Ethyl isocyanate

HCID 8022CAS 109-90-0

Basic information

Standard SMILES
CCN=C=O
InChIKey
WUDNUHPRLBTKOJ-UHFFFAOYSA-N
Molecular formula
C3H5NO
Average molar mass
71.08 g/mol
Monoisotopic mass
71.03711378

Overview

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.

Names & identifiers

Preferred name
Ethyl isocyanate
IUPAC
isocyanatoethane
English name
Ethyl isocyanate
Molecular formula
C3H5NO
Molecular weight
71.08

Names & synonyms

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

Database identifiers

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

Properties

Computed structural properties

XLogP
1.4
Topological polar surface area
29.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

Chemical Classes · 2 items

Toxic Gases & Vapors -> Monoisocyanates

Flammable agents - 3rd degree

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

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 items

Miscible in ethanol, ether

Soluble in chlorinated and aromatic hydrocarbons

Physicochemical properties

Melting point
-50 · <-50
Boiling point
60 °C · 60 °C(lit.)
Density
0.898 g/mL · 0.898 g/mL at 25 °C(lit.)
vapor pressure
4.34 psi · 4.34 psi ( 20 °C)
refractive index
20 · n20/D 1.381(lit.)
Flash point
20 °F · 20 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

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

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 items

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 items

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.

Hazards Summary · 1 item

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.

Safety & protection

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

· 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 items

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

General First Aid:

Exposure Control and Personal Protection · 2 items

· 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 items

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/

Toxicology

Interactions · 1 item

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 items

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 item

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 item

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 items

/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/

Regulatory information

TSCA Requirements · 2 items

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.

Safety data

F
10-19-21
wgk
3
tsca
TSCA listed
rtecs
NQ8825000
ridadr
UN 2481
hs_code
29291090

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

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 items

... 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/

Uses & manufacturing

Uses · 2 items

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 items

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

Applications · 4 items

UsesEthyl 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.

UsesEthyl 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.

UsesPharmaceutical and pesticide intermediate.

General DescriptionA colorless liquid. Less dense than water and insoluble in water. Flash point below 30°F. May irritate skin, eyes, and mucous membranes. May be lethal by Inhalation . Used to make pharmaceuticals and pesticides.

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
阿诺西(上海)生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北成丰化工有限公司13125175253 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Additional notes

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

Related reactions

1,259 records

Linked notes

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