in 1973 and is a
clear, colorless, nonflammable general liquid with a mild, sweet odor. Although relatively stable
chemically, enflurane does not attack aluminum, copper, iron, or brass and is soluble in rubber
(partition coefficient = 74), which can prolong induction/recovery times, as seen with halothane.Enflurane has an intermediate solubility in blood and significant potency. Most of its
pharmacological properties are similar to those of halothane, although there may be slightly less
nausea, vomiting, arrhythmias, and postoperative shivering than observed with halothane. High
concentrations of enflurane, however, are more likely to produce convulsions and circulatory
depression. Enflurane also relaxes the uterus and, thus, should not be used as an anesthetic
during labor. Metabolism via CYP2E1 accounts for 2% of an inhaled dose and includes
transformation to the fluoride ion and fluoromethoxydifluoroacetic acid. During
recovery, enflurane leaves the fatty tissues rapidly and, therefore, is not available for a prolonged
period of time for significant metabolism to proceed. | [Synthesis]
Enflurane is prepared by dichlorination of
the methyl group of 1-chloro-1,2,2-trifluoro-2-
methoxyethane and replacement of these two
chlorine atoms by fluorine , :
 | [storage]
Store at -20°C |
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