Ethyl formate

HCID 8025CAS 109-94-4

Basic information

Standard SMILES
CCOC=O
InChIKey
WBJINCZRORDGAQ-UHFFFAOYSA-N
Molecular formula
C3H6O2
Average molar mass
74.08 g/mol
Monoisotopic mass
74.03677943

Overview

Ethyl formate appears as a clear colorless liquid with a pleasant odor. Flash point -4 °F. Less dense than water. Vapors heavier than air.

Names & identifiers

Preferred name
Ethyl formate
IUPAC
ethyl formate
English name
Ethyl formate
Molecular formula
C3H6O2
Molecular weight
74.08

Names & synonyms

ETHYL FORMATE109-94-4AreginalFormic acid, ethyl esterEthyl methanoateEthyl formic esterAethylformiatFormic etherEthylformiaatMrowczan etyluCarboxylic acid oxaethaneEthyle (formiate d')
Show more names
FORMIC ACID ETHYL ESTEREthyl forMatEthylformiatethyl formiateHCOOC2H5FEMA 2434
Etile (formiato di)FEMA No. 2434Ethyl ester of formic acidEthylester kyseliny mravenciDTXSID60401170K3E2L5553NSC-406578CHEBI:52342

Database identifiers

CAS
109-94-4
PubChem CID
8025
DTXSID
DTXSID6040117
ChEMBL
CHEMBL44215、CHEMBL55595
ChEBI
CHEBI:52342
UNII
0K3E2L5553
EC Number
203-721-0
Nikkaji
J1.971B

Properties

Computed structural properties

XLogP
0.5
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
5

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Esters (<C12)
SpringerMaterials PropertiesCoriolis coupling
FragrancesFragrance Ingredient (Ethyl formate) -> IFRA transparency List
Pesticides · 2 items

Insecticides

Active substance -> EU Pesticides database: Not approved

LogP · 4 items

0.23

0.23

0.23

0.27

Physicochemical properties

Melting point
-80 °C · -80 °C (lit.)
Boiling point
52 · 52-54 °C (lit.)
Density
0.921 g/mL · 0.921 g/mL at 20 °C (lit.)
vapor density
2.5 · 2.5 (vs air)
vapor pressure
15.16 psi · 15.16 psi ( 55 °C)
refractive index
20 · n20/D 1.359(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P317, P303+P361+P353, P304+P340, P305+P351+P338, P317, P319, P330, P337+P317, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.6% (11 of 1923) of reports.

Danger

H225 (99.4%): Highly Flammable liquid and vapor [Danger Flammable liquids]

Hazard information

Regulatory Information · 4 items

Chemical: Formic acid, ethyl ester

Status: Active Update: 30-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/17274

Formic acid, ethyl ester: HSNO Approval: HSR001148 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 - Formic acid, ethyl ester: Human health tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 items

Behavior in Fire: Vapor is heavier than air and may travel long distance to a source of ignition and flash back. (USCG, 1999)

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

Highly flammable. Vapour/air mixtures are explosive. Heating will cause rise in pressure with risk of bursting. Risk of fire and explosion on contact with strong oxidants.

Fire Potential · 2 items

Burning Rate: 3.6 mm/min.

DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS.

Health Hazards · 2 items

Inhalation of vapor causes slight irritation of the eyes and rapidly increasing irritation of the nose. High concentrations cause deep narcosis within a few minutes followed by death within a few hours. Contact with liquid causes moderate irritation of eyes and mild irritation of skin. Ingestion causes irritation of mouth and stomach; may cause deep narcosis and death if not treated. (USCG, 1999)

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

Safety & protection

Fire Fighting · 2 items

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

Use powder, alcohol-resistant foam, water spray, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

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. Refer for medical attention .

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 · 3 items

Excerpt from NIOSH Pocket Guide for Ethyl formate:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants. Cool.
Firefighting HazardsVapor is heavier than air and may travel long distance to a source of ignition and flash back.

Toxicology

Target OrgansEyes, respiratory system, central nervous system
Environmental Fate · 3 items

TERRESTRIAL FATE: If released to soil, ethyl formate would readily volatilize from the surface layers of soil as well as leach. While no data were located concerning the degradation in soil, it would be expected to readily degrade by chemical hydrolysis, especially in alkaline soil, and biodegrade. (SRC)

AQUATIC FATE: Ethyl formate has a relatively high Henry's Law constant of 3.85X10-4 atm-cu m/mol(1) and if released to water, it will be lost due to evaporation. A volatilization half-life of 4.5 hrs was predicted for ethyl formate from a model river 1 m deep, flowing at 1 m/sec with a wind velocity of 3 m/sec(2,SRC). It would not be expected to sorb to sediment or bioconcentrate in aquatic organisms. Chemical hydrolysis will be an important fate process, especially in alkaline waters. The hydrolytic half-life is 3.1 days and 7.5 hr at pH 7 and 8, respectively(3,SRC). Based on limited data from screening tests supplemented by predictions of mathematical models and data on similar chemicals, ethyl formate should rapidly biodegrade(SRC).

ATMOSPHERIC FATE: The half-life of ethyl formate in the atmosphere is estimated to be 11 days as a result of reaction with photochemically-produced hydroxyl radicals(1). Being fairly soluble in water, it should be readily washed out of the air by rain(SRC).

Food Survey ValuesEthyl formate was identified, but not quantified, in roasted filberts(1), beer(2), wine(6,7), Korean chamchwi(3), blue cheese(4), and apples and pears(5).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure Routes · 2 items

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

inhalation, ingestion, skin and/or eye contact

Signs and Symptoms · 5 items

Cough. Shortness of breath. Headache. Drowsiness.

Redness.

Redness. Pain.

Sore throat. Further see Inhalation.

irritation eyes, upper respiratory system; In Animals: narcosis

Regulatory information

FDA RequirementsSubstance added directly to human food affirmed as generally recognized as safe (GRAS).
FIFRA Requirements · 3 items

The food additive ethyl formate may be safely used in or on specified dried fruits in accordance with the following conditions: it is used or intended for use in or on raisins and dried Zante currants as a bulk and package fumigant.

The food additive ethyl formate may be safely used in or on specified dried fruits in accordance with the following conditions: it is used in accordance with directions registered with the U.S. EPA, and so used that the total formic acid present free and combined, in the finished product shall not exceed 250 ppm.

The food additive ethyl formate may be safely used in or on specified dried fruits in accordance with the following conditions: to assure safe use of the additive, its label and labeling shall conform to that registered with the USEPA.

Safety data

OEB
A
OEL
TWA: 100 ppm (300 mg/m3)
PPE
Eyeshields, Faceshields, Gloves
wgk
1
IDLA
1,500 ppm
tsca
TSCA listed

Chemistry & industry

Pharmacology

Mechanism of ActionIt has been assumed, but not proved, that hydrolysis and release of formic acid on the moist surfaces are responsible for the irritant action of ethyl formate.
Metabolism/Metabolites · 2 items

A MUCH STRONGER IRRITANT THAN ETHYL ACETATE, PROBABLY BECAUSE OF HYDROLYSIS TO FORMIC ACID.

Ethyl formate is metabolized by esterases in Streptomyces nitrificans.

Absorption, Distribution and Excretion · 2 items

BECAUSE OF RELATIVELY GOOD SOLUBILITY IN PLASMA, ETHYL FORMATE PASSES READILY THROUGH THE PULMONARY ALVEOLI AND, DUE TO HIGH WATER SOLUBILITY, HAS A HIGH BLOOD-AIR DISTRIBUTION COEFFICIENT.

ETHYL FORMATE IS ABSORBED BY THE LUNGS AND THE GI TRACT; SLIGHT PENETRATION OF THE SKIN IS SAID TO OCCUR...

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 6 items

Used as flavoring agent, solvent for nitrocellulose, and reagent in organic synthesis; Also used as a fungicide/larvicide for tobacco, cereals, and dried fruit; [ACGIH]

Farming (Pesticides) [Category: Industry]

IN LACQUER INDUSTRY, IN ARTIFICIAL SILK MFR AS SOLVENT FOR CELLULOSE ACETATE; IN MFR OF SAFETY GLASS; IN SHOE INDUSTRY AS SOLVENT FOR CELLULOID

SOLVENT FOR OILS AND GREASES

FLAVOR FOR LEMONADE & ESSENCES; MFR OF ARTIFICIAL RUM & ARRAC; SOLVENT FOR NITROCELLULOSE; FUNGICIDE AND LARVICIDE; IN ORGANIC SYNTHESIS

ACETONE SUBSTITUTE; IN SYNTHETIC RESINS

U.S. Production · 2 items

(1978) PROBABLY GREATER THAN 4.54X10+5 G

(1982) PROBABLY GREATER THAN 9.08X10+5 G

Methods of Manufacturing · 3 items

ESTERIFICATION OF FORMIC ACID WITH ETHYL ALCOHOL IN THE PRESENCE OF SULFURIC ACID

/IT IS/...PREPARED BY ESTERIFICATION OF ETHYL ALCOHOL AND FORMIC ACID OR BY DISTILLATION OF ETHYL ACETATE & FORMIC ACID IN PRESENCE OF CONCN SULFURIC ACID.

Produced by carbonylation of ethanol with carbon monoxide...

Formulations/Preparations · 3 items

AREGINAL.../IS/ MIXTURE OF METHYL FORMATE AND ETHYL FORMATE.

ASSAY: 95% MINIMUM.

GRADES: TECHNICAL; FCC.

Use Classification · 4 items

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information · 4 items

Formic acid, ethyl ester: ACTIVE

USE IN FOODS RESTRICTED TO 0.0015%.

NON-ALCOHOLIC BEVERAGES 9.4 PPM, ALCOHOLIC BEVERAGES 10 PPM, ICE CREAM, ICES, ETC 21 PPM, CANDY 50 PPM, BAKED GOODS 98 PPM, GELATINS AND PUDDINGS 0.35-11 PPM, CHEWING GUM 430 PPM.

OF DIRECT FOOD ADDITIVES: LIMITATIONS- SYNTHETIC FLAVOR.

Applications · 4 items

DescriptionEthyl formate is an ester formed when ethanol (an alcohol) reacts with formic acid (a carboxylic acid). It is also known as ethyl methanoate because formic acid is also known as methanoic acid. Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries.

OccurrenceReported in the oil of Boronia dentigeroides; it has been identified in Florida orange juice, several varieties of honey, apple and pear and in distilled liquors, such as rum. Also reported found in peach, raspberry, strawberry, pineapple, cabbage, vinegar, cheeses, butter, cream, milk powder, cooked beef, beer, coffee, tea, honey, corn oil, brandy and mussels.

UsesEthyl Formate is a flavoring agent that occurs naturally in some plant oils, fruits, and juices but does not occur naturally in the ani- mal kingdom. it is used in food at a maximum level, as served, of 0.05% in baked goods; 0.04% in chewing gum, hard candy, and soft candy; 0.02% in frozen dairy desserts; 0.03% in gelatins, puddings, and fillings; and 0.01% in all other food categories.Ethyl formate is also used as a solvent for nitrocellulose; as fungicide and larvicide for tobacco, cereals, dried fruits, etc.; in organic synthesis.

General DescriptionA clear colorless liquid with a pleasant odor. Flash point -4°F. Less dense than water. Vapors heavier than air.

Preparation methods

PreparationEthyl Formate is an ester of formic acid and is prepared by esterification of formic acid with ethyl alcohol or by distillation of ethyl acetate and formic acid in the presence of concentrated sulfuric acid.

Additional notes

DefinitionChEBI: Ethyl formate is a formate ester resulting from the formal condensation of formic acid with ethanol. It has a role as a fumigant and a plant metabolite. It is a formate ester and an ethyl ester.

Related reactions

1,399 records

Linked notes

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