Product Name

  • Name

    Methyl 2-tetrahydrofuroate

  • EINECS 420-670-1
  • CAS No. 37443-42-8
  • Article Data31
  • CAS DataBase
  • Density 1.108 g/cm3
  • Solubility
  • Melting Point
  • Formula C6H10O3
  • Boiling Point 158.8 °C at 760 mmHg
  • Molecular Weight 130.144
  • Flash Point 55.2 °C
  • Transport Information
  • Appearance Colourless clear and volatile liquid
  • Safety 26-39
  • Risk Codes 41
  • Molecular Structure Molecular Structure of 37443-42-8 (Methyl 2-tetrahydrofuroate)
  • Hazard Symbols IrritantXi
  • Synonyms 2-Furoicacid, tetrahydro-, methyl ester (6CI);Methyl tetrahydro-2-furancarboxylate;Tetrahydro-2-furancarboxylic acid methyl ester;Tetrahydro-2-furoic acid methylester;
  • PSA 35.53000
  • LogP 0.33840

Synthetic route

tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

methanol
67-56-1

methanol

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
With dimesitylammonium pentafluorobenzenesulfonate at 20℃; for 24h;92%
With dimesitylammonium pentafluorobenzenesulfonate at 22℃; for 11h;91%
dimesitylammonium pentafluorobenzenesulfonate at 20℃; for 11h; Product distribution / selectivity;91%
2-furoic acid methyl ester
611-13-2

2-furoic acid methyl ester

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
With methanol; nickel at 120℃; Hydrogenation.Unter Druck;
at 160℃; Leiten ueber Palladium/Asbest im Wasserstoff-Strom;
With palladium/alumina; hydrogen; Cinchonidin In isopropyl alcohol at 20℃; under 22501.8 Torr;
With hydrogen In methanol at 99.84℃; under 30003 Torr; for 1h; Autoclave;12 %Chromat.
With hydrogen In methanol at 30℃; under 75007.5 Torr; for 72h; Reagent/catalyst; Temperature; Pressure; Autoclave;
tetrahydrofuran-2-carbonyl chloride
52449-98-6

tetrahydrofuran-2-carbonyl chloride

methanol
67-56-1

methanol

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2
View Scheme
2-furoic acid methyl ester
611-13-2

2-furoic acid methyl ester

argon

argon

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
palladium-carbon In methanol
palladium-carbon In methanol
palladium-carbon In methanol
2-furoic acid methyl ester
611-13-2

2-furoic acid methyl ester

A

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

B

methyl 5-hydroxypentanoate
14273-92-8

methyl 5-hydroxypentanoate

Conditions
ConditionsYield
With hydrogen In methanol at 99.84℃; under 30003 Torr; for 1h; Autoclave;A 30 %Chromat.
B 41 %Chromat.
methanol
67-56-1

methanol

2-furanoic acid
88-14-2

2-furanoic acid

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

C

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

D

methyl 5-hydroxypentanoate
14273-92-8

methyl 5-hydroxypentanoate

Conditions
ConditionsYield
With hydrogen at 99.84℃; under 30003 Torr; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Pressure; Concentration; Autoclave;A 6 %Chromat.
B 9 %Chromat.
C 11 %Chromat.
D 47 %Chromat.
...Expand
methanol
67-56-1

methanol

2-furanoic acid
88-14-2

2-furanoic acid

A

tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

B

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

C

methyl 5-hydroxypentanoate
14273-92-8

methyl 5-hydroxypentanoate

Conditions
ConditionsYield
With hydrogen at 99.84℃; under 30003 Torr; for 1h; Catalytic behavior; Reagent/catalyst; Autoclave;
...Expand
methanol
67-56-1

methanol

2-furanoic acid
88-14-2

2-furanoic acid

A

tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

B

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen at 99.84℃; under 30003 Torr; for 1h; Autoclave;
...Expand
2-furanoic acid
88-14-2

2-furanoic acid

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
2: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
2: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: hydrogen / 4 h / 99.84 °C / 30003 Torr / Autoclave
2: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: hydrogen; 5%-palladium/activated carbon / 1 h / 99.84 °C / 30003 Torr / Autoclave
2: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
View Scheme
Multi-step reaction with 2 steps
1: hydrogen / isopropyl alcohol / 1 h / 99.84 °C / 30003 Torr / Autoclave
2: hydrogen / 1 h / 99.84 °C / 30003 Torr / Autoclave
View Scheme
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

N-Methyl-1,3-propanediamine
6291-84-5

N-Methyl-1,3-propanediamine

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide
81403-67-0

N-<3-(methylamino)propyl>tetrahydrofuran-2-carboxamide

Conditions
ConditionsYield
With calcium iodide at 25℃; for 1h; Green chemistry; chemoselective reaction;94%
at 110℃; for 4h;83%
In methanol at 30 - 42℃; for 48h;
In methanol at 25 - 45℃; for 40h;
piperazine
110-85-0

piperazine

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

N-(tetrahydro-2-furoyl)-piperazine
63074-07-7

N-(tetrahydro-2-furoyl)-piperazine

Conditions
ConditionsYield
at 110℃; for 5h;91%
79%
at 110℃; for 5h;16%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

2-(hydroxymethyl)tetrahydrofuran-d2
144091-56-5

2-(hydroxymethyl)tetrahydrofuran-d2

Conditions
ConditionsYield
With lithium aluminium deuteride In diethyl ether for 1h; Heating;89%
With lithium aluminium deuteride In tetrahydrofuran at 0 - 20℃;67%
With lithium aluminium deuteride In diethyl ether at 0℃; for 2h; Reflux;
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

acetyl chloride
75-36-5

acetyl chloride

methyl 2-(acetyloxy)-5-iodopentanoate

methyl 2-(acetyloxy)-5-iodopentanoate

Conditions
ConditionsYield
With sodium iodide In acetonitrile at 20℃; for 24h; Cooling with ice;86%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

hexan-1-amine
111-26-2

hexan-1-amine

N-hexyltetrahydrofuran-2-carboxamide

N-hexyltetrahydrofuran-2-carboxamide

Conditions
ConditionsYield
With zirconium(IV) oxide In diethylene glycol dimethyl ether at 160℃; under 3750.38 Torr; Flow reactor; Green chemistry;83%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

tetrahydrofuran-2-carboxylic acid hydrazide
59293-11-7

tetrahydrofuran-2-carboxylic acid hydrazide

Conditions
ConditionsYield
With hydrazine In methanol at 80℃; for 72h;74%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

methyl 2-(bromomethyl)propenoate
4224-69-5

methyl 2-(bromomethyl)propenoate

2-(2-methoxycarbonyl-allyl)-tetrahydro-furan-2-carboxylic acid methyl ester

2-(2-methoxycarbonyl-allyl)-tetrahydro-furan-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Alkylation;73%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

tetrahydro-2-furancarboximidamide hydrochloride
619329-27-0

tetrahydro-2-furancarboximidamide hydrochloride

Conditions
ConditionsYield
With trimethylaluminum; ammonium chloride In hexane; toluene at 0 - 80℃;69%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Benzyloxymethyl chloride
3587-60-8

Benzyloxymethyl chloride

methyl 2-((benzyloxy)methyl)tetrahydrofuran-2-carboxylate

methyl 2-((benzyloxy)methyl)tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
Stage #1: methyl tetrahydrofuran-2-carboxylate With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: Benzyloxymethyl chloride In tetrahydrofuran at -78 - 20℃; for 2h;		55%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

A

3-tetrahydro[2]furyl-pentan-3-ol

3-tetrahydro[2]furyl-pentan-3-ol

B

1-(tetrahydrofuran-2-yl)cyclopropan-1-ol

1-(tetrahydrofuran-2-yl)cyclopropan-1-ol

C

tetrahydrofuranyl-2-ethyl ketone
67234-00-8

tetrahydrofuranyl-2-ethyl ketone

Conditions
ConditionsYield
With titanium(IV) isopropylate In tetrahydrofuran Cooling;A 55%
B 11%
C 14%
...Expand
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

diisopropylamine
108-18-9

diisopropylamine

isobutyraldehyde
78-84-2

isobutyraldehyde

2-(1-hydroxy-2-methyl-propyl)-2-tetrahydrofuroic acid
327618-78-0

2-(1-hydroxy-2-methyl-propyl)-2-tetrahydrofuroic acid

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In tetrahydrofuran44%
...Expand
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

carbon dioxide
124-38-9

carbon dioxide

2-methoxycarbonyl-2-tetrahydrofuroic acid
327618-73-5

2-methoxycarbonyl-2-tetrahydrofuroic acid

Conditions
ConditionsYield
Stage #1: methyl tetrahydrofuran-2-carboxylate With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1h;
Stage #2: carbon dioxide In tetrahydrofuran		32%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-[(±)-tetrahydro-2-furanyl]ethanone
25252-64-6

1-[(±)-tetrahydro-2-furanyl]ethanone

Conditions
ConditionsYield
With N,O-dimethylhydroxylamine*hydrochloride In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;26%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

(R)-(-)-methyl tetrahydrofuran-2-carboxylate
87324-00-3

(R)-(-)-methyl tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
With ammonium hydroxide at 30℃; pH=6.9;23.4%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

methyl 2-(2-tertbutoxy-2-oxoethyl)tetrahydrofuran-2-carboxylate

methyl 2-(2-tertbutoxy-2-oxoethyl)tetrahydrofuran-2-carboxylate

Conditions
ConditionsYield
Stage #1: methyl tetrahydrofuran-2-carboxylate With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 1.25h;
Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran at 20℃;		23%
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

acetic anhydride
108-24-7

acetic anhydride

2-acetoxy-5-hydroxy-valeric acid methyl ester

2-acetoxy-5-hydroxy-valeric acid methyl ester

Conditions
ConditionsYield
With zinc(II) chloride
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

A

2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

B

2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

C

methanol
67-56-1

methanol

D

Cyclopropanecarboxaldehyde
1489-69-6

Cyclopropanecarboxaldehyde

Conditions
ConditionsYield
at 500℃; Leiten ueber Aluminiumoxid auf Bimsstein;
at 400℃; Leiten ueber Silicagel;
at 500℃; Leiten ueber Natriumphosphat und Phosphorsaeure auf Bimsstein;
...Expand
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

A

2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

B

butyraldehyde
123-72-8

butyraldehyde

Conditions
ConditionsYield
at 375℃; Leiten ueber Silicagel;
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Cyclopropanecarboxaldehyde
1489-69-6

Cyclopropanecarboxaldehyde

methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

A

(S)-tetrahydrofuran-2-carboxaldehyde
7681-84-7, 22170-11-2, 22170-12-3

(S)-tetrahydrofuran-2-carboxaldehyde

B

(R)-tetrahydrofuran-2-carboxaldehyde
7681-84-7, 22170-12-3, 22170-11-2

(R)-tetrahydrofuran-2-carboxaldehyde

Conditions
ConditionsYield
With diisobutylaluminium hydride In diethyl ether; hexane at -60℃; for 0.5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

Acetyl bromide
506-96-7

Acetyl bromide

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

acetic anhydride
108-24-7

acetic anhydride

acetic acid
64-19-7

acetic acid

A

5-bromo-2-hydroxy-valeric acid
745058-06-4

5-bromo-2-hydroxy-valeric acid

B

methyl 2-acetoxy-5-bromopentanoate
61427-26-7

methyl 2-acetoxy-5-bromopentanoate

C

2-acetoxy-5-bromo-valeric acid

2-acetoxy-5-bromo-valeric acid

...Expand
methyl tetrahydrofuran-2-carboxylate
37443-42-8

methyl tetrahydrofuran-2-carboxylate

propionyl fluoride
430-71-7

propionyl fluoride

ZnCl2

ZnCl2

5-fluoro-2-propionyloxy-valeric acid propyl ester

5-fluoro-2-propionyloxy-valeric acid propyl ester

...Expand

Methyl 2-tetrahydrofuroate Chemical Properties

Molecular Formula: C6H10O3
 Density: 1.108 g/cm3
EINECS: 420-670-1
Flash Point: 55.2 °C
Index of Refraction: 1.441 
Molecular Weight: 130.141800 g/mol 
IUPAC Name: methyl oxolane-2-carboxylate
Product Name: Methyl 2-tetrahydrofuroate
Enthalpy of Vaporization: 39.54 kJ/mol 
Boiling Point: 158.8 °C at 760 mmHg 
Vapour Pressure: 2.59 mmHg at 25°C  
Appearance:Colorless, transparent volatile liquid
synonyms: 2-Tetrahydrofuroic acid methyl ester ; Methyl tetrahydrofuran-2-carboxylate ; Methyltetrahydrofuroate ; Methyl tetrahydro-2-furoate ; Methyl 2-tetrahydrofuroate ; Methfat ; Tetrahydrofuran-2-carboxylic acid methyl ester ; Tetra hydro-2-methyl furoate
Following is the molecular structure of Methyl 2-tetrahydrofuroate (37443-42-8):

 
 
 

Methyl 2-tetrahydrofuroate Uses

Methyl 2-tetrahydrofuroate (37443-42-8) used as pharmaceutical intermediates and solvents.

Methyl 2-tetrahydrofuroate Safety Profile

Safety Information of Methyl 2-tetrahydrofuroate (37443-42-8):
Hazard Codes: Xi
Xi: Irritant
Risk Statements: 41 
41: Risk of serious damage to eyes 
Safety Statements: 26-39 
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
39: Wear eye/face protectio

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