イソシアン酸 エチル

Ethyl isocyanate

HCID 8022CAS 109-90-0

基本情報

標準SMILES
CCN=C=O
InChIKey
WUDNUHPRLBTKOJ-UHFFFAOYSA-N
分子式
C3H5NO
平均分子量
71.08 g/mol
単同位体質量
71.03711378

概要

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.

名称と識別子

優先名称
Ethyl isocyanate
IUPAC
isocyanatoethane
現地名
イソシアン酸 エチル
英語名
Ethyl isocyanate
分子式
C3H5NO
分子量
71.08

名称と別名

ETHYL ISOCYANATEIsocyanatoethane109-90-0Ethane, isocyanato-Isocyanic acid, ethyl esterB02YQ4MIR0CHEBI:85107NSC-89687DTXSID5059379RefChem:138962DTXCID4033132203-717-9
名称をさらに表示
イソシアン酸 エチルイソシアン酸エチルエチルイソシアナートエチル=イソシアナートisocyanatoetheneC2H5NCOethyl爄socyanateisocyanato-ethanisocyanated’ethyleethane,isocyanato-
Isocyanic acid ethyl esterisocyanato-ethaneethylisocyanateMFCD00002042HSDB 6318EINECS 203-717-9NSC 89687UN2481

データベース識別子

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

物性

構造計算による物性

XLogP
1.4
極性表面積
29.4 Ų
水素結合供与体数
0
水素結合受容体数
2
回転可能結合数
1
重原子数
5

実験および物理化学的性質

Chemical Classes · 2 件

Toxic Gases & Vapors -> Monoisocyanates

Flammable agents - 3rd degree

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

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 件

Miscible in ethanol, ether

Soluble in chlorinated and aromatic hydrocarbons

物理化学的性質

融点
-50 · <-50
沸点
60 °C · 60 °C(lit.)
比重(密度)
0.898 g/mL · 0.898 g/mL at 25 °C(lit.)
蒸気圧
4.34 psi · 4.34 psi ( 20 °C)
屈折率
20 · n20/D 1.381(lit.)
闪点
20 °F · 20 °F

化学的性質

化学的特性Ethyl Isocyanate is a clear, colorless liquid with a pungent odor.

安全と法規制

GHS分類

GHS Classification · 4 件

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.

危険有害性情報

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

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 件

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 件

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 件

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.

安全と保護具

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

· 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 件

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

General First Aid:

Exposure Control and Personal Protection · 2 件

· 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 件

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/

毒性情報

Interactions · 1 件

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 件

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 件

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 件

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 件

/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/

法規制情報

TSCA Requirements · 2 件

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.

安全データ

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

化学と産業

薬理情報

Mechanism of Action · 1 件

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 件

... 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/

用途と製造

Uses · 2 件

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 件

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

応用分野 · 2 件

使用Ethyl 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.

一般的な説明A 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.

調製方法

純化方法Fractionate the isocyanate through an efficient column preferably in an inert atmosphere and store it in aliquots in sealed tubes [Bieber J Am Chem Soc 74 4700 1952, Slocombe et al. J Am Chem Soc 72 1888 1950]. [Beilstein 4 IV 402.]

サプライヤー50 社

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]

補足説明

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

関連反応

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