109-94-4

Basic information

• Product Name: Ethyl formate
• Synonyms: FEMA 2434;FORMIC ACID ETHYL ESTER;FORMIC ETHER;ETHYL METHANOATE;ETHYL FORMATE;Aethylformiat;Areginal;Ethyl ester of formic acid
• CAS NO: 109-94-4
• Molecular Formula: C₃H₆O₂
• Molecular Weight: 74.08
• EINECS: 203-721-0
• Product Categories: Organics;Analytical Chemistry;Solvents for HPLC & Spectrophotometry;Solvents for Spectrophotometry;Organic synthesis
• Mol File: 109-94-4.mol
• Article Data: 254

Chemical Properties

• Melting Point: −80 °C(lit.)
• Boiling Point: 52-54 °C(lit.)
• Flash Point: 7 °F
• Appearance: Clear/Liquid
• 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.)
• Storage Temp.: Flammables area
• Solubility: Miscible with alcohol, benzene, and ether (Hawley, 1981)
• Explosive Limit: 16%
• Water Solubility: 11 g/100 mL (18 ºC)
• Sensitive: Moisture Sensitive
• Stability: Stable. Extremely flammable. May form explosive mixtures with air. Note low flash point and wide explosive limits. Incompatible
• Merck: 14,3807
• BRN: 906769
• CAS DataBase Reference: Ethyl formate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl formate(109-94-4)
• EPA Substance Registry System: Ethyl formate(109-94-4)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-20/22-36/37
• Safety Statements: 9-16-24-26-33
• RIDADR: UN 1190 3/PG 2
• WGK Germany: 1
• RTECS: LQ8400000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 109-94-4(Hazardous Substances Data)

Usage

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.

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.

Physical properties

Colorless and transparent liquid, volatile, with a pleasant, fruity odor. Miscible with ethanol and ether, soluble in acetone. The solubility in water is 11.8g/100ml.

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.

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.Ethyl formate is also used as a solvent for nitrocellulose; as fungicide and larvicide for tobacco, cereals, dried fruits, etc.; in organic synthesis.

Definition

ChEBI: 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.

Preparation

Ethyl 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.

Taste threshold values

Taste characteristics at 60 ppm: sweet, chemical with clean, fresh, fruity lift.

General Description

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

Air & Water Reactions

Highly flammable. Soluble in water. Slowly decomposed by water to formic acid, a corrosive material and ethyl alcohol, another flammable liquid.

Reactivity Profile

Ethyl formate 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. Ethyl formate is incompatible with the following: Nitrates; strong oxidizers, alkalis & acids [Note: Decomposes slowly in water to form ethyl alcohol and formic acid.] .

Health Hazard

The irritant action of ethyl formate inthe eyes, nose, and mucous membranes ismilder than that of methyl formate. How ever it is more narcotic than the methylester. Cats exposed to 10,000 ppm died after90 minutes, after deep narcosis. A 4-hourexposure to 8000 ppm was lethal to rats.Inhalation of 5000 ppm for a short periodproduces eye and nasal irritation and salivation in rats. The toxic effects from ingestion include somnolence, narcosis, gastritis,and dyspnea. The oral LD50 values in various test animals range between 1000 and2000 mg/kg.

Fire Hazard

Highly flammable liquid. Vapor is heavier than air and may travel long distance to a source of ignition and flash back. 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.

Flammability and Explosibility

Flammable

Agricultural 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.

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.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.

Potential Exposure

In industry, Ethyl formate 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 lacquersduring the manufacture of safety glassWhen 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).

Shipping

UN1190 Ethyl formate, Hazard Class: 3; Labels: 3-Flammable liquid

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.]

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

Waste Disposal

Spray into a furnace in admixture with a flammable solvent

InChI:InChI=1/C3H6O2/c1-2-5-3-4/h3H,2H2,1H3

Synthetic route

formic acid (64-18-6) + ethyl difluoroacetate (454-31-9) → Difluoroacetic acid (381-73-7) + formic acid ethyl ester (109-94-4)

Conditions	Yield
sulfuric acid at 70℃; Product distribution / selectivity;	A 96% B n/a

4-oxopentanoic acid ethyl ester (539-88-8) + orthoformic acid triethyl ester (122-51-0) → ethyl 4,4-diethoxypentanoate (92557-39-6) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol at 145℃; ketalization;	A 94% B n/a

ethanol (64-17-5) + formic acid cyanomethyl ester (150760-95-5) → formic acid ethyl ester (109-94-4)

Conditions	Yield
With 1H-imidazole for 24h; Ambient temperature;	93%
With 1H-imidazole Yield given;

orthoformic acid triethyl ester (122-51-0) → ethyl bromide (74-96-4) + ethyl trimethylsilyl ether (1825-62-3) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With chloro-trimethyl-silane; sodium bromide for 2h; Product distribution; Heating; Me3SiBr generated in situ;	A n/a B n/a C 92%

ethanol (64-17-5) + sodium salt of β-mercaptonaphthalene (39689-37-7) → ethyl 2-naphthyl sulfide (32551-87-4) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With carbon monoxide at 150℃; under 75006 Torr; for 21h;	A 90% B n/a

ethyl vinyl ether (109-92-2) → formaldehyd (50-00-0) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With ozone at 24.85℃; under 100 Torr; for 0.416667h; Kinetics;	A n/a B 86%
With dihydrogen peroxide at 98.85℃; under 100 Torr; for 4h; Kinetics; Further Variations:; Temperatures; Pressures; Reagents; Irradiation;	A n/a B 83%
With ozone at 24.84℃; under 760.051 Torr; Kinetics; Concentration; Time; Gas phase;	A 15 %Chromat. B 80 %Chromat.

methyl chloroformate (79-22-1) + dibutyl (diethoxymethyl)phosphine (82833-74-7) → chloroethane (75-00-3) + dibutyl(methoxycarbonyl)phosphine (112499-32-8) + formic acid ethyl ester (109-94-4)

Conditions	Yield
In diethyl ether for 4h; Heating;	A n/a B 85% C n/a

tris(2-diphenylphosphanylethyl)aminerhodium(I) hydride (85233-91-6) + ethyl cyanoformate (623-49-4) → N(CH2CH2P(C6H5)2)3RhCN (118681-53-1) + formic acid ethyl ester (109-94-4)

Conditions	Yield
In tetrahydrofuran soln. of formate added to stirred suspn. of complex (N2), gently warmed to 40°C (1 h), cooled to room temp.; mixt. of ethanol/n-hexane (1:1) added, concd. (brisk current of N2), sepd., collected on sintered glass frits, washed (EtOH, pentane), dried (N2);	A 71% B 85%

Triethyl orthoacetate (78-39-7) + allyl alcohol (107-18-6) → ethanol (64-17-5) + ethyl 4-pentenoate (1968-40-7) + C9H18O3 + ethyl acetate (141-78-6) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With formic acid at 150℃; for 16h; Reagent/catalyst; Johnson-Claisen Rearrangement; Autoclave;	A n/a B 83% C n/a D n/a E n/a

formic acid (64-18-6) + diethyl (trichloromethyl)phosphonate (866-23-9) → formic acid ethyl ester (109-94-4)

Conditions	Yield
at 120℃; for 24h;	82%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) + ethanol (64-17-5) → 5-(ethoxymethyl)furfural (1917-65-3) + 4-oxopentanoic acid ethyl ester (539-88-8) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With sulfuric acid at 75℃; for 24h; Reagent/catalyst; Temperature; Sealed tube;	A 81% B 16% C n/a

Dichloromethyl methyl ether (4885-02-3) + ethyl P-(diethoxymethyl)phosphonite (65600-72-8) → diethyl phosphorylchloridite (589-57-1) + chloroethane (75-00-3) + Methyl formate (107-31-3) + formic acid ethyl ester (109-94-4)

Conditions	Yield
at 60 - 70℃; Product distribution; argon atmosphere;	A 80% B n/a C n/a D n/a

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + Ethyl diethoxyacetate (6065-82-3) → 2,2-diethoxy-N,N-dimethylacetamide (34640-92-1) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With lithium methanolate In methanol at 80℃; for 10h; Product distribution / selectivity;	A 80% B n/a

tris(2-diphenylphosphanylethyl)phosphanerhodium(I) hydride (109786-30-3) + ethyl cyanoformate (623-49-4) → RhCN(tris(2-(diphenylphosphino)ethyl)phosphine) (118681-54-2) + formic acid ethyl ester (109-94-4)

Conditions	Yield
In tetrahydrofuran neat formate pipetted into soln. of complex, heated at ca. 40°C (20-30 min), cooled to room temp.; ethanol/n-hexane 1:1 added, concd. (N2), crystals collected on sintered glass frits, washed (EtOH, pentane), dried (N2);	A 70% B 80%

3,4-methylenedioxyphenyl formate (80592-18-3) → Sesamol (533-31-3) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With ethanol; sodium hydroxide at 82 - 96℃; for 4.5h; Reflux; elimination of ethyl formate;	A 79% B n/a

Dichloromethyl methyl ether (4885-02-3) + (diethoxymethyl)diisopropylphosphine oxide (95987-39-6) → chloroethane (75-00-3) + Methyl formate (107-31-3) + Chlorodiisopropylphosphane (40244-90-4) + formic acid ethyl ester (109-94-4)

Conditions	Yield
at 60℃; for 1h; Product distribution; argon atmosphere;	A n/a B n/a C 76% D n/a

pentacarbonylhydridomanganese (16972-33-1) + Et-oxycarbonylcobalt tetracarbonyl → (CO)5MnCo(CO)4 (35646-82-3) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With carbon monoxide In n-heptane Kinetics; heptane, 25°C, CO atmosphere, 24 h; evapd. in vac. at 0°C, crystd. at -79°C;	A 71% B n/a

formic acid (64-18-6) + ethanol (64-17-5) → formic acid ethyl ester (109-94-4)

Conditions	Yield
With phosphorus pentoxide; copper(II) sulfate; sodium sulfate for 20h; Ambient temperature;	70%
With Ag2(4,4'-bipy)2(O3SCH2CH2SO3)*4H2O-based polymer Reflux;	70%
With sulfuric acid; mercury(II) sulfate unter Durchleiten von Acetylen;

dicyclohexyl peroxydicarbonate (1561-49-5) + orthoformic acid triethyl ester (122-51-0) → diethoxycyclohexyloxymethane (25604-46-0) + formic acid ethyl ester (109-94-4) + Diethyl carbonate (105-58-8)

Conditions	Yield
at 60℃; for 2h;	A 70% B n/a C n/a

orthoformic acid triethyl ester (122-51-0) → diethoxycyclohexyloxymethane (25604-46-0) + formic acid ethyl ester (109-94-4) + Diethyl carbonate (105-58-8)

Conditions	Yield
With dicyclohexyl peroxydicarbonate at 60℃; for 2h;	A 70% B n/a C n/a
With dicyclohexyl peroxydicarbonate at 60℃; for 4h;	A 0.56 mmol B 0.37 mmol C 0.17 mmol

styrene (292638-84-7) + ethanol (64-17-5) → formaldehyd (50-00-0) + benzoic acid ethyl ester (93-89-0) + benzaldehyde (100-52-7) + formic acid ethyl ester (109-94-4)

Conditions	Yield
Stage #1: styrene; ethanol With ozone Stage #2: at 90 - 100℃; Further byproducts given;	A 6% B 63.4% C 6.3% D 20.4%

5-hydroxymethyl-2-furfuraldehyde (67-47-0) + ethanol (64-17-5) → 4-oxopentanoic acid ethyl ester (539-88-8) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With sulfuric acid at 120℃; for 30h; Reagent/catalyst; Sealed tube;	A 62% B n/a

Acetyl bromide (506-96-7) + ethyl P-(diethoxymethyl)phosphonite (65600-72-8) → ethyl bromide (74-96-4) + formic acid ethyl ester (109-94-4) + diethyl acetylphosphonate (919-19-7)

Conditions	Yield
for 1h; Heating; argon atmosphere;	A n/a B n/a C 61%

bromoethyl ethyl ether (116779-75-0) + orthoformic acid triethyl ester (122-51-0) → diethyl acetal (105-57-7) + formic acid ethyl ester (109-94-4)

Conditions	Yield
at 25℃;	A 61% B n/a

2-oxo-propionic acid ethyl ester (617-35-6) + orthoformic acid triethyl ester (122-51-0) → ethyl 2,2-diethoxypropionate (7476-20-2) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol	A 61% B n/a

1-chloroethyl ethyl ether (7081-78-9) + orthoformic acid triethyl ester (122-51-0) → diethyl acetal (105-57-7) + formic acid ethyl ester (109-94-4)

Conditions	Yield
for 12h;	A 59% B n/a

ethanol (64-17-5) + D-glucose (50-99-7) → formic acid (64-18-6) + formic acid ethyl ester (109-94-4)

Conditions	Yield
With H8[PMo7V5O40]; oxygen In water at 90℃; under 15001.5 Torr; for 24h; Autoclave;	A 56% B 40%

ethanol (64-17-5) + chloroform (67-66-3) → formic acid ethyl ester (109-94-4)

Conditions	Yield
at 20℃; for 6h; UV-irradiation;	55%

formic acid (64-18-6) + diethyl sulphite (623-81-4) → formic acid ethyl ester (109-94-4)

Conditions	Yield
sulfuric acid Heating;	53%

tryptamine (61-54-1) + formic acid ethyl ester (109-94-4) → Nb-formyltryptamine (6502-82-5)

Conditions	Yield
for 24h; Reflux;	100%
for 6h; Reflux;	100%
With triethylamine In methanol at 100℃; for 16h; Inert atmosphere;	97%

isobutylamine (78-81-9) + formic acid ethyl ester (109-94-4) → N-isobutylformamide (6281-96-5)

Conditions	Yield
for 12h; Reflux; Inert atmosphere;	100%

phenylacetonitrile (140-29-4) + formic acid ethyl ester (109-94-4) → phenyl(formyl)acetonitrile (5841-70-3)

Conditions	Yield
With sodium hydride	100%
With sodium hydride In tetrahydrofuran at 50℃; for 0.333333h;	86%
With sodium In ethanol at 0 - 40℃;	78.7%

ethanolamine (141-43-5) + formic acid ethyl ester (109-94-4) → (2-hydroxyethyl)-formamide (693-06-1)

Conditions	Yield
Stage #1: ethanolamine With sodium ethanolate at 20℃; for 0.5h; Stage #2: formic acid ethyl ester In ethanol for 1h; Heating; Further stages.;	100%
at 10 - 20℃; for 12h;	100%
	99%

chloroacetic acid ethyl ester (105-39-5) + formic acid ethyl ester (109-94-4) → ethyl 2-chloro-3-oxopropanoate (33142-21-1)

Conditions	Yield
With sodium ethanolate In tert-butyl methyl ether at 0 - 20℃; Inert atmosphere; Large scale;	100%
With sodium ethanolate In tert-butyl methyl ether at 0 - 20℃; Inert atmosphere; Large scale;	100%
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;	95%

rac-methylbenzylamine (618-36-0) + formic acid ethyl ester (109-94-4) → N-formyl-α-methylbenzylamine (6948-01-2)

Conditions	Yield
for 8h; Reflux;	100%
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction;	94%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 70℃; for 15h; Microwave irradiation; Sealed tube; Inert atmosphere;	81%

propan-1-ol-3-amine (156-87-6) + formic acid ethyl ester (109-94-4) → 3-(N-formylamino)propan-1-ol (49807-74-1)

Conditions	Yield
	100%
Reflux;	100%
at 50℃; for 2.25h; Cooling with ice;	95%

n-Dodecylamine (124-22-1) + formic acid ethyl ester (109-94-4) → N-(dodecyl)formamide (7402-57-5)

Conditions	Yield
for 20h; Inert atmosphere; Reflux;	100%

formic acid ethyl ester (109-94-4) + succinic acid diethyl ester (123-25-1) → diethyl 2-formylbutanedioate (5472-38-8)

Conditions	Yield
With sodium In diethyl ether at 40℃; for 5h;	100%
With sodium In diethyl ether at 40℃; for 5h;	100%
With sodium hydride In toluene at 20℃; for 16h; Reagent/catalyst;	95.1%

1-amino-2-propene (107-11-9) + formic acid ethyl ester (109-94-4) → N-allylformamide (16250-37-6)

Conditions	Yield
at 60℃; for 6h;	100%
for 1h; Heating;	86%
at 0 - 20℃; Inert atmosphere;	80%

1-bromo-4-butene (5162-44-7) + formic acid ethyl ester (109-94-4) → 1,8-nonadiene-5-ol (94427-72-2)

Conditions	Yield
Stage #1: 1-bromo-4-butene With magnesium In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: formic acid ethyl ester In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	100%
Stage #1: 1-bromo-4-butene With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: formic acid ethyl ester In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;	98%
Stage #1: 1-bromo-4-butene With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: formic acid ethyl ester In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	94%

cyclobutylamine (2516-34-9) + formic acid ethyl ester (109-94-4) → N-cyclobutylformamide (87055-64-9)

Conditions	Yield
for 4h; Heating;	100%
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction;	98%
With toluene-4-sulfonic acid

(S)-1-phenyl-ethylamine (2627-86-3) + formic acid ethyl ester (109-94-4) → (S)-N-formyl-1-phenylethylamine (19145-06-3)

Conditions	Yield
In toluene for 15h; Heating;	100%
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction;	95%

(R)-1-phenyl-ethyl-amine (3886-69-9) + formic acid ethyl ester (109-94-4) → (R)-(+)-α-methylbenzyl formamide (6948-01-2, 19145-06-3, 31502-34-8, 42412-77-1)

Conditions	Yield
for 8h; Reflux;	100%
With amberlyst 15 In tetrahydrofuran for 21h; Reflux; Inert atmosphere;	99%
With Novozyme 435 CALB In tetrahydrofuran at 20℃; Green chemistry; Enzymatic reaction;	92%

4-butanolide (96-48-0) + formic acid ethyl ester (109-94-4) → sodium salt of (Z)-3-(hydroxymethylene)dihydro-2(3H)-furanone (51270-64-5, 54211-97-1, 93698-26-1)

Conditions	Yield
With sodium hydride	100%
With sodium In diethyl ether at -20 - -15℃; for 5h;

4-butanolide (96-48-0) + formic acid ethyl ester (109-94-4) → sodium salt of (E)-3-(hydroxymethylene)dihydro-2(3H)-furanone (54211-97-1)

Conditions	Yield
With sodium hydride	100%
With ethanol; sodium hydride In 1,2-dimethoxyethane at 40℃; for 22h; cross-Claisen acylation;	97%
With sodium methylate In diethyl ether for 12h;	69%
With sodium hydroxide In 1,2-dimethoxyethane at 60℃; for 16h;	66%

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9) + formic acid ethyl ester (109-94-4) → Sodium; [2-oxo-dihydro-pyran-(3Z)-ylidene]-methanolate

Conditions	Yield
With sodium hydride	100%

(2-aminomethylpyridine) (3731-51-9) + formic acid ethyl ester (109-94-4) → N-((pyridin-2-yl)methyl)formamide (56625-03-7)

Conditions	Yield
for 1.5h; Reflux;	100%
at 25℃; for 8h;

cyclohexanone (108-94-1) + formic acid ethyl ester (109-94-4) → 2-(hydroxymethylene)cyclohexanone (823-45-0)

Conditions	Yield
With sodium hydride In tetrahydrofuran; paraffin oil at 10 - 20℃;	100%
With sodium methylate In toluene for 24h;	94%
With ethanol; sodium hydride In diethyl ether; mineral oil at 20℃;	92%

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + formic acid ethyl ester (109-94-4) → N-[2-(3,4-dimethoxyphenyl)ethyl]formamide (14301-36-1)

Conditions	Yield
at 70℃; for 20h;	100%
at 70℃;	100%
Reflux;	99%

Cyclopentamine (1003-03-8) + formic acid ethyl ester (109-94-4) → N-cyclopentylcarboxamide (41215-40-1)

Conditions	Yield
for 4h; Heating;	100%
for 3h; Heating;	97%
Heating;
Reflux;
In ethanol at 90℃; for 9h;

Cyclopropylamine (765-30-0) + formic acid ethyl ester (109-94-4) → N-cyclopropylformamide (58644-54-5)

Conditions	Yield
for 4h; Heating;	100%
at 50℃; for 5h;	84%
With sodium carbonate In ethanol for 20h; Ambient temperature;	59%

2-(3-methoxyphenyl)-1-ethanamine (2039-67-0) + formic acid ethyl ester (109-94-4) → N-[2-(3-methoxy-phenyl)-ethyl]-formamide (110339-54-3)

Conditions	Yield
In toluene for 6h; Heating;	100%

(S)-1-Pyrrolidin-2-yl-methanol (23356-96-9) + formic acid ethyl ester (109-94-4) → (S)-(-)-1-Formyl-2-(hydroxymethyl)pyrrolidine (55456-46-7)

Conditions	Yield
at 50℃;	100%

5-methyl-2-hydroxyacetophenone (1450-72-2) + formic acid ethyl ester (109-94-4) → 2,3-dihydro-2-hydroxy-6-methyl-1-benzopyran-4-one (90617-36-0)

Conditions	Yield
With sodium methylate In tetrahydrofuran at 20℃; for 0.5h;	100%
With sodium In diethyl ether Heating;	74%

2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine (22231-61-4) + formic acid ethyl ester (109-94-4) → N-formyl-2-[3-methoxy-4-(benzyloxy)phenyl]ethylamine (55803-41-3)

Conditions	Yield
In tetrahydrofuran for 12h; Reflux;	100%
for 12h; Inert atmosphere; Reflux;	95%
for 1h; Heating;	78%
at 70 - 80℃; for 8h;	50.72%

(S)-valinol (2026-48-4) + formic acid ethyl ester (109-94-4) → (S)-N-[1-(hydroxymethyl)-2-methylpropyl]formamide (89876-66-4)

Conditions	Yield
for 4h; Heating;	100%
Reflux;	99%
for 2h; Heating;	95%

1-dodecyl alcohol (112-53-8) + formic acid ethyl ester (109-94-4) → 1-dodecanyl formate (28303-42-6)

Conditions	Yield
cerium (IV) sulfate; silica gel for 1h; Heating;	100%

1-dimethylamino-butan-2-one (114049-99-9) + formic acid ethyl ester (109-94-4) → Sodium; (Z)-4-dimethylamino-2-methyl-3-oxo-but-1-en-1-olate

Conditions	Yield
With sodium hydride In toluene	100%

ethyl 2-fluoroacetate (459-72-3) + formic acid ethyl ester (109-94-4) → (1-ethoxy-2-fluoro-1,3-dioxopropan-2-yl) sodium (1652-39-7)

Conditions	Yield
With sodium hydride In diethyl ether; ethanol; mineral oil at 20℃; Inert atmosphere; Cooling with ice;	100%
With sodium ethanolate In tetrahydrofuran at 0 - 20℃;	94.7%
With sodium hydride In diethyl ether for 2h; Ambient temperature;
With ethanol; sodium hydride In diethyl ether; mineral oil at 20℃; Inert atmosphere; Cooling with ice;

Upstream product

• 64-17-5 Etanol 

Downstream Products

• 485-47-2 Ninhydrin hydrate 
• 23676-63-3 5-Acetamidomethyl-4-Amino-2-Methyl pyrimidine 
• 80471-63-2 EPOSTANE 
• 3967-53-1 A-(HYDROXYMETHYL)BENZENACETIC ACID METHYL ESTER 
• 38071-22-6 4,5-DIBROMOTHIOPHENE-2-CARBOXALDEHYDE 
• 1753-48-6 2-Aminopyrimidine-5-carbonitrile 
• 1514-96-1 4-CHLORO-2-(TRIFLUOROMETHYL)PYRIMIDINE 
• 1546-80-1 4-Hydroxy-2-(trifluoromethyl)pyrimidine 
• 35629-70-0 2-AMINO-4-METHYLOXAZOLE 
• 128537-47-3 4-CHLORO-1-ETHYL-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER 
• 23707-37-1 7-Aminoisoquinoline 
• 13750-81-7 1-Methyl-2-imidazolecarboxaldehyde 
• 51550-40-4 AMITRAZ METABOLITE HYDROCHLORIDE 
• 114077-82-6 4-Chloropyridine-3-carboxaldehyde 
• 28900-10-9 2-Chloro-6-methyl-3-pyridinecarbonitrile 
• 118-70-7 4,5,6-TRIAMINOPYRIMIDINE 
• 2954-52-1 5-PROPYL-2-THIOURACIL 
• 1123-54-2 1H-1,2,3-Triazolo[4,5-d]pyrimidin-7-amine 
• 4652-27-1 4-METHOXY-3-BUTEN-2-ONE 
• 1608-83-9 α-Dimethoxymethyl-methoxypropionitrile 
• 529-64-6 Tropic acid 
• 3230-65-7 3,4-DIHYDROISOQUINOLINE 
• 112068-01-6 (S)-(?)-α,α-Diphenyl-2-pyrrolidinemethanol 
• 79173-38-9 6-Methyl-1H-pyrazolo[3,4-b]pyridin-3-amine 
• 80360-23-2 1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBALDEHYDE 
• 19030-75-2 5-N-PROPYLURACIL 
• 4241-27-4 3-Cyano-6-methyl-2(1H)-pyridinone 
• 57401-76-0 2-AMINO-PYRIMIDINE-5-CARBOXYLIC ACID ETHYL ESTER 
• 58794-09-5 7-Bromoisoquinoline 
• 59-43-8 Thiamine chloride 
• 62541-59-7 7-NITRO-3,4-DIHYDROISOQUINOLINE 
• 672-42-4 2-(TRIFLUOROMETHYL)PYRIMIDIN-4-AMINE 
• 67383-35-1 4-HYDROXY-2-METHYLPYRIMIDINE 
• 7492-66-2 1,1-Diethoxy-3,7-dimethylocta-2,6-diene 
• 82437-64-7 Methyl 3-amino-4-phenylthiophene-2-carboxylate 

Recommend Products

• 2591-86-8  N-Formylpiperidine 
• 110-89-4  piperidine 
• 7755-92-2  piperazine-1-carbaldehyde 
• 4164-39-0  N,N'-diformylpiperazine 
• 110-85-0  piperazine 
• 1192-79-6  formyl-2 methyl-5 pyrrole 
• 636-41-9  2-methyl-1H-pyrrole 
• 60-29-7  diethyl ether 
• 925-90-6  ethylmagnesium bromide 
• 98-03-3  thiophene-2-carbaldehyde 
• 1003-09-4  2-bromothiophene 
• 89941-77-5  2-methoxy-tetrahydro-furan-3-carboxylic acid methyl ester 
• 96-48-0  4-butanolide 
• 22236-96-0  3-N-formylaminopyridine