Ethyl Nitrite

HCID 8026CAS 109-95-5

Basic information

Standard SMILES
CCON=O
InChIKey
QQZWEECEMNQSTG-UHFFFAOYSA-N
Molecular formula
C2H5NO2
Average molar mass
75.07 g/mol
Monoisotopic mass
75.0320284

Overview

Ethyl nitrite, solution appears as a clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31 °F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.

Names & identifiers

Preferred name
Ethyl Nitrite
IUPAC
ethyl nitrite
English name
Ethyl nitrite
Molecular formula
C2H5NO2
Molecular weight
75.07

Names & synonyms

ETHYL NITRITE109-95-5Nitrosyl ethoxideHyponitrous etherNitrous acid, ethyl esterNitrous ethyl etherFEMA No. 2446Ethylester kyseliny dusiteDTXSID90465748C7CJ279RVDTXCID7026574RefChem:55164
Show more names
Ethy nitritenitrousetherhyponitrousethernitrousethylethersweetspiritofnitresweetspiritofniterNitrous acid ethylspiritofethylnitrite
203-722-6Nitrous etherEthyl-nitrite-NCGC00166242-01nitrous acid ethyl esterHSDB 416Ethylester kyseliny dusite [Czech]EINECS 203-722-6

Database identifiers

CAS
109-95-5
PubChem CID
8026
DTXSID
DTXSID9046574
ChEMBL
CHEMBL1551365
ChEBI
CHEBI:173313
UNII
8C7CJ279RV
EC Number
203-722-6
Nikkaji
J47.917I

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
38.7 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
5

Experimental & physicochemical properties

Chemical Classes · 2 items

Nitrogen Compounds -> Nitrates and Nitrites

Flammable agents - 4th degree

OdorSWEET, RUM-LIKE ODOR
Taste · 2 items

FRUITY TASTE

Burning, sweetish taste

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 3 items

0.9 at 59 °F (USCG, 1999) - Less dense than water; will float

0.90 @ 15 °C/15 °C

0.900 @ 15.5°C

Color/FormColorless or yellowish, clear liquid

Physicochemical properties

Boiling point
17 ° · bp 17°
Density
0.792 g/mL · 0.792 g/mL at 25 °C
refractive index
20 · n20/D 1.36
FEMA
2446 · 2446 | ETHYL NITRITE
Flash point
59 °F · 59 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H220: Extremely flammable gas [Danger Flammable gases]

P203, P210, P222, P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P377, P381, P403, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 13.2% (36 of 272) of reports.

Danger

H220 (86.8%): Extremely flammable gas [Danger Flammable gases]

Hazard information

Regulatory Information · 3 items

Chemical: Nitrous acid, ethyl ester

Nitrous acid, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard

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 Poison
Fire Hazards · 2 items

Special Hazards of Combustion Products: Toxic oxides of nitrogen are generated.

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

Fire PotentialFlammable liquid.
Health Hazards · 2 items

Inhalation or ingestion causes headache, increased pulse rate, decreased blood pressure, and unconsciousness. Contact with liquid irritates eyes and skin. (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

Hazards Summary · 1 item

Inhalation or ingestion can cause headache, rapid pulse, hypotension, and unconsciousness. [CHRIS] One fatality was reported after the breakage of a 4 liter bottle containing 24% ethyl nitrite in alcohol. Three cases of methemoglobinemia were reported in workers exposed during the synthesis of hydantoin (glycolylurea). [HSDB] Inhalation of high concentrations causes narcosis; Chronic exposure to chemicals with this reactive group can cause hepatitis; [CAMEO]

Safety & protection

Fire FightingExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
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

INHALATION: remove victim from exposure; if breathing has stopped, give artificial respiration; call physician.

General First Aid:

Firefighting HazardsClosed containers may rupture violently when heated.
Exposure Control and Personal Protection · 2 items

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

Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH]

Fire Fighting Procedures · 3 items

Use water spray, dry chemical, foam, or carbon dioxide. Use water spry to keep fire-exposed containers cool. Fight fire from protected location or maximum possible distance.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or 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 water 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.

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that ethyl nitrite is expected to have very high mobility in soil(SRC). Volatilization of ethyl nitrite from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.7X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(3). The potential for volatilization of ethyl nitrite from dry soil surfaces may exist(SRC) based upon an estimated vapor pressure of 620 mm Hg(SRC), determined from a fragment constant method(4). A decomposition rate has not been published, however it is known that ethyl nitrite is slightly soluble(5) and decomposes in water(5). In addition, decomposition of ethyl nitrite is hastened by air, light, and moisture(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that ethyl nitrite 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 8.7X10-5 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 7 and 146, respectively(SRC). A decomposition rate has not been published, however it is known that ethyl nitrite is slighlty soluable in water and is decomposed by it(7). In addition, decomposition of ethyl nitrite is hastened by air, light, and moisture(7). According to a classification scheme(5), an estimated BCF of 2(SRC), from an estimated log Kow(8) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.

ATMOSPHERIC FATE: A decomposition rate has not been published, however it is known that decomposition of ethyl nitrite is hastened by air, light,and moisture(4). According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethyl nitrite, which has an estimated vapor pressure of 620 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Vapor-phase ethyl nitrite 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 34.5 days(SRC), calculated from its rate constant of 1.75X10-12 cu cm/molecule-sec at 25 °C(3).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 item

Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethyl nitrite can be estimated to be 81(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethyl nitrite is expected to have high mobility in soil.

Human Toxicity Excerpts · 5 items

MAY CAUSE METHEMOGLOBINEMIA & HYPOTENSION, &, IN HIGH CONCN.../SRP: CNS DEPRESSION/.

Industrial intoxications characterized by headache, tachycardia, and methemoglobinemia have occurred. A fatality has been described following the inhalation of ethyl nitrite after accidental breakage of a 4 liter bottle containing 24% ethyl nitrite in alcohol.

Three cases of ethyl nitrite intoxication have been reported from Czechoslovakia during a synthesis of hydantoin (glycolylurea). Symptoms of both "nitrite" effect and methemoglobinemia were noted. In addition, there was a vasodilator effect upon the blood vessels of the sclerae, producing a peculiar redness of the eyes, ... No Heinz bodies were seen.

ADMIN OF SWEET SPIRITS OF NITRE (4% ETHYL NITRITE IN 70% ETHANOL) WAS FOLLOWED BY ACUTE METHEMOGLOBINEMIA & SEVERE ANOXIC METABOLIC ACIDOSIS IN INFANT TWINS, METHYLENE BLUE ADMIN REVERSED METHEMOGLOBINEMIA IN BOTH, BUT ONE TWIN DIED FROM THE CONSEQUENCES OF HYPOXEMIA.

For more Human Toxicity Excerpts (Complete) data for ETHYL NITRITE (6 total), please visit the HSDB record page.

Artificial Pollution SourcesEthyl nitrite's production and use for preparing spirit nitrous ether(1), in exhaust from alcohol-fueled vehicles(2), and also for use in organic reactions(3) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 2 was calculated for ethyl nitrite(SRC), using an estimated log Kow of 1.4(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low.

Regulatory information

FDA Requirements · 1 item

Ethyl nitrite is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

DHS Chemicals of Interest (COI) · 4 items

Ethyl nitrite

1

10000

Flammable chemical that can be released at a facility.

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
WGK 1
tsca
TSCA listed
rtecs
RA0810000
ridadr
UN 1194
Toxicity
cat,LC,inhalation,> 200mg/m3/15M (200mg/m3),Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(1), Pg. 62, 1983.

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

THE REACTIONS OF HUMAN HEMOGLOBIN WITH SODIUM NITRITE AND ETHYL NITRITE IN DEOXYGENATED MEDIA HAVE BEEN EXAMINED IN KINETIC DETAIL. ETHYL NITRITE REACTS WITH HEMOGLOBIN AT RATES THAT ARE AT LEAST 10 TIMES SLOWER THAN THOSE EXTRAPOLATED FOR NITROUS ACID, & HYDROLYSIS OF ALKYL NITRITE IS NOT COMPETITIVE WITH OXIDATION OF HEMOGLOBIN. THE EXPERIMENTAL RESULTS ARE INTERPRETED TO DESCRIBE ALKYL NITRITE, AND PRESUMABLY, NITROUS ACID ASSOCIATION WITH HEMOGLOBIN FOLLOWED BY RATE-LIMITED ELECTRON TRANSFER RESULTING IN NITRIC OXIDE AND ALKOXIDE (OR HYDROXIDE) PRODN. PROTON TRANSFER RESULTING IN ALC (OR WATER) FORMATION OCCURS SUBSEQUENT TO THE RATE-LIMITING STEP AS DO REACTIONS OF HEMOGLOBIN WITH NITRIC OXIDE.

THE REACTION OF HUMAN HEMOGLOBIN AND SPERM WHALE MYOGLOBIN UNDER AEROBIC CONDITIONS WITH ETHYL NITRITE HAVE BEEN EXAMINED. ETHYL NITRITE CONVERTS TWO EQUIVALENTS OF OXYHEMOGLOBIN TO THEIR OXIDIZED COUNTERPARTS WITH CONCURRENT PRODN OF ONE EQUIVALENT OF MOLECULAR OXYGEN, NITRATE ION, & ETHYL ALCOHOL.

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 5 items

Used to flavor foods and to synthesize other organic chemicals; [HSDB]

For preparing spirit nitrous ether

CHEM INTERMEDIATE; FLAVOR IN FOODS & BEVERAGES

Organic reactions, synthetic flavoring

FLAVORS USEFUL IN RUM, BRANDY, FRUIT FLAVORS.

U.S. Production(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Methods of Manufacturing · 2 items

REACTION OF NITROUS ACID & ETHANOL

Made by action of sodium nitrite on mixture of alcohol and sulfuric acid in the cold. In lab ethyl nitrite gas is ... Generated by placing 20 L of 90% ethanol in suitable vessel, diluting with 200 L of water ... While stirring, adding to dilute alcohol 18.3 kg of nitrosyl chloride @ the rate of 2.25 kg/hr ... Chase, US patent 2,615,896 (1952).

Formulations/PreparationsArticle of commerce contains 90-95% ethyl nitrite, remainder is chiefly alcohol as preservative.
General Manufacturing Information · 4 items

Nitrous acid, ethyl ester: ACTIVE

FEMA LIST OF GRAS SUBSTANCES REPORT USAGE AS SYNTHETIC FLAVOR INGREDIENT IN NON-ALCOHOLIC BEVERAGES 3.0 PPM, ICE CREAM, ICES...4.5 PPM; CANDY 0.10-8.0 PPM; BAKED GOODS 0.10 PPM; CHEWING GUM 3.9 PPM; SYRUPS 52 PPM; ICINGS 13 PPM.

FEMA NUMBER 2446

In prepn of spirit nitrous ether by mixing with 21 parts alcohol by weight.

Applications · 4 items

DescriptionThe chemical compound ethyl nitrite is an alkyl nitrite. It may be prepared from ethanol Ethyl nitrite is the main ingredient in a traditional ethanol-based South African remedy for colds and flu known as Witdulsies and sold in pharmacies. It is known as a traditional Afrikaans remedy and may have Dutch roots, as the same remedy is apparently made by the Germano-Dutch Amish people in the USA. However FDA has blocked over-the-counter sales of this same remedy, known in the USA as sweet nitrite or sweet spirit of nitre since 1980 .

UsesOrganic reactions, synthetic flavoring.

UsesEthyl Nitrite is an S-nitrosylating agent that improve tissue oxygenation in humans and sheep at normoxia and at reduced fraction of inspired oxygen during microvasculature. Ethyl Nitrite is also used as a therapeutic gas utilized in neonatal Intensive Care Unit.

General DescriptionA clear colorless to yellow liquid with a pleasant odor. Flammable over a wide range of vapor-air concentrations. Flash point -31°F. Less dense than water and insoluble in water. Vapors are heavier than air and narcotic in high concentrations. Produces toxic oxides of nitrogen during combustion.

Preparation methods

PreparationFrom sodium nitrite in aqueous solution by displacing the acid with H2SO4 in the presence of ethyl alcohol; it forms azeotropic mixtures with isopentane (85%), amyl bromide (40%) and carbon disulfide (96%).

Additional notes

DefinitionChEBI: Ethyl nitrite is a nitroso compound.

Related reactions

21 records

Linked notes

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