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[(2R)-2-oxolanyl]methanol
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Tetrahydrofurfuryl alcohol CAS: 97-99-4
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97-99-4 Tetrahydrofurfuryl alcohol
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97-99-4 Usage

Preparation

By catalytic reduction of furfural with Raney-Ni; also by destructive hydrogenation of lignin.

Chemical Properties

Colorless to light yellow liqui

Uses

Solvent for vinyl resins; dyes for leather; chlorinated rubber; cellulose esters; solvent softener for nylon; vegetable oils; coupling agent; organic synthesis.

General Description

A clear colorless liquid with a mild odor. Flash point 167°F. Vapors are heavier than air.

Air & Water Reactions

Denser than water and soluble in water.

Health Hazard

Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Reactivity Profile

Acetyl bromide reacts violently with alcohols or water [Merck 11th ed. 1989]. Mixtures of alcohols with concentrated sulfuric acid and strong hydrogen peroxide can cause explosions. Example: An explosion will occur if dimethylbenzylcarbinol is added to 90% hydrogen peroxide then acidified with concentrated sulfuric acid. Mixtures of ethyl alcohol with concentrated hydrogen peroxide form powerful explosives. Mixtures of hydrogen peroxide and 1-phenyl-2-methyl propyl alcohol tend to explode if acidified with 70% sulfuric acid [Chem. Eng. News 45(43):73. 1967; J, Org. Chem. 28:1893. 1963]. Alkyl hypochlorites are violently explosive. They are readily obtained by reacting hypochlorous acid and alcohols either in aqueous solution or mixed aqueous- carbon tetrachloride solutions. Chlorine plus alcohols would similarly yield alkyl hypochlorites. They decompose in the cold and explode on exposure to sunlight or heat. Tertiary hypochlorites are less unstable than secondary or primary hypochlorites [NFPA 491 M 1991]. Base-catalysed reactions of isocyanates with alcohols should be carried out in inert solvents. Such reactions in the absence of solvents often occur with explosive violence [Wischmeyer 1969].

Occurrence

Reported found in shoyu (fermented soya hydrolysate), coffee and fresh mango.

Chemical Properties

Tetrahydrofurfuryl alcohol has a faint, warm, oily, caramellic odor with a coffee and nut-like flavor at very low levels (0.03 to 1 ppm).

Carcinogenicity

Tetrahydro-2-furanmethanol was not mutagenic to S. typhimurium strains TA100, TA1535, TA1537, or TA98 in an in vitro gene mutation assay or to E. coliWP2uvrA/pKM101 with or withoutmetabolic activation. No chromosomal aberrations or polypoidy were observed when tetrahydro-2-furanmethanol was added to cultured Chinese hamster lung cells with or without metabolic activation .
InChI:InChI=1/C5H10O2/c6-4-5-2-1-3-7-5/h5-6H,1-4H2

97-99-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A17078)  (±)-Tetrahydrofurfuryl alcohol, 98%    97-99-4 100ml 226.0CNY Detail
Alfa Aesar (A17078)  (±)-Tetrahydrofurfuryl alcohol, 98%    97-99-4 500ml 397.0CNY Detail
Alfa Aesar (A17078)  (±)-Tetrahydrofurfuryl alcohol, 98%    97-99-4 2500ml 599.0CNY Detail
Aldrich (185396)  Tetrahydrofurfurylalcohol  99% 97-99-4 185396-5G 308.88CNY Detail
Aldrich (185396)  Tetrahydrofurfurylalcohol  99% 97-99-4 185396-250G 321.75CNY Detail
Aldrich (185396)  Tetrahydrofurfurylalcohol  99% 97-99-4 185396-1KG 870.48CNY Detail
Aldrich (T12653)  Tetrahydrofurfurylalcohol  98% 97-99-4 T12653-500ML 205.92CNY Detail
Aldrich (T12653)  Tetrahydrofurfurylalcohol  98% 97-99-4 T12653-1KG 1,049.49CNY Detail
Aldrich (T12653)  Tetrahydrofurfurylalcohol  98% 97-99-4 T12653-2.5L 576.81CNY Detail
Aldrich (T12653)  Tetrahydrofurfurylalcohol  98% 97-99-4 T12653-3KG 2,577.51CNY Detail

97-99-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetrahydrofurfuryl Alcohol

1.2 Other means of identification

Product number -
Other names 2-Furanmethanol, tetrahydro-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:97-99-4 SDS

97-99-4Synthetic route

furfural
98-01-1

furfural

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With hydrogen In ethanol at 60℃; under 15001.5 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Pressure; Autoclave; Green chemistry;100%
With hydrogen In butan-1-ol at 80℃; under 30003 Torr; for 5h; Catalytic behavior; Temperature; Reagent/catalyst;99%
With hydrogen In isopropyl alcohol at 179.84℃; under 22502.3 Torr; for 1.25h; Reagent/catalyst;99%
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With 3% Pd/C; hydrogen In isopropyl alcohol at 219.84℃; under 25858.1 Torr; for 5h; Inert atmosphere;100%
With hydrogen In isopropyl alcohol at 25℃; under 7500.75 Torr; for 3h; Green chemistry;100%
With palladium on activated charcoal; ammonia; hydrogen In tetrahydrofuran at 160℃; for 4h; Reagent/catalyst; Autoclave;100%
5-hydroxy-1,2-epoxypentane
21915-56-0

5-hydroxy-1,2-epoxypentane

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With Hexafluorobenzene at 20℃; for 22h;100%
With C10H12NO(1+)*BF4(1-) In dichloromethane
With hydrogenchloride In water; tert-butyl alcohol at 20℃; for 2h; Green chemistry;
With Hexafluorobenzene In dichloromethane-d2 at 20℃; Kinetics; Reagent/catalyst; Solvent;
n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With pyridine-3-carbonitrile; dihydrogen peroxide; methyltrioxorhenium(VII) In dichloromethane at 24℃; for 18h;97%
With C10H12NO(1+)*BF4(1-) In dichloromethane for 3.5h; Ambient temperature;95%
With molecular sieve; dihydrogen peroxide In water at 59.85℃; for 3h;99 % Chromat.
tetrahydrofurfuryl acetate
637-64-9

tetrahydrofurfuryl acetate

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With ytterbium(III) triflate In isopropyl alcohol for 8h; Deacetylation; Heating;95%
With MetProLeuAspGlnProThrAlaAlaPheLeuAspPheLeuArgSerSerGlyGlyLysProLeuTyrGluLeuProLeuAlaGluAlaArgAlaAlaMetAlaMetGlySerGlnLeuGlyAlaProProAlaAspValGlyArgIleValAspArgSerIleAspValProGlyGlyAlaValAlaLeuArgIleTyrThrProAlaThrThrLysAlaGlyGlyLeuLeuProAlaIleLeuGlnTyrHisGlyGlyGlyPheValLeuGlyAsnLeuAspThrHisGluSerIleAlaArgPheTyrCysAlaHisAlaGlyAlaValValIleSerValAspTyrArgLeuAlaProGluHisArgPheProThrGlnValGluAspSerPheAlaAlaLeuThrTrpValSerGluHisAlaSerGluLeuGlyValAspProAlaArgValAlaValAlaGlyAspSerAlaGlyGlyAsnLeuAlaThrValMetCysLeuLeuAlaLysAlaArgGlyGlyProArgIleAlaCysGlnAlaLeuLeuTyrProValAlaAspPheArgProGluGlnValTyrAlaSerHisAlaGlnPheGlyAspGlySerTyrPheLeuSerSerLysAspMetAspTrpPheArgAlaSerTyrPheThrAspValAlaSerGlnAlaAlaGluProThrAlaSerProMetAlaThrThrAspLeuSerGlyLeuProProAlaLeuValThrThrAlaGlyCysAspProLeuLeuAspGluGlyArgAlaTyrAlaAspArgLeuLysAlaAlaGlyValProValAspTyrArgCysPheGluThrThrIleHisAlaCysAlaSerPheAlaGlyThrIleProAlaGlyLeuAspMetLeuGlyPheValAlaAspTrpLeuAlaAlaHisThrLys In aq. phosphate buffer at 37℃; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;
tetrahydrofurfuryl tetrahydropyranyl ether
710-14-5

tetrahydrofurfuryl tetrahydropyranyl ether

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With methanol; zirconium(IV) chloride at 20℃; for 7h;93%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

tetrahydrofuran-2-carbaldehyde
7681-84-7

tetrahydrofuran-2-carbaldehyde

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In water at 2℃; under 60006 Torr; for 2h; Reagent/catalyst; Autoclave;A 91.9%
B n/a
With hydrogen In water at 1.84℃; under 60006 Torr; for 4h; Catalytic behavior; Autoclave;
With palladium on activated charcoal; hydrogen In toluene at 170℃; under 52505.3 Torr; for 1h; Solvent; Autoclave;A 52.2%Chromat.
B 7.6%Chromat.
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

TETRAHYDROFURFURYLAMINE
4795-29-3

TETRAHYDROFURFURYLAMINE

Conditions
ConditionsYield
With ammonia; hydrogen In tetrahydrofuran at 180℃; for 12h; Autoclave;A 5.1%
B 91%
Multi-step reaction with 2 steps
1: ammonia; hydrogen / tetrahydrofuran / 2 h / 80 °C / Autoclave
2: ammonia; hydrogen / tetrahydrofuran / 24 h / 160 °C / Autoclave
View Scheme
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
With hydrogen at 90℃; under 15001.5 Torr; Reagent/catalyst;A 90.5%
B 8.4%
With hydrogen In butan-1-ol at 40℃; under 30003 Torr; for 7h; Catalytic behavior; Reagent/catalyst;A 12%
B 85%
With hydrogen In tetrahydrofuran at 175℃; under 7500.75 Torr; for 8h; Catalytic behavior; Pressure; Temperature; Time; chemoselective reaction;A 10%
B 79.5%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1,4-Pentanediol
626-95-9

1,4-Pentanediol

Conditions
ConditionsYield
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;A 9%
B 90%
With hydrogen In water at 140℃; under 11251.1 Torr; for 4h; Kinetics; Temperature; Autoclave;A 7%
B 87%
2-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran
69406-23-1

2-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With 4,4'-bipyridine; (phthalocyaninato)iron(II); oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; under 3000.3 Torr; for 24h; Autoclave;86%
With 4,4'-bipyridine; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 120℃; under 3750.38 Torr; for 7h; Autoclave; Green chemistry;65%
With ammonium peroxydisulfate; 9-(2-mesityl)-10-methylacridinium perchlorate In dichloromethane; water at 20 - 30℃; for 3.5h; Irradiation; Green chemistry;65%
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In monoethylene glycol diethyl ether at 120℃; under 1500.15 Torr; for 1.5h;
With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 100℃; under 760.051 Torr; for 1h;
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

2-methylfuran
534-22-5

2-methylfuran

Conditions
ConditionsYield
With hydrogen at 250℃; under 760.051 Torr;A 6.2%
B 83.3%
With hydrogen In methanol at 25℃; under 750.075 Torr; for 1h; Reagent/catalyst; Sealed tube; Green chemistry;A 69.4%
B 14.3%
With hydrogen In ethanol at 25℃; for 1h; Sealed tube; Green chemistry;A 43%
B 50%
tetrahydro-2-furancarboxylic acid
16874-33-2

tetrahydro-2-furancarboxylic acid

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 160℃; under 37503.8 Torr; for 24h;83%
Stage #1: tetrahydro-2-furancarboxylic acid With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at -20 - 20℃;
Stage #2: With water In tetrahydrofuran; diethyl ether; ethyl acetate at 0 - 20℃;
With tin(II) trifluoromethanesulfonate; tris(2,4-pentanedionato)ruthenium(III); hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In water; toluene at 160℃; under 45004.5 Torr; for 24h; Autoclave;80 %Chromat.
2-methylfuran
534-22-5

2-methylfuran

A

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

B

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With carbon dioxide; 5% Pd(II)/C(eggshell); hydrogen at 300℃; under 112511 Torr; Supercritical conditions;A 82%
B 6%
tert-butyldimethyl((tetrahydrofuran-2-yl)methoxy)silane
126680-80-6

tert-butyldimethyl((tetrahydrofuran-2-yl)methoxy)silane

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
With zinc tetrafluoroborate In water for 5h; Ambient temperature;80%
With Nafion-H(R); sodium iodide In methanol at 20℃; for 7h;
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1,2-pentanediol
5343-92-0

1,2-pentanediol

Conditions
ConditionsYield
With 5%PtO2-Al2O3; hydrogen In ethanol at 0 - 5℃; under 750.075 Torr; for 5h;A 15%
B 80%
With hydrogen; 5 % platinum dioxide on gamma-aluminum oxide In ethanol at 0 - 5℃; under 750.075 Torr; for 5h;A n/a
B 80%
With water; hydrogen at 120℃; under 22502.3 Torr; for 4h; chemoselective reaction;
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

Cyclopentanol
96-41-3

Cyclopentanol

C

cyclopentanone
120-92-3

cyclopentanone

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 30003 Torr; for 2.5h; Reagent/catalyst; Autoclave;A n/a
B n/a
C 79%
With hydrogen In water at 175℃; under 60006 Torr; for 0.5h;A 9.7 mol
B n/a
C n/a
With 20% Ni/Co3O4; hydrogen In water at 149.84℃; under 30003 Torr; for 6h; Reagent/catalyst; Autoclave; chemoselective reaction;
furfural
98-01-1

furfural

A

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

B

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Conditions
ConditionsYield
Stage #1: furfural With hydrogen at 160℃; under 760.051 Torr; Flow reactor;
Stage #2: With hydrogen at 130℃; under 760.051 Torr; Flow reactor;
A 13.7%
B 78.2%
With hydrogen In 1,4-dioxane; isopropyl alcohol at 200℃; under 48754.9 Torr; for 6h; Reagent/catalyst;A 36%
B 45%
Multi-step reaction with 2 steps
1: isopropyl alcohol; 10% Pd/C / 7.5 h / 150 °C / Inert atmosphere
2: isopropyl alcohol; 10% Pd/C / 7.5 h / 180 °C / Inert atmosphere
View Scheme
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

furan
110-00-9

furan

C

2-methylfuran
534-22-5

2-methylfuran

D

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
With hydrogen In methanol at 119.84℃; under 7500.75 Torr; for 1h; Catalytic behavior; Solvent; Reagent/catalyst; Autoclave;A 6.2%
B 8.9%
C 7.7%
D 75.5%
With hydrogen In isopropyl alcohol at 180℃; under 15001.5 Torr; for 5h; Kinetics; Catalytic behavior; Time; Autoclave; Sealed tube;A 13%
B 22%
C 54%
D 8%
With hydrogen at 250℃; under 760.051 Torr;A 10.2%
B 13.5%
C 38.6%
D 19%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

2-methylfuran
534-22-5

2-methylfuran

C

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
With hydrogen In isopropyl alcohol at 229.84℃; under 30003 Torr; for 5h;A 18%
B 14%
C 71%
With hydrogen In isopropyl alcohol at 229.84℃; under 30003 Torr; for 2h;A 7.2%
B 61%
C 8%
With hydrogen at 30℃; Kinetics;
furfural
98-01-1

furfural

A

2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

B

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

C

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
Stage #1: furfural With hydrogen at 160℃; under 760.051 Torr; Flow reactor;
Stage #2: With hydrogen at 120℃; under 760.051 Torr; Flow reactor;
A 13.1%
B 70%
C 9.1%
With Ni3Sn2; hydrogen In isopropyl alcohol at 20 - 179.84℃; for 12h; Autoclave;A 5 %Chromat.
B 5 %Chromat.
C 91 %Chromat.
With hydrogen In isopropyl alcohol at 50℃; under 3750.38 Torr; Autoclave;
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

C

(+/-)-2-pentanol
6032-29-7

(+/-)-2-pentanol

D

pentan-1-ol
71-41-0

pentan-1-ol

Conditions
ConditionsYield
With hydrogen In isopropyl alcohol at 150℃; under 30003 Torr; for 8h; Temperature; Pressure; Autoclave;A 68.7%
B 24.2%
C n/a
D n/a
2,5-dihydrofuran
1708-29-8

2,5-dihydrofuran

carbon monoxide
201230-82-2

carbon monoxide

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

3-tetrahydrofuranmethanol
124391-75-9, 124506-31-6, 15833-61-1

3-tetrahydrofuranmethanol

Conditions
ConditionsYield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 2-(dicyclohexylphosphanyl)-1-(2-methoxyphenyl)-1H-imidazole; hydrogen In toluene at 160℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; Overall yield = 60 %Chromat.; regioselective reaction;A n/a
B 66%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

carbon monoxide
201230-82-2

carbon monoxide

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

3-tetrahydrofuranmethanol
124391-75-9, 124506-31-6, 15833-61-1

3-tetrahydrofuranmethanol

Conditions
ConditionsYield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); 2-(dicyclohexylphosphanyl)-1-(2-methoxyphenyl)-1H-imidazole; hydrogen In toluene at 160℃; under 37503.8 Torr; for 24h; Autoclave; Inert atmosphere; Overall yield = 60 %Chromat.; regioselective reaction;A n/a
B 66%
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

methanol
67-56-1

methanol

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

methyl tetrahydrofurfuryl ether
19354-27-9

methyl tetrahydrofurfuryl ether

C

O-methyl-pentamethylene glycol
4799-62-6

O-methyl-pentamethylene glycol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;A 64.5%
B n/a
C n/a
(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1,4-Pentanediol
626-95-9

1,4-Pentanediol

C

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With palladium on activated charcoal; water; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;A 64%
B n/a
C n/a
methanol
67-56-1

methanol

5-hydroxymethyl-2-furfuraldehyde
67-47-0

5-hydroxymethyl-2-furfuraldehyde

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

methyl tetrahydrofurfuryl ether
19354-27-9

methyl tetrahydrofurfuryl ether

C

O-methyl-pentamethylene glycol
4799-62-6

O-methyl-pentamethylene glycol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen at 170℃; under 52505.3 Torr; for 2h; Autoclave;A 63.4%
B n/a
C n/a
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

1,4-Pentanediol
626-95-9

1,4-Pentanediol

C

5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

Conditions
ConditionsYield
With hydrogen; toluene-4-sulfonic acid In water at 140℃; under 11251.1 Torr; for 4h; Autoclave;A 19%
B 63%
C 8%
With carbon dioxide; hydrogen In water at 80℃; under 30003 Torr; for 20h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave;A 8%
B 57%
C 15%
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

C

2-furaldehyde dimethyl acetal
1453-62-9

2-furaldehyde dimethyl acetal

Conditions
ConditionsYield
With hydrogen In methanol at 100℃; under 15001.5 Torr; Catalytic behavior; Reagent/catalyst; Autoclave;A n/a
B 60%
C n/a
furfural
98-01-1

furfural

A

Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

B

furan
110-00-9

furan

C

(2-furyl)methyl alcohol
98-00-0

(2-furyl)methyl alcohol

Conditions
ConditionsYield
With MnO2#dotPd; hydrogen In isopropyl alcohol at 180℃; under 15001.5 Torr; for 5h; Kinetics; Catalytic behavior; Time; Autoclave; Sealed tube;A 8.3%
B 14.11%
C 59.76%
With hydrogen In isopropyl alcohol at 120℃; under 45004.5 Torr; for 3h; Reagent/catalyst;
With Ni-doped silica; hydrogen at 140℃; under 760.051 Torr; for 2h; Flow reactor;
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate
34583-63-6

rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 1h;100%
With potassium hydroxide93%
With potassium iodide; silver(l) oxide In dichloromethane at 40℃;91%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

3-(diphenylphosphono)-2-(N-cyanoimino)thiazolidine
449813-82-5

3-(diphenylphosphono)-2-(N-cyanoimino)thiazolidine

<(tetrahydrofurfuryl)oxy>diphenyphosphine
33026-82-3

<(tetrahydrofurfuryl)oxy>diphenyphosphine

Conditions
ConditionsYield
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.5h; Product distribution; Further Variations:; Reagents; reaction times;100%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

but-3-enoic acid
625-38-7

but-3-enoic acid

tetrahydrofurfuryl vinylacetate
1198472-55-7

tetrahydrofurfuryl vinylacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;100%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

titanium(IV) isopropylate
546-68-9

titanium(IV) isopropylate

C16H32O6Ti
1346523-06-5

C16H32O6Ti

Conditions
ConditionsYield
In cyclohexane Inert atmosphere; Reflux;100%
In cyclohexane for 0.5h; Schlenk technique; Inert atmosphere; Reflux;100%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

tetrahydrofurfuryl tetrahydropyranyl ether
710-14-5

tetrahydrofurfuryl tetrahydropyranyl ether

Conditions
ConditionsYield
With zirconium(IV) chloride In dichloromethane for 3h;99%
With Envirocat EPZG at 0 - 5℃; for 1h;98%
With 1-butyl-3-methylimidazolium hydrogen sulfate at 20℃; for 0.166667h;98%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

acetic anhydride
108-24-7

acetic anhydride

tetrahydrofurfuryl acetate
637-64-9

tetrahydrofurfuryl acetate

Conditions
ConditionsYield
With phosphoric acid In acetonitrile at 50℃; for 3h;99%
With zirconium sulfophenyl phosphonate In dichloromethane at 20℃; for 3h; Acetylation;97%
With aluminum triflate at 20℃; for 0.00555556h;96%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Diethyl carbonate
105-58-8

Diethyl carbonate

carbonate d'ethyle et de (2-tetrahydrofuryl) methyle
108106-20-3

carbonate d'ethyle et de (2-tetrahydrofuryl) methyle

Conditions
ConditionsYield
aluminum oxide; cesium fluoride at 129.85℃; for 0.5h;99%
With MgLa mixed oxide at 125℃; for 4h;99%
tiveTMNano*MgO*Plus*(NAP-MgO,*Aerogel*prepared) at 125℃; for 3h;99%
With immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene on magnetic γ-Fe2O3 nanoparticles at 125℃; for 10h;93%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

1,1,3,3-tetramethyldisilazane
15933-59-2

1,1,3,3-tetramethyldisilazane

1,1,3,3-tetramethyl-1,3-bis[(tetrahydrofuran-2-yl)methoxy]disiloxane
1333319-95-1

1,1,3,3-tetramethyl-1,3-bis[(tetrahydrofuran-2-yl)methoxy]disiloxane

Conditions
ConditionsYield
With 1.2% Pd/C at 20℃; for 20h; Inert atmosphere;99%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

uranyl nirate hexahydrate

uranyl nirate hexahydrate

C13H26N2O10U

C13H26N2O10U

Conditions
ConditionsYield
In chloroform at 20℃; for 0.166667h;99%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

5-bromo-6-chloropyridine-2-carboxylic acid
959958-25-9

5-bromo-6-chloropyridine-2-carboxylic acid

5-bromo-6-(tetrahydrofuran-2-ylmethoxy)pyridine-2-carboxylic acid
1415899-56-7

5-bromo-6-(tetrahydrofuran-2-ylmethoxy)pyridine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: 5-bromo-6-chloropyridine-2-carboxylic acid With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: Tetrahydrofurfuryl alcohol In dimethyl sulfoxide at 20℃; for 24h;
99%
Stage #1: 5-bromo-6-chloropyridine-2-carboxylic acid With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: Tetrahydrofurfuryl alcohol In dimethyl sulfoxide at 20℃; for 24h;
Stage #3: With hydrogenchloride In water
99%
Stage #1: 5-bromo-6-chloropyridine-2-carboxylic acid With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: Tetrahydrofurfuryl alcohol In dimethyl sulfoxide at 20℃; for 24h;
99%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester
76578-14-8

(R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester

(RS)-tetrahydrofuran-2-ylmethyl (R)-2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionate
200509-41-7

(RS)-tetrahydrofuran-2-ylmethyl (R)-2-[4-(6-chloro-2-quinoxalinyloxy)phenoxy]propionate

Conditions
ConditionsYield
Stage #1: Tetrahydrofurfuryl alcohol; (R)-2-[4-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoic acid ethyl ester In toluene at 115℃; for 2h;
Stage #2: With tetraisopropanoyl titanate In toluene at 80 - 130℃; for 4h;
98.6%
With di(n-butyl)tin oxide at 75 - 130℃; for 8h; Temperature; Concentration;98%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

tetrahydro-2-furanmethanol methanesulfonate (ester)
72641-13-5

tetrahydro-2-furanmethanol methanesulfonate (ester)

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 36h;98%
With triethylamine In dichloromethane at 0℃; for 14h;92%
With pyridine at 20℃; for 60h; Inert atmosphere; Cooling with ice;77%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

(tetrahydrofuran-2-ylmethoxy)butanedioic acid

(tetrahydrofuran-2-ylmethoxy)butanedioic acid

Conditions
ConditionsYield
With lanthanum(III) chloride at 140℃; for 7.7h;97%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

neodymium chloride tris(isopropanol)

neodymium chloride tris(isopropanol)

neodymium chloride tris(tetrahydrofurfuryl alcohol)

neodymium chloride tris(tetrahydrofurfuryl alcohol)

Conditions
ConditionsYield
In benzene addn. of lanthanide-compd. to anhyd. benzene containing ligand, refluxing for 4 h under exclusion of moisture; removal of isopropanol by azeotropical distn., removal of benzene, filtn., washing with dry benzene, drying for 4 h under reduced pressure, elem. anal.;97%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

titanium tetrachloride
7550-45-0

titanium tetrachloride

A

hydrogenchloride
7647-01-0

hydrogenchloride

B

titanium(IV) trichloride(tetrahydrofuran-2-methanolate)

titanium(IV) trichloride(tetrahydrofuran-2-methanolate)

Conditions
ConditionsYield
In hexane N2-atmosphere; alcohol dropvise addn. with stirring (pptn.); washing (n-hexane), drying (vac.); elem. anal.;A n/a
B 97%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

uranyl nirate hexahydrate

uranyl nirate hexahydrate

[UO2(κ2-nitrate)2(tetrahydrofurfuryl alcohol)]*H2O

[UO2(κ2-nitrate)2(tetrahydrofurfuryl alcohol)]*H2O

Conditions
ConditionsYield
In chloroform at 20℃; for 48h;97%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

benzoyl chloride
98-88-4

benzoyl chloride

(tetrahydrofuran-2-yl)methyl benzoate
2217-32-5

(tetrahydrofuran-2-yl)methyl benzoate

Conditions
ConditionsYield
With iron In 1,2-dichloro-ethane at 84℃; for 3h; Schlenk technique; Inert atmosphere; regioselective reaction;97%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

carbon monoxide
201230-82-2

carbon monoxide

tert-butyl alcohol
75-65-0

tert-butyl alcohol

(tetrahydrofuran-2-yl)methyl 3-methylbutanoate

(tetrahydrofuran-2-yl)methyl 3-methylbutanoate

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; toluene-4-sulfonic acid at 120℃; under 15001.5 Torr; for 20h; Autoclave; Inert atmosphere;97%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

trimethyl(tetrahydro-2-furylmethoxy)silane
3067-36-5

trimethyl(tetrahydro-2-furylmethoxy)silane

Conditions
ConditionsYield
With aluminum tris(dihydrogen phosphate) at 20℃; for 0.2h;96%
With zinc(II) oxide at 20℃; for 1.83333h;95%
With Al2O3*HClO4 In acetonitrile at 20℃; for 0.116667h;93%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

3-chloro-3-oxopropanoic acid methyl ester
37517-81-0

3-chloro-3-oxopropanoic acid methyl ester

methyl tetrahydrofurfuryl malonate
1198472-57-9

methyl tetrahydrofurfuryl malonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃; for 1.5h; Inert atmosphere;96%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

m-methoxyphenylacetic acid
1798-09-0

m-methoxyphenylacetic acid

tetrahydrofurfuryl 3-methoxyphenylacetate
1198472-48-8

tetrahydrofurfuryl 3-methoxyphenylacetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;96%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

o-methylphenylacetic acid
644-36-0

o-methylphenylacetic acid

C14H18O3

C14H18O3

Conditions
ConditionsYield
With β-cyclodextrin-SO3H In neat (no solvent) at 70℃; for 3h;96%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate
2455-24-5

(tetrahydrofuran-2-yl)methyl 2-methylprop-2-enoate

Conditions
ConditionsYield
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; di(n-butyl)tin oxide In 2-Methylpentane; cyclohexane at 85 - 100℃; for 12h; Temperature;95%
2-methyl-propan-2-ol; lanthanum tri-tert-butylate at 25℃; for 2h;32 %Chromat.
sodium ethanolate15 %Chromat.
With sulfuric acid; benzene
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

Carbonic acid benzyl ester 6-trifluoromethyl-benzotriazol-1-yl ester
112380-58-2

Carbonic acid benzyl ester 6-trifluoromethyl-benzotriazol-1-yl ester

Carbonic acid benzyl ester furan-2-ylmethyl ester
112380-52-6

Carbonic acid benzyl ester furan-2-ylmethyl ester

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 0℃; for 24h;95%
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

sodium succinate
150-90-3

sodium succinate

A

malic acid
617-48-1

malic acid

B

(tetrahydrofuran-2-ylmethoxy)butanedioic acid

(tetrahydrofuran-2-ylmethoxy)butanedioic acid

Conditions
ConditionsYield
With lanthanum(III) chloride at 116℃; for 19h; Product distribution; also with other alcohols; variation of reaction time, temperature and proportion of reagents;A 3%
B 95%

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