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Ethylthiocyanat

Ethyl thiocyanate

HCID 10968
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Grundinformationen

CAS
542-90-5
Standard-SMILES
CCSC#N
InChIKey
WFCLYEAZTHWNEH-UHFFFAOYSA-N
Summenformel
C3H5NS
Durchschnittliche Molmasse
87,15 g/mol
Monoisotopische Masse
87,01427016

Überblick

Ethylthiocyanate is a liquid. Used as an agricultural insecticide. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Ethyl thiocyanate
IUPAC
ethyl thiocyanate
Lokaler Name
Ethylthiocyanat
Englischer Name
Ethylthiocyanate
Summenformel
C3H5NS
Molmasse
87.14

Namen und Synonyme

ETHYL THIOCYANATE542-90-5EthylthiocyanateThiocyanic acid, ethyl esterEthyl rhodanateEthyl sulfocyanateAethylrhodanidEthyl rhodanideEthane, thiocyanato-Ethylthiokyanat(ethylsulfanyl)carbonitrileThiocyanic Acid Ethyl Ester
Weitere Namen anzeigen
ai3-18429ethyl rhodonateethyl thiocyanidethiocyanato-ethanethyl sulfocyanide
MFCD00001834PF9AD5G86ZNSC-8827Aethylrhodanid [German]Ethylthiokyanat [Czech]HSDB 6394NSC 8827EINECS 208-833-3

Datenbank-Bezeichner

CAS
542-90-5
PubChem CID
10968
DTXSID
DTXSID7060259
UNII
PF9AD5G86Z
EC Number
208-833-3
Nikkaji
J1.602K

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
1,3
Polarare Oberfläche (TPSA)
49,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
5
Formalladung
0
Komplexität
51,2

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesBoiling point
PesticidesPesticides -> Other Insecticides
Density · 3 Einträge

1.007 at 73.4 °F (EPA, 1998) - Denser than water; will sink

1.0071 @ 23 °C

1.020 @ 16°C

Color/FormVolatile liquid
SolubilityInsoluble in water; miscible in ethanol, ethyl ether; soluble in chloroform
Boiling Point · 3 Einträge

295 °F at 760 mmHg (EPA, 1998)

146 °C

145 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits very toxic fumes of NOx and SOx.
Melting Point · 3 Einträge

-122 °F (EPA, 1998)

-85.5 °C

-85.5 °C

Vapor Pressure · 2 Einträge

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Thiocyanic acid, ethyl ester

Ethyl thiocyanate: 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 Flammable Liquid
Fire HazardsWhen heated to decomposition, it emits very toxic fumes of oxides of nitrogen and sulfur. (EPA, 1998)
Health HazardsThis material is highly toxic if ingested. (EPA, 1998)
Hazards Summary · 1 Eintrag

In high-dose animal studies, causes somnolence, convulsions, ataxia, paralysis, and changes to the liver and kidneys; [RTECS] Thiocyanates are goitrogenic; [HSDB] A severe irritant capable of causing serious injury in high concentrations; A lachrymator; Effects in high-dose animal studies include convulsions; [MSDSonline] See CYANIDES.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

Verwendung und Herstellung

Uses · 5 Einträge

Used as agricultural insecticide; as insecticidal fumigant; [HSDB]

Farming (Pesticides) [Category: Industry]

Agricultural insecticide

Sometimes employed as insecticidal fumigants.

The thiocyanates have also been used on the skin as delousing preparations and as livestock sprays. /Aliphatic thiocyanates/

General Manufacturing InformationThiocyanic acid, ethyl ester: ACTIVE

Anwendungen

VerwendenEthyl thiocyanate was used in the synthesis of hydrogen cyanide by undergoing in situ reduction with dithiothreitol.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

diazoethanethiourethaneRhodanwasserstoffsäurexanthogenamideTriethyloxoniumtetrafluoroborat(1-)Ethylisothiocyanat

Zugehörige Reaktionen

8
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 8412
HRID 8412als Eduktuspto-grants-2006_08
Reaktionsgleichung von HRID 392863
HRID 392863als Eduktuspto-grants-2004_10
Reaktionsgleichung von HRID 496853
HRID 496853als Eduktuspto-grants-2005_09
Reaktionsgleichung von HRID 949193
HRID 949193als EduktValidation data from https://doi.org/10.1039/C8SC04228D
Reaktionsgleichung von HRID 1062352
HRID 1062352als Eduktuspto-grants-2005_11
Reaktionsgleichung von HRID 1110126
HRID 1110126als Eduktuspto-grants-1994_06
Reaktionsgleichung von HRID 1790387
HRID 1790387als Eduktuspto-grants-2006_07
Reaktionsgleichung von HRID 2260828
HRID 2260828als Eduktuspto-grants-1995_12

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4.83 [mmHg]

4 [mm Hg] @25 °C

Refractive IndexIndex of refraction: 1.4684 @ 15 °C/D
Physical Description · 2 Einträge

Ethylthiocyanate is a liquid. Used as an agricultural insecticide. (EPA, 1998)

Volatile liquid; [HSDB] Clear faintly yellow liquid; [MSDSonline]

Physikochemische Eigenschaften

Schmelzpunkt
-85.5 °C · -85.5°C
Siedepunkt
145 °C · 145 °C(lit.)
Dichte
1.012 g/mL · 1.012 g/mL at 25 °C(lit.)
Brechungsindex
20 · n20/D 1.462(lit.)
Flammpunkt
109 °F · 109 °F
storage temp.
Flammables area
Aggregatzustand
liquid
Farbe
Colorless to Almost colorless
BRN
1737620 · 1737620
Henry's Law Constant
1.7 · 1.7×10-1 mol/(m3Pa) at 25℃, HSDB (2015)
Dielectric constant
29.6 · 29.6(20℃)
InChI
InChI=1S/C3H5NS/c1-2-5-3-4/h2H2,1H3
InChIKey
WFCLYEAZTHWNEH-UHFFFAOYSA-N
SMILES
S(CC)C#N
LogP
1.011 · 1.011 (est)
CAS Datenbank
542 · 542-90-5(CAS DataBase Reference)
NIST chemische Informationen
Thiocyanic acid, ethyl ester(542-90-5)
EPA chemische Informationen
Ethyl thiocyanate (542-90-5)
Reactive Group
Isocyanates and Isothiocyanates
Reactivity ProfileNitric acid violently oxidized a thiocyanate solution [Bretherick, 1979 p. 121]. Caution should be exercised in treating a thiocyanate with an oxidizing agent such as a peroxide or chlorate as such mixtures have been known to explode.
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
CERCLA Reportable Quantities · 1 Eintrag

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. Ethylthiocyanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.

Hazard Classes and CategoriesFlam. Liq. 3 (100%)
Skin, Eye, and Respiratory Irritations... irritant to skin & eyes. ... /Aliphatic thiocyanates/

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

(Non-Specific -- Pesticide, Liquid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First AidNote: Ethylthiocyanate is very readily absorbed through the skin.
Nonfire Spill Response · 1 Eintrag

(Non-Specific -- Pesticide, Liquid, n.o.s.) Do not touch spilled material; stop leak if you can do so without risk. Use water spray to reduce vapors. For small spills, absorb with sand or other noncombustible absorbent material and place into containers for later disposal. For large spills, dike far ahead of spill for later disposal. (EPA, 1998)

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Protective Action Criteria (PAC) · 3 Einträge

1.5 [mg/m3]

17 [mg/m3]

84 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Toxikologische Informationen

Treatment · 1 Eintrag

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

InteractionsThe thiocyanates have synergistic insecticidal effects in combination with DDT, carbaryl and organophosphates like parathion. /Aliphatic thiocyanates/
Health Effects · 1 Eintrag

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 15(SRC), determined from a structure estimation method(2), indicates that ethyl thiocyanate is expected to have very high mobility in soil(SRC). Volatilization of ethyl thiocyanate from moist soil surfaces may be important(SRC) given an estimated Henry's Law constant of 5.82X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethyl thiocyanate from dry soil surfaces may exist(SRC) based on an estimated vapor pressure of 5 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data for ethyl thiocyanate are not readily available(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 15(SRC), determined from a structure estimation method(2), indicates that ethyl thiocyanate is not expected to adsorb to suspended solids and sediment in water(SRC). Ethyl thiocyanate may volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 5.82X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated volatilization half-lives for a model river and model lake are 16.8 hours and 191.1 hours, respectively(3,SRC). According to a classification scheme(5), an estimated BCF of 5.0(3,SRC), from an estimated log Kow of 1.22(6,SRC), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation data for ethyl thiocyanate are not readily available(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl thiocyanate, which has an estimated vapor pressure of 4.8 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl thiocyanate 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 about 2.2 days(3,SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesOral (L96) ; inhalation (L96) ; dermal (L96)
Toxicity Summary · 1 Eintrag

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Signs and SymptomsCyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethyl thiocyanate can be estimated to be about 15(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that ethyl thiocyanate is expected to have very high mobility in soil(SRC).

Natural Pollution Sources · 1 Eintrag

Food-borne goitrogens are often characterized by the presence of sulfur and most are thiocyanates or closely related compounds. Because of their widespread occurrence in Cruciferae, eg, cabbage, kale, onions, cress, broccoli, cauliflower, rutabaga, turnip & radish, goitrogens are among the most common and longest recognized substances of toxic nature in the human food supply. ... It has ... been demonstrated that the quantity of the precursor found in plant materials is related to the available sulfur in the soil. /Goitrogens/

Human Toxicity Excerpts · 3 Einträge

All /aliphatic thiocyanates/ have an appreciable percutaneous toxicity, although this is not regarded as an important hazard with the concentrations usually employed in agriculture. Primary irritation of skin and eyes due to local contact, however, is not a negligible hazard, and the undiluted liquids may produce very severe cutaneous reactions ... /Aliphatic thiocyanates/

... important qualitative distinctions are recognized among the various organic thiocyanates. ... ethyl ... thiocyanate .. /is a/ rapidly acting poison of high potency.

Food-borne goitrogens are often characterized by the presence of sulfur and most are thiocyanates ... /Goitrogens/ are among the most common and longest recognized substances of toxic nature in the human food supply. /Goitrogens/

Artificial Pollution SourcesEthyl thiocyanate's production and use in industry and research(1) as well as an intermediate for pesticides(2) may result in its release to the environment through various waste streams(SRC).

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

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. Ethylthiocyanate is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.

Sicherheitsdaten

F
13-19-21
wgk
3
tsca
TSCA listed
ridadr
UN 2929 6.1/PG 2
hs_code
29309070
RTECS-Nr.
XK9900000
risk_code
10-20/21/22-36/37/38
hazard_code
Xn
safety_code
26-36/37-24/25-16
hazard_class
3.2
packing_group
III
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
542-90-5(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralFlam. Liq. 3
Bromethan
Ethanol
Ethyltoluol-4-sulfonat
Kaliumthiocyanat

Nachgelagerte Produkte

EthansulfonylchloridEthylchlorthiolformiatPiperidinocarbonitril1,3-dihydrobenzo[c]thiophene5-(Ethylthio)-1H-tetrazole