4-Iodotetrahydro-2H-pyran supplier

Name
4-IODOTETRAHYDRO-2H-PYRAN
EINECS
CAS No. 25637-18-7
Article Data14
CAS DataBase
Density 1.777 g/cm³
Solubility
Melting Point
Formula C₅H₉IO
Boiling Point 208.154 °C at 760 mmHg
Molecular Weight 212.03
Flash Point 79.689 °C
Transport Information
Appearance
Safety 26-36/37/39
Risk Codes 36-36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Iodooxacyclohexane;
PSA 9.23000
LogP 1.60040

Synthetic route

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

: 25637-18-7
4-iodotetrahydropyran

Conditions

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 16h; Cooling with ice; Inert atmosphere;	65%
With 1H-imidazole; iodine; triphenylphosphine In tetrahydrofuran at 0 - 20℃;	64.3%
Stage #1: Tetrahydro-pyran-4-ol With 1H-imidazole; triphenylphosphine In dichloromethane for 0.25h; Inert atmosphere; Stage #2: With iodine In dichloromethane for 16h; Inert atmosphere;	51%

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

: 25637-18-7
4-iodotetrahydropyran

Conditions

Conditions	Yield
With acetone; sodium iodide

: 108-97-4
4-pyrone

: 25637-18-7
4-iodotetrahydropyran

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Raney nickel / Hydrogenation 2: pyridine 3: acetone; sodium iodide View Scheme

: 25637-18-7
4-iodotetrahydropyran

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: N-(tert-butyl)tetrahydro-2H-pyran-4-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-iodotetrahydropyran; tert-butylisonitrile With bis(1,5-cyclooctadiene)nickel (0); water; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; sodium t-butanolate In tert-butyl alcohol at 100℃; for 12h; Inert atmosphere; Stage #2: With hydrogenchloride In tert-butyl alcohol at 20℃; for 0.0833333h; Inert atmosphere;	98%

: 25637-18-7
4-iodotetrahydropyran

: 159862-82-5
((triisopropylsilyl)ethynyl)magnesium bromide

: triisopropyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane

Conditions

Conditions	Yield
With iron(II) bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Inert atmosphere; Glovebox;	96%

: 25637-18-7
4-iodotetrahydropyran

: 86953-79-9
tert-butyl pyrrolidine-1-carboxylate

: 1448219-22-4
(R)-tert-butyl 2-(tetrahydro-2H-pyran-4-yl)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl pyrrolidine-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; cyclohexane at -78℃; for 3.5h; Inert atmosphere; Stage #2: With zinc(II) iodide In tetrahydrofuran; diethyl ether; cyclohexane at -78 - 20℃; for 1.5h; Cooling with acetone-dry ice; Inert atmosphere; Stage #3: 4-iodotetrahydropyran With (1,2-dimethoxyethane)dichloronickel(II); (1S,2S)-N,N’-dimethyl-1,2-di(naphthalen-1-yl)ethane-1,2-diamine In tetrahydrofuran; diethyl ether; cyclohexane at 20℃; for 60h; Reagent/catalyst; Negishi Coupling; Inert atmosphere; enantioselective reaction;	94%

Yield

Stage #1: tert-butyl pyrrolidine-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; cyclohexane at -78℃; for 3.5h; Inert atmosphere;
Stage #2: With zinc(II) iodide In tetrahydrofuran; diethyl ether; cyclohexane at -78 - 20℃; for 1.5h; Cooling with acetone-dry ice; Inert atmosphere;
Stage #3: 4-iodotetrahydropyran With (1,2-dimethoxyethane)dichloronickel(II); (1S,2S)-N,N’-dimethyl-1,2-di(naphthalen-1-yl)ethane-1,2-diamine In tetrahydrofuran; diethyl ether; cyclohexane at 20℃; for 60h; Reagent/catalyst; Negishi Coupling; Inert atmosphere; enantioselective reaction;

94%

: 25637-18-7
4-iodotetrahydropyran

: 201230-82-2
carbon monoxide

: 501-65-5
diphenyl acetylene

: (E)-2,3-diphenyl-1-(tetrahydro-2H-pyran-4-yl)prop-2-en-1-ol

Conditions

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); potassium methanolate In tetrahydrofuran at 20℃; under 4560.31 Torr; for 15h;	94%

...Expand

: 25637-18-7
4-iodotetrahydropyran

: C18H20BrNOZn

: C23H29NO2

Conditions

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); 1,5-bis-(diphenylphosphino)pentane; C17H20N2O In tetrahydrofuran at 5℃; stereoselective reaction;	91%

: 25637-18-7
4-iodotetrahydropyran

: 1616634-99-1
3-bromo-2-phenyl-1,2-dihydrobenzo[e][1,2]azaborinine

: 1616695-73-8
2-phenyl-3-(4-tetrahydro-2H-pyranyl)-2,1-borazaronaphthalene

Conditions

Conditions	Yield
With 4-Ethylpyridine; manganese; sodium tetrafluoroborate; 4,4'-dimethyl-2,2'-bipyridines; (1,2-dimethoxyethane)dichloronickel(II) In N,N-dimethyl acetamide; cyclohexane at 40℃; for 18h; Inert atmosphere; Sealed tube;	90%

: 25637-18-7
4-iodotetrahydropyran

: 14918-21-9
5-hexynonitrile

: (E)-6-(tetrahydro-2H-pyran-4-yl)hex-5-enenitrile

Conditions

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); (tpy')NiI; lithium isopropoxide; HSiPh3 In 1,2-dimethoxyethane at 25℃; for 2h; Inert atmosphere; diastereoselective reaction;	90%

: 25637-18-7
4-iodotetrahydropyran

: 1149-23-1
diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

: diethyl 2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Conditions

Conditions	Yield
With dimanganese decacarbonyl In dichloromethane at 20℃; for 12h; Inert atmosphere; Irradiation; Schlenk technique;	88%

: 25637-18-7
4-iodotetrahydropyran

: C14H6F2MnN2

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

Conditions

Conditions	Yield
With iron(II) chloride In tetrahydrofuran at -20 - 25℃; for 16h; Inert atmosphere; Schlenk technique;	86%

: 25637-18-7
4-iodotetrahydropyran

: 106-53-6
para-bromobenzenethiol

: 165119-50-6
4-[(4-bromophenyl)sulfanyl]tetrahydro-2H-pyran

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;	85%

: 25637-18-7
4-iodotetrahydropyran

: 64920-29-2
2-oxo-4-phenylbutanoic acid ethyl ester

: 109-73-9
N-butylamine

: ethyl 2-(butylamino)-4-phenyl-2-(tetrahydro-2H-pyran-4-yl)butanoate

Conditions

Conditions	Yield
Stage #1: 2-oxo-4-phenylbutanoic acid ethyl ester; N-butylamine With propionic acid In dichloromethane at 20℃; for 4h; Inert atmosphere; Molecular sieve; Stage #2: 4-iodotetrahydropyran With tris-(trimethylsilyl)silane; t-butyldimethylsiyl triflate In dichloromethane at 20℃; for 6h; Inert atmosphere; Molecular sieve; Irradiation;	85%

...Expand

: 25637-18-7
4-iodotetrahydropyran

: 2038-57-5
3-Phenylpropan-1-amine

: N-(3-phenylpropyl)tetrahydro-2H-pyran-4-amine

Conditions

Conditions	Yield
With copper(l) iodide; tert-butylimino-tri(pyrrolidino)phosphorane; 1,1'-bi-2-naphthol In N,N-dimethyl-formamide; acetonitrile at -10℃; for 24h; Irradiation;	84%

: 25637-18-7
4-iodotetrahydropyran

: 77758-51-1
methyl hex-5-ynoate

: methyl 6-(tetrahydro-2H-pyran-4-yl)hex-5-ynoate

Conditions

Conditions	Yield
With potassium carbonate; copper(l) chloride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In methanol; acetonitrile at 25℃; for 24h; Glovebox; Inert atmosphere; Irradiation;	84%

: 25637-18-7
4-iodotetrahydropyran

: 201230-82-2
carbon monoxide

: 185990-03-8
dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

: (dimethyl(phenyl)silyl)(tetrahydro-2H-pyran-4-yl)methanone

Conditions

Conditions	Yield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium phenoxide In 1,4-dioxane at 60℃; under 4560.31 Torr; for 12h; Glovebox;	84%

...Expand

: 25637-18-7
4-iodotetrahydropyran

: 98-01-1
furfural

: 5-(tetrahydro-2H-pyran-4-yl)furan-2-carbaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	84%

: 25637-18-7
4-iodotetrahydropyran

: 196789-82-9
Triisopropyl-trifluoromethanesulfonylethynyl-silane

: triisopropyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane

Conditions

Conditions	Yield
With bis(tri-n-butyltin) In benzene at 35℃; for 8h; Irradiation;	83%

: 25637-18-7
4-iodotetrahydropyran

: 498-60-2
furan-3-carboxaldehyde

: 2-(tetrahydro-2H-pyran-4-yl)furan-3-carbaldehyde

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	83%

: 25637-18-7
4-iodotetrahydropyran

: 617-90-3
2-furancarbonitrile

: 5-(tetrahydro-2H-pyran-4-yl)furan-2-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	83%

: 25637-18-7
4-iodotetrahydropyran

: 271-89-6
1-benzofurane

: 2-(tetrahydro-2H-pyran-4-yl)benzofuran

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	83%

: 25637-18-7
4-iodotetrahydropyran

: 61210-52-4
(trimethylsilyl)ethynylmagnesium bromide

: 1604039-54-4
trimethyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane

Conditions

Conditions	Yield
With iron(II) bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Inert atmosphere; Glovebox;	82%

: 25637-18-7
4-iodotetrahydropyran

: 88537-43-3
1-p-toluenesulfonyloxy-3-(4-methoxyphenyl)propane

: C15H22O4S

Conditions

Conditions	Yield
With sodium metabisulfite; tetrabutylammomium bromide; potassium formate; caesium carbonate In dimethyl sulfoxide at 100℃; for 10h; Inert atmosphere;	82%

: 25637-18-7
4-iodotetrahydropyran

: 91361-92-1
(4-mercapto-phenyl)-acetic acid methyl ester

: 1328997-80-3
methyl 2-(4-tetrahydropyran-4-ylsulfanylphenyl)acetate

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;	80%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;
Stage #1: (4-mercapto-phenyl)-acetic acid methyl ester With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 4-iodotetrahydropyran In N,N-dimethyl-formamide at 20℃;
Stage #1: (4-mercapto-phenyl)-acetic acid methyl ester With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: 4-iodotetrahydropyran In N,N-dimethyl-formamide at 20℃;

: 25637-18-7
4-iodotetrahydropyran

: C18H25BO4

: C24H37BO5

Conditions

Conditions	Yield
With potassium fluoride; C18H16N2O2; diethoxymethylane; nickel dichloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 40h; enantioselective reaction;	79%

: 25637-18-7
4-iodotetrahydropyran

: tert-butyl 4-(furan-2-carbonyl)piperazine-1-carboxylate

: tert-butyl 4-(5-(tetrahydro-2H-pyran-4-yl)furan-2-carbonyl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	79%

: 25637-18-7
4-iodotetrahydropyran

: 1,3-dimethoxy-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene

: 4-(2-(3,5-dimethoxyphenyl)-3,3-difluoroallyl)tetrahydro-2H-pyran

Conditions

Conditions	Yield
With nickel(II) bromide dimethoxyethane; cesium fluoride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; zinc In tetrahydrofuran; N,N-dimethyl acetamide for 16h;	78%

: 25637-18-7
4-iodotetrahydropyran

: 1192-62-7
1-(2-furyl)-1-ethanone

: 1-(5-(tetrahydro-2H-pyran-4-yl)furan-2-yl)ethan-1-one

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	78%

: 25637-18-7
4-iodotetrahydropyran

: 118264-44-1
(cyclohex-1-en-1-ylethynyl)magnesium bromide

: 1604039-53-3
4-(cyclohex-1-en-1-ylethynyl)tetrahydro-2H-pyran

Conditions

Conditions	Yield
With iron(II) bromide In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 16h; Inert atmosphere; Glovebox;	77%

: 25637-18-7
4-iodotetrahydropyran

: 17113-33-6
2-phenylfuran

: 4-(5-phenylfuran-2-yl)tetrahydro-2H-pyran

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene at 110℃; for 48h; Inert atmosphere; Schlenk technique; regioselective reaction;	77%

: 25637-18-7
4-iodotetrahydropyran

: 1105596-88-0
C16H31ClSi

: 1105596-90-4
C21H40OSi

Conditions

Conditions	Yield
Stage #1: 4-iodotetrahydropyran With iodine; zinc In N,N-dimethyl acetamide at 80℃; for 6h; Inert atmosphere; Stage #2: C16H31ClSi With 2,2':6,2''-terpyridine; (1,2-dimethoxyethane)dichloronickel(II) In N,N-dimethyl acetamide at 20℃; for 16h; Negishi coupling reaction; Inert atmosphere;	76%

: 25637-18-7
4-iodotetrahydropyran

: 16939-57-4
(E)-1-Phenyl-1,3-butadiene

: 103-67-3
benzyl-methyl-amine

: (E)-N-benzyl-N-methyl-4-phenyl-1-(tetrahydro-2H-pyran-4-yl)but-3-en-2-amine

Conditions

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; palladium dichloride; silver(I) triflimide In tetrahydrofuran at 20℃; for 15h; Inert atmosphere; Glovebox; Schlenk technique; Irradiation; regioselective reaction;	76%

...Expand

4-Iodotetrahydro-2H-pyran Chemical Properties

Molecular Structure:

Molecular Formula: C₅H₉IO
Molecular Weight: 212.0288
IUPAC Name: 4-Iodooxane
Synonyms of 4-Iodotetrahydro-2H-pyran (CAS NO.25637-18-7): 4-Iodo-tetrahydro-pyran ; 4-Iodotetrahydro-2H-pyran 97%
CAS NO: 25637-18-7
Index of Refraction: 1.546
Molar Refractivity: 37.795 cm³
Molar Volume: 119.328 cm³
Surface Tension: 37.18 dyne/cm
Density: 1.777 g/cm³
Flash Point: 79.689 °C
Enthalpy of Vaporization: 42.628 kJ/mol
Boiling Point: 208.154 °C at 760 mmHg
Vapour Pressure of 4-Iodotetrahydro-2H-pyran (CAS NO.25637-18-7): 0.313 mmHg at 25°C

4-Iodotetrahydro-2H-pyran Safety Profile

Hazard Codes of 4-Iodotetrahydro-2H-pyran (CAS NO.25637-18-7): Xi
Hazard Note: Irritant

Product Name

4-IODOTETRAHYDRO-2H-PYRAN

Synthetic route

4-Iodotetrahydro-2H-pyran Chemical Properties

4-Iodotetrahydro-2H-pyran Safety Profile

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