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Ethylisocyanat

Ethyl isocyanate

HCID 8022
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Grundinformationen

CAS
109-90-0
Standard-SMILES
CCN=C=O
InChIKey
WUDNUHPRLBTKOJ-UHFFFAOYSA-N
Summenformel
C3H5NO
Durchschnittliche Molmasse
71,08 g/mol
Monoisotopische Masse
71,03711378

Überblick

Ethyl isocyanate appears as a colorless liquid. Less dense than water and insoluble in water. May irritate skin, eyes, and mucous membranes. May be lethal by Inhalation. Used to make pharmaceuticals and pesticides.

Namen und Bezeichner

Bevorzugter Name
Ethyl isocyanate
IUPAC
isocyanatoethane
Lokaler Name
Ethylisocyanat
Englischer Name
Ethyl isocyanate
Summenformel
C3H5NO
Molmasse
71.08

Namen und Synonyme

ETHYL ISOCYANATEIsocyanatoethane109-90-0Ethane, isocyanato-Isocyanic acid, ethyl esterB02YQ4MIR0CHEBI:85107NSC-89687DTXSID5059379RefChem:138962DTXCID4033132203-717-9
Weitere Namen anzeigen
isocyanatoetheneC2H5NCOethyl爄socyanateisocyanato-ethanisocyanated’ethyleethane,isocyanato-
Isocyanic acid ethyl esterisocyanato-ethaneethylisocyanateMFCD00002042HSDB 6318EINECS 203-717-9NSC 89687UN2481

Datenbank-Bezeichner

CAS
109-90-0
PubChem CID
8022
DTXSID
DTXSID5059379
ChEBI
CHEBI:85107
UNII
B02YQ4MIR0
EC Number
203-717-9
Nikkaji
J53.650D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,4
Polarare Oberfläche (TPSA)
29,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
1
Schwere Atome
5
Formalladung
0
Komplexität
53,9

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Toxic Gases & Vapors -> Monoisocyanates

Flammable agents - 3rd degree

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
OdorPungent smelling
Density · 3 Einträge

0.9031g/cu cm

Isocyanates...are highly reactive and undergo addition reactions across the carbon-nitrogen double bond of the NCO group. Reactions with alcohols, carboxylic acids, and amines have been widely exploited...The basis for the high reactivity of the isocyanates is the low electron density of the central carbon...Electron withdrawing or donating substituents alter the electrophilic nature of the isocyanate...The reactivity of the isocyanates is also manifested in their tendency to react with themselves to form dimers, trimers, or higher oligomers and polymers. /Isocyanates/

0.9031 @25 °C

Color/FormLiquid
Solubility · 2 Einträge

Miscible in ethanol, ether

Soluble in chlorinated and aromatic hydrocarbons

Boiling Point

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

Danger

H225 (95.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P284, P301+P316, P301+P317, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P320, P321, P330, P332+P317, P337+P317, P342+P316, P362+P364, P370+P378, P403, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazards IdentificationToxic/poison by inhalation (TIH/PIH)
Regulatory Information · 2 Einträge

Ethyl isocyanate: HSNO Approval: HSR004473 Approved with controls

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 Inhalation Hazard Flammable Liquid
Fire Hazards · 2 Einträge

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Health Hazards · 2 Einträge

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 1 Eintrag

The inactivation of guinea pig liver transglutaminase was investigated using aliphatic isocyanates. It was found that one equivalent of ethyl isocyanate reduced transglutaminase activity to less than 25% within 3 minutes. ... The isocyanates reacted slowly with the sulfhydryl groups of reduced glutathione, indicating enzyme inactivation with transglutaminase. The investigators concluded that alkyl isocyanates inactivate guinea pig liver transglutaminase by forming N-alkylthiocarbamyl ester with the single active site sulfhydryl group of the enzyme.

Metabolism/Metabolites · 2 Einträge

... Reactive isocyanates in general, can react with biological molecules containing amino, alcohol, or sulfhydryl groups, as well as with water. While hydrolysis in an aqueous environment, such as the lung, is theoretically possible, measurements show that alkyl isocyanates are relatively resistant (compared to arylisocyanates) to such hydrolysis.

Isocyanates ... form labile glutathione conjugates from which they can be released. /Isocyanate/

Verwendung und Herstellung

Uses · 2 Einträge

Used as an intermediate for pharmaceuticals and pesticides; [Hawley]

Pharmaceutical and pesticide intermediate.

Methods of ManufacturingThe reaction of phosgene with amines or amine salts and the thermal cleavage of urethanes, preformed from the appropriate amine, urea,and an alcohol, are used commercially on a large scale. /Isocyanates/
General Manufacturing Information · 3 Einträge

Ethane, isocyanato-: ACTIVE

... L-cysteine hydrochloride was converted into S-ethylcarbamyl-L-cysteine by treatment with ethyl isocyanate in dimethylformamide solution.

Ethyl isocyanate ... was reduced with lithium aluminum deuteride and nitrosated with sodium nitrite to yield, the carcinogen nitrosomethyl (d3) ethylamine

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· 2 Einträge

60 °C

60 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits toxic fumes of /nitrogen oxides/.
Vapor Density2.45 (Air = 1)
Vapor Pressure · 2 Einträge

17.5 [mmHg]

200 [mm Hg] @25 °C

Optical RotationSpecific optical rotation = 1.3808 at 20 °C/D
Refractive IndexIndex of refraction: 1.3808 at 20 °C/D

Physikochemische Eigenschaften

Schmelzpunkt
-50 · <-50
Siedepunkt
60 °C · 60 °C(lit.)
Dichte
0.898 g/mL · 0.898 g/mL at 25 °C(lit.)
Dampfdruck
4.34 psi · 4.34 psi ( 20 °C)
Brechungsindex
20 · n20/D 1.381(lit.)
Flammpunkt
20 °F · 20 °F
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand
Oil
Farbe
Colourless
Wasserlöslichkeit
Insoluble
BRN
773743 · 773743
Stabilität
Hygroscopic, Moisture sensitive, Volatile
CAS Datenbank
109 · 109-90-0(CAS DataBase Reference)
NIST chemische Informationen
Ethane, isocyanato-(109-90-0)
EPA chemische Informationen
Ethyl isocyanate (109-90-0)
Hazards Summary · 1 Eintrag

An irritant that can cause acute inhalation injury; [HSDB] A strong irritant; [Hawley] Highly flammable; May react with water forming a corrosive liquid and carbon dioxide gas; May cause irritation; Inhalation may be fatal; [CAMEO] A lachrymator; A severe skin, eye, and respiratory tract irritant capable of causing severe injury and permanent damage; Inhalation may cause sufficient damage to lungs and respiratory system to cause death; Symptoms include convulsions, chemical bronchitis, pulmonary edema, and coma; A possible skin and respiratory sensitizer; [CHEMINFO] A dermal sensitizer; [ACGIH] A skin and eye irritant; May cause respiratory sensitization after prolonged contact; [eChemPortal: ERMA] A lachrymator; An irritant; May cause respiratory sensitization after prolonged contact; Effects in high-dose animal studies include convulsions and lacrimation; [MSDSonline] See MONOISOCYANATES.

DOT ID and Guide2481 155
Reactive GroupIsocyanates and Isothiocyanates
TSCA Requirements · 2 Einträge

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethane, isocyanato is included on this list.

Reactivity AlertsHighly Flammable
Reactivity ProfileWhen heated to decomposition ETHYL ISOCYANATE emits toxic fumes of nitrogen oxides [Sax, 9th ed., 1996, p. 1572].
DOT Emergency Guidelines · 5 Einträge

If ... THERE IS NO FIRE, go directly to the Table of Initial Isolation and Protective Action Distances /(see table below)/ ... to obtain initial isolation and protective action distances. IF THERE IS A FIRE, or IF A FIRE IS INVOLVED, go directly to the appropriate guide /(see guide(s) below)/ and use the evacuation information shown under PUBLIC SAFETY.

/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Health: TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Bromoacetates and chloroacetates are extremely irritating/lachrymators. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

/GUIDE 155: SUBSTANCES - TOXIC and/or CORROSIVE (Flammable/Water-Sensitive)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.

For more DOT Emergency Guidelines (Complete) data for ETHYL ISOCYANATE (9 total), please visit the HSDB record page.

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

General First Aid:

Exposure Control and Personal Protection · 2 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].

Fire Fighting Procedures · 2 Einträge

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

Persons involved in fighting fires should wear a self-contained breathing apparatus with a full facepiece operated in a pressure-demand or other positive pressure mode. ... /Methyl isocyanate/

Cleanup MethodsFor small quantities absorb on paper towels. /Methyl isocyanate/
Nonfire Spill ResponseExcerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:
Disposal Methods · 2 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

/For small quantities/ evaporate material in a fume hood. /Methyl isocyanate/

Preventive Measures · 5 Einträge

... Employees should change into uncontaminated clothing before leaving the work premises. Contaminated clothing should be placed in closed containers until it can either be discarded or until provision can be made for the removal of the contaminant. Employees should also be provided with emergency eyewash stations ... . /Methyl isocyanate/

Do not allow this material to enter a confined space, such as a sewer, because of the possibility of an explosion. /Methyl isocyanate/

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.

For more Preventive Measures (Complete) data for ETHYL ISOCYANATE (6 total), please visit the HSDB record page.

Isolation and Evacuation · 4 Einträge

Excerpt from ERG Guide 155 [Substances - Toxic and/or Corrosive (Flammable / Water-Sensitive)]:

Immediate precautionary measure

Small spill:

Small spill:

Threshold Limit Values (TLV) · 2 Einträge

0.02 [ppm]

0.06 [ppm]

Protective Action Criteria (PAC) · 3 Einträge

0.0031 [ppm]

0.034 [ppm]

0.10 [ppm]

Toxikologische Informationen

Interactions · 1 Eintrag

The effects of 2-chloroethylisocyanate, ethylisocyanate and sodium cyanate on the uptake of isotope-labeled thymidine, leucine and H2O were compared in rat liver and hepatomas. The data suggested that carbamoylating agents may have a common property of inhibiting uptake of compounds in hepatomas under conditions in which there is a smaller effect or no action in the liver of tumor-bearing rats. The distinction between tissues may have been mediated, in part, through effects on tumor circulation and was less apparent when isolated cells were studied in vitro. Preferential inhibitory effects of carbamoylating agents on the uptake of leucine and H2O were also observed with a murine hepatoma, but they were not as great as with rat hepatomas.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Isocyanates undergo rapid hydrolysis under environmental conditions with half-lives of less than 10 minutes(1). Therefore, hydrolysis is expected to be the dominant fate process for ethyl isocyanate in moist soil(SRC). Soil adsorption, biodegradation, and volatilization from moist soil are not expected to compete with hydrolysis as important fate and transport processes(SRC). Ethyl isocyanate may volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 200 mm Hg(2).

AQUATIC FATE: Isocyanates undergo rapid hydrolysis under environmental conditions with half-lives of less than 10 minutes(1). Therefore, hydrolysis is expected to be the dominant fate process for ethyl isocyanate in water(SRC). Sorption to sediments, volatilization, bioconcentration, and biodegradation are not expected to compete with hydrolysis as important fate and transport processes in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl isocyanate, which has an estimated vapor pressure of 200 mm Hg at 25 °C(SRC), determined from a structure estimation method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl isocyanate 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 15 days(SRC), calculated from its rate constant of 1.1X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Ethyl isocyanate does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

Adverse EffectsDermatotoxin - Skin burns.
Medical Surveillance · 1 Eintrag

Initial Medical Examination: A complete history and physical examination should be performed to detect pre-existing conditions that might place the exposed employee at an increased risk and to establish a baseline for future health monitoring. Examination of the eyes and respiratory tract should be stressed and the skin should be examined for evidence of chronic disorders. The aforementioned medical examinations should be repeated on an annual basis. /Methyl isocyanate/

Soil Adsorption/Mobility · 1 Eintrag

Isocyanates undergo rapid hydrolysis under environmental conditions with half-lives of less than 10 minutes(1). Therefore, hydrolysis is expected to be the dominant fate process for ethyl isocyanate in moist soil and water(SRC). Adsorption to soil and sediment is not expected to compete with hydrolysis as an important environmental process(SRC).

Human Toxicity Excerpts · 4 Einträge

/SIGNS AND SYMPTOMS/ Exposure of humans to high concn may cause cough, dyspnea, chest pain and an increase in secretions. /Methyl isocyanate/

/SIGNS AND SYMPTOMS/ Isocyanates are irritating to the skin and the mucous membranes, the skin conditions ranging from localized itching to more or less widespread eczema. Eye affections are less common and, although lacrimation is often found, conjunctivitis is rare. The commonest and most serious troubles, however, are those affecting the respiratory systems. /Isocyanates/

/SIGNS AND SYMPTOMS/ Isocyanates ... produce lung disease /in/ manufacture of plastics and chemical industry. Acute effects /include/ airway irritation, cough, /and/ dyspnea; chronic effects /include asthma, and/ reduced pulmonary function. /From table, isocyanates/

/EPIDEMIOLOGY STUDIES/ /During/ 0.5 to 4 yr of follow-up after leaving work, /among total of 104/ subjects with occupational asthma /from isocyanate exposure/, 50 to 82% /had/ persistence of symptoms and 58 to 77% of bronchial hyperresponsiveness. /From table, isocyanates/

Artificial Pollution SourcesEthyl isocyanate's production and use as an intermediate in the production of pharmaceuticals and pesticides(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

Isocyanates undergo rapid hydrolysis under environmental conditions with half-lives of less than 10 minutes(1). Therefore, hydrolysis is expected to be the dominant fate process for ethyl isocyanate in moist soil and water(SRC). Biodegradation is not expected to compete with hydrolysis as an important fate process(SRC).

Environmental Bioconcentration · 1 Eintrag

Isocyanates undergo rapid hydrolysis under environmental conditions with half-lives of less than 10 minutes(1). Therefore, hydrolysis is expected to be the dominant fate process for ethyl isocyanate in water(SRC). Bioconcentration is not expected to compete with hydrolysis as an important environmental process(SRC).

Volatilization from Water/Soil · 1 Eintrag

Isocyanates undergo rapid hydrolysis under environmental conditions with half-lives of less than 10 minutes(1). Therefore, hydrolysis is expected to be the dominant fate process for ethyl isocyanate in moist soil and water(SRC). Volatilization from moist soil and water surfaces is not expected to compete with hydrolysis as an important removal process(SRC). Ethyl isocyanate may volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 200 mm Hg at 25 °C(SRC), determined using a structure estimation method(2).

Non-Human Toxicity Excerpts/ALTERNATIVE and IN VITRO TESTS/ ... Of the isocyanates, bone marrow toxicity was highest with chloroethyl isocyanate and cyclohexyl isocyanate, intermediate with ethyl isocyanate, and lowest with KOCN and ethyl isothiocyanate.
Populations at Special Risk · 2 Einträge

2% of some worker populations /with the genetic factor of / immunologic hypersensitivity /have increased risk when exposed to/ isocyanates. /From table, Isocyanates/

Persons with a history of asthma, allergies ... or impaired lung or pulmonary function may be at an increased risk. /Methyl isocyanate/

Regulatorische Informationen

TSCA Requirements · 2 Einträge

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Ethane, isocyanato is included on this list.

Sicherheitsdaten

F
10-19-21
wgk
3
tsca
TSCA listed
ridadr
UN 2481
hs_code
29291090
RTECS-Nr.
NQ8825000
risk_code
11-20/21-25-36/37/38-42
hazard_code
F,T
safety_code
16-26-36/37/39-45
hazard_class
6.1
packing_group
I
Giftige Stoffe Daten
109-90-0(Hazardous Substances Data)
Anwendungen · 1 Eintrag

VerwendenEthyl isocyanate is part of a group of isocyanates that react with primary and secondary amines to form urea derivatives and carbamates. Ethyl isocyanate (among other isocyanate compounds, such as toluene isocyanate) are also thought to be the most common cause of occupational asthma.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

[3-[(Ethylimidocarbonyl)amino]propyl]trimethylammoniumiodidN'-(Ethylkohlenstoffimidoyl)-N,N-dimethylpropan-1,3-diaminN-(4-broMopyridin-2-yl)-N'-ethylureaUrea, N-ethyl-N'-(2-ethynylphenyl)-Ethyl-carbaMicacidpiperidin-4-ylesterCarbamic acid, ethyl-, 1-ethynylcyclohexyl ester (6CI)ABL-IN-291-m-tolyl-1H-1,2,4-triazole-3-carboxylic acidEthylsulfamidsure

Ergänzende Hinweise

DefinitionChEBI: An isocyanate having an ethyl group attached to the nitrogen.