Tetrahydro-4-pyranol supplier

Name
Tetrahydro-4-pyranol
EINECS 218-210-8
CAS No. 2081-44-9
Article Data16
CAS DataBase
Density 1.08 g/cm³
Solubility
Melting Point
Formula C₅H₁₀O₂
Boiling Point 183 °C at 760 mmHg
Molecular Weight 102.133
Flash Point 87.8 °C
Transport Information
Appearance Yellow powder
Safety 26-39-36/37/39-23
Risk Codes 41-36/37/38-20/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 2H-Pyran-4-ol,tetrahydro-;Pyran-4-ol,tetrahydro- (6CI,7CI);4-Hydroxytetrahydro-2H-pyran;4-Hydroxytetrahydropyran;Tetrahydro-2H-pyran-4-ol;Tetrahydro-2H-pyranol-4-ol;
PSA 29.46000
LogP 0.15770

Synthetic route

: 29943-42-8
Tetrahydro-4H-pyran-4-one

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
Stage #1: Tetrahydro-4H-pyran-4-one With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With sodium hydroxide In tetrahydrofuran; water	99%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 5℃; for 3h;	96%
With C15H18BF3; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane In tetrahydrofuran at 75℃; under 75007.5 Torr; for 40h; Glovebox;	93%

: 110-88-3
1,3,5-Trioxan

: 627-27-0
homoalylic alcohol

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
Stage #1: 1,3,5-Trioxan; homoalylic alcohol With formic acid at 80℃; for 4h; Stage #2: With isopropyl alcohol; methanesulfonic acid at 64℃; Product distribution / selectivity;	84%
Stage #1: 1,3,5-Trioxan; homoalylic alcohol With formic acid at 80℃; for 4 - 12.5h; Stage #2: With ethanol; methanesulfonic acid at 20 - 64℃; Product distribution / selectivity;	81%
Stage #1: 1,3,5-Trioxan; homoalylic alcohol With formic acid at 80℃; for 4h; Stage #2: With methanol; methanesulfonic acid at 64℃; Product distribution / selectivity;	79%

: 50-00-0
formaldehyd

: 187737-37-7
propene

A: 1120-97-4
4-methyl-1,3-dioxane

B: 2081-44-9
Tetrahydro-pyran-4-ol

C: 18826-95-4, 107-88-0
1.3-butanediol

Conditions

Conditions	Yield
With cerium(IV) oxide Reagent/catalyst;	A 26% B 11% C 60%

...Expand

: 542-05-2
acetonedicarboxylic acid

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 1h; Inert atmosphere;	17%

: 108-97-4
4-pyrone

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
With nickel Hydrogenation;
Multi-step reaction with 2 steps 1: Raney nickel; ethanol / Hydrogenation.bei Raumtemperatur unter Normaldruck 2: Raney nickel / Hydrogenation View Scheme

: 50-00-0
formaldehyd

: 627-27-0
homoalylic alcohol

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
With sulfuric acid; water

: 50-00-0
formaldehyd

: 627-27-0
homoalylic alcohol

A: 2081-44-9
Tetrahydro-pyran-4-ol

B: 5684-93-5
2-[1,3]dioxan-4-yl-ethanol

Conditions

Conditions	Yield
With sulfuric acid

...Expand

: 78870-52-7
(1SR,6RS)-3,7-dioxa-bicyclo[4.1.0]heptane

A: 19752-84-2
Oxan-3-ol

B: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In pentane for 4h; Ambient temperature;

pyrone-(4): pyrone-(4)

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
With water; platinum Hydrogenation;

: 108-97-4
4-pyrone

: 67-56-1
methanol

Raney nickel: Raney nickel

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
at 110℃; under 36775.4 Torr; Hydrogenation;

...Expand

: 108-97-4
4-pyrone

: 64-17-5
ethanol

copper oxide-chromium oxide: copper oxide-chromium oxide

A: 2081-44-9
Tetrahydro-pyran-4-ol

B: 29943-42-8
Tetrahydro-4H-pyran-4-one

Conditions

Conditions	Yield
at 120℃; under 73550.8 - 147102 Torr; Hydrogenation;

...Expand

: 5337-03-1
tetrahydro-2H-pyran-4-carboxylic acid

: 7732-18-5
water

A: 2081-44-9
Tetrahydro-pyran-4-ol

B: 4677-17-2
octahydro-[4,4']bipyranyl

C: tetrahydro-pyran-4-carboxylic acid tetrahydropyran-4-yl ester

Conditions

Conditions	Yield
Anodischen Oxydation des Kalium-Salzes;

...Expand

: 50-00-0
formaldehyd

: 627-27-0
homoalylic alcohol

: 7664-93-9
sulfuric acid

A: 2081-44-9
Tetrahydro-pyran-4-ol

B: 5684-93-5
2-[1,3]dioxan-4-yl-ethanol

...Expand

: 50-00-0
formaldehyd

: 627-27-0
homoalylic alcohol

: 7664-93-9
sulfuric acid

: 7732-18-5
water

A: 2081-44-9
Tetrahydro-pyran-4-ol

B: 5684-93-5
2-[1,3]dioxan-4-yl-ethanol

...Expand

: 99-32-1
chelidonic acid

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: copper-powder / 350 °C 2: Raney nickel; ethanol / Hydrogenation.bei Raumtemperatur unter Normaldruck 3: Raney nickel / Hydrogenation View Scheme

: 68854-18-2
2,4,6-trioxo-heptanedioic acid diethyl ester

: 2081-44-9
Tetrahydro-pyran-4-ol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: concentrated aqueous hydrochloric acid 2: copper-powder / 350 °C 3: Raney nickel; ethanol / Hydrogenation.bei Raumtemperatur unter Normaldruck 4: Raney nickel / Hydrogenation View Scheme

: 142-68-7
TETRAHYDROPYRANE

A: 96-47-9
2-methyltetrahydrofuran

B: 2081-44-9
Tetrahydro-pyran-4-ol

C: 96-48-0
4-butanolide

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

E: 29943-42-8
Tetrahydro-4H-pyran-4-one

F: 1487-44-1
3-chloropropyl formate

Conditions

Conditions	Yield
With clorine at 24.84℃; under 800 Torr; Kinetics; Inert atmosphere; Gas phase;

...Expand

: 50-00-0
formaldehyd

: 187737-37-7
propene

A: 2081-44-9
Tetrahydro-pyran-4-ol

B: 3174-74-1
dihydropyran

C: 627-27-0
homoalylic alcohol

D: 123-72-8
butyraldehyde

Conditions

Conditions	Yield
With zeolite Zn/H-beta In 1,4-dioxane at 119.84℃; for 2.5h; Catalytic behavior; Reagent/catalyst; Temperature;

...Expand

: 50-00-0
formaldehyd

: 187737-37-7
propene

A: 1120-97-4
4-methyl-1,3-dioxane

B: 2081-44-9
Tetrahydro-pyran-4-ol

C: 3174-74-1
dihydropyran

D: 627-27-0
homoalylic alcohol

E: 123-72-8
butyraldehyde

Conditions

Conditions	Yield
With zeolite Zn/H-beta In 1,4-dioxane at 119.84℃; for 2.5h; Catalytic behavior; Reagent/catalyst; Temperature;

...Expand

: 2081-44-9
Tetrahydro-pyran-4-ol

: 124-63-0
methanesulfonyl chloride

: 134419-59-3
4-oxanyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 2.5h;	100%
With triethylamine In dichloromethane at 0℃; for 1.5h;	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 760994-01-2
6-ethyl-5-hydroxyindan-1-one

: 760994-03-4
6-ethyl-5-(tetrahydro-2H-pyran-4-yloxy)indan-1-one

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; PS-triphenylphosphine In tetrahydrofuran	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 3943-97-3
methyl 4-hydroxycinnamate

: 871109-62-5
methyl 4-(tetrahydro-4H-pyran-4-yloxy)cinnamate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 25h; Ultrasonification;	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 1100768-37-3
1-[3-(5-chloro-thiophen-2-yl)-4-fluoro-phenyl]-ethanone

: 1100768-38-4
1-[3-(5-chloro-thiophen-2-yl)-4-(tetrahydro-pyran-4-yloxy)-phenyl]-ethanone

Conditions

Conditions	Yield
Stage #1: Tetrahydro-pyran-4-ol With sodium hydride In dimethyl sulfoxide at 0 - 10℃; for 0.5h; Stage #2: 1-[3-(5-chloro-thiophen-2-yl)-4-fluoro-phenyl]-ethanone In dimethyl sulfoxide at 20℃; for 1h;	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 103095-47-2
(2-hydroxy-5-nitrophenoxy)acetic acid ethyl ester

: 1111236-81-7
C15H19NO7

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 3h; Mitsunobu reaction;	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 35213-00-4
2,6-dinitrobenzonitrile

: 1093204-86-4
2-nitro-6-(tetrahydro-2H-pyran-4-yloxy)benzonitrile

Conditions

Conditions	Yield
	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 2,6-dichloro-4-(pyrrolidin-1-yl)pyrido[3,4-d]pyrimidine

: 6-chloro-4-(pyrrolidin-1-yl)-2-((tetrahydro-2H-pyran-4-yl)oxy)pyrido[3,4-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: Tetrahydro-pyran-4-ol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2,6-dichloro-4-(pyrrolidin-1-yl)pyrido[3,4-d]pyrimidine In tetrahydrofuran at 20℃; for 2h;	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 5470-18-8
2-Chloro-3-nitropyridine

: 1211758-67-6
3-nitro-2-(tetrahydropyran-4-oxy)pyridine

Conditions

Conditions	Yield
Stage #1: Tetrahydro-pyran-4-ol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: 2-Chloro-3-nitropyridine In tetrahydrofuran; mineral oil at 20℃;	100%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 32315-10-9
bis(trichloromethyl) carbonate

: 89641-80-5
tetrahydro-2H-pyran-4-yl carbonochloridate

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate With pyridine In tetrahydrofuran for 0.166667h; Cooling with ice; Stage #2: Tetrahydro-pyran-4-ol In tetrahydrofuran at 20℃; for 1h;	99%
With pyridine In dichloromethane at 20℃; for 3h;	90%
With pyridine In dichloromethane at 0 - 20℃; for 2h;	86%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 598-40-3
ethyl iodoacetate

: C8H14O3

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.5h; Green chemistry;	99%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 61915-52-4
2,2-Dimethylpropanoyl iodide

: tetrahydro-2H-pyran-4-yl pivalate

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.5h; Green chemistry;	99%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 21524-39-0
2,3-difluorobenzonitrile

: 3-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)benzonitrile

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	98%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 75-44-5
phosgene

: 89641-80-5
tetrahydro-2H-pyran-4-yl carbonochloridate

Conditions

Conditions	Yield
In dichloromethane; toluene at 20℃; for 18h;	98%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 4-methyl-6-bromo-8-hydroxyquinazoline

: 6-bromo-4-methyl-8-((tetrahydro-2H-pyran-4-yl)oxy)quinazoline

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu Displacement; Inert atmosphere;	98%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Inert atmosphere;	98%

: 2081-44-9
Tetrahydro-pyran-4-ol

: N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide

: N-(3-(trifluoromethyl)benzyl)-2-(2-nitro-5-(tetrahydro-2H-pyran-4-yloxy)phenyl)isonicotinamide

Conditions

Conditions	Yield
Stage #1: Tetrahydro-pyran-4-ol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: N-(3-(trifluoromethyl)benzyl)-2-(5-fluoro-2-nitrophenyl)isonicotinamide In N,N-dimethyl-formamide at 80℃; for 2h;	97%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 1036738-12-1
2,4,6-trichloropyrido[3,2-d]pyrimidine

: C12H11Cl2N3O2

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 16h;	97%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 40530-18-5
5-bromo-2-hydroxybenzonitrile

: 876918-62-6
5-bromo-2-((tetrahydro-2H-pyran-4-yl)oxy)benzonitrile

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 18h;	96%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 18h;	96%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 124811-71-8
4-hydroxy-3-(trifluoromethyl)benzonitrile

: 1241910-75-7
4-(tetrahydro-2H-pyran-4-yloxy)-3-(trifluoromethyl)benzonitrile

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	96%
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	96%

: 2081-44-9
Tetrahydro-pyran-4-ol

: isopropyl (S)-2-(tert-butoxy)-2-(4‘-(4,4-dimethylpiperidin-1-yl)-5-hydroxy-6’-methyl-[2,3‘-bipyridin]-5‘-yl)acetate

: (S)-isopropyl 2-tert-butoxy-2-(4'-(4,4-dimethylpiperidin-1-yl)-6'-methyl-5-(tetrahydro-2H-pyran-4-yloxy)-2,3'-bipyridin-5'-yl)acetate

Conditions

Conditions	Yield
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; Inert atmosphere;	96%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 3964-56-5
4-bromo-2-chlorophenol

: 1056465-06-5
4-(4-bromo-2-chlorophenoxy)tetrahydropyrane

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate In dichloromethane at 0 - 20℃; for 2h;	95%
With di-tert-butyl-diazodicarboxylate In dichloromethane at 0 - 20℃; for 2h; Mitsunobu reaction;	95%
With di-tert-butyl-diazodicarboxylate In dichloromethane at 0 - 20℃; for 2.08333h; Mitsunobu reaction;	95%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 598-40-3
ethyl iodoacetate

: 5-iodopentane-1,3-diyl dipropionate

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.5h; Green chemistry;	95%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 61915-52-4
2,2-Dimethylpropanoyl iodide

: 5-iodopentane-1,3-diyl dipivalate

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.5h; Green chemistry;	95%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 611-35-8
4-chloroquinoline

: 4-((tetrahydro-2H-pyran-4-yl)oxy)quinoline

Conditions

Conditions	Yield
Stage #1: Tetrahydro-pyran-4-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-chloroquinoline In N,N-dimethyl-formamide; mineral oil at 50℃; for 5h; Inert atmosphere;	95%

: 2081-44-9
Tetrahydro-pyran-4-ol

: methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

: methyl 2-[(tetrahydropyran-4-yl)oxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 72h;	94%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 72684-95-8
3,5-dimethoxy-4-hydroxybenzonitrile

: 1319736-48-5
3,5-dimethoxy-4-(4-tetrahydropyranyloxy)benzonitrile

Conditions

Conditions	Yield
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	94%
Stage #1: Tetrahydro-pyran-4-ol; 3,5-dimethoxy-4-hydroxybenzonitrile With di-tert-butyl-diazodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Stage #2: With formic acid at 50℃; for 2h;	94%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: C11H24O2Si

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 3h; Inert atmosphere; Schlenk technique;	94%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 104-92-7
1-bromo-4-methoxy-benzene

: 1240042-03-8
4-(4-methoxyphenoxy)-tetrahydro-2H-pyran

Conditions

Conditions	Yield
With copper(l) iodide; N1, N2-diphenethyloxalamide; sodium t-butanolate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating;	94%

: 2081-44-9
Tetrahydro-pyran-4-ol

: 98-59-9
p-toluenesulfonyl chloride

: 97986-34-0
toluene-4-sulfonic acid tetrahydropyran-4-yl ester

Conditions

Conditions	Yield
Stage #1: Tetrahydro-pyran-4-ol With trimethylamine hydrochloride; triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 0 - 20℃; for 17h;	93%
Stage #1: Tetrahydro-pyran-4-ol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 15h;	92%
With pyridine; dmap In dichloromethane for 168h;	90%

: 2081-44-9
Tetrahydro-pyran-4-ol

: (4-chlorophenyl)(pyridin-2-yl)methyl 2,2,2-trichloroacetimidate

: 2-[(4-chlorophenyl)(tetrahydro-2H-pyran-4-yloxy)methyl]pyridine

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere; Cooling with ice;	93%

Tetrahydro-4-pyranol Chemical Properties

Empirical Formula: C₅H₁₀O₂
Molecular Weight: 102.1317
EINECS: 218-210-8
Index of Refraction: 1.467
Molar Refractivity: 26.25 cm³
Molar Volume: 94.4 cm³
Surface Tension: 36 dyne/cm
Density: 1.08 g/cm³
Flash Point: 87.8 °C
Enthalpy of Vaporization: 48.8 kJ/mol
Boiling Point: 183 °C at 760 mmHg
Vapour Pressure: 0.227 mmHg at 25 °C
Structure of Tetrahydro-4-pyranol (CAS NO.2081-44-9):

IUPAC Name: Oxan-4-ol
Canonical SMILES: C1COCCC1O
InChI: InChI=1S/C5H10O2/c6-5-1-3-7-4-2-5/h5-6H,1-4H2
InChIKey: LMYJGUNNJIDROI-UHFFFAOYSA-N
Product Category of Tetrahydro-4-pyranol (CAS NO.2081-44-9): Alcohols and Derivatives;Heterocycles;Pyrans, Piperidines & Piperazines

Tetrahydro-4-pyranol Safety Profile

Hazard Codes of Tetrahydro-4-pyranol (CAS NO.2081-44-9): Irritant Xi, Harmful Xn
Risk Statements: 41-36/37/38-20/22
R20/22:Harmful by inhalation and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
R41:Risk of serious damage to the eyes.
Safety Statements: 26-39-36/37/39-23
S23:Do not breathe vapour.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S39:Wear eye / face protection.
WGK Germany: 3
Hazard Note: Irritant

Tetrahydro-4-pyranol Specification

Tetrahydro-4-pyranol , its cas register number is 2081-44-9. It also can be called Tetrahydropyran-4-ol ; 4-Hydroxytetrahydropyran ; and 2H-Pyran-4-ol, tetrahydro .

Product Name

Tetrahydro-4-pyranol

Synthetic route

Tetrahydro-4-pyranol Chemical Properties

Tetrahydro-4-pyranol Safety Profile

Tetrahydro-4-pyranol Specification

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