Halothane

Halothane Basic information
Product Name:Halothane
Synonyms:1,1,1-Trifluoro-2-bromo-2-chloroethane;1,1,1-Trifluoro-2-chloro-2-bromoethane;HALOTHANE;2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE;1-BROMO-1-CHLORO-2,2,2-TRIFLUOROETHANE;Halothane (1 mL);2-Bromo-1,1,1-trifluoroethane-2-chloro-;2-Bromo-2-chloro-1,1,1-trifluoroethane, Halothane
CAS:151-67-7
MF:C2HBrClF3
MW:197.38
EINECS:205-796-5
Product Categories:Organics;SOLAQUIN FORTE
Mol File:151-67-7.mol
Halothane Structure
Halothane Chemical Properties
Melting point -115.75°C
Boiling point 50.2 °C(lit.)
density 1.872 g/mL at 25 °C(lit.)
vapor pressure 4.5 psi ( 20 °C)
refractive index n20/D 1.369(lit.)
Fp 49-50°C
storage temp. 2-8°C
solubility Slightly soluble in water, miscible with anhydrous ethanol and with trichloroethylene.
form Colorless liquid
Water Solubility Soluble in water (8 mg/ml).
Sensitive Light Sensitive
Merck 14,4603
BRN 1736947
Exposure limitsTLV-TWA 50 ppm (~400 mg/m3) (ACGIH).
CAS DataBase Reference151-67-7(CAS DataBase Reference)
EPA Substance Registry SystemHalothane (151-67-7)
Safety Information
Hazard Codes T,Xi,Xn
Risk Statements 61-37/38-41-40-20
Safety Statements 53-23-26-36/37-45-36
RIDADR UN 3334
WGK Germany 3
RTECS KH6550000
8-19
Hazard Note Irritant
HS Code 2937990000
Hazardous Substances Data151-67-7(Hazardous Substances Data)
ToxicityLD50 oral in rat: 5680mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Halothane Usage And Synthesis
DescriptionHalothane was introduced into medical practice in the United States in 1956 as a nonflammable, nonexplosive, halogenated volatile anesthetic that usually is mixed with air or oxygen. The presence of the carbon–halogen bonds contributes to its nonflammability. This clear liquid with a sweet odor was developed based on predictions that its halogenated structure would provide chemical stability, an intermediate blood solubility, and significant anesthetic potency. Halothane is the only useful volatile anesthetic possessing a bromine atom, which has been suggested to contribute to its potency. Similarly, the addition of fluorine atoms, of which halothane has three, is thought to contribute to the increased potency, volatility, and increased chemical stability of the hydrocarbon skeleton.
Halothane produces rapid onset and recovery from anesthesia with high potency when used alone or in combination with nitrous oxide. Most metals, with the exception of chromium, nickel, and titanium, are easily tarnished by halothane. Although halothane is relatively stable, it is subject to spontaneous oxidative decomposition to hydrochloric acid, hydrobromic acid, and phosgene. For this reason, it is available in dark, amber glass containers with thymol added as a preservative to minimize decomposition. Halothane may permeate into the rubber components of the anesthetic delivery devices, which might account for some slowing of the induction onset and recovery. Approximately 20% of an administered dose is metabolized, which accounts, in part, for the increased hepatotoxicity observed with this agent.
Chemical PropertiesClear, colourless, mobile, heavy, non-flammable liquid
Chemical PropertiesHalothane is a highly volatile, nonflammable, colorless liquid. Sweet odor.
OriginatorFluothane,Ayerst,US,1958
Usesdepigmentor, antioxidant
UsesHalothane is used as a clinical anesthetic.
Uses2-Bromo-2-chloro-1,1,1-trifluoroethane, or halothane, has been used in a study that combined molecular simulations with free energy simulations to study solvation of halothane in polarizable water and methanol. Halothane has also been used in a study to investigate the interaction of anesthetics with the Rho GTPase regulator Rho GDP dissociation inhibitor.
DefinitionChEBI: A haloalkane comprising ethane having three flouro substituents at the 1-position as well as bromo- and chloro substituents at the 2-position.
DefinitionA colorless nonflammable liquid halocarbon used as a general anesthetic. The systematic name is 1-chloro-1-bromo-2,2,2-trifluoroethane.
Manufacturing ProcessAccording to US Patent 2,849,502, the apparatus used consisted of a 2" x 24" silica tube packed with silica chips and enclosed in a vertical electric furnace. 1,1,1-trifluoro-2-chloroethane as vapor and bromine as liquid were introduced into a narrow tube passing down the inside of the reaction tube. The mixed reactants then passed up through the reaction tube which was maintained at a temperature of about 465°C. The reaction products were passed through a water-cooled condenser which condensed out most of the desired 1,1,1- trifluoro-2-bromo-2-chloroethane along with any high boiling by-products and unchanged bromine.
This condensate was washed with dilute caustic soda solution and dried over calcium chloride. The exit gases from this condenser were scrubbed with water and dilute caustic soda solution, dried and passed to a condenser cooled with a mixture of solid carbon dioxide and trichloroethylene which caused the unchanged 1,1,1-trifluoro-2-chloroethane to condense. This second condensate was then combined with the first and the mixture was fractionally distilled.
During a run of 2 hours 620 grams of 1,1,1-trifluoro-2-chloroethane and 630 grams of bromine were fed to the reactor and the product was worked up as described above. On fractional distillation there was obtained a first cut up to 50°C consisting of unchanged 1,1,1-trifluoro-2-chloroethane, then a middle cut between 50° and 52°C consisting of substantially pure 1,1,1-trifluoro-2- bromo-chloroethaneand a higher boiling residue that contained a further quantity of the desired product together with some 1,1,1-trifluoro-2,2- dibromo-2-chloroethane. On redistillation of the middle fraction pure 1,1,1- trifluoro-2-bromo-2-chloroethane was obtained with BP 50° to 50.5°C.

Brand nameFluothane (Wyeth).
Therapeutic FunctionInhalation anesthetic
Biological FunctionsHalothane (Fluothane) depresses respiratory function, leading to decreased tidal volume and an increased rate of ventilation. Since the increased rate does not adequately compensate for the decrease in tidal volume, minute ventilation will be reduced; plasma PaCO2 rises, and hypoxic drive is depressed.With surgical anesthesia, spontaneous ventilation is inadequate, and the patient’s ventilation must be controlled.
Halothane administration can result in a marked reduction in arterial blood pressure that is due primarily to direct myocardial depression, which reduces cardiac output. The fall in pressure is not opposed by reflex sympathetic activation, however, since halothane also blunts baroreceptor and carotid reflexes. Systemic vascular resistance is unchanged, although blood flow to various tissues is redistributed. Halothane also sensitizes the heart to the arrhythmogenic effect of catecholamines. Thus, maintenance of the patient’s blood pressure with epinephrine must be done cautiously.
General DescriptionHalothane is a nonflammable, nonpungent, volatile, liquid,halogenated (F, Cl, and Br) ethane (bp=50°C), introducedin 1956. Halothane may increase heart rate, cause cardiacarrhythmias, increase cerebral blood flow, and increase intracranialpressure.It can undergo spontaneous oxidationwhen exposed to ultraviolet light to yield HCl, HBr, Cl ,Br- , and phosgene (COCl2). To prevent oxidation it ispackaged in amber bottles with a low concentration of thymol(0.01%) as a stabilizer. The drug has a high potency(MAC=0.75%), a blood:gas partition coefficient of 2.4,and high adipose solubility. Halothane undergoes both reductiveand oxidative processes with up to 20% of the doseundergoing metabolism .The trifluoroacetylchloride metabolite is electrophilic and can form covalentbonds with proteins leading to immune responses andhalothane hepatitis upon subsequent halothane exposure.Halothane hepatitis is rare with 1 case reported for every6,000 to 35,000 patients exposed.
General DescriptionClear colorless highly volatile liquid with a sweet chloroform-like odor . Density 1.875 g / cm3. Boiling point 122.4°F (50.2°C). Noncombustible.
Air & Water ReactionsSlightly water soluble.
Reactivity Profile2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE is sensitive to exposure to light. Incompatible with oxidizing materials. Tarnishes or corrodes most metals, with the exception of chromium, nickel and titanium. When moisture is present, 2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE attacks aluminum, brass and lead, but not copper. Contact causes rubber and some plastics to deteriorate rapidly.
Health HazardHealth hazard may arise from exposure tohigh concentrations of vapors. The target sites are the central nervous system, car diovascular system, and liver. The toxiceffects include depression of the central ner vous system, nausea, vomiting, increasedbody temperature, excitability, arrhythmias,vasodilatation, hepatitis, and liver necrosis.An anesthetic effect in humans is noted atan exposure level of 10,000 ppm. Repeatedexposure to halothane at anesthetic concen trations may result in hepatic lesions andnecrosis. Contact of liquid with the eyes mayresult in severe irritation. The lethal con centration in humans for a 3-hour exposureperiod is in the range of 7000 ppm.
LC50 value, inhalation (mice): 22,000 ppm/10 min
LD50 value, oral (guinea pigs): 6000 mg/kg
No mutagenic effect was observed. Carcino genicity in animals has not been reported.


Fire HazardLiterature sources indicate that 2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE is nonflammable.
Biochem/physiol ActionsInhalation anesthetic. In an effect believed to be independent of anesthesia, halothane inhibits synthesis of 5-hydroxytryptamine in brain tissue, probably at the tryptophan hydroxylase step.
Clinical UseThe use of inhaled anesthetics and halothane in particularcan produce malignant hyperthermia (MH) in geneticallysusceptible individuals. This results in an increase inbody temperature, tachycardia, tachypnea, acidosis, andrhabdomylolysis. MH is a result of the excessive release ofcalcium from the sarcoplasmic reticulum (SR). Patientswith an inherited mutation in the ryanodine receptor(RYR1), which is located in the SR, are at an increased riskof developing MH when exposed to an inhaled anesthetictriggering agent. Treatment entails discontinuing the anestheticagent, rapid cooling, intravenous dantrolene sodium,and supportive measures. MH has been reported to occurwith all anesthetics agents and with succinylcholine, a depolarizingneuromuscular blocker. The combination ofhalothane and succinylcholine appears to trigger a great extentof the MH episodes. Patients with a family history ofMH can be genetically screened for MH susceptibility viathe caffeine–halothane contracture test. This test is invasiverequiring a piece of skeletal muscle to conduct and it isexpensive costing approximately $5,000 (cost in 2008).Noninvasive molecular genetic screening is currently beingdeveloped.
Potential ExposureHalothane is used as an inhalation anesthetic. It has been estimated that halothane accounts for two-thirds of all anesthetics.
Veterinary Drugs and TreatmentsHalothane remains a useful general anesthetic in veterinary medicine due to its relative safety, potency, controllability, non-flammability, and comparatively low cost. However, its use has been largely supplanted by newer agents such as isoflurane and sevoflurane that have less cardiodepressant effects.
ShippingUN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz ardous material, Technical Name Required.
IncompatibilitiesMay attack rubber and some plastics; sensitive to light. Light causes decomposition. May be stabilized with 0.01% thymol. Halothane is incompatible with oxidizers (chlorates, nitrates, peroxides, permanga nates, perchlorates, chlorine, bromine, fluorine, etc.); con tact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Tarnishes or corrodes most metals, with the exception of copper, chromium, nickel, and titanium. Attacks aluminum, brass and lead in the presence of moisture. Attacks rubber and causes some plastics to deteriorate rapidly.
Waste DisposalThe compound is mixed with a combustiblesolvent and burned in a chemical incineratorequipped with an afterburner and scrubber.
2-Bromo-1-chloro-1,1,2-trifluoroethane 2-bromo-1-chloro-1,2,2-trifluoroethan FLUOROETHANE 1,2-DICHLOROTETRAFLUOROETHANE 2-Bromo-2-chloro-1,1,1-trifluoroethane-d 1,2-DIBROMO-2-CHLOROPENTAFLUOROPROPANE 1-CHLORO-1,1-DIBROMO-2,2,2-TRIFLUOROETHANE Fluoxetine 2-CHLORO-1,1,1-TRIFLUOROETHANE 1,1,1,2,3,3,3-Heptafluoropropane 2-BROMO-1,1,1-TRIFLUOROETHANE 1-BROMO-1,1-DICHLOROTRIFLUOROETHANE 1,1,1-Trifluoroethane 2,3-DIBROMO-2-CHLORO-1,1,1,4,4,4-HEXAFLUOROBUTANE [S,(-)]-2-Bromo-2-chloro-1,1,1-trifluoroethane 1,1,1,2-Tetrafluoroethane DIBROMODIFLUOROMETHANE HALOTHANE=2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE

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