Product Name

  • Name

    2-HYDROXYTETRAHYDROPYRAN

  • EINECS 229-509-8
  • CAS No. 694-54-2
  • Article Data104
  • CAS DataBase
  • Density 1.08 g/cm3
  • Solubility
  • Melting Point
  • Formula C5H10O2
  • Boiling Point 170.5 °C at 760 mmHg
  • Molecular Weight 102.133
  • Flash Point 71.4 °C
  • Transport Information
  • Appearance
  • Safety 36/37/39-26
  • Risk Codes 36/37/38-20/22
  • Molecular Structure Molecular Structure of 694-54-2 (2-HYDROXYTETRAHYDROPYRAN)
  • Hazard Symbols HarmfulXn
  • Synonyms Pyran-2-ol,tetrahydro- (6CI,7CI);2-Hydroxytetrahydro-2H-pyran;2-Hydroxytetrahydropyran;NSC 244915;Tetrahydro-2-hydroxy-2H-pyran;Tetrahydro-2H-pyran-2-ol;Tetrahydropyran-2-ol;d-Valerolactol;
  • PSA 29.46000
  • LogP 0.50530

Synthetic route

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

3,4-dihydro-2H-pyran

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With hydrogenchloride; water at 0 - 20℃; for 1.25h; Inert atmosphere;96%
With hydrogenchloride In water at 0 - 20℃; for 1.5h;93%
With hydrogenchloride; water In water at 0 - 20℃; for 1.25h;87%
2,2′-peroxybis(tetrahydro-2H-pyran)

2,2′-peroxybis(tetrahydro-2H-pyran)

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With methanol; iodine; magnesium at 40℃; for 3h;96%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

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

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With diisobutylaluminium hydride In diethyl ether; hexane at -78℃; for 2h; Reduction;93%
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 2h;91%
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 0.25h;88%
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

1,6-hexanediol
629-11-8

1,6-hexanediol

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

6-(tetrahydro-2H-pyranyloxy)hexan-1-ol
28659-22-5

6-(tetrahydro-2H-pyranyloxy)hexan-1-ol

C

1,6-bis(tetrahydropyranyloxy)hexane
15057-15-5

1,6-bis(tetrahydropyranyloxy)hexane

Conditions
ConditionsYield
With Dowex 50W x 2 In toluene at 30℃; for 2.5h; Etherification; hydration;A n/a
B 89%
C 2%
ethyl 2-<1-(2-tetrahydropyranylperoxy)ethyl>propenoate
157136-52-2

ethyl 2-<1-(2-tetrahydropyranylperoxy)ethyl>propenoate

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

n-butyl formate
592-84-7

n-butyl formate

C

ethyl 2-cyclohexylmethyl-2,3-epoxybutanoate

ethyl 2-cyclohexylmethyl-2,3-epoxybutanoate

D

ethyl 2,3-epoxy-2-<5-(formyloxy)pentyl>butanoate

ethyl 2,3-epoxy-2-<5-(formyloxy)pentyl>butanoate

Conditions
ConditionsYield
With tert-butyl peroxyacetate In cyclohexane at 110℃; under 0.001 Torr; for 12h; further solvents;A 1 % Chromat.
B 6 % Chromat.
C 7%
D 75%
5-triphenylmethoxypentanal
258331-72-5

5-triphenylmethoxypentanal

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
Stage #1: 5-triphenylmethoxypentanal With boron trichloride In dichloromethane at -30℃; for 0.75h; Substitution;
Stage #2: With methanol Cyclization; methanolysis; Further stages.;
75%
(E)-pent-2-ene-1,5-diol
25073-26-1

(E)-pent-2-ene-1,5-diol

carbon monoxide
201230-82-2

carbon monoxide

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

C

2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
123703-40-2

2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan

D

3-hydroxymethyltetrahydropyran-2-ol

3-hydroxymethyltetrahydropyran-2-ol

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In dichloromethane at 120℃; under 45003.6 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents;A n/a
B n/a
C 72%
D n/a
(E)-pent-2-ene-1,5-diol
25073-26-1

(E)-pent-2-ene-1,5-diol

carbon monoxide
201230-82-2

carbon monoxide

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
123703-40-2

2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan

Conditions
ConditionsYield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In dichloromethane at 120℃; under 45003.6 Torr; for 20h;A n/a
B 72%
Iodoethanol
624-76-0

Iodoethanol

acrolein
107-02-8

acrolein

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With copper(l) iodide; zinc In water ultrasonic irradiation;70%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

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

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

5-hydroxypentanal
4221-03-8

5-hydroxypentanal

Conditions
ConditionsYield
With diisobutylaluminium hydride In dichloromethane; toluene at -70℃; for 3h; Inert atmosphere; Overall yield = 0.71 g;A 65%
B 25%
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

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

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

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 22℃; for 2h;A 58%
B 29%
2-(prop-2-en-1-yloxy)oxane
69161-61-1, 4203-49-0

2-(prop-2-en-1-yloxy)oxane

trimethylaluminum
75-24-1

trimethylaluminum

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

2-(2-Methyl-hex-5-enyloxy)-tetrahydro-pyran

2-(2-Methyl-hex-5-enyloxy)-tetrahydro-pyran

Conditions
ConditionsYield
bis(triphenylphosphine)nickel(II) chloride In tolueneA n/a
B 48%
pent-2-ene-1,5-diol
29293-07-0

pent-2-ene-1,5-diol

carbon monoxide
201230-82-2

carbon monoxide

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
123703-40-2

2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan

C

3-hydroxymethyltetrahydropyran-2-ol

3-hydroxymethyltetrahydropyran-2-ol

Conditions
ConditionsYield
With hydrogen; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 120℃; under 45004.5 Torr; for 20h;A 7%
B 35%
C 34%
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
platinum In sulfuric acid; water at 35℃; for 1.15h; Product distribution; electrolysis, also with PtO2, RuO2;91 % Turnov.
platinum In sulfuric acid; water at 35℃; for 1.15h; electrolysis;91 % Turnov.
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

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

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

Conditions
ConditionsYield
With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane In dichloromethane at 0℃; for 0.25h; Yield given. Yields of byproduct given;
lead dioxide In sulfuric acid; water at 35℃; for 7.83333h; electrolysis;A 5.4 % Turnov.
B 73 % Turnov.
With oxone; methyltrifluoromethyldioxirane In dichloromethane at -15℃;A 37 % Chromat.
B 63 % Chromat.
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

bis-tetrahydropyran-2-yl ether
709-84-2

bis-tetrahydropyran-2-yl ether

C

5-(2-tetrahydropyranyloxy)pentanal
14194-86-6

5-(2-tetrahydropyranyloxy)pentanal

D

5-hydroxypentanal
4221-03-8

5-hydroxypentanal

Conditions
ConditionsYield
With hydrogenchloride for 0.25h; Product distribution; Ambient temperature; other times and temperatures, other hydration reagent;
With hydrogenchloride; sodium sulfite at 25℃; for 24h; Yield given;
With hydrogenchloride at 25℃; for 0.25h; Yield given. Yields of byproduct given;
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

bis-tetrahydropyran-2-yl ether
709-84-2

bis-tetrahydropyran-2-yl ether

C

5-hydroxypentanal
4221-03-8

5-hydroxypentanal

Conditions
ConditionsYield
With hydrogenchloride 1.) 25 deg C, 1 h, 2.) reflux, 24 h; Yield given. Yields of byproduct given;
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

5-(2-tetrahydropyranyloxy)pentanal
14194-86-6

5-(2-tetrahydropyranyloxy)pentanal

C

5-hydroxypentanal
4221-03-8

5-hydroxypentanal

Conditions
ConditionsYield
With sodium metabisulfite; water at 25℃; for 24h; Yield given. Yields of byproduct given;
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

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

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

C

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

D

1,7-dioxacyclododecane-2,6-dione

1,7-dioxacyclododecane-2,6-dione

Conditions
ConditionsYield
With H4Ru4(CO)84; hydrogen In diethyl ether; toluene at 200℃; under 98800 Torr; for 48h;A 2.9 % Chromat.
B 28.7 % Chromat.
C 47.7 % Chromat.
D 20.7 % Chromat.
2-phenoxytetrahydropyran
4203-50-3

2-phenoxytetrahydropyran

octanol
111-87-5

octanol

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

2-octyloxy-tetrahydro-pyran
70690-19-6

2-octyloxy-tetrahydro-pyran

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
tris(2,2'-bipyridyl)ruthenium dichloride; Paraquat In acetonitrile at 20℃; for 30h; Product distribution; Irradiation; also with H2O, or molecular sieves 4 Angstroem;
2-phenoxytetrahydropyran
4203-50-3

2-phenoxytetrahydropyran

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

2-octyloxy-tetrahydro-pyran
70690-19-6

2-octyloxy-tetrahydro-pyran

C

phenol
108-95-2

phenol

Conditions
ConditionsYield
With water; tris(2,2'-bipyridyl)ruthenium dichloride; (MV)Cl2 In acetonitrile for 30h; Irradiation; Yields of byproduct given;
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
Thermodynamic data; protonation, ΔG0;
hexanal
66-25-1

hexanal

2-Acetyl-2-methyl-5-oxo-hexanoic acid allyl ester
139048-07-0

2-Acetyl-2-methyl-5-oxo-hexanoic acid allyl ester

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

3-(1-Hydroxy-hexyl)-3-methyl-heptane-2,6-dione
139025-72-2, 139025-73-3

3-(1-Hydroxy-hexyl)-3-methyl-heptane-2,6-dione

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; zinc In N,N-dimethyl-formamide at 40℃; for 5h; Yield given. Title compound not separated from byproducts;
homoalylic alcohol
627-27-0

homoalylic alcohol

carbon monoxide
201230-82-2

carbon monoxide

A

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

B

(R)-3-Methyl-tetrahydro-furan-2-ol

(R)-3-Methyl-tetrahydro-furan-2-ol

C

(S)-3-Methyl-tetrahydro-furan-2-ol

(S)-3-Methyl-tetrahydro-furan-2-ol

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); (R,S)-binaphos; hydrogen In benzene at 60℃; under 22800 Torr; Yield given. Yields of byproduct given;
With acetylacetonatodicarbonylrhodium(l); (R,S)-binaphos; hydrogen In benzene at 60℃; under 22800 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
2-(prop-2-en-1-yloxy)oxane
69161-61-1, 4203-49-0

2-(prop-2-en-1-yloxy)oxane

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With triethylaluminum; bis(triphenylphosphine)nickel(II) chloride In toluene
α-bromopropionate de tetrahydropyrannyle
74266-26-5

α-bromopropionate de tetrahydropyrannyle

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism;
2,2-Dimethyl-propionic acid tetrahydro-pyran-2-yl ester

2,2-Dimethyl-propionic acid tetrahydro-pyran-2-yl ester

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism;
2-Chloro-propionic acid tetrahydro-pyran-2-yl ester

2-Chloro-propionic acid tetrahydro-pyran-2-yl ester

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism;
3-Chloro-propionic acid tetrahydro-pyran-2-yl ester

3-Chloro-propionic acid tetrahydro-pyran-2-yl ester

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism;
Ethoxy-acetic acid tetrahydro-pyran-2-yl ester

Ethoxy-acetic acid tetrahydro-pyran-2-yl ester

tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism;
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

(5R,7S)-7,8-Dimethyl-non-8-ene-1,5-diol

(5R,7S)-7,8-Dimethyl-non-8-ene-1,5-diol

Conditions
ConditionsYield
With triethyl borane; bis(acetylacetonate)nickel(II) In tetrahydrofuran; hexane at 20℃; for 40h;99%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

2,5-dimethoxyphenol
18113-18-3

2,5-dimethoxyphenol

2,5-Dimethoxy-1-(tetrahydro-2H-pyran-2-yloxy)-benzol
109765-65-3

2,5-Dimethoxy-1-(tetrahydro-2H-pyran-2-yloxy)-benzol

Conditions
ConditionsYield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere;99%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

2-oxo-3-(phenyl)propionic acid
156-06-9

2-oxo-3-(phenyl)propionic acid

C14H16O4

C14H16O4

Conditions
ConditionsYield
With 2-Sulfanylpyridine; FeIIFeIII2(μ3-O)(μ2-OOCCF3)6(OH2)3 In 1,2-dichloro-ethane at 60℃; for 24h; Reagent/catalyst;99%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

9-bromononan-1-ol
55362-80-6

9-bromononan-1-ol

2-(9-bromononyloxy)tetrahydropyran
55695-90-4

2-(9-bromononyloxy)tetrahydropyran

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃;99%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

(3-bromopropyl)(methyl)sulfane
68731-27-1

(3-bromopropyl)(methyl)sulfane

8-(methylthio)octane-1,5-diol

8-(methylthio)octane-1,5-diol

Conditions
ConditionsYield
Stage #1: (3-bromopropyl)(methyl)sulfane With iodine; magnesium In tetrahydrofuran Reflux; Inert atmosphere;
Stage #2: tetrahydro-2H-2-pyranol In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
99%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

(carbethoxyethylidene)triphenylphosphorane
21382-82-1

(carbethoxyethylidene)triphenylphosphorane

(E)-7-hydroxy-2-methyl-hept-2-enoic acid ethyl ester
74844-86-3

(E)-7-hydroxy-2-methyl-hept-2-enoic acid ethyl ester

Conditions
ConditionsYield
98%
In benzene for 12h; Ambient temperature;80%
In toluene at 90℃; for 1h;
In benzene Wittig Olefination;1.87 g
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

isopropyl alcohol
67-63-0

isopropyl alcohol

2-isopropoxytetrahydropyran
1927-70-4

2-isopropoxytetrahydropyran

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine at 20℃; for 16h;97%
With titanium(IV) tetrabutoxide; (R)-Mandelic Acid at 20℃; for 24h;94%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

benzyl alcohol
100-51-6

benzyl alcohol

tetrahydro-2-(benzyloxy)-2H-pyran
1927-62-4

tetrahydro-2-(benzyloxy)-2H-pyran

Conditions
ConditionsYield
With pyrrolidine hydrochloride In toluene at 100℃; for 5h; Inert atmosphere;96%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

O-(tert-butyldimethylsilanyl)hydroxylamine
41879-39-4

O-(tert-butyldimethylsilanyl)hydroxylamine

5-hydroxypentanal O-tert-butyldimethylsilyloxime
873692-60-5

5-hydroxypentanal O-tert-butyldimethylsilyloxime

Conditions
ConditionsYield
With magnesium sulfate In diethyl ether at 20℃; for 1h;94%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

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

3,4-dihydro-2H-pyran

bis-tetrahydropyran-2-yl ether
709-84-2

bis-tetrahydropyran-2-yl ether

Conditions
ConditionsYield
With N.N'-bis[3,5-bis(trifluoromethyl)phenyl]thiourea at 20℃; for 19h;94%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

(E)-8-Hydroxy-oct-3-en-2-one
172877-31-5

(E)-8-Hydroxy-oct-3-en-2-one

Conditions
ConditionsYield
93%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

4-but-1-enylmagnesium bromide
7103-09-5

4-but-1-enylmagnesium bromide

non-8-ene-1,5-diol
198637-27-3

non-8-ene-1,5-diol

Conditions
ConditionsYield
In tetrahydrofuran for 1.5h; Ambient temperature;93%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

8-bromooctanol
50816-19-8

8-bromooctanol

(R)-1-bromo-2-methyldecane
130236-39-4

(R)-1-bromo-2-methyldecane

(R)-10-methyloctadecyl-1-tetrahydropyranyl ether

(R)-10-methyloctadecyl-1-tetrahydropyranyl ether

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; Li2CuCl4 In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique;93%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

5-hydroxypentylamine
2508-29-4

5-hydroxypentylamine

Conditions
ConditionsYield
With ammonium hydroxide; hydrogen In water at 80℃; under 15001.5 Torr; for 6h; Pressure; Temperature;93%
With ammonia; hydrogen In water at 80℃; under 15001.5 Torr; for 1h; Reagent/catalyst; Autoclave;
With ammonium hydroxide; hydrogen In water at 60℃; under 15001.5 Torr; for 1h; Catalytic behavior; Temperature; Autoclave;
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

Benzeneselenol
645-96-5

Benzeneselenol

tetrahydro-2-(phenylseleno)-2H-Pyran
64042-26-8

tetrahydro-2-(phenylseleno)-2H-Pyran

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene at 25℃;92%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

benzyltriphenylphosphonium chloride
1100-88-5

benzyltriphenylphosphonium chloride

6-phenylhex-5-en-1-ol
98078-15-0

6-phenylhex-5-en-1-ol

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium chloride With potassium tert-butylate In tert-butyl alcohol at 20℃; for 0.5h;
Stage #2: tetrahydro-2H-2-pyranol In tert-butyl alcohol at 20℃; for 0.5h;
92%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

2-(2-nitro-vinyl)-phenol
3156-43-2

2-(2-nitro-vinyl)-phenol

A

(4aR,5S,10aS)-5-(nitromethyl)-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene

(4aR,5S,10aS)-5-(nitromethyl)-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene

B

5-(nitromethyl)-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene

5-(nitromethyl)-2,3,4,4a,5,10a-hexahydropyrano[2,3-b]chromene

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 23℃; for 24h; Michael Addition; enantioselective reaction;A 92%
B n/a
Stage #1: tetrahydro-2H-2-pyranol; 2-(2-nitro-vinyl)-phenol With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 25℃; for 24h;
Stage #2: With hydrogenchloride In dichloromethane; water for 2h; Overall yield = 92 %;
A n/a
B n/a
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

phenylacetic acid
103-82-2

phenylacetic acid

Cyclohexyl isocyanide
931-53-3

Cyclohexyl isocyanide

6-hydroxy-1-[(cyclohexyl)amino]-1-oxohexan-2-yl phenylacetate

6-hydroxy-1-[(cyclohexyl)amino]-1-oxohexan-2-yl phenylacetate

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 18h; Passerini Condensation;92%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

3-Pyrroline
109-96-6

3-Pyrroline

5-(1H-pyrrol-1-yl)pentan-1-ol

5-(1H-pyrrol-1-yl)pentan-1-ol

Conditions
ConditionsYield
With benzoic acid In toluene at 110℃; for 24h; Inert atmosphere;90%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

n-undecyltriphenylphosphonium bromide
60669-22-9

n-undecyltriphenylphosphonium bromide

5-(Z,E)-hexadecenol
149011-67-6

5-(Z,E)-hexadecenol

Conditions
ConditionsYield
Stage #1: n-undecyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h;
Stage #2: tetrahydro-2H-2-pyranol In tetrahydrofuran; hexane at 0 - 20℃; Wittig reaction;
89%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

2-phenylethanol
60-12-8

2-phenylethanol

2-(2-phenylethoxy)tetrahydro-2H-pyran
1927-61-3

2-(2-phenylethoxy)tetrahydro-2H-pyran

Conditions
ConditionsYield
With rhenium(VII) oxide In dichloromethane at 20℃; Time; Inert atmosphere;89%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

phenylacetic acid
103-82-2

phenylacetic acid

n-butyl isonitrile
2769-64-4

n-butyl isonitrile

6-hydroxy-1-[(n-butyl)amino]-1-oxohexan-2-yl phenylacetate

6-hydroxy-1-[(n-butyl)amino]-1-oxohexan-2-yl phenylacetate

Conditions
ConditionsYield
In neat (no solvent) at 20℃; for 18h; Passerini Condensation;89%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

(2-trimethylsilylethylidene)triphenylphosphorane
63922-69-0

(2-trimethylsilylethylidene)triphenylphosphorane

7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol
119554-49-3

7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol

Conditions
ConditionsYield
88%
In tetrahydrofuran -78 deg C to r.t.;80%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl cis/trans-7-hydroxy-2-heptenoate
96251-91-1, 105198-41-2, 110935-49-4

ethyl cis/trans-7-hydroxy-2-heptenoate

Conditions
ConditionsYield
In dichloromethane for 1.5h; Wittig reaction; Heating;88%
85%
79%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

ethyl (E)-7-hydroxyhept-2-enoate
96251-91-1

ethyl (E)-7-hydroxyhept-2-enoate

Conditions
ConditionsYield
In tetrahydrofuran Wittig reaction; Heating;88%
In dichloromethane for 48h; Ambient temperature;83%
In dichloromethane at 23℃; for 96h; Inert atmosphere;80%
tetrahydro-2H-2-pyranol
694-54-2

tetrahydro-2H-2-pyranol

2-methyl-5-(phenylsulfonyl)-2-pentene
59555-69-0

2-methyl-5-(phenylsulfonyl)-2-pentene

9-methyl 6-phenylsulphonyl 8-decen 1,5-diol
116893-79-9, 116893-80-2

9-methyl 6-phenylsulphonyl 8-decen 1,5-diol

Conditions
ConditionsYield
With lithium diisopropyl amide at 20℃; for 18h;87%

2H-Pyran-2-ol,tetrahydro- Specification

The 2H-Pyran-2-ol,tetrahydro- is an organic compound with the formula C5H10O2. The IUPAC name of this chemical is Oxan-2-ol. With the CAS registry number 694-54-2, it is also named as 2-Tetrahydropyranol. Besides, it is clear colorless liquid, which should be stored in a cool, sealed, dry place.

Physical properties about 2H-Pyran-2-ol,tetrahydro- are: (1)ACD/LogP: -0.36; (2)ACD/LogD (pH 5.5): -0.36; (3)ACD/LogD (pH 7.4): -0.36; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 15.15; (7)ACD/KOC (pH 7.4): 15.15; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 18.46 Å2; (12)Index of Refraction: 1.467; (13)Molar Refractivity: 26.25 cm3; (14)Molar Volume: 94.4 cm3; (15)Polarizability: 10.4×10-24 cm3; (16)Surface Tension: 36 dyne/cm; (17)Density: 1.08 g/cm3; (18)Flash Point: 71.4 °C; (19)Enthalpy of Vaporization: 47.37 kJ/mol; (20)Boiling Point: 170.5 °C at 760 mmHg; (21)Vapour Pressure: 0.471 mmHg at 25 °C.

Preparation: this chemical can be prepared by Tetrahydro-pyran-2-one. This reaction will need reagent diisobutylaluminum hydride (DIBAL-H) and solvent toluene. The reaction time is 1 hour with reaction temperature of -70 °C.

2H-Pyran-2-ol,tetrahydro- can be obtained by Tetrahydro-pyran-2-one

Uses of 2H-Pyran-2-ol,tetrahydro-: it can be used to produce 2-Phenylselanyl-tetrahydro-pyran at temperature of 25 °C. It will need reagent p-toluenesulfonic acid and solvent benzene. The yield is about 92%.

2H-Pyran-2-ol,tetrahydro- and Benzeneselenol can be used to produce 2-Phenylselanyl-tetrahydro-pyran

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation and if swallowed. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)InChI: InChI=1/C5H10O2/c6-5-3-1-2-4-7-5/h5-6H,1-4H2
(2)InChIKey: CELWCAITJAEQNL-UHFFFAOYAE
(3)Std. InChI: InChI=1S/C5H10O2/c6-5-3-1-2-4-7-5/h5-6H,1-4H2
(4)Std. InChIKey: CELWCAITJAEQNL-UHFFFAOYSA-N

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