Conditions | Yield |
---|---|
With oxygen at 120℃; under 3750.38 Torr; for 12h; Temperature; Reagent/catalyst; Autoclave; | 99.9% |
at 100℃; under 4137.29 - 15514.9 Torr; for 3h; Temperature; Pressure; | 98% |
With dihydrogen peroxide; Al1.3SiW12O40 at 80 - 250℃; Reagent/catalyst; | 96% |
Conditions | Yield |
---|---|
magnesium(II) perchlorate In nitromethane at 40℃; for 16h; | 99% |
With dmap In tetrahydrofuran for 88h; | 97% |
Conditions | Yield |
---|---|
With phosphotungstic acid for 4h; Reflux; | 98% |
With sulfuric acid for 4h; Reflux; | 93% |
With potassium carbonate In ethyl acetate for 1.5h; Heating; | 92% |
Conditions | Yield |
---|---|
at 20℃; for 24h; | 97% |
for 1h; Heating; Yield given; | |
With triethylamine at 20℃; for 1h; Inert atmosphere; |
Conditions | Yield |
---|---|
With dihydrogen peroxide for 3h; Irradiation; | 96% |
With PdCoBi/C; oxygen; potassium carbonate at 60℃; under 760.051 Torr; for 14h; Schlenk technique; Green chemistry; | 96% |
With oxygen at 20℃; for 12h; Irradiation; | 93% |
furan
methanol
tetrachloromethane
A
2-furoic acid methyl ester
B
furan-2,5-dicarboxylic acid dimethyl ester
Conditions | Yield |
---|---|
With copper(l) iodide at 120℃; for 6h; Inert atmosphere; Autoclave; | A 95% B 5% |
With copper(l) iodide at 140℃; for 0.5h; Inert atmosphere; Autoclave; | A 60% B 40% |
Conditions | Yield |
---|---|
With IRA 904 In acetonitrile 2.) 25 deg C, 10 h; | 94% |
Conditions | Yield |
---|---|
With sulfuric acid at 80 - 85℃; for 7.5h; Neat (no solvent); | 92.4% |
Conditions | Yield |
---|---|
With potassium bromide In N,N-dimethyl-formamide at 130℃; for 12h; Schlenk technique; chemoselective reaction; | 90% |
methanol
3-(furan-2-carbonyl)oxazolidin-2-one
2-furoic acid methyl ester
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 25℃; for 12h; Sealed tube; Inert atmosphere; Green chemistry; chemoselective reaction; | 88% |
methyl 3-aminofuran-2-carboxylate
2-furoic acid methyl ester
Conditions | Yield |
---|---|
With isopentyl nitrite In tetrahydrofuran at 120℃; under 5250.53 Torr; for 0.333333h; | 88% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; bis(1,5-cyclooctadiene)nickel (0) In toluene at 20℃; for 1h; Sealed tube; chemoselective reaction; | 87% |
Conditions | Yield |
---|---|
With sodium cyanide; potassium iodide at 15℃; Electrochemical reaction; | 86% |
Conditions | Yield |
---|---|
With triethylamine for 2.5h; | 83% |
N-methoxyfuran-2-carboxamide
2-furoic acid methyl ester
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 85℃; for 1.5h; Electrolysis; | 83% |
Conditions | Yield |
---|---|
at 400℃; for 0.05h; Temperature; Supercritical conditions; Flow reactor; High pressure; | 82% |
Conditions | Yield |
---|---|
With copper(II) chloride monohydrate; dihydrogen peroxide; oxygen; potassium carbonate; calcium chloride at 80℃; for 15h; Sealed tube; Green chemistry; | 81% |
furfural
methanol
A
2-furoic acid methyl ester
B
trans-azobenzene
C
trans-azoxybenzene
Conditions | Yield |
---|---|
With nitrobenzene; triethylamine; N-methyl-4,5-dimethylthiazolium iodide at 60℃; for 96h; Heating; | A 79% B n/a C n/a |
Conditions | Yield |
---|---|
With tellurium; bismuth (III) nitrate pentahydrate; 5%-palladium/activated carbon; oxygen In methanol at 60℃; under 760.051 Torr; for 8h; | 76% |
2-bromofuran
methanol
carbon monoxide
A
2-furanoic acid
B
2-furoic acid methyl ester
Conditions | Yield |
---|---|
With tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 42h; Irradiation; | A 2% B 72% |
2-bromofuran
carbon monoxide
A
2-furanoic acid
B
2-furoic acid methyl ester
Conditions | Yield |
---|---|
With methanol; tert-Amyl alcohol; sodium hydride; cobalt(II) acetate In tetrahydrofuran at 40℃; under 760 Torr; for 42h; Irradiation; | A 2% B 72% |
furan-2-carbonyl fluoride
tris(2,4,6-trimethoxyphenyl)phosphine
2-furoic acid methyl ester
Conditions | Yield |
---|---|
In toluene at 130℃; for 24h; Schlenk technique; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
With copper doped mesoporous polymelamine-formaldehyde In water; dimethyl sulfoxide at 100℃; for 16h; Catalytic behavior; | 65% |
With copper quinolate In water; dimethyl sulfoxide at 120℃; for 24h; | 44% |
Stage #1: tert.-butylhydroperoxide; 2-furanoic acid In water; dimethyl sulfoxide Stage #2: In water; dimethyl sulfoxide at 100℃; for 20h; Sealed tube; | 82 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: furan With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; cadmium(II) chloride-N,N,N',N'-tetramethylethylenediamine In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; Stage #2: methyl chloroformate In tetrahydrofuran; hexane at 0 - 20℃; Inert atmosphere; chemoselective reaction; | 60% |
Conditions | Yield |
---|---|
Stage #1: 2-(furan-2-yl)-5,5-dimethyl-[1,3,2]dioxaborinane; di-tert-butyl dicarbonate With 4,4'-dimethyl-2,2'-bipyridines; lithium methanolate; copper(l) chloride In N,N-dimethyl acetamide at 30℃; for 6h; Inert atmosphere; Schlenk technique; Stage #2: methyl iodide In N,N-dimethyl acetamide at 30℃; for 2h; Schlenk technique; | 43% |
furfural
ethanol
A
3-furan-2-yl-propenal
B
2-furoic acid methyl ester
Conditions | Yield |
---|---|
With oxygen; potassium carbonate at 140℃; under 2250.23 Torr; for 4h; Reagent/catalyst; | A 21% B n/a |
With oxygen at 140℃; under 2250.23 Torr; for 4h; Reagent/catalyst; Autoclave; | A 61.6 %Chromat. B 37 %Chromat. |
Conditions | Yield |
---|---|
With tellurium; bismuth (III) nitrate pentahydrate; 5%-palladium/activated carbon; oxygen In methanol at 60℃; under 760.051 Torr; for 8h; | 19% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; calcium chloride at 65℃; for 48h; | A n/a B 9% |
Conditions | Yield |
---|---|
With methanol; magnesium methanolate; Petroleum ether | |
Multi-step reaction with 2 steps 1: 18-crown-6 ether; potassium fluoride / tetrahydrofuran / 24 h / 40 °C / Schlenk technique; Inert atmosphere 2: toluene / 24 h / 130 °C / Schlenk technique; Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution; | 100% |
With potassium fluoride; thiophenol In various solvent(s) at 190℃; for 0.166667h; | 90% |
With potassium fluoride; thiophenol In 1-methyl-pyrrolidin-2-one for 0.166667h; Heating; | 90% |
2,5-bis(methylsulfonyl)-thiophene-1,1-dioxide
2-furoic acid methyl ester
Conditions | Yield |
---|---|
In 1,1,2,2-tetrachloroethylene at 100℃; | 100% |
2-furoic acid methyl ester
2-chloro-5-methylsulfonyl-thiophene-1,1-dioxide
Conditions | Yield |
---|---|
In 1,1,2,2-tetrachloroethylene at 100℃; | 100% |
2-furoic acid methyl ester
N,O-dimethylhydroxylamine*hydrochloride
N-methoxy-N-methyl-2-furancarboxamide
Conditions | Yield |
---|---|
With dimethylaluminum chloride In hexane; dichloromethane for 0.5h; Ambient temperature; | 99% |
Stage #1: 2-furoic acid methyl ester; N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at -20℃; for 0.0833333h; Inert atmosphere; Stage #2: With isopropylmagnesium chloride In tetrahydrofuran; diethyl ether at -20℃; for 0.416667h; Inert atmosphere; | 85% |
Conditions | Yield |
---|---|
With ethanol; [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II) at 100℃; for 24h; Inert atmosphere; Sealed tube; Darkness; | 99% |
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 100℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere; | 95% |
With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen In toluene at 80℃; under 37503.8 Torr; for 10h; | 80% |
Conditions | Yield |
---|---|
With zinc(II) chloride In dichloromethane at 50℃; for 24h; Temperature; Solvent; Reagent/catalyst; | 99% |
Multi-step reaction with 2 steps 1: formic acid; aqueous sulfuric acid 2: aqueous nitric acid View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid 2: aqueous nitric acid View Scheme | |
Multi-step reaction with 2 steps 1: chloroform; iron (III)-chloride; sodium sulfate / Reagens 4: Chlorwasserstoff 2: aqueous nitric acid View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; sulfuric acid; paraformaldehyde 2: aqueous nitric acid View Scheme |
2-furoic acid methyl ester
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With (iPrPNP)CoCH2SiMe3 In neat (no solvent) at 23℃; for 0.166667h; Reagent/catalyst; Temperature; Inert atmosphere; Glovebox; | 99% |
With (iPrPNP)CoCH2SiMe3 In neat (no solvent) at 23℃; for 0.166667h; Reagent/catalyst; | 99% |
2-furoic acid methyl ester
benzylamine
furan-2-carboxylic acid benzylamide
Conditions | Yield |
---|---|
With 14C2H2F3O(1-)*6C4H8O*La2Na8(14+) at 80℃; for 6h; Inert atmosphere; | 99% |
With niobium(V) oxide In neat (no solvent) at 140℃; for 30h; Molecular sieve; Inert atmosphere; | 87% |
2-furoic acid methyl ester
tris(methylthio)methane
A
tetrathioorthocarbonic acid tetramethyl ester
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane 1.) -95 deg C, 2 h, 2.) -78 deg C, 30 min; | A n/a B 97% |
Conditions | Yield |
---|---|
With hydrogenchloride; sulfuric acid; zinc(II) chloride In dichloromethane; water at 0 - 20℃; | 95% |
With hydrogenchloride; zinc(II) chloride In dichloromethane at 35℃; for 2.5h; | 67% |
With hydrogenchloride; zinc(II) chloride In dichloromethane at 35℃; | 66% |
Conditions | Yield |
---|---|
Stage #1: ethyl bromoacetate With zinc In tetrahydrofuran at 50 - 55℃; for 0.333333h; Stage #2: 2-furoic acid methyl ester In tetrahydrofuran for 8h; Heating; | 95% |
Conditions | Yield |
---|---|
Stage #1: 2-furoic acid methyl ester; acetic anhydride With aluminium(III) chloride hexahydrate In dichloromethane at 0 - 20℃; for 4h; Stage #2: With sodium hypochlorite; water; sodium hydroxide at 0℃; for 2h; | 95% |
2-furoic acid methyl ester
ethanolamine
N-(2-hydroxyethyl)amide of furan-2-carboxylic acid
Conditions | Yield |
---|---|
94% | |
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine In acetonitrile at 20℃; for 15h; Schlenk technique; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
Stage #1: 2-furoic acid methyl ester; acetyl chloride With iron(III) chloride In dichloromethane at 0 - 20℃; for 4h; Stage #2: With sodium hypochlorite; water; sodium hydroxide at 0℃; for 2h; Solvent; Reagent/catalyst; | 94% |
2-furoic acid methyl ester
1-(furan-2-yl)-2-phenylethanone
Conditions | Yield |
---|---|
With lithium tert-butoxide In tetrahydrofuran at 23℃; for 3h; Glovebox; | 94% |
2-furoic acid methyl ester
A
methyl furan-2-carbodithioate
B
O-methyl furan-2-carbothiono ester
Conditions | Yield |
---|---|
With Lawessons reagent In xylene for 10h; Heating; | A n/a B 93% |
Conditions | Yield |
---|---|
Stage #1: 2-furoic acid methyl ester; 1-octadecanol In xylene for 0.5h; Heating; Stage #2: With TiO(acac)2 In xylene for 13h; Heating; | 93% |
Conditions | Yield |
---|---|
Stage #1: 2-furoic acid methyl ester With nitric acid; acetic anhydride at -5℃; for 2h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 20℃; for 2h; | 90% |
Stage #1: 2-furoic acid methyl ester With nitric acid; acetic anhydride at -5℃; for 2h; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 20℃; for 15h; | 90% |
With nitric acid In dichloromethane; acetic anhydride 1.) Ac2O,CH2Cl2, -5 deg C, 2h 2.) Ac2O,CH2Cl2, room temp, 5h; | 85% |
With nitric acid; acetic anhydride; N-ethyl-N,N-diisopropylamine 1) -5 deg C, 4 h; 2) CH2Cl2, rt, 15 h; Yield given. Multistep reaction; |
2-furoic acid methyl ester
potassium trimethylsilonate
potassium furan-2-carboxylate
Conditions | Yield |
---|---|
In tetrahydrofuran | 90% |
Conditions | Yield |
---|---|
With amino(methyl)aluminum chloride In benzene at 50℃; for 12h; | 89% |
Conditions | Yield |
---|---|
With N,N'-Mes2imidazol-2-ylidene In tetrahydrofuran at 23℃; for 24h; | 89% |
With 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In tetrahydrofuran at 23 - 25℃; Inert atmosphere; | 75% |
Molecular Structure of Methyl furoate (CAS NO.611-13-2):
IUPAC Name: Methyl furan-2-carboxylate
Molecular Formula: C6H6O3
Molecular Weight: 126.11
EINECS: 210-254-6
FEMA: 2703
Index of Refraction: 1.462
Molar Refractivity: 30.32 cm3
Molar Volume: 110.1 cm3
Surface Tension: 34 dyne/cm
Density: 1.145 g/cm3
Flash Point: 58.6 °C
Enthalpy of Vaporization: 41.76 kJ/mol
Boiling Point: 181.3 °C at 760 mmHg
Vapour Pressure: 0.858 mmHg at 25 °C
Water Solubility: slightly soluble
Sensitive: Lachrymatory
Appearance: Colorless to light yellow liquid
Canonical SMILES: COC(=O)C1=CC=CO1
InChI: InChI=1S/C6H6O3/c1-8-6(7)5-3-2-4-9-5/h2-4H,1H3
InChIKey: HDJLSECJEQSPKW-UHFFFAOYSA-N
Classification Code: Drug / Therapeutic Agent; Skin / Eye Irritant
Product Categories: Aromatic Esters; Furan & Benzofuran; ester Flavor
Methyl furoate (CAS NO.611-13-2) can be used in organic synthesis, also used as a solvent.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 1250mg/kg (1250mg/kg) | Food and Cosmetics Toxicology. Vol. 17, Pg. 869, 1979. | |
rat | LD50 | oral | 300mg/kg (300mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | National Technical Information Service. Vol. OTS0559247, |
rat | LDLo | intraperitoneal | 75mg/kg (75mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 174, 1936. |
Reported in EPA TSCA Inventory.
Safety Information of Methyl furoate (CAS NO.611-13-2):
Hazard Codes: Xn,
Xi
Risk Statements: 36/37/38-21/22-22
R36/37/38:Irritating to eyes, respiratory system and skin.
R21/22:Harmful in contact with skin and if swallowed.
R22:Harmful if swallowed.
Safety Statements: 26-36-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2810 6.1/PG 3
WGK Germany: 3
RTECS: LV1950000
Hazard Note: Irritant
HazardClass: 6.1
PackingGroup: III
Poison by intraperitoneal route. A skin irritant and lachrymator. When heated to decomposition it emits acrid smoke and irritating fumes.
Methyl furoate (CAS NO.611-13-2), its Synonyms are 2-(Methoxycarbonyl)furan ; 2-Furancarboxylic acid, methyl ester ; 2-Furoic acid, methyl ester ; Methyl 2-furancarboxylate ; Methyl 2-furoate ; Methyl 2-furylcarboxylate ; Methyl pyromucate ; Pyromucic acid methyl ester .
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