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
Show more names
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
- Formal charge
- 0
- Complexity
- 26.1
Experimental & physicochemical properties
Pesticides
Insecticides
Active substance -> EU Pesticides database: Not approved
LogP
0.23
0.23
0.23
0.27
Density
0.922 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9168 @ 20 °C
CONVERSION FACTORS: 1 MG/L EQUIV TO 330 PPM; 1 PPM EQUIV TO 3.03 MG/CU M; DENSITY OF SATURATED AIR: 1.25 (AIR= 1)
Relative density (water = 1): 0.92
0.917-0.922
0.92
Color/Form
MOBILE LIQUID
WATER-WHITE LIQ
Colorless liquid.
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.)
- FEMA
- 2434 · 2434 | ETHYL FORMATE
- FLAVIS Number
- 9.072 · 09.072 | Ethyl formate
- Flash point
- 7 °F · 7 °F
- storage temp.
- 2 · 2-8°C
- solubility
- Miscible with alcohol, benzene, and ether (Hawley, 1981)
- form
- Liquid
- color
- Clear
- Odor
- Characteristic; pleasant aromatic.
- biological source
- synthetic
- Odor Type
- ethereal
- Odor Threshold
- 2.7 ppm · 2.7ppm
- explosive limit
- 16 % · 16%
- Water Solubility
- 11 g/100 · 11 g/100 mL (18 ºC)
- Thermal Conductivity
- 0.16 W/ · 0.16 W/(m·K) at 25 ℃
- Specific Heat Capacity
- 2.02 J/ · Cp(liquid): 2.02 J/(g·K), at 25℃
- Sensitive
- Moisture Sensitive
- JECFA Number
- 26 · 26
- Merck
- 14 · 14,3807
- BRN
- 906769 · 906769
- Henry's Law Constant
- 0.097 · 0.097(x 10-3 atmm3/mol) at 5.00 °C, 0.13 at 10.00 °C, 0.17 at 15.00 °C, 0.23 at 20.00 °C, 0.29 at 25.00 °C (column stripping-UV, Kutsuna et al., 2005)
- Dielectric constant
- 8.4 · 8.4(6℃)
- Exposure limits
- 100 ppm · ACGIH:TLV-STEL 100 ppm (303 mg/m3)OSHA:PEL-TWA 100 ppm (300 mg/m3)NIOSH:REL-TWA 100 ppm
- Stability
- Stable. Extremely flammable. May form explosive mixtures with air. Note low flash point and wide explosive limits. Incompatible with strong oxidizing agents, strong bases, strong acids, nitrates.
- Major Application
- agriculturecleaning productscosmeticsenvironmentalflavors and fragrancesfood and beveragespersonal care
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- 1S/C3H6O2/c1-2-5-3-4/h3H,2H2,1H3
- InChIKey
- WBJINCZRORDGAQ-UHFFFAOYSA-N
- SMILES
- CCOC=O
- LogP
- 1.504 at · 1.504 at 25℃
- CAS DataBase Reference
- 109 · 109-94-4(CAS DataBase Reference)
- SCOGS (Select Committee on GRAS Substances)
- Ethyl formate
- Substances Added to Food (formerly EAFUS)
- ETHYL FORMATE
- FDA 21 CFR
- 184.1295 · 184.1295
- EWG's Food Scores
- 2 · 2
- FDA UNII
- 0 K3E2L5553 · 0K3E2L5553
- NIST Chemistry Reference
- Formic acid, ethyl ester(109-94-4)
- EPA Substance Registry System
- Ethyl formate (109-94-4)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 2 · GHS02,GHS07,GHS08
- Signal word
- Danger
- Hazard statements
- 302 · H302+H332-H319-H360-H370-H373-H350-H335-H336-H225
- Precautionary statements
- 501 · P501-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P308+P311-P303+P361+P353-P301+P312+P330-P304+P340+P312-P403+P233-P403+P235-P405
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves
- Hazard Codes
- F,Xn
- Risk Statements
- 11 · 11-20/22-36/37
- Safety Statements
- 9 · 9-16-24-26-33
- OEB
- A
- OEL
- 100 ppm · TWA: 100 ppm (300 mg/m3)
- RIDADR
- 1190 · UN 1190
- WGK Germany
- 1 · 1
- RTECS
- 8400000 · LQ8400000
- Autoignition Temperature
- 851 °F · 851 °F
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29151300 · 29151300
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 4 InhalationAcute · Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2STOT SE 3
- Hazardous Substances Data
- 109 · 109-94-4(Hazardous Substances Data)
- Toxicity
- 50 orally · LD50 orally in rats: 4.29 g/kg (Smyth)
- IDLA
- 1 · 1,500 ppm
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
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
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.)
Fire Hazards
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
Burning Rate: 3.6 mm/min.
DANGEROUS, WHEN EXPOSED TO HEAT, FLAME, OR OXIDIZERS.
Health Hazards
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.
Hazards Summary
Liquid causes second degree burns after contact for a few minutes. [CHRIS] The anesthetic potency of ethyl formate is greater than ethanol, acetone, and alkanes such as pentane, but less than chlorinated hydrocarbons and ethyl ether. TLV Basis = upper respiratory tract irritant; Reported to be irritating at 321 ppm; [ACGIH] Esters may induce narcosis in animals, but workers' exposures are limited by irritating effects. See appendix in: [Dick RB, et al. Chemicals in the workplace: incorporating human neurobehavioral testing into the regulatory process. Am J Ind Med. 1998 May;33(5):439-53.] Inhalation of high concentrations causes drowsiness and unconsciousness; A skin, eye, and respiratory tract irritant; [ICSC]
DOT ID and Guide
1190 129
1190 129
Safety & protection
Fire Fighting
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
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
· 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
Excerpt from NIOSH Pocket Guide for Ethyl formate:
General First Aid:
(General first aid procedures)
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
100.0 [ppm]
Cleanup Methods
1. REMOVE ALL IGNITION SOURCES. 2. VENTILATE AREA OF SPILL OR LEAK. 3. FOR SMALL QUANTITIES, ABSORB ON PAPER TOWELS. EVAPORATE IN A SAFE PLACE (SUCH AS A FUME HOOD). ALLOW SUFFICIENT TIME FOR EVAPORATING VAPORS TO COMPLETELY CLEAR THE HOOD DUCTWORK. BURN THE PAPER IN A SUITABLE LOCATION AWAY FROM COMBUSTIBLE MATERIALS. LARGE QUANTITIES CAN BE COLLECTED AND ATOMIZED IN A SUITABLE COMBUSTION CHAMBER. ETHYL FORMATE SHOULD NOT BE ALLOWED TO ENTER A CONFINED SPACE, SUCH AS A SEWER, BECAUSE OF THE POSSIBILITY OF AN EXPLOSION.
Disposal Methods
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.
1. BY ABSORBING IT IN VERMICULITE, DRY SAND, EARTH OR A SIMILAR MATERIAL AND DISPOSING IN A SECURED SANITARY LANDFILL. 2. BY ATOMIZING IN A SUITABLE COMBUSTION CHAMBER.
Toxicology
Environmental Fate
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).
Exposure Routes
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
Cough. Shortness of breath. Headache. Drowsiness.
Redness.
Redness. Pain.
Sore throat. Further see Inhalation.
irritation eyes, upper respiratory system; In Animals: narcosis
Medical Surveillance
Employees should be screened for history of certain medical conditions which might place the employee at increased risk from ethyl formate exposure. /These include/ chronic respiratory disease ... skin disease ... liver disease ... kidney disease. ... Any employee developing the above-listed conditions should be referred for further medical examination.
Soil Adsorption/Mobility
Using a reported water solubility of 88.25 g/L(1) for ethyl formate, an estimated Koc of 8 was calculated using a regression equation(2,SRC). A Koc of 4 was estimated from molecular structure(3). According to a suggested classification scheme(3), this estimated Koc suggests that ethyl formate will be highly mobil in soil (SRC).
Natural Pollution Sources
/IT IS/ REPORTED IN OIL OF BORONIA DENTIGEROIDES. IT HAS BEEN IDENTIFIED IN FLORIDA ORANGE JUICE, SEVERAL VARIETIES OF HONEY, APPLES AND PEARS, & DISTILLED LIQUORS, SUCH AS RUM.
Ethyl formate occurs widely in fruit(1).
Human Toxicity Excerpts
/IT IS/ IRRITATING TO SKIN, MUCOUS MEMBRANES, & IN HIGH CONCENTRATIONS.../A CNS DEPRESSANT/.
No irritation was noted after a 48 hr closed-patch test of 4% ethyl formate on human subjects.
Slight eye irritation in human subjects and strong persistent nasal irritation were noted on exposure to 330 ppm in the air. ... The irritating effects on the eyes and respiratory tract are probably due to rapid hydrolysis of the ester on contact with water, with the formation of alcohol and formic acid.
THERE ARE NO REPORTS OF TOXIC EFFECTS ON HUMANS EXCEPT SLIGHT IRRITATION OF THE EYES AND NOSE...10,500 PPM CAUSES MODERATE BUT PROGRESSIVE IRRITATION OF EYES AND NOSE, REMAINING 4 HR AFTER EXPOSURE.
THE ANESTHETIC POTENCY /IS/ ... LESS THAN THAT OF CHLORINATED HYDROCARBONS & ETHYL ETHER, BUT IT /IS/ ... MORE ACTIVE ... THAN ETHANOL, ACETONE AND ALIPHATIC HYDROCARBONS ... .
Artificial Pollution Sources
Ethyl formate maybe released to the environment as a result of its production, transport, disposal and use as a synthetic flavoring agent in lemonades, chewing gum, ice cream, essences (apple, pineapple, banana, and peach flavors), artificial rum and arrac; as a fungicide and larvicide for tobacco, cereals, dried fruit, and other crops(1,3) and as a solvent for cellulose nitrate and acetate, as an acetone substitute and fumigant in packaged food, and in organic synthesis(2-4).
Regulatory information
FIFRA Requirements
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
- rtecs
- LQ8400000
- ridadr
- UN 1190
- hs_code
- 29151300
- Toxicity
- LD50 orally in rats: 4.29 g/kg (Smyth)
- risk_code
- 11-20/22-36/37
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07,GHS08
- hazard_code
- F,Xn
- safety_code
- 9-16-24-26-33
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H302+H332-H319-H360-H370-H373-H350-H335-H336-H225
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2STOT SE 3
- Autoignition Temperature
- 851 °F
- Precautionary statements
- P501-P270-P202-P240-P260-P210-P233-P201-P243-P241-P242-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P308+P311-P303+P361+P353-P301+P312+P330-P304+P340+P312-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 109-94-4(Hazardous Substances Data)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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
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...
Uses & manufacturing
Uses
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
(1978) PROBABLY GREATER THAN 4.54X10+5 G
(1982) PROBABLY GREATER THAN 9.08X10+5 G
Methods of Manufacturing
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
AREGINAL.../IS/ MIXTURE OF METHYL FORMATE AND ETHYL FORMATE.
ASSAY: 95% MINIMUM.
GRADES: TECHNICAL; FCC.
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
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
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.
Upstream & downstream products
Upstream raw materials
Downstream products
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
Linked notes
Loading…