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methyl formate

Chemical Structure

General Material Information

Preferred name methyl formate
Trivial Name Methyl formate
Short Description formic acid, methyl ester
Formula C2 H4 O2
CAS Number 107-31-3
Flavis Number 9.642
ECHA Number 203-481-7
FDA UNII 1MPH591FTG
Nikkaji Number J4.064I
Beilstein Number 1734623
MDL MFCD00003291
COE Number 10795
NMR Predictor External link
Synonyms
  • formic acid methyl ester
  • formic acid, methyl ester
  • formicacidmethylester
  • methyl ester of formic acid
  • methyl methanoate
  • methylformate
  • Methanoic acid methyl ester
  • R 611
  • Greenmate

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Literature & References

methyl formate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:107-31-3
Pubchem (cid):7865
Pubchem (sid):134972417
Publications by PubMed
Correction to "ab initio reaction kinetics of hydrogen abstraction from methyl formate by hydrogen, methyl, oxygen, hydroxyl, and hydroperoxy radicals".
Detection and Identification of the Keto-Hydroperoxide (HOOCH2OCHO) and Other Intermediates during Low-Temperature Oxidation of Dimethyl Ether.
Sonophotodeposition of Bimetallic Photocatalysts Pd-Au/TiO2 : Application to Selective Oxidation of Methanol to Methyl Formate.
Dynamical, spectroscopic and computational imaging of bond breaking in photodissociation: roaming and role of conical intersections.
Comparison of sample preparation methods for the quantitative analysis of eicosanoids and other oxylipins in plasma by means of LC-MS/MS.
Formation of complex organic molecules in methanol and methanol-carbon monoxide ices exposed to ionizing radiation--a combined FTIR and reflectron time-of-flight mass spectrometry study.
Methyl N-phenyl carbamate synthesis from aniline and methyl formate: carbon recycling to chemical products.
Addition-elimination versus Tishchenko reaction in the gas phase.
The formation of glycine and other complex organic molecules in exploding ice mantles.
Low-energy electron-induced chemistry of condensed methanol: implications for the interstellar synthesis of prebiotic molecules.
Mass spectral characterisation of a polar, esterified fraction of an organic extract of an oil sands process water.
Theoretical spectroscopic characterization at low temperatures of S-methyl thioformate and O-methyl thioformate.
Homogeneous hydrogenation of CO₂ to methyl formate utilizing switchable ionic liquids.
Electrocatalytic oxidation and adsorption rate of methanol at Pt stepped single-crystal electrodes and effect of Ru step decoration: a DEMS study.
Ag/Au mixed sites promote oxidative coupling of methanol on the alloy surface.
Accurate bond energies of biodiesel methyl esters from multireference averaged coupled-pair functional calculations.
Surface treatment with methyl formate-methyl acetate increased the shear bond strength between reline resins and denture base resin.
Molecular hydrogen formation from photocatalysis of methanol on anatase-TiO₂(101).
Roads leading to roam. Role of triple fragmentation and of conical intersections in photochemical reactions: experiments and theory on methyl formate.
The α-effect and competing mechanisms: the gas-phase reactions of microsolvated anions with methyl formate.
Variation in concentration of perfluorooctanoic acid in methanol solutions during storage.
Shape-controlled solvothermal synthesis of Bi2S3 for photocatalytic reduction of CO2 to methyl formate in methanol.
Graphene-supported Au-Pd bimetallic nanoparticles with excellent catalytic performance in selective oxidation of methanol to methyl formate.
LC-MS/MS method for rapid and concomitant quantification of pro-inflammatory and pro-resolving polyunsaturated fatty acid metabolites.
DFT investigations for the reaction mechanism of dimethyl carbonate synthesis on Pd(II)/β zeolites.
Mechanisms of lactone hydrolysis in neutral and alkaline conditions.
Mechanisms of lactone hydrolysis in acidic conditions.
Accurate treatment of two-dimensional non-separable hindered internal rotors.
Photocatalytic cross-coupling of methanol and formaldehyde on a rutile TiO2(110) surface.
An exchangeable-tip scanning probe instrument for the analysis of combinatorial libraries of electrocatalysts.
Sequential photo-oxidation of methanol to methyl formate on TiO2(110).
Influence of the O-protonation in the O═C-O-Me Z preference. A QTAIM study.
High-temperature measurements of the reactions of OH with small methyl esters: methyl formate, methyl acetate, methyl propanoate, and methyl butanoate.
Synchrotron FTIR spectroscopy of weak torsional bands: a case study of cis-methyl formate.
Ab initio reaction kinetics of hydrogen abstraction from methyl formate by hydrogen, methyl, oxygen, hydroxyl, and hydroperoxy radicals.
Spontaneous electric fields in films of cis-methyl formate.
Computational mechanistic study of the hydrogenation of carbonate to methanol catalyzed by the Ru(II)PNN complex.
Volatile compounds and sensory analysis of both harvests of double-cut Yakima peppermint (Mentha piperita L.).
Dissociative electron-ion recombination of the interstellar species protonated glycolaldehyde, acetic acid, and methyl formate.
Transient Ru-methyl formate intermediates generated with bifunctional transfer hydrogenation catalysts.
Mechanistic investigations on dimethyl carbonate formation by oxidative carbonylation of methanol over a CuY zeolite: an operando SSITKA/DRIFTS/MS study.
Methyl 2,2'-dimethyl-4'-[2-(methyl-sulfan-yl)eth-yl]-1,3-dioxo-2,3-dihydro-1H,4'H-spiro-[isoquinoline-4,5'-oxazole]-4'-carboxyl-ate.
Carbonylation of nitrobenzene in methanol with palladium bidentate phosphane complexes: an unexpectedly complex network of catalytic reactions, centred around a Pd-imido intermediate.
Acute airway irritation of methyl formate in mice.
Quantifying temperature and flow rate effects on the performance of a fixed-bed chromatographic reactor.
Structure of complexes formed by dissolution of palladium diacetate in methanol and chloroform. In situ NMR study.
Methyl formate and its mono and difluoro derivatives: conformational manifolds, basicity, and interaction with HF theoretical investigation.
Potential energy surface and rotational cross sections for methyl formate colliding with helium.
[Spectralsignatures of nickel and vanadium supported photocatalysts and their photocatalytic properties].
Thermal decomposition of methyl 2-azidopropionate studied by UV photoelectron spectroscopy and matrix isolation IR spectroscopy: heterocyclic intermediate vs imine formation.
Spatial distributions and interstellar reaction processes.
Effect of ionization on infrared and electronic absorption spectra of methyl and ethyl formate in the gas phase and in astrophysical H2O ice: a computational study.
Fuel-specific influences on the composition of reaction intermediates in premixed flames of three C5H10O2 ester isomers.
Molecular elimination of methyl formate in photolysis at 234 nm: roaming vs. transition state-type mechanism.
Magnetic hyperfine coupling of a methyl group undergoing internal rotation: a case study of methyl formate.
The effect of chemical surface treatments on the flexural strength of repaired acrylic denture base resin.
On the temperature dependence of flammability limits of gases.
Photocatalytic reduction of CO2 in methanol to methyl formate over CuO-TiO2 composite catalysts.
Atmospheric chemistry of C2F5CH2OCH3 (HFE-365mcf).
Elevated formic acid concentrations in putrefied post-mortem blood and urine samples.
Product study of the OH radical and Cl atom initiated oxidation of 1,3-dioxane.
A Study of Micronucleus Induction with Methyl Formate and 2-Methylbutane in Bone Marrow Cells of Male ICR Mice.
Electronic state spectroscopy of methyl formate probed by high resolution VUV photoabsorption, He(i) photoelectron spectroscopy and ab initio calculations.
Reactivity of heteropolytungstate and heteropolymolybdate metal transition salts in the synthesis of dimethyl carbonate from methanol and CO₂.
Ab initio chemical kinetics of methyl formate decomposition: the simplest model biodiesel.
Guaiane sesquiterpenes from seaweed Ulva fasciata Delile and their antibacterial properties.
Insights into the mechanistic photodissociation of methyl formate.
Nanoporous gold catalysts for selective gas-phase oxidative coupling of methanol at low temperature.
Removal of high concentration dimethyl methylphosphonate in the gas phase by repeated-batch reactions using TiO2.
Binuclear TiOMn charge-transfer chromophore in mesoporous silica.
Metabolism and cometabolism of cyclic ethers by a filamentous fungus, a Graphium sp.
Methanol electrooxidation on PtRu bulk alloys and carbon-supported PtRu nanoparticle catalysts: a quantitative DEMS study.
N-formylation of amines via the aerobic oxidation of methanol over supported gold nanoparticles.
Selectivity control in gold-mediated esterification of methanol.
Gas-phase fragmentation of protonated C60-pyrimidine derivatives.
Flow through reactors for organic chemistry: directly electrically heated tubular mini reactors as an enabling technology for organic synthesis.
Analysis of potassium formate in airport storm water runoff by headspace solid-phase microextraction and gas chromatography-mass spectrometry.
Photodissociation dynamics of methyl formate at 193.3 nm: Branching ratios, kinetic-energy distributions, and angular anisotropies of products.
Molecular dynamics prediction of the mechanism of ester hydrolysis in water.
Photochemical study of the transport properties of gases in polymer films.
A study on flammability limits of fuel mixtures.
Biodiesel production by supercritical process with crude bio-methanol prepared by wood gasification.
Improved efficiency of focal point conformational analysis with truncated correlation consistent basis sets.
Catalytic oxidation of methanol on Pd metal and oxide clusters at near-ambient temperatures.
The relationship of methanol and formate concentrations in fatalities where methanol is detected.
Methanol oxidation using ozone on titania-supported vanadia catalyst.
Towards predictive inhibitor design for the EGFR autophosphorylation activity.
Carbon dioxide fixation into chemicals (methyl formate) at high yields by surface coupling over a Pd/Cu/ZnO nanocatalyst.
Conformational equilibria in formic acid and the adduct of formic acid and hexafluoroacetone, HCO2C(CF3)2OH.
Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder.
Sevoflurane breakdown produces flammable concentrations of hydrogen.
Structures and properties of zirconia-supported ruthenium oxide catalysts for the selective oxidation of methanol to methyl formate.
On gas phase alpha-effects. 1. The gas-phase manifestation and potential SET character.
Interferometric observations of large biologically interesting interstellar and cometary molecules.
Photocatalytic oxidation of methyl ethyl ketone over sol-gel and commercial TiO2 for the improvement of indoor air.
Active control of methanol carbonylation selectivity over Au/carbon anode by electrochemical potential.
Collision-energy-resolved penning ionization electron spectroscopy of HCOOH, CH3COOH, and HCOOCH3 by collision with He*(2(3)S) metastable atoms.
Extended Le Chatelier's formula for carbon dioxide dilution effect on flammability limits.
Recognition of small polar molecules with an ionic crystal of alpha-Keggin-type polyoxometalate with a macrocation.
Solvent effects on the structural and formyl substrate reactivity properties of a nitrogen/sulfur-ligated zinc hydroxide complex.
Production of methyl-oxonium ion and its complexes in the core-excited (HC(O)OCH3)n clusters: H/H+ transfer from the alpha carbonyl.
Mechanism of the aminolysis of methyl benzoate: a computational study.
Dimethyl ether oxidation at elevated temperatures (295-600 K).
Some basic parameters of microspheres fabricated from a branched oligoester by a rapid procedure.
Multiple isotope effect study of the acid-catalyzed hydrolysis of methyl formate.
Electrochemical oxidation of methanol using dppm-bridged Ru/Pd, Ru/Pt and Ru/Au catalysts.
[Hygienic standards of the occupational air quality established by the Experts on Chemical Agents, 2002].
Synthesis of porritoxin.
Alcohol dehydrogenases that catalyse methyl formate synthesis participate in formaldehyde detoxification in the methylotrophic yeast Candida boidinii.
Effect of oil substitution in chiral microemulsion electrokinetic chromatography.
[Diagnostic importance of formic acid detection in methyl alcohol poisoning].
Photocatalytic oxidation of gaseous 2-chloroethyl ethyl sulfide over TiO2.
Mechanistic study of the gas-phase decomposition of methyl formate.
Post-mortem analysis of formic acid disposition in acute methanol intoxication.
In situ FTIR studies on the effect of temperature on the electro-oxidation of small organic molecules at the Ru(0001) electrode.
Metal-catalyzed silacyclopropanation of mono- and disubstituted alkenes.
A theoretical analysis of the free-energy profile of the different pathways in the alkaline hydrolysis of methyl formate in aqueous solution.
Hydroxide as general base in the saponification of ethyl acetate.
Methyl rotational barriers in amides and thioamides.
Ellipsometric study of undersaturated critical adsorption.
Synthesis, structure, and reactions of (acylimino)triaryl-lambda(5)-bismuthanes: first comparative study of the (acylimino)pnictorane series.
Barriers to rotation in methyl formate by dynamic NMR spectroscopy and barriers to 1,3 oxygen-to-oxygen migration in methyl formate and trifluoromethyl formate by ab initio calculations.
Verification of NEXAFS assignments by a comparison of fragmentation between gaseous and condensed methyl formate.
Multiple isotope effects on the acyl group transfer reactions of amides and esters.
Formate species in the low-temperature oxidation of dimethyl ether.
The gas-phase reaction between hydroxide ion and methyl formate: a theoretical analysis of the energy surface and product distribution.
Solvent effects on oxygen-17 chemical shifts in methyl formate: linear solvation shift relationships.
Isopropanol and methylformate exposure in a foundry: exposure data and neurobehavioural measurements.
Toxicokinetic modelling of methyl formate exposure and implications for biological monitoring.
Branched oligoester microspheres fabricated by a rapid emulsion solvent extraction method.
Urinary methanol and formic acid as indicators of occupational exposure to methyl formate.
Experimental exposure to methylformate and its neurobehavioral effects.
Substitutes for methylene chloride as dental softening agent.
Growth of Candida boidinii on methanol and the activity of methanol-degrading enzymes as affected from formaldehyde and methylformate.
Analysis of methanol or formic acid in body fluids by headspace solid-phase microextraction and capillary gas chromatography.
Hemiacetal dehydrogenation activity of alcohol dehydrogenases in Saccharomyces cerevisiae.
Ester synthesis by NAD(+)-dependent dehydrogenation of hemiacetal: production of methyl formate by cells of methylotrophic yeasts.
Purification and properties of methyl formate synthase, a mitochondrial alcohol dehydrogenase, participating in formaldehyde oxidation in methylotrophic yeasts.
Oxidative cleavage of esters and amides to carbonyl products by cytochrome P450.
A novel formaldehyde oxidation pathway in methylotrophic yeasts: methylformate as a possible intermediate.
Insertion reactions of metal carbonyl anions with methyl formate in the gas phase as revealed by (13)C- and D-labeling.
The spectrum of Orion-KL at 2 millimeters (150-160 GHz).
Interferometric observations for oxygen-containing organic molecules toward Orion-KL.
Dye-linked dehydrogenase activities for formate and formate esters in Amycolatopsis methanolica. Characterization of a molybdoprotein enzyme active with formate esters and aldehydes.
Determination of prostaglandins in human seminal fluid by solid-phase extraction, pyridinium dichromate derivatization and high-performance liquid chromatography.
Observations of some oxygen-containing and sulfur-containing organic molecules in cold dark clouds.
In vivo enzymology: a deuterium NMR study of formaldehyde dismutase in Pseudomonas putida F61a and Staphylococcus aureus.
Seed Dormancy in Red Rice : VII. Structure-Activity Studies of Germination Stimulants.
Gas chromatographic analysis of methyl formate and application in methanol poisoning cases.
Rapid quantification of 11 prostanoids by combined capillary column gas chromatography and negative ion chemical ionization mass spectrometry: application to prostanoids released from normal human embryonic lung fibroblasts WI38 in a culture medium.
Polymerization of phenols catalyzed by peroxidase in nonaqueous media.
Determination of 2,3-dinor-6-ketoprostaglandin F1 alpha in urine samples by liquid chromatography and radioimmunoassay.
Studies on the decomposition of the oxime HI 6 in aqueous solution.
Peroxidases depolymerize lignin in organic media but not in water.
Proposed structure for the noncovalently associated heme prosthetic group of dissimilatory nitrite reductases. Configuration of substituents of acrylochlorin.
Simultaneous extraction and preparation for high-performance liquid chromatography of prostaglandins and phospholipids.
Measurement of human venous plasma prostacyclin and metabolites by radioimmunoassay: a reappraisal.
Factors influencing the resistance of biological monitors to ethylene oxide.
Rapid extraction of oxygenated metabolites of arachidonic acid from biological samples using octadecylsilyl silica.
Gas chromatographic head-space assay of formic acid as methyl formate in biologic fluids: potential application to methanol poisoning.
Sorption processes in gas sterilization in the medical sector.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
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(IUPAC):Periodic Table of the Elements
FDA Indirect Additives used in Food Contact Substances:View
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CHEMBL:View
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2915.13.5000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
grade: technical, refined, fcc

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 60.052280426025
Specific gravity @ 25 °C
Pounds per Gallon 8.105 to 8.113
Refractive Index 1.341 to 1.346 @ 20 °C
Boiling Point 31.5 to 31.8°C @ 760 mm Hg
Boiling Point 8 to 9°C @ 300 mm Hg
Vapor Pressure 731.903992 mmHg @ 25 °C
Vapor Density 2.1
Flash Point TCC Value -26.67 °C TCC
logP (o/w) 0.03
Solubility
alcohol Yes
water, 1.293e+005 mg/L @ 25 °C (est) Yes
water, 2.30E+05 mg/L @ 25 °C (exp) Yes

Organoleptic Properties

Odor Type: Fruity
fruity, plum, estery
General comment At 10.00 % in dipropylene glycol. fruity plum estery
Flavor Type: Fruity
plum, estery
General comment Plum

Occurrences

Potential Uses

Applications
Flavoring purposes Arrack, Berry mixed berry, Cherry, Lemon, Plum
Other purposes Fumigant

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 12 - Extremely flammable.
R 20/22 - Harmful by inhalation and if swallowed.
R 36/37 - Irritating to eyes and respiratory system.
S 02 - Keep out of the reach of children.
S 09 - Keep container in a well-ventilated place.
S 16 - Keep away from sources of ignition - No Smoking.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 33 - Take precautionary measures against static discharge.
S 36/37/39 - Wear suitable clothing, gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50 1500 mg/kg
(BASF AG, 1979)

oral-rat LD50 475 mg/kg
(Eastman Kodak Co., 1994a)

oral-mouse LD50 475 mg/kg
(Eastman Kodak Co., 1994a)

oral-rabbit LD50 1600 mg/kg
(Munch,1972)

oral-rabbit LD50 1600 mg/kg
(Gosselin et al., 1984)

oral-rabbit LD50 1622 mg/kg
(RTECS,2002)

oral-mouse LD50 675 mg/kg
National Technical Information Service. Vol. OTS0556689

oral-rabbit LD50 1622 mg/kg
Industrial Medicine and Surgery. Vol. 41, Pg. 31, 1972.

oral-rat LD50 475 mg/kg
National Technical Information Service. Vol. OTS0556689

Dermal Toxicity:
skin-guinea pig LD50 > 20 ml/kg
National Technical Information Service. Vol. OTS0556689

skin-rabbit LD50 > 5000 mg/kg
National Technical Information Service. Vol. OTS0556797

skin-rat LD50 > 4000 mg/kg
National Technical Information Service. Vol. OTS0556791

Inhalation Toxicity:
inhalation-rat LC50 5200 mg/m3/4H
National Technical Information Service. Vol. OTS0556791

Safety in use information

Category:
flavoring agents
Recommendation for methyl formate usage levels up to:
not for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.97 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 2700 (μg/person/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 5.0000035.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 5.0000025.00000
Edible ices, including sherbet and sorbet (03.0): 10.0000050.00000
Processed fruit (04.1): 7.0000035.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 5.0000050.00000
Chewing gum (05.3): --
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 5.0000025.00000
Bakery wares (07.0): 5.0000050.00000
Meat and meat products, including poultry and game (08.0): 2.0000010.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): --
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 5.0000025.00000
Foodstuffs intended for particular nutritional uses (13.0): 10.0000050.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): 2.0000025.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 5.0000050.00000
Ready-to-eat savouries (15.0): 20.00000100.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 5.0000025.00000

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 2, Revision 1 (FGE.02) : Branched- and straight-chain aliphatic saturated primary alcohols and related esters of primary alcohols and straight-chain carboxylic acids and one straight-chain aldehyde from chemical groups 1 and 2 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

EPI System: View
NIOSH International Chemical Safety Cards:search
NIOSH Pocket Guide:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):107-31-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :7865
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1243
WGK Germany:1
methyl formate
Chemidplus:0000107313
EPA/NOAA CAMEO:hazardous materials
RTECS:107-31-3