25637-18-7

Basic information

• Product Name: 4-IODOTETRAHYDRO-2H-PYRAN
• Synonyms: 4-IODOTETRAHYDRO-2H-PYRAN;4-IODO-TETRAHYDRO-PYRAN;4-Iodotetrahydro-2H-pyrane;4-Iodotetrahydro-2H-pyran 97%;2H-Pyran, tetrahydro-4-iodo-;4-iodooxane;Tetrahydro-4-iodo-2H-pyran
• CAS NO: 25637-18-7
• Molecular Formula: C₅H₉IO
• Molecular Weight: 212.03
• Mol File: 25637-18-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 79 °C
• Flash Point: 79.689 °C
• Appearance: /
• Density: 1.777 g/cm³
• Vapor Pressure: 0.313mmHg at 25°C
• Refractive Index: 1.546
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 4-IODOTETRAHYDRO-2H-PYRAN(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODOTETRAHYDRO-2H-PYRAN(25637-18-7)
• EPA Substance Registry System: 4-IODOTETRAHYDRO-2H-PYRAN(25637-18-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 25637-18-7(Hazardous Substances Data)

Usage

General Description

4-IODOTETRAHYDRO-2H-PYRAN is a chemical compound with the molecular formula C5H9IO. It is a heterocyclic compound containing a pyran ring with an iodine substituent at the 4-position. 4-IODOTETRAHYDRO-2H-PYRAN has potential applications in organic synthesis and as a building block for the preparation of various organic molecules. It is known for its use as a versatile synthetic intermediate in the production of pharmaceuticals, agrochemicals, and other fine chemicals. Additionally, 4-IODOTETRAHYDRO-2H-PYRAN has been studied for its potential biological activities and pharmacological properties, making it a versatile and important chemical in various fields of research and industry.

InChI:InChI=1/C5H9IO/c6-5-1-3-7-4-2-5/h5H,1-4H2

Synthetic route

Tetrahydro-pyran-4-ol (2081-44-9) → 4-iodotetrahydropyran (25637-18-7)

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%

toluene-4-sulfonic acid tetrahydropyran-4-yl ester (97986-34-0) → 4-iodotetrahydropyran (25637-18-7)

Conditions	Yield
With acetone; sodium iodide

4-pyrone (108-97-4) → 4-iodotetrahydropyran (25637-18-7)

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

4-iodotetrahydropyran (25637-18-7) + tert-butylisonitrile (119072-55-8, 7188-38-7) → N-(tert-butyl)tetrahydro-2H-pyran-4-carboxamide

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%

4-iodotetrahydropyran (25637-18-7) + ((triisopropylsilyl)ethynyl)magnesium bromide (159862-82-5) → triisopropyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane

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

4-iodotetrahydropyran (25637-18-7) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (R)-tert-butyl 2-(tetrahydro-2H-pyran-4-yl)pyrrolidine-1-carboxylate (1448219-22-4)

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%

4-iodotetrahydropyran (25637-18-7) + carbon monoxide (201230-82-2) + diphenyl acetylene (501-65-5) → (E)-2,3-diphenyl-1-(tetrahydro-2H-pyran-4-yl)prop-2-en-1-ol

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%

4-iodotetrahydropyran (25637-18-7) + C18H20BrNOZn → C23H29NO2

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

4-iodotetrahydropyran (25637-18-7) + 3-bromo-2-phenyl-1,2-dihydrobenzo[e][1,2]azaborinine (1616634-99-1) → 2-phenyl-3-(4-tetrahydro-2H-pyranyl)-2,1-borazaronaphthalene (1616695-73-8)

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%

4-iodotetrahydropyran (25637-18-7) + 5-hexynonitrile (14918-21-9) → (E)-6-(tetrahydro-2H-pyran-4-yl)hex-5-enenitrile

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%

4-iodotetrahydropyran (25637-18-7) + diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1149-23-1) → diethyl 2,6-dimethyl-4-(tetrahydro-2H-pyran-4-yl)-1,4-dihydropyridine-3,5-dicarboxylate

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

4-iodotetrahydropyran (25637-18-7) + C14H6F2MnN2 → 2-fluoro-3-(tetrahydro-2H-pyran-4-yl)benzonitrile

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

4-iodotetrahydropyran (25637-18-7) + para-bromobenzenethiol (106-53-6) → 4-[(4-bromophenyl)sulfanyl]tetrahydro-2H-pyran (165119-50-6)

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

4-iodotetrahydropyran (25637-18-7) + 2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) + N-butylamine (109-73-9) → ethyl 2-(butylamino)-4-phenyl-2-(tetrahydro-2H-pyran-4-yl)butanoate

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%

4-iodotetrahydropyran (25637-18-7) + 3-Phenylpropan-1-amine (2038-57-5) → N-(3-phenylpropyl)tetrahydro-2H-pyran-4-amine

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%

4-iodotetrahydropyran (25637-18-7) + methyl hex-5-ynoate (77758-51-1) → methyl 6-(tetrahydro-2H-pyran-4-yl)hex-5-ynoate

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%

4-iodotetrahydropyran (25637-18-7) + carbon monoxide (201230-82-2) + dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8) → (dimethyl(phenyl)silyl)(tetrahydro-2H-pyran-4-yl)methanone

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%

4-iodotetrahydropyran (25637-18-7) + furfural (98-01-1) → 5-(tetrahydro-2H-pyran-4-yl)furan-2-carbaldehyde

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%

4-iodotetrahydropyran (25637-18-7) + Triisopropyl-trifluoromethanesulfonylethynyl-silane (196789-82-9) → triisopropyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane

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

4-iodotetrahydropyran (25637-18-7) + furan-3-carboxaldehyde (498-60-2) → 2-(tetrahydro-2H-pyran-4-yl)furan-3-carbaldehyde

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%

4-iodotetrahydropyran (25637-18-7) + 2-furancarbonitrile (617-90-3) → 5-(tetrahydro-2H-pyran-4-yl)furan-2-carbonitrile

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%

4-iodotetrahydropyran (25637-18-7) + 1-benzofurane (271-89-6) → 2-(tetrahydro-2H-pyran-4-yl)benzofuran

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%

4-iodotetrahydropyran (25637-18-7) + (trimethylsilyl)ethynylmagnesium bromide (61210-52-4) → trimethyl((tetrahydro-2H-pyran-4-yl)ethynyl)silane (1604039-54-4)

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

4-iodotetrahydropyran (25637-18-7) + 1-p-toluenesulfonyloxy-3-(4-methoxyphenyl)propane (88537-43-3) → C15H22O4S

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

4-iodotetrahydropyran (25637-18-7) + (4-mercapto-phenyl)-acetic acid methyl ester (91361-92-1) → methyl 2-(4-tetrahydropyran-4-ylsulfanylphenyl)acetate (1328997-80-3)

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℃;

4-iodotetrahydropyran (25637-18-7) + C18H25BO4 → C24H37BO5

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%

4-iodotetrahydropyran (25637-18-7) + 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	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%

4-iodotetrahydropyran (25637-18-7) + 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	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%

4-iodotetrahydropyran (25637-18-7) + 1-(2-furyl)-1-ethanone (1192-62-7) → 1-(5-(tetrahydro-2H-pyran-4-yl)furan-2-yl)ethan-1-one

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%

4-iodotetrahydropyran (25637-18-7) + (cyclohex-1-en-1-ylethynyl)magnesium bromide (118264-44-1) → 4-(cyclohex-1-en-1-ylethynyl)tetrahydro-2H-pyran (1604039-53-3)

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

4-iodotetrahydropyran (25637-18-7) + 2-phenylfuran (17113-33-6) → 4-(5-phenylfuran-2-yl)tetrahydro-2H-pyran

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%

4-iodotetrahydropyran (25637-18-7) + C16H31ClSi (1105596-88-0) → C21H40OSi (1105596-90-4)

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%

4-iodotetrahydropyran (25637-18-7) + (E)-1-Phenyl-1,3-butadiene (16939-57-4) + benzyl-methyl-amine (103-67-3) → (E)-N-benzyl-N-methyl-4-phenyl-1-(tetrahydro-2H-pyran-4-yl)but-3-en-2-amine

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%

Upstream product

• 2081-44-9 Tetrahydro-pyran-4-ol 
• 108-97-4 4-pyrone 
• 97986-34-0 toluene-4-sulfonic acid tetrahydropyran-4-yl ester 

Downstream Products

• 1100767-95-0 1-[3-chloro-4-(tetrahydro-pyran-4-ylsulfanyl)-phenyl]-ethanone 
• 1276024-95-3 methyl 4-(tetrahydro-2H-pyran-4-yl)benzoate 
• 1448219-22-4 (R)-tert-butyl 2-(tetrahydro-2H-pyran-4-yl)pyrrolidine-1-carboxylate 
• 1426955-70-5 (R_S,R)-N-[phenyl(tetrahydro-2H-pyran-4-yl)methyl]-2-methylpropane-2-sulfinamide 
• 1427064-46-7 5-(tetrahydropyran-4-yl)-6-(2,2,2-trifluoroethoxy)nicotinic acid N′-methyl-N′-phenylhydrazide 
• 1227159-77-4 N'-hydroxy-4-(tetrahydro-2H-pyran-4-yl)benzenecarboximide amide 
• 1227160-25-9 5-(5-methyl-1H-pyrazol-3-yl)-3-[4-(tetrahydro-2H-pyran-4-yl)phenyl]-1,2,4-oxadiazole 
• 1227159-78-5 4-(tetrahydro-2H-pyran-4-yl)benzonitrile 
• 1350351-52-8 4,4,5,5-tetramethyl-2-(4-tetrahydropyran-4-ylsulfonylphenyl)-1,3,2-dioxaborolane 
• 1021169-68-5 4-[(4-bromophenyl)sulfonyl]tetrahydro-2H-pyran 
• 165119-50-6 4-[(4-bromophenyl)sulfanyl]tetrahydro-2H-pyran 
• 1328997-80-3 methyl 2-(4-tetrahydropyran-4-ylsulfanylphenyl)acetate 
• 885133-28-8 3-ethyl-6-{1-[4-(methylsulfonyl)phenyl]-1H-pyrazol-5-yl}-1-(tetrahydro-2H-pyran-4-yl)-1H-indazole 
• 646055-93-8 ethyl aminotetrahydropyran-4-ylacetate 

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