2-Fluoracetamid

Fluoroacetamide

HCID 12542

Grundinformationen

CAS
640-19-7
Standard-SMILES
NC(=O)CF
InChIKey
FVTWJXMFYOXOKK-UHFFFAOYSA-N
Summenformel
C2H4FNO
Durchschnittliche Molmasse
77,06 g/mol
Monoisotopische Masse
77,02769191

Überblick

Fluoroacetamide is a colorless crystalline powder. Used as a rodenticide. Highly toxic.

Namen und Bezeichner

Bevorzugter Name
Fluoroacetamide
IUPAC
2-fluoroacetamide
Lokaler Name
2-Fluoracetamid
Englischer Name
Fluoroacetamide
Summenformel
C2H4FNO
Molmasse
77.06

Namen und Synonyme

FLUOROACETAMIDE2-Fluoroacetamide640-19-7MonofluoroacetamideAcetamide, 2-fluoro-FluorkillFussolMegatoxYanockNavronFluoroacetic acid amideFluorakil 100
Weitere Namen anzeigen
1081RODEXRHODEXafl1081APHITOX
Compound 1081Fluoroakil 100Flutritex 1FluoracetamideBaranAFL 1081RCRA waste number P057Caswell No. 461

Datenbank-Bezeichner

CAS
640-19-7
PubChem CID
12542
DTXSID
DTXSID2034255
ChEMBL
CHEMBL160811
ChEBI
CHEBI:53124
UNII
B18R611M38
EC Number
211-363-1
Nikkaji
J2.102D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1
Polarare Oberfläche (TPSA)
43,1 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
5

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesSchoenflies notation
Pesticides · 3 Einträge

Rodenticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Rodenticides

LogP · 3 Einträge

log Kow= -1.05

-1.05

-1.05

Color/Form · 2 Einträge

Colorless crystalline powder

White...solid

Solubility · 3 Einträge

Freely sol in water, sol in acetone; sparingly sol in chloroform

Moderately sol in ethanol; sparingly sol in aliphatic and aromatic hydrocarbons

Solubility in water: very good

Boiling Point · 3 Einträge

Sublimes on heating (EPA, 1998)

Sublimes

250 °C @760 [mm Hg]

Physikochemische Eigenschaften

Schmelzpunkt
106 · 106-108 °C(lit.)
Siedepunkt
259 · 259.0±10.0 °C(Predicted)
Dichte
1.117 · 1.1170 (estimate)
Löslichkeit
DMSO (Soluble), Methanol (Slightly)
Aggregatzustand
Solid
pka
14.6 · 14.60±0.40(Predicted)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 4 Einträge

T - indicates a substance that is the subject of a final TSCA section 4 test rule.

2004/129/EC

Acetamide, 2-fluoro-: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire Hazards · 2 Einträge

Emits very toxic fumes of fluorine containing compounds and nitrogen oxides when heated to decomposition. Avoid decomposing heat. (EPA, 1998)

Gives off irritating or toxic fumes (or gases) in a fire.

Health Hazards · 1 Eintrag

This material is super toxic; probable oral lethal dose in humans is less than 5 mg/kg, or a taste (less than 7 drops) for a 150-lb. person. Chemically inhibits oxygen metabolism by cells with critical damage occurring to the heart, brain, and lungs resulting in heart failure, respiratory arrest, convulsions, and death. (EPA, 1998)

Hazards Summary · 2 Einträge

Can be absorbed through skin; In animal experiments, toxic to the heart (fatal arrhythmias) and reproductive system; [ICSC] A testicular poison in animal studies; [HSDB] Probable oral lethal dose in humans is less than 5 mg/kg (less than 7 drops); Inhibits oxygen metabolism by cells; [CAMEO] Converted to fluoroacetic acid in vivo causing buildup of fluorocitric acid and inhibiting Krebs cycle; [UNEP] May cause irritation; Can be absorbed through skin; Metabolized to fluoroacetate (highly toxic); [MSDSonline] See Sodium fluoroacetate.

The major hazards encountered in the use and handling of fluoroacetamide stem from its toxicologic properties. Exposure to this colorless, crystalline powder may occur from its manufacture, formulation, and use as a rodenticide. Effects from exposure may include nausea, convulsions, cyanosis, ventricular fibrillation, and death. Effects may be delayed up to 20 hours following exposure. If contact should occur, remove clothing and vigorously wash skin, hair, and nails with soap. Fluoroacetamide should be stored in closed containers in a cool, closed area.

Reactive GroupAmides and Imides

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer for medical attention .

First AidWarning: Effects usually appear within 30 minutes of exposure but may be delayed as long as 20 hours. Caution is advised. Vital signs should be monitored closely.
Safe StorageSeparated from acids.
Storage ConditionsSTORE IN CLOSED CONTAINERS IN CLOSED AREA.
Nonfire Spill Response · 1 Eintrag

Caution : Fluoroacetamide is extremely toxic. There is no known antidote. Immediately transport victims to a health care facility. Highly toxic fumes of fluorine-containing compounds and nitrogen oxides will be emitted when fluoroacetamide is heated to decomposition. Avoid sources of extreme heat including fire.

Toxikologische Informationen

Treatment · 1 Eintrag

Consider gastric lavage after ingestion, and/or administer charcoal as a slurry. In case of refractory seizures after following ingestion, consider continuous infusion of midazolam, propofol, and/or pentobarbital. Hyperthermia, lactic acidosis and muscle destruction may necessitate use of neuromuscular blocking agents with continuous EEG monitoring. If the exposure occurred through inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of acute lung injury, maintain ventilation and oxygenation and evaluate with frequent arterial blood gas or pulse oximetry monitoring. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. In case of dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. (T36)

InteractionsTOXIC EFFECTS OF SUCROSE-CONTAINING SODIUM FLUOROSILICATE FED TO HOUSEFLIES IS DELAYED WHEN DIFLUBENZURON IS ADDED. A SIMILAR, THOUGH LESS PRONOUNCED, EFFECT IS EXERTED BY DFB IN FLUOROACETAMIDE TOXICITY.
Health Effects · 1 Eintrag

Metabolic acidosis, hyperglycemia, hyperuricemia, elevated serum levels of hepatic transaminases, and elevated serum creatinine levels may occur. Tachycardia, ventricular tachycardia or fibrillation, and sudden onset of asystole may occur (T36).

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc of 6.4(2), indicates that fluoroacetamide is expected to have very high mobility in soil(SRC). Volatilization of fluoroacetamide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of fluoroacetamide from dry soil surfaces may exist (SRC) based upon an estimated vapor pressure of 0.99 mm Hg(SRC), determined from a fragment constant method(4). The persistence of fluoroacetamide was studied in garden soil by determining its toxicity to aphids(5); at a concn of 50 ppm, toxicity had ceased after 11 weeks of incubation; at a conc of 10 ppm, toxicity lasted only 3 weeks; in a control soil that had been steam sterilized, toxicity was still evident at both concns after 17 weeks suggesting that the degradation was microbial in nature(5).

AQUATIC FATE: Based on a classification scheme(1), a Koc of 6.4(2), indicates that fluoroacetamide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.2X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The neutral hydrolysis rate constant for fluoroacetamide at 25 °C was experimentally determined to be 3.3X10-5/hr which corresponds to an aqueous hydrolysis half-life of 2.4 yr at pH 7(8). This indicates that hydrolysis is slow(SRC). It has been suggested that fluoroacetamide should be degradable by biological sewage treatment provided suitable acclimatization can be achieved(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluoroacetamide, which has an estimated vapor pressure of 0.99 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase fluoroacetamide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC). The half-life for this reaction in air is estimated to be 7.8 days(SRC), calculated from its rate constant of 2.1X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.

Inhalation (L1160) ; oral (L1160) ; dermal (L1160) ; eye contact (L1160).

Regulatorische Informationen

RCRA Requirements · 1 Eintrag

P057; As stipulated in 40 CFR 261.33, when fluoroacetamide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).

FIFRA Requirements · 1 Eintrag

In 1988, Congress amended FIFRA to strengthen and accelerate EPA's reregistration program which applies to each registered pesticide product containing an active ingredient initially registered before November 1, 1984. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for exposure and other factors, with List B being of highest concern and D of least. List: C; Case: fluoroacetic acid derivatives; Case No.: 3073; Pesticide type: insecticide, rodenticide; Case Status: RED Approved 6/95; OPP has made a decision that some/all uses of the pesticide are eligible for reregistration, as reflected in a Reregistration Eligibility Decision (RED) document. ; Active Ingredient (AI): fluoroacetamide; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled.".

CERCLA Reportable Quantities · 2 Einträge

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.5 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Fluoroacetamide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered for and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Sicherheitsdaten

wgk
2
tsca
TSCA listed
ridadr
UN 2811 6.1/PG 2
hs_code
29241200
RTECS-Nr.
AC1225000
risk_code
24-28

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

FLUOROACETATE PRODUCES ITS TOXIC ACTION BY INHIBITING THE CITRIC ACID CYCLE. THE FLUORINE SUBSTITUTED ACETATE BECOMES INCORPORATED, AS A NORMAL ACETATE, INTO FLUOROACETYL COENZYME A, WHICH CONDENSES WITH OXALOACETATE TO FORM FLUOROCITRATE. FLUOROCITRATE INHIBITS THE ENZYME ACONITASE & THEREBY INHIBITS THE CONVERSION OF CITRATE TO ISOCITRATE. AS A RESULT THERE IS AN ACCUMULATION OF LARGE QUANTITIES OF CITRATE IN THE TISSUE, & THE CYCLE IS BLOCKED. ... THE HEART & CNS ARE THE MOST CRITICAL TISSUES INVOLVED IN POISONING BY GENERAL INHIBITION OF OXIDATIVE ENERGY METABOLISM. /FLUOROACETATE/

FLUOROACETAMIDE ... /IS/ TOXIC TO MAMMALS PRESUMABLY BECAUSE OF METABOLIC ... /HYDROLYSIS/ TO FLUOROACETATE.

Moderately fast-acting rodenticide which is less likely to lead to poison shyness because of sublethal dosing. It acts chiefly on the heart, with secondary effects on CNS.

Metabolism/Metabolites · 4 Einträge

INVESTIGATORS ARE AGREED THAT FLUOROACETAMIDE IS LESS TOXIC THAN FLUOROACETATE. THIS HAS BEEN ATTRIBUTED TO THE FACT THAT METABOLISM OF THE FORMER TO THE LATTER IS SLOW. ... RECOVERED, FROM THE URINE OF RATS RECEIVING FLUOROACETAMIDE AT A RATE OF 3 MG/KG/DAY, 62% OF THE TOTAL INTAKE UNMETABOLIZED ... .

2,4-Dinitrofluorobenzene reacts with glutathione to form a stable product similar to that formed with the model glutathione-S-transferase substrate, 1-chloro-2,4-dinitrobenzene. ... Fluoroacetamide, like fluoroacetate, undergoes no discernable chemical defluorinantion. Its enzymatic defluorination is approx 10% of that observed for fluoroacetate and only 0.2% of the rate for 2,4-dinitrofluorobenzene. An antibody raised to the fluoroacetate specific dehalogenase precipitated both fluoroacetate ad fluoroacetamide defluorinating activity but had no effect on either 1-chloro-2,4-dinitrobenzene or 2,4-dinitrofluorobenzene activity. ... 2,4-Dinitrofluorobenzene is metabolized by the glutathione-S-transferase while fluoroacetamide is metabolized by the fluoroacetate specific dehalogenase.

Fluoroacetate administered ip to rats and mice is defluorinated to give fluoride ion evident in urine and kidney by (19)F NMR. The use of 2-(13)C-, 1,2-(13)C-, and 1,2-(14)C-fluoroacetate, ... reveals a complex mixture of urinary metabolites including an S-(carboxymethyl) conjugate complex in rats and mice and sulfoxidation products ... in rats. ... Bile, following treatment with 2-(13)C- fluoroacetate, shows the presence of S-(carboxymethyl)glutathione or a related conjugate and an O-conjugate of fluoracetate. Incubation of (13)C-fluoroacetate with rat and mouse liver cytosol involves formation of S-((13)C-carboxymethyl) glutathione and fluoride ion. Fluorocitrate is also /detected in/ fluoracetate incubations with mouse liver cytosol. Fluoroacetamide administered ip to rats and mice yields urinary fluoride ion formed via fluoroacetate which is liberated on hydrolysis by an organophosphate-sensitive amidase. (19)F NMR ... of other metabolites of fluoroacetamide are consistent with fluoroacetohydroxamic acid in the liver of mice and fluorocitrate in the urine of rats. Fluoroethanol gives rinary fluoroacetate and fluoride ion in rats and mice and is converted to fluoroacetaldehyde by mouse and rat liver microsomes. (-)- and (+)-erythro- fluorocitrates administered ip to rats yield mostly the parent compounds in urine at 6 hr with increasing amounts of fluoride ion thereafter. ... Rat and mouse liver cytosols defluorinate (-)-erythro-fluorocitrate. Metabolic defluorination and pig heart aconitase also defluorinates (-)-erythro- fluorocitrate. Metabolic defluorination of fluoracetate and its progenitors, fluoroacetamide and fluoroethanol, is therefore attributable to both conjucation of fluoracetate with glutathione and conversion to (-)-erythro-fluorocitrate, which is both an inhibitor of and a substrate for aconitase. ... Urine of rats and mice poisoned with fluoroacetate or (-)-erythro-fluorocitrate show elevated citrate and glucose and diminished urea consistent with disruptions in the tricarboxylic acid cycle and ammonia metabolism.

Fluoroacetamide is metabolized by the fluoroacetate specific dehalogenase (A323).

Absorption, Distribution and ExcretionTHE CMPD IS ABSORBED BY THE SKIN.

Verwendung und Herstellung

Uses · 6 Einträge

Used as rodenticide and insecticide; [HSDB] Used as a rodenticide in the US and as pesticide in other countries; The only continued registration in the US after 1980 was for rat control in sewers with application by certified professionals and highly restricted; [EPA OHM/TADS]

No longer registered with the EPA for use in the US; [HSDB] Banned in the EU for use as pesticide; [eChemPortal: ESIS] Use in Israel and Japan (insecticide for citrus) requires special permit from the government (as of 1991); [UNEP]

Farming (Pesticides) [Category: Industry]

For Fluoroacetamide (USEPA/OPP Pesticide Code: 075002) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Rodenticide, insecticide proposed mainly for use on fruits to combat scale insects, aphids, mites. /Former use/

Normally it is used as a bait /(20 g ai/kg)/ in areas to which the public has no access such as sewers and locked warehouses. /Former use/

ImpuritiesSometimes colored with black dye, nigrosine.
Consumption PatternsESSENTIALLY 100% AS A RODENTICIDE.
Methods of Manufacturing · 3 Einträge

Fluoroacetamide is made by reacting fluoroacetyl chloride and ammonia.

Sodium fluoroacetate + ammonia (amide formation)

Made from chloroacetamide by fluorination process using KF.

Formulations/Preparations · 4 Einträge

USEPA/OPP Pesticide Code 075002; Trade Names: Fluorkill, compound 1081, 1081.

BAIT, DYED CEREAL BASE (30 G AI/KG) WHICH IS MIXED WITH WATER FOR USE.

Poisoned grains; bait pellets

Usually packed in 8 oz (227 g) or 5 kg cans

General Manufacturing Information · 5 Einträge

Acetamide, 2-fluoro-: ACTIVE

The WHO Recommended Classification of Pesticides by Hazard identifies Fluoroacetamide (technical grade) as Class IB: highly hazardous; Main Use: rodenticide. According to the PIC /Prior Informed Consent/ Convention, export of /Fluoroacetamide/ can only take place with the prior informed consent of the importing Party. ...(further information can be found at: http://www.pic.int/).

/FLUOROACETAMIDE/ USE IS LARGELY RESTRICTED TO LICENSED PEST CONTROL OPERATORS.

THE POISONING OF FARM ANIMALS BY EFFLUENTS FROM A FACTORY THAT MFR FLUOROACETAMIDE CAUSED THE MINISTRY OF AGRICULTURE, FISHERIES, & FOOD TO RECOMMEND THAT THE CMPD SHOULD NOT BE USED AS AN INSECTICIDE IN AGRICULTURE, HOME GARDENS, OR FOOD STORAGE IN GREAT BRITAIN, & IT WAS WITHDRAWN FROM THE MARKET.

A rebuttable presumption against registration was issued by EPA on November 22, 1976 on the basis of toxicity to nontarget species ... . The RPAR was terminated on February 28, 1980

Anwendungen · 3 Einträge

BeschreibungDas Fluoracetamid bildet farblose, mäßig wasserlösliche, sehr giftige Kristalle. Die Verbindung besitzt nur wissenschaftliches Interesse.

BeschreibungFluoroacetamide is an odourless, tasteless, white, crystalline water soluble. It is a fluorinated amide and reacts with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Fluoroacetamide is used as a rodenticide and insecticide to control rabbits but is dangerous for other species of pests, farm livestock, and humans. Fluoroacetamide is a noncombustible substance itself and does not burn but may decompose upon heating to produce irritating, corrosive, and/or toxic fumes. On decomposition, fluoroacetamide releases nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, HF gas, and nitrogen gas.

VerwendenRodenticide. Insecticide proposed mainly for use on fruits to combat scale insects, aphids, and mites.

Ergänzende Hinweise

DefinitionChEBI: Acetamide substituted at C-2 by a fluorine atom.

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