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109-94-4

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Identification

Name
Ethyl formate
CAS
109-94-4
Synonyms
ETHYL FORMATE
ETHYL METHANOATE
FEMA 2434
FORMIC ACID ETHYL ESTER
FORMIC ETHER
Aethylformiat
Areginal
Ethyl ester of formic acid
Ethyle(formiate d')
ethyle(formiated’)
ethyle(formiated’)(french)
Ethylester kyseliny mravenci
ethylesterkyselinymravenci
ethylformate(dot)
Ethylformiaat
Ethylformic ester
ethylformicester
Etile(formiato di)
etile(formiatodi)
femanumber2434.
EINECS(EC#)
203-721-0
Molecular Formula
C3H6O2
MDL Number
MFCD00003294
Molecular Weight
74.08
MOL File
109-94-4.mol

Chemical Properties

Appearance
colourless liquid with an aromatic odour
Appearance
Ethyl formate is a colorless liquid with a fruity odor.
mp 
−80 °C(lit.)

Melting point 
-80 °C (lit.)
Boiling point 
52-54 °C (lit.)
bp 
52-54 °C(lit.)

density 
0.921 g/mL at 20 °C(lit.)

vapor density 
2.5 (vs air)

vapor pressure 
15.16 psi ( 55 °C)

refractive index 
n20/D 1.359(lit.)

FEMA 
2434
Fp 
7 °F

storage temp. 
Flammables area
solubility 
Miscible with alcohol, benzene, and ether (Hawley, 1981)
form 
Liquid
color 
Clear
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.
Odor
Characteristic; pleasant aromatic.
Odor Threshold
2.7ppm
explosive limit
16%
Water Solubility 
11 g/100 mL (18 ºC)
Sensitive 
Moisture Sensitive
Merck 
14,3807
JECFA Number
26
BRN 
906769
Henry's Law Constant
0.097(x 10-3 atm?m3/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)
Exposure limits
TLV-TWA 100 ppm (~300 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 8000 ppm (NIOSH).
InChIKey
WBJINCZRORDGAQ-UHFFFAOYSA-N
Uses
Plant volatiles such as ethyl formate have been shown to have insecticidal properties as fumigant. The efficacy of ethyl formate against insect pests of food commodities, bagged cereals, spices, pulses, dry fruits and oilcakes had been proved. The fumigant was known to provide a high mortality of mixed stage cultures of the key stored product pests, with limited efficacy against the pupal stage of few pests like S. oryzae. The advantages of ethyl formate include natural occurrence in food; rapid kill of insects (2-4 hours); fast breakdown of residues to natural products and low human toxicity. However the fumigant exhibits poor penetration characteristics and high doses (>120 g/t of grain) were required to control internal feeders, which was higher than the flammable limit of 85 g/t. Formulations of ethyl formate in liquid carbon dioxide were found to overcome the problems of flammability and poor penetration.
Uses
Ethyl 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. it 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.
CAS DataBase Reference
109-94-4(CAS DataBase Reference)
NIST Chemistry Reference
Formic acid, ethyl ester(109-94-4)
EPA Substance Registry System
109-94-4(EPA Substance)

Safety Data

Hazard Codes 
F,Xn
Risk Statements 
R11:Highly Flammable.
R20/22:Harmful by inhalation and if swallowed .
R36/37:Irritating to eyes and respiratory system .
Safety Statements 
S9:Keep container in a well-ventilated place .
S16:Keep away from sources of ignition-No smoking .
S24:Avoid contact with skin .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S33:Take precautionary measures against static discharges .
RIDADR 
UN 1190 3/PG 2

WGK Germany 
1

RTECS 
LQ8400000

Autoignition Temperature
851 °F
TSCA 
Yes
HazardClass 
3
PackingGroup 
II
HS Code 
29151300
Safety Profile
Moderately toxic by ingestion and subcutaneous routes. Mddly toxic by skin contact and inhalation. A powerful inhalation irritant in humans. A skin and eye irritant. Questionable carcinogen with experimental tumorigenic data. Highly flammable liquid. A very dangerous fire and explosion hazard when exposed to heat, flame, or oxilzers. To fight fire, use alcohol foam, spray, mist, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTERS.
Hazardous Substances Data
109-94-4(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 4.29 g/kg (Smyth)

Raw materials And Preparation Products

Raw materials
Etanol-->Formic acid-->Calcium chloride-->Aluminium chloride hexahydrate
Preparation Products
2-Aminopyrimidine-5-carbonitrile-->4-Chloropyridine-3-carboxaldehyde-->4-METHOXY-3-BUTEN-2-ONE-->2-(TRIFLUOROMETHYL)PYRIMIDIN-4-AMINE-->METHYL 3-AMINO-6-METHYLTHIOPHENO[2,3-B]PYRIDINE-2-CARBOXYLATE-->7-Aminoisoquinoline-->6-Methyl-1H-pyrazolo[3,4-b]pyridin-3-amine-->5-Acetamidomethyl-4-Amino-2-Methyl pyrimidine-->2-AMINO-4-METHYLOXAZOLE-->5-BROMO-4-HYDROXY-2-METHYLPYRIMIDINE-->Thiamine chloride-->AMITRAZ METABOLITE HYDROCHLORIDE-->Tropic acid-->4-CHLORO-2-(TRIFLUOROMETHYL)PYRIMIDINE-->Methyl 3-amino-4-phenylthiophene-2-carboxylate-->3-Cyano-6-methyl-2(1H)-pyridinone-->N-Methylformamide-->3,4-DIHYDROISOQUINOLINE-->7-NITRO-3,4-DIHYDROISOQUINOLINE-->2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER-->4,5,6-TRIAMINOPYRIMIDINE-->2-Chloro-6-methyl-3-pyridinecarbonitrile-->1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine-->Ninhydrin hydrate-->4-METHYLPYRIMIDIN-2-OL HYDROCHLORIDE-->1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBALDEHYDE-->A-(HYDROXYMETHYL)BENZENACETIC ACID METHYL ESTER-->4-Hydroxy-2-(trifluoromethyl)pyrimidine-->4-chloro-5-fluoropyrimidine-->1-Methyl-2-imidazolecarboxaldehyde-->5-N-PROPYLURACIL-->5-PROPYL-2-THIOURACIL-->4-HYDROXY-2-METHYLPYRIMIDINE-->4,5-DIBROMOTHIOPHENE-2-CARBOXALDEHYDE-->7-Bromoisoquinoline-->4-CHLORO-1-ETHYL-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER-->α-Dimethoxymethyl-methoxypropionitrile-->EPOSTANE-->alpha,alpha-Diphenyl-L-prolinol-->1,1-Diethoxy-3,7-dimethylocta-2,6-diene

Hazard Information

General Description
A clear colorless liquid with a pleasant odor. Flash point-4°F. Less dense than water. Vapors heavier than air.
Reactivity Profile
ETHYL FORMATE(109-94-4) is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. This compound is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids [Note: Decomposes slowly in water to form ethyl alcohol and formic acid.] .
Air & Water Reactions
Highly flammable. Soluble in water. Slowly decomposed by water to formic acid, a corrosive material and ethyl alcohol, another flammable liquid.
Hazard
Narcotic and irritant to skin and eyes; use in foods restricted to 0.0015%. Highly flammable, dangerous fire and explosion risk. Questionable carcinogen.
Health Hazard
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.
Potential Exposure
This material is used as an emulsifier; food and feed additive; flavor, packaging material; as a solvent for cellulose nitrate and acetate; it is used as a fumigant and in the production of synthetic flavors. It is also a raw material in pharmaceutical manufacture
First aid
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 24 to 48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy
Fire Hazard
Behavior in Fire: Vapor is heavier than air and may travel long distance to a source of ignition and flash back.
Shipping
UN1190 Ethyl formate, Hazard Class: 3; Labels: 3-Flammable liquid
Incompatibilities
May form explosive mixture with air. Reacts violently with nitrates, strong oxidizers, strong alkalis, and strong acids. Decomposes slowly in water, forming ethyl alcohol and formic acid. May accumulate static electrical charges, and may cause ignition of its vapors
Description
Ethyl 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.
Ethyl formate
Chemical Properties
Ethyl Formate occurs widely in fruits. It is a liquid with a slightly pungent, fruity, ethereal odor and is used in fruit flavors.
Chemical Properties
Ethyl formate has a characteristic, pungent odor similar to ethyl acetate and reminiscent of pineapple and a slightly bitter taste. It has been also reported to have a rum-like odor. The ester is slightly soluble in water (9 parts/100 at 18 °C) with gradual decomposition into formic acid and ethanol; it is miscible in ethanol, ether, and acetone (HSDB, 2013), as well as in benzene.
Waste Disposal
Spray into a furnace in admixture with a flammable solvent
Physical properties
Colorless, clear liquid with a pleasant, fruity odor. An odor threshold concentration of 2.7 ppmv was reported by Nagata and Takeuchi (1990).
History
Astronomers have identified ethyl formate in dust clouds in an area of the Milky Way galaxy called Sagittarius B2. The astronomers, from the Max Planck Institute for Radio Astronomy in Bonn, Germany, used the 30 meter IRAM radio telescope in Spain to analyze the spectra of radiation emitted from hot regions near a new star. It is among 50 molecules identified by the astronomers.
Occurrence
Reported 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.
Definition
ChEBI: A formate ester resulting from the formal condensation of formic acid with ethanol.
Production Methods
Ethyl formate is manufactured via esterfication of formic acid and ethanol in the presence of sulfuric acid and alternatively by distillation of ethyl acetate and formic acid in the presence of sulfuric acid.
Aroma threshold values
Detection: 17 ppm
Taste threshold values
Taste characteristics at 60 ppm: sweet, chemical with clean, fresh, fruity lift.
Chemical Reactivity
Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
Agricultural Uses
Fumigant, Insecticide: Used as a fumigant, especially on dried fruit, Also used as a solvent for cellulose nitrate and acetate and in the production of synthetic flavors. Not currently registered for agricultural use in EU countries and the U.S. Used in Australia and there are 63 global suppliers.
Safety
Ethyl methanoate is generally recognized as safe by the U.S. Food and Drug Administration.
According to the U.S Occupational Safety and Health Administration (OSHA), ethyl formate can irritate eyes, skin, mucous membranes, and the respiratory system of humans and other animals; it is also a central nervous system depressant.In industry, it is used as a solvent for cellulose nitrate, cellulose acetate, oils, and greases. It can be used as a substitute for acetone; workers may also be exposed to it under the following circumstances:
during spray, brush, or dip applications of lacquers
during the manufacture of safety glass
When fumigating tobacco, cereals, and dried fruits (as an alternative to methyl bromide under the U.S. Department of Agriculture quarantine system ).
Environmental Fate
Photolytic. Reported rate constants for the reaction of ethyl formate and OH radicals in the atmosphere (296 K) and aqueous solution are 1.02 x 10-11 and 6.5 x 10-13 cm3/molecule?sec, respectively (Wallington et al., 1988b).
Chemical/Physical. Slowly hydrolyzes in water forming ethanol and formic acid (Windholz et al., 1983).
Purification Methods
Free acid or alcohol is removed by standing the ester over anhydrous K2CO3, with occasional shaking, then decanting and distilling from P2O5. Alternatively, the ester can be kept over CaH2 for several days, then distilled from fresh CaH2. It cannot be dried with CaCl2 because it reacts rapidly with the ester to form a crystalline compound. [Beilstein 2 IV 23.]

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