Ethyl Nitrate

HCID 12259

Basic information

CAS
625-58-1
Standard SMILES
CCO[N+](=O)[O-]
InChIKey
IDNUEBSJWINEMI-UHFFFAOYSA-N
Molecular formula
C2H5NO3
Average molar mass
91.07 g/mol
Monoisotopic mass
91.02694302

Overview

Ethyl nitrate appears as a clear colorless liquid with a pleasant odor. Prolonged exposure to fire or heat may cause vigorous decomposition and rupturing of the container. Denser than water and insoluble in water. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion.

Names & identifiers

Preferred name
Ethyl Nitrate
IUPAC
ethyl nitrate
English name
Ethyl nitrate
Molecular formula
C2H5NO3
Molecular weight
91.07

Names & synonyms

ETHYL NITRATE625-58-1Nitric etherNitric acid, ethyl esterEthylester kyseliny dusicneE1ZT886LR5NSC-8826DTXSID0060806NSC8826RefChem:139016DTXCID7043374210-903-3
Show more names
1-NitrooxyethaneNitric acid ethylNicorandil Impurity 23Nicorandil Impurity 13 (Ethyl Nitrate)
nitric acid ethyl esterHSDB 415Ethylester kyseliny dusicne [Czech]NSC 8826EINECS 210-903-3BRN 1700275UNII-E1ZT886LR5AI3-24234

Database identifiers

CAS
625-58-1
PubChem CID
12259
DTXSID
DTXSID0060806
UNII
E1ZT886LR5
EC Number
210-903-3
Nikkaji
J1.687J

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
55.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Nitrates and Nitrites

Flammable agents - 3rd degree

SpringerMaterials PropertiesSchoenflies notation
OdorPleasant odor
TasteSweet taste
Density · 2 items

1.1084 @ 20 °C/4 °C

1.004 @ 20°C

Color/FormColorless liquid

Physicochemical properties

Melting point
-94.59 °C · -94.59°C
Boiling point
87.25 °C · 87.25°C
Density
1.1084 · 1.1084
refractive index
1.3852 · 1.3852
solubility
1.3 ml · 1.3 ml soluble in 100 ml water at 55°C; miscible with alcohol and ether
Henry's Law Constant
1.6 · 1.6×10-2 mol/(m3Pa) at 25℃, Burkholder et al. (2019)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H200: (Deleted) Unstable Explosive [Danger Explosives]

P201, P202, P281, P372, P373, P380, P401, and P501 (click each P-code to see the statement)

Danger

H200: (Deleted) Unstable Explosive [Danger Explosives]

P201, P202, P281, P372, P373, P380, P401, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 2 items

Chemical: Nitric acid, ethyl ester

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 LabelFlammable Liquid
Fire HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Fire PotentialSPONTANEOUS HEATING: NO
Health HazardsExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Hazards SummaryInhalation can cause CNS depression and methemoglobinemia; [HSDB]

Safety & protection

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
First AidExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Fire Fighting Procedures · 4 items

FOAM, CARBON DIOXIDE, DRY CHEM...

EXTINGUISHING METHOD... WATER MAY BE INEFFECTIVE EXCEPT AS BLANKET.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply watt from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.

Evacuation: If fire becomes uncontrollable or container is exposed to direct flame - consider evacuation of one-half (1/2) mile radius.

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 1 item

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.

Preventive Measures · 4 items

Precautions should be taken to prevent the spread of any liq that may accidentally escape from a container. ...should not be exposed in.../poorly/ ventilated conditions.

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.

Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amount of water or soap and water.

If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from a structure estimation method(2), indicates that ethyl nitrate is expected to have very high mobility in soil(SRC). Volatilization of ethyl nitrate from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethyl nitrate from dry soil surfaces may exist(SRC) based upon a vapor pressure of 64 mm Hg(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 24(SRC), determined from an estimation method(2), indicates that ethyl nitrate is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 2.6X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.1 and 120 hours, respectively(SRC). According to a classification scheme(5), an estimated BCF of 1.8(SRC), from an estimated log Kow of 24(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl nitrate, which has a vapor pressure of 64 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethyl nitrate 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 80 days(SRC), calculated from its rate constant of 2.7X10-13 cu cm/molecule-sec at 25 °C(3).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethyl nitrate can be estimated to be 24(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl nitrate is expected to have very high mobility in soil(2).

Natural Pollution Sources · 2 items

The atmospheric photochemistry of the organosulfur compounds methyl sulfide, ethyl sulfide, & methanethiol was studied with emphasis on gaseous & particulate reaction products & their modes of formation when exposed to sunlight irradiation & various NO(x) mixtures. Experimental results show that ethyl nitrate is a gas-phase photooxidation product of ethyl sulfide.

The yields of alkyl nitrates formed in the NOx-air photooxidations of the homologous series of n-alkanes from ethane through n-octane have been determined at 299 +/- 2 K & 735 torr total pressure for 2 different chemical systems. Alkyl peroxy radicals were generated by reaction of the n-alkanes with OH radicals (generated from the photolysis of methyl nitrite in air) or Cl atoms (from photolysis of CL2 in air). The alkyl nitrate yields obtained from the 2 systems, corrected for secondary reactions, were in agreement within the exptl errors & incr monotonically with the carbon number of the n-alkane, from equal to or less than 1% for ethane to approx 33% for n-octane, with the yields apparently approaching a limit of approx 35% for larger n-alkanes. Data are consistent with the alkyl nitrates being formed almost entirely from the reaction of peroxy radicals with NO, & the ratios of the corrected alkyl nitrate yields reflect the fraction of RO2 radicals which react with NO to form alkyl nitrates.

Atmospheric Concentrations · 3 items

SOURCE DOMINATED: Ethyl nitrate was detected in air samples collected between November 1988 and April 1989 from Juelich, a city surrounded by five lignite-coal-burning power plants in the Black Forest region of Germany at a mean concn of 47.7 parts per trillion(1).

URBAN/SUBURBAN: Ethyl nitrate was detected not quantified in air samples from Vancouver, British Columbia, Canada(1).

RURAL/REMOTE: Ethyl nitrate was detected in air samples collected in May/June 1989 from Schauinsland, southwest of Juelich in the Black Forest region of Germany at a mean concn of 9.5 parts per trillion(1).

Human Toxicity Excerpts · 3 items

...HIGHLY TOXIC & IN LARGE DOSES MAY CAUSE DIZZINESS, ABDOMINAL CRAMPS, VOMITING, BLOODY DIARRHEA, WEAKNESS, CONVULSIONS, & COLLAPSE. SMALL, REPEATED DOSES MAY LEAD TO WEAKNESS, GENERAL DEPRESSION, HEADACHE, & MENTAL DISORDERS. /ALKYL NITRATES/

IT IS SAID THAT ETHYL NITRATE HAS ANESTHETIC PROPERTIES & ON INHALATION CAUSES HEADACHE.../PRC: CNS DEPRESSION/ & VOMITING.

A poison by intraperitoneal route. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. A moderate explosion hazard when exposed to heat (explodea @ 185 °F).

Safety data

tsca
TSCA listed
ridadr
0473
risk_code
2
Signal word
Danger
Symbol(GHS)
GHS01
hazard_code
E

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used as a chemical intermediate for production of other organic chemicals; [HSDB]

Organic synthesis of drugs, perfumes, and dyes, and as rocket propellant.

CHEM INT FOR DRUGS, PERFUMES; COMPONENT OF ROCKET PROPELLANTS

Methods of Manufacturing · 2 items

REACTION OF ETHANOL, UREA NITRATE, AND NITRIC ACID, FOLLOWED BY DISTILLATION

By heating alcohol, urea nitrate, and nitric acid, with subsequent distillation.

General Manufacturing InformationNitric acid, ethyl ester: ACTIVE
Applications · 3 items

DescriptionEthyl nitrate has formula C2H5NO3. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes. Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. Originally thought to be a pollutant, formed mainly by the combustion of fossil fuels, recent analysis of ocean water samples reveal that in places where cool water rises from the deep, the water is saturated with alkyl nitrates, likely formed by natural processes.

UsesOrganic synthesis, drugs, perfumes, dyes, rocket propellant.

General DescriptionA clear colorless liquid with a pleasant odor. Flash point 50°F. Prolonged exposure to fire or heat may cause vigorous decomposition and rupturing of the container. Denser than water and insoluble in water. Vapors are heavier than air. Produces toxic oxides of nitrogen during combustion.

Preparation methods

PreparationEthyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at 10 °C . The reaction was subsequently studied in detail.

Suppliers20 total

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
SelectLab Chemicals GmbH+49-(0)2383-919350 · [email protected]
广东方信生物科技有限公司0751-2838688 13376594225 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]

Related reactions

7 records

Compound notes

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