Methyl formate

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Methyl formate
Structural formula of methyl formate Structural formula of methyl formate.svg
Structural formula of methyl formate
Ball-and-stick model of the methyl formate molecule Methyl-formate-3D-balls.png
Ball-and-stick model of the methyl formate molecule
Commercial methyl formate.jpg
Preferred IUPAC name
Methyl formate
Systematic IUPAC name
Methyl methanoate
Other names
3D model (JSmol)
ECHA InfoCard 100.003.166 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-282-1
PubChem CID
  • InChI=1S/C2H4O2/c1-4-2-3/h2H,1H3 Yes check.svgY
  • InChI=1/C2H4O2/c1-4-2-3/h2H,1H3
  • O=COC
Molar mass 60.052 g·mol−1
AppearanceColorless liquid
Odor pleasant [1]
Density 0.98 g/cm3
Melting point −100 °C (−148 °F; 173 K)
Boiling point 32 °C (90 °F; 305 K)
30% (20°C) [1]
Vapor pressure 634 hPa (476 mmHg) (20°C) [1]
-32.0·10−6 cm3/mol
GHS labelling: [2]
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
H224, H302, H319, H332, H335
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
Flash point −19 °C; −2 °F; 254 K [1]
Explosive limits 4.5%-23% [1]
Lethal dose or concentration (LD, LC):
1622 mg/kg (oral, rabbit) [3]
50,000 ppm (guinea pig, 20 min) [3]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 100 ppm (250 mg/m3) [1]
REL (Recommended)
TWA 100 ppm (250 mg/m3) ST 150 ppm (375 mg/m3) [1]
IDLH (Immediate danger)
4500 ppm [1]
Safety data sheet (SDS) Oxford MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of an ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest. [4]



In the laboratory, methyl formate can be produced by the condensation reaction of methanol and formic acid, as follows:


Industrial methyl formate, however, is usually produced by the combination of methanol and carbon monoxide (carbonylation) in the presence of a strong base, such as sodium methoxide: [4]

Base-catalyzed carbonylation of methanol with carbon monoxide to methyl formate Industrial synthesis of methyl formate.svg
Base-catalyzed carbonylation of methanol with carbon monoxide to methyl formate

This process, practiced commercially by BASF among other companies gives 96% selectivity toward methyl formate. The catalyst for this process is sensitive to water, which can be present in the carbon monoxide feedstock, which is commonly derived from synthesis gas. Very dry carbon monoxide is, therefore, essential. [5]


Methyl formate is used primarily to manufacture formamide, dimethylformamide, and formic acid. These compounds are precursors or building blocks for many useful derivatives.

Because of its high vapor pressure, it is used for quick-drying finishes and as a blowing agent for some polyurethane foam applications and as a replacement for CFCs, HCFCs, and HFCs. Methyl formate has zero ozone depletion potential and zero global warming potential [ citation needed ]. It is also used as an insecticide.

A historical use of methyl formate, which sometimes brings it attention, was in refrigeration. Before the introduction of less-toxic refrigerants, methyl formate was used as an alternative to sulfur dioxide in domestic refrigerators, such as some models of the famous GE Monitor Top.

Related Research Articles

<span class="mw-page-title-main">Methanol</span> Organic compound (CH3OH); simplest alcohol

Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colourless, flammable liquid with a distinctive alcoholic odour similar to that of ethanol (potable alcohol). A polar solvent, methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide.

<span class="mw-page-title-main">Formic acid</span> Simplest carboxylic acid (HCOOH)

Formic acid, systematically named methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH and structure H−C(=O)−O−H. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts and the anion derived from formic acid are called formates. Industrially, formic acid is produced from methanol.

<span class="mw-page-title-main">Iodoform</span> Chemical compound

Iodoform (also known as triiodomethane and, inaccurately, as carbon triiodide) is the organoiodine compound with the chemical formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Methyl acetate</span> Chemical compound

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Formamide</span> Chemical compound

Formamide is an amide derived from formic acid. It is a colorless liquid which is miscible with water and has an ammonia-like odor. It is chemical feedstock for the manufacture of sulfa drugs and other pharmaceuticals, herbicides and pesticides, and in the manufacture of hydrocyanic acid. It has been used as a softener for paper and fiber. It is a solvent for many ionic compounds. It has also been used as a solvent for resins and plasticizers. Some astrobiologists suggest that it may be an alternative to water as the main solvent in other forms of life.

Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is structurally related to formamide, having two methyl groups in the place of the two hydrogens. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Methyl methacrylate</span> Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

<span class="mw-page-title-main">Ethyl formate</span> Chemical compound

Ethyl formate is an ester formed when ethanol reacts with formic acid. Ethyl formate has the characteristic smell of rum and is also partially responsible for the flavor of raspberries. It occurs naturally in the body of ants and in the stingers of bees.

Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.

<span class="mw-page-title-main">Maleic anhydride</span> Chemical compound

Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and polymers.

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

<span class="mw-page-title-main">Isobutanol</span> Chemical compound

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

<span class="mw-page-title-main">Methacrylic acid</span> Chemical compound

Methacrylic acid, abbreviated MAA, is an organic compound. This colorless, viscous liquid is a carboxylic acid with an acrid unpleasant odor. It is soluble in warm water and miscible with most organic solvents. Methacrylic acid is produced industrially on a large scale as a precursor to its esters, especially methyl methacrylate (MMA), and to poly(methyl methacrylate) (PMMA). MAA occurs naturally in small amounts in the oil of Roman chamomile.

<span class="mw-page-title-main">Dimethoxymethane</span> Chemical compound

Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimethoxymethane is soluble in three parts water and miscible with most common organic solvents.

<span class="mw-page-title-main">2-Methoxyethanol</span> Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

<span class="mw-page-title-main">Nitroethane</span> Chemical compound

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates.


  1. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0417". National Institute for Occupational Safety and Health (NIOSH).
  2. "Methyl formate". Retrieved 19 December 2021.
  3. 1 2 "Methyl formate". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 Werner Reutemann and Heinz Kieczka "Formic Acid" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a12_013
  5. W. Couteau, J. Ramioulle, US Patent US4216339