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Name	4-Iodotetrahydro-2H-pyran	EINECS	N/A
CAS No.	25637-18-7	Density	1.777 g/cm³
PSA	9.23000	LogP	1.60040
Solubility	N/A	Melting Point	N/A
Formula	C₅H₉IO	Boiling Point	208.154 °C at 760 mmHg
Molecular Weight	212.03	Flash Point	79.689 °C
Transport Information	N/A	Appearance	N/A
Safety	26-36/37/39	Risk Codes	36-36/37/38
Molecular Structure		Hazard Symbols	Xi
Synonyms	4-Iodooxacyclohexane;	Article Data	14

4-Iodotetrahydro-2H-pyran 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%

: 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%

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

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