Nitroethane

HCID 6587CAS 79-24-3

基本情報

標準SMILES
CC[N+](=O)[O-]
InChIKey
MCSAJNNLRCFZED-UHFFFAOYSA-N
分子式
C2H5NO2
平均分子量
75.07 g/mol
単同位体質量
75.0320284

概要

Nitroethane appears as a colorless oily liquid with a pleasant odor. Flash point of 82 °F. Decomposes above 350 °F. Density 1.052 g / cm3. Vapors much heavier than air. and insoluble in water. Vapors may irritate skin, eyes and mucous membranes. Produces toxic oxides of nitrogen during combustion. Used as a propellant and as a solvent.

名称と識別子

優先名称
Nitroethane
IUPAC
1-nitroethane
現地名
ニトロエタン
英語名
Nitroethane
分子式
C2H5NO2
分子量
75.07

名称と別名

NITROETHANEEthane, nitro-79-24-3NitroetanNitroethanDTXSID80209696KEL3ZAU0VNSC-8800DTXCID80969CHEBI:16268RefChem:6065201-188-9
名称をさらに表示
ニトロエタン1-ニトロエタン2-ニトロエタンモノニトロエタンニトロエタン REAGENT GRADE,≥98.0%C2H5NO2Nitroparaffinnitro-ethan2-NitroethaneEthane,nitro-Nitroethane,99%nitroetan(polish)NITROETHANE,REAGENT
1-NitroethaneNitroetan [Polish]CCRIS 3088HSDB 105UNII-6KEL3ZAU0VNSC 8800EINECS 201-188-9UN2842

データベース識別子

CAS
79-24-3
PubChem CID
6587
DTXSID
DTXSID8020969
ChEMBL
CHEMBL15625
ChEBI
CHEBI:16268
UNII
6KEL3ZAU0V
EC Number
201-188-9
Nikkaji
J3.837G

物性

構造計算による物性

XLogP
0.2
極性表面積
45.8 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
0
重原子数
5

実験および物理化学的性質

Chemical Classes · 2 件

Nitrogen Compounds -> Nitros, Aliphatic

Flammable agents - 3rd degree

pHpH of 0.01 M aqueous solution at 25 °C = 6.0
SpringerMaterials PropertiesSchoenflies notation
LogP · 2 件

log Kow = 0.18

0.2

Odor · 3 件

Moderate to strong disagreeable odor

Mild, fruity odor

Pleasant odor

Density · 6 件

1.05 at 68 °F (USCG, 1999) - Denser than water; will sink

1.0448 g/cu cm at 25 °C

Bulk density: 8.75 lb/gal at 20 °C

1.051 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.03

1.05

物理化学的性質

融点
-90 °C · -90 °C
沸点
114 · 114-115 °C(lit.)
比重(密度)
1.045 g/mL · 1.045 g/mL at 25 °C(lit.)
蒸気密度
2.58 · 2.58 (vs air)
蒸気圧
15.6 mm · 15.6 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.391(lit.)

化学的性質

化学的特性Nitroethane is a colorless, oily liquid with a mild, fruity odor. The Odor Threshold is 163 ppm.

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P317, P330, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

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

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P273, P280, P301+P317, P303+P361+P353, P304+P340, P316, P317, P318, P321, P330, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: Ethane, nitro-

List I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)

Ethane, nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, nitro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 09-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/10513

Ethane, nitro-: HSNO Approval: HSR001205 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.)

Other Safety InformationIMAP assessments - Ethane, nitro-: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 件

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. (USCG, 1999)

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

Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 28 °C explosive vapour/air mixtures may be formed. Risk of explosion on contact with many substances. See Chemical Dangers.

Fire Potential · 2 件

Sudden absorption of the anhydous liquid or gas on activated carbon or Hopcalite may result in flames.

Contact with metal oxides increase sensitivity of... nitroethane... to heat.

Health Hazards · 2 件

Inhalation causes moderate irritation of respiratory tract. Ingestion causes irritation of mouth and stomach. Contact with liquid causes irritation of eyes and mild irritation of skin. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Use powder, foam, carbon dioxide, water spray. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Rinse and then wash skin with water and soap.

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

Rinse mouth. Do NOT induce vomiting. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.

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 · 3 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Well closed. Separated from : see Chemical Dangers.
Firefighting Hazards · 2 件

Flashback along vapor trail may occur.

Special hazards arising from the substance or mixture: Carbon oxides, nitrogen oxides (NOx).

毒性情報

Interactions · 1 件

When 3 consecutive generations of Swiss mice were exposed to a mixture of 7.8 ppm diethylhydroxylamine and 11.5 ppm nitroethane for 8.25 hr/day from conception to sexual maturity, no statistically significant differences in any of the litter sizes were found. Furthermore, there were no increases in embryotoxicity or terata in the second and third generations.

Target OrgansSkin, respiratory system, central nervous system, kidneys, liver
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that nitroethane is expected to have very high mobility in soil(SRC). Some adsorption may occur in high organic-content peat or clay(3,4). Volatilization of nitroethane from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 4.76X10-5 atm-cu m/mole(5). Nitroethane is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 20.8 mm Hg at 25 °C(6). Limited biodegradation data suggest that nitroethane may biodegrade under aerobic conditions but not under anaerobic conditions(SRC). Mineralization of nitroethane reached 23.9% in five days using an activated sludge inoculum, but less than 1% of the initial nitroethane was biodegraded in 28 days using the closed bottle test(7). In anaerobic soil, nitroethane was not biodegraded over a 35 day period(7). Nitroethane is expected to undergo direct photolysis on soil surfaces exposed to sunlight(SRC) based on 76.1-83% degradation within 24 hours measured during photodegradation tests(8,9).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 20(SRC), determined from a structure estimation method(2), indicates that nitroethane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 4.76X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 18 hrs and 8 days, respectively(SRC). According to a classification scheme(5), a BCF of 1 measured in fish (golden orfe)(6), suggests bioconcentration in aquatic organisms is low(SRC). Limited biodegradation data suggest that nitroethane may biodegrade under aerobic conditions but not under anaerobic conditions(SRC). Mineralization of nitroethane reached 23.9% in five days using an activated sludge inoculum, but less than 1% of the initial nitroethane was biodegraded in 28 days using the closed bottle test(6). In anaerobic soil, nitroethane was not biodegraded over a 35 day period(6). Nitroethane is expected to undergo direct photolysis at water surfaces exposed to sunlight(SRC) based on 76.1-83% degradation within 24 hours measured during photodegradation tests(7,8). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(3).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nitroethane, which has a vapor pressure of 20.8 mm Hg at 25 deg(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nitroethane 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 110 days(SRC), calculated from its rate constant of 1.50X10-13 cu cm/molecule-sec at 25 °C(3). Nitroethane is expected to undergo direct photolysis in the atmosphere based on 76.1-83% degradation within 24 hours measured during photodegradation tests(4,5).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 2 件

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

inhalation, ingestion, skin and/or eye contact

Toxicity Summary · 1 件

IDENTIFICATION AND USE: Nitroethane is a colorless oily liquid. It is used as solvent, artificial fingernail glue remover; in organic syntheses. It is also used experimentally as liquid propellant. HUMAN EXPOSURE AND TOXICITY: Adverse effects resulting from human exposure to nitroethane have been primarily through accidental ingestion of artificial nail remover products by children. Methemoglobinemia results from accidental oral exposure and can be successfully treated with iv methylene blue therapy. Because methemoglobinemia may be delayed, individuals who ingest nitroethane should be monitored closely for at lease 24 hours after ingestion. if nitroethane is spilled on clothing and allowed to remain, it may cause smarting and reddening of skin. If inhaled will cause coughing or difficult breathing. Liquid: if swallowed will cause nausea and vomiting. Inhalation causes moderate irritation of respiratory tract. Ingestion causes irritation of mouth and stomach. ANIMAL STUDIES: Nitroethane was considered less toxic to rats ip or by inhalation than 1- and 2-nitropropanes. Even in cases of acute intoxication, only low levels of methemoglobin were induced by nitroethane. The 2 year study in male and female rats found no biologically significant effects of nitroethane exposure on organ weights, and no significant difference in the nonneoplastic or neoplastic pathology related to exposure to nitroethane. Developmental study in mice found no effect on the dams and there was no evidence of nitroethane-induced terata, variation in sex ratio, embryotoxicity or inhibition of fetal growth and development. Negative results were obtained from studies of nitroethane in Salmonella typhimurium/mammalian microsome (Ames) test (with and without microsomal activation), and in an in vivo mutagenic (micronucleus) test.

法規制情報

FDA Requirements · 1 件

The following chemicals have been specifically designated by the Administrator of the Drug Enforcement Administration as the listed chemicals subject to the provisions of this part and parts 1309 and 1313 of this chapter. Each chemical has been assigned the DEA Chemical Code Number set forth opposite it. Nitroethane (DEA Code: 6724) is included on this list.

TSCA Requirements · 1 件

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. Nitroethane is included on this list. Effective date: 4/13/89?; Sunset date: 12/19/95.

Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Nitroethane is produced, as an intermediate or a final product, by process units covered under this subpart.

安全データ

OEB
A
OEL
TWA: 100 ppm (310 mg/m3)
wgk
2
IDLA
1,000 ppm
tsca
TSCA listed
rtecs
KI5600000

化学と産業

薬理情報

Metabolism/Metabolites · 2 件

... Nitroethane is readily converted by glucose oxidase in vitro to acetaldehyde, nitrite, nitrate, hydrogen peroxide and dinitroethane. However, the role of this enzyme in vivo is unknown ... A small amount of a mercapturic acid metabolite /was recovered/ from the urine of rabbits dosed with nitroethane.

A peak blood nitroethane conc of 1.10 mg/mL was recorded after oral administration of 1.26 g/kg to rabbits. Following inhalation exposure of rabbits to about 13,500 ppm or 2700 ppm, peak nitroethane blood conc were 2.70 mg/mL after 360 min, and 0.36 mg/mL after 500 min, respectively. Blood nitrite and nitrate conc increased during the exposures, indicating that nitrite was formed as a result of the metabolism of nitroethane, and was oxidized to nitrate.

Absorption, Distribution and Excretion · 3 件

Nitroethane was partially excreted by the lungs when given to rabbits iv (1 g) or orally (1 or 2 g/kg). It was eliminated from the blood within 30 hr after the iv dose.

Absorption of nitroethane during inhalation exposure occurs in both the upper and lower respiratory tract of rats. The isolated upper, lower and intact respiratory tract absorbed 65, 71 and 58%, respectively, of the nitroethane presented at a rate comparable to a normal respiratory minute volume for rats. The absorption of nitroethane by the upper respiratory tract was linear over a 10-fold exposure range. During exposures only 2.8 and 2.0% of nitroethane was excreted from the upper and lower respiratory tract, respectively.

...Inhalation exposure reportedly leads to increased nitrite concentrations in the blood of rabbits. Distribution studies of nitroethane in animals showed rapid disappearance from the body. Within 3 hr only 14% of the dose was recovered in rats, and by 30 hr, essentially all of the dose had been cleared from the tissues, the blood, lungs, liver, and muscle.

用途と製造

Uses · 6 件

Used as a propellant, a solvent for resins and waxes, and an intermediate for organic chemicals; [ACGIH]

Plastic Composites Manufacturing [Category: Industry]

Solvent for cellulose esters, vinyl, alkyd & other resins & waxes.

Solvent, artificial fingernail glue remover; in organic syntheses. Experimentally as liquid propellant.

Principally a propellant for military use; chemical intermediate for a nitroplasticizer for solid propellants, for nitro alcohols.

Solvent for nitrocellulose, cellulose acetate, cellulose acetopropionate, cellulose acetobutyrate, vinyl, alkyd, and many other resins, waxes, fats and dyestuffs, Friedel-Crafts synthesis; propellant research; fuel additive.

U.S. Production · 6 件

2023: 5,360,646 lb

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Nitroethane is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Ethane, nitro-. Aggregated National Production Volume: 1 to < 10 million pounds.

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethane, nitro-. National Production Volume: Withheld.

Consumer UsesSolvent
Industry UsesWetting agent (non-aqueous)
Methods of Manufacturing · 3 件

Obtained by vapor phase nitration of ethane with nitric acid.

By reaction of propane with nitric acid under pressure.

Industrial production of nitroethane is by vapor-phase nitration of propane with nitric acid, followed by fractional distillation.

Formulations/PreparationsGRADE: Commercial, 92.5+%
応用分野 · 4 件

解説ニトロエタン.クロロエタンと亜硝酸銀を加熱するか,工業的には,気相でエタンをNO2でニトロ化すると得られる.無色の液体.融点約-50 ℃,沸点114~115 ℃.d20201.052.n20D1.3917.ほとんどの有機溶剤に可溶,水に難溶,有機溶媒やアルカリ水溶液に可溶.芳香臭を有する.セルロース誘導体,ビニル樹脂などの合成樹脂,染料,油脂などの有機溶剤として工業的に重要である.眼,粘膜などを刺激する.

用途安定剤、農薬原料、溶剤、爆薬、ロケット燃料

使用Solvent, artificial fingernail glue remover; in organic syntheses. Experimentally as liquid propellant.

一般的な説明A colorless oily liquid with a pleasant odor. Flash point of 82°F. Decomposes above 350°F. Density 1.052 g / cm3. Vapors much heavier than air. and insoluble in water. Vapors may irritate skin, eyes and mucous membranes. Produces toxic oxides of nitrogen during combustion. Used as a propellant and as a solvent.

調製方法

Industrial production of nitroethane is by vapor-phase nitration of propane with nitric acid, followed by fractional distillation (Baker and Bollmeier 1978). U.S. production was greater than 454 kg in 1975 (HSDB 1988).

純化方法Purify it as described for nitromethane below. A spectroscopic impurity can be removed by shaking it with activated alumina, decanting and distilling it rapidly. [Beilstein 1 IV 170.]

補足説明

定義ChEBI: A nitroalkane that is ethane substituted by a nitro group.

関連反応

369 件

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