2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene supplier

Name
2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene
EINECS 618-312-6
CAS No. 898566-17-1
Article Data11
CAS DataBase
Density 1.533 g/cm³
Solubility
Melting Point 109-110 °C
Formula C₁₈H₁₄FIS
Boiling Point 450.2 °C at 760 mmHg
Molecular Weight 408.278
Flash Point 226.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-(4-fluorophenyl)-5-(5-iodo-2-methylbenzyl)thiophene;2-(5-iodo-2-methylbenzyl)-5-(4-fluoro-phenyl)thiophene;THI045;
PSA 28.24000
LogP 6.05800

Synthetic route

: (5-(4-fluorophenyl)thiophen-2-yl)(5-iodo-2-methylphenyl)methanone

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions

Conditions	Yield
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 35℃;	85%
With sodium tetrahydroborate; chloro-trimethyl-silane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 5 - 35℃; for 0.5h;	81.1%
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 0 - 28℃; Inert atmosphere;	70.3%
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In chlorobenzene at 10 - 50℃; Reagent/catalyst; Solvent; Concentration; Temperature; Industrial scale;	65.2 kg
With aluminum (III) chloride In chlorobenzene at 10 - 50℃; for 4h;	11.48 g

: 58861-48-6
2-(4-fluorophenyl)thiophene

: 108440-70-6
5-iodo-2-methylbenzoyl chloride

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions

Conditions	Yield
With aluminum (III) chloride Solvent; Temperature; Friedel-Crafts Acylation;	80%
Stage #1: 5-iodo-2-methylbenzoyl chloride With aluminum (III) chloride In dichloromethane at 2℃; for 0.25h; Stage #2: 2-(4-fluorophenyl)thiophene In dichloromethane at 2 - 20℃; for 2.41667h; Product distribution / selectivity;

: 1030825-20-7
2-[(5-bromo-2-methyl-phenyl)methyl]-5-(4-fluorophenyl)thiophene

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions

Conditions	Yield
With sodium iodide; N,N`-dimethylethylenediamine; copper(l) iodide In diethylene glycol dimethyl ether; toluene at 110℃;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene at 20℃; Inert atmosphere; Reflux;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In diethylene glycol dimethyl ether; toluene for 36h; Inert atmosphere; Reflux;	94.9 g

: 118-90-1
ortho-methylbenzoic acid

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: iodic acid / 20 °C / Molecular sieve 2: thionyl chloride 3: aluminum (III) chloride View Scheme

: 54811-38-0
5-iodo-2-methylbenzoic acid

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride 2: aluminum (III) chloride View Scheme
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C / Inert atmosphere 2: aluminum (III) chloride / dichloromethane / 7.5 h / 0 - 20 °C / Inert atmosphere 3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 28 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; thionyl chloride / chlorobenzene / 4 h / 65 - 70 °C / Inert atmosphere; Industrial scale 2: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale 3: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / chlorobenzene / 4 h / 65 - 70 °C / Inert atmosphere 2: aluminum (III) chloride / chlorobenzene / 4 h / 10 - 55 °C 3: aluminum (III) chloride / chlorobenzene / 4 h / 10 - 50 °C View Scheme

: 108440-70-6
5-iodo-2-methylbenzoyl chloride

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 7.5 h / 0 - 20 °C / Inert atmosphere 2: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0 - 28 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: aluminum (III) chloride / chlorobenzene / 4 h / 50 - 55 °C / Industrial scale 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / chlorobenzene / 10 - 50 °C / Industrial scale View Scheme

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: (3-bromo-4, 4, 4-trifluorobutyl)benzene

: (S)-2-(4-fluorophenyl)-5-(2-methyl-5-(1,1,1-trifluoro-4-phenylbutan-2-yl)benzyl)thiophene

Conditions

Conditions	Yield
With nickel(II) bromide dimethoxyethane; manganese; (4R,4'R)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-2,2'-bioxazole; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at -10℃; for 22h; Sealed tube; Inert atmosphere; enantioselective reaction;	95%

: 67-56-1
methanol

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1030825-21-8
(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With magnesium In tetrahydrofuran at 0 - 25℃; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0℃; Inert atmosphere; Stage #3: methanol With methanesulfonic acid In tetrahydrofuran at 20℃; Inert atmosphere;	93.3%
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With s-butylmagnesium chloride; lithium chloride In tetrahydrofuran at -25 - -20℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -25 - -20℃; for 2h; Stage #3: methanol With methanesulfonic acid for 18h; Reagent/catalyst;	93.7%
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In dibutyl ether; toluene Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In toluene Stage #3: methanol With methanesulfonic acid In toluene
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at -18 - -13℃; for 1h; Inert atmosphere; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -15 - -10℃; for 1h; Large scale; Stage #3: methanol With hydrogenchloride at 20℃; for 1h; Large scale;	23.5 kg

...Expand

: 19879-84-6
tetraacetyl thioglucose

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: C32H33FO9S2

Conditions

Conditions	Yield
With palladium; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	90%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 3-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}-4-methylbenzonitrile

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper(II) nitrate trihydrate; water; acetic acid at 130℃; for 48h;	87%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 20574-98-5
4-(p-methoxyphenyl)but-1-ene

: 2-(4-fluorophenyl)-5-(5-(1-(4-methoxyphenyl)butyl)-2-methylbenzyl)thiophene

Conditions

Conditions	Yield
With dimethylsulfide borane complex; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; lithium methanolate In N,N-dimethyl acetamide at -19℃; for 12h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction;	87%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: 1283129-18-9
(2S,3S,4R,5R,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-thiyl tris(2,2-dimethylpropanoate)

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium; zinc dibromide In n-heptane; dibutyl ether; toluene at -10 - 25℃; for 2.5h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide In n-heptane; dibutyl ether; toluene at 95℃; for 6.5h; Product distribution / selectivity;	86.6%
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at 0 - 10℃; for 1h; Large scale; Stage #2: 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide In tetrahydrofuran at 0 - 10℃; for 3h; Large scale;	85%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 866607-35-4
(3R,4R,5S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With isopropylmagnesium chloride In tetrahydrofuran at 0 - 10℃; for 2h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide In tetrahydrofuran at -15 - 10℃; for 2h; Reagent/catalyst; Inert atmosphere;	86.2%
With bis(acetylacetonate)nickel(II); magnesium chloride; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine; zinc In tetrahydrofuran for 20h; Schlenk technique; Inert atmosphere; Cooling with ice;	75%
With magnesium chloride In tetrahydrofuran at 15℃; stereoselective reaction;	60%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 124-38-9
carbon dioxide

: C19H15FO2S

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 10h; Temperature; Solvent; Inert atmosphere;	86.1%

: 873-66-5
1-propenylbenzene

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: (R)-2-(4-fluorophenyl)-5-(2-methyl-5-(1-phenylpropyl)benzyl)thiophene

Conditions

Conditions	Yield
With potassium fluoride; dimethoxymethylsilane; (1,2-dimethoxyethane)dichloronickel(II); (4R,4'R)-1,1'-bis(3-(tert-butyl)phenyl)-4,4'-di(heptan-4-yl)-4,4',5,5'-tetrahydro-1H,1'H-2,2'-biimidazole at 22 - 26℃; for 24h; Sealed tube; enantioselective reaction;	85%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: (2R,3S,4R,5R)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-one

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -70℃; Industrial scale; Stage #2: With trifluoroacetic acid In tetrahydrofuran; hexane; water; toluene at 0℃; for 3h; Solvent; Reagent/catalyst; Temperature; Industrial scale;	84.23%

Yield

Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -70℃; Industrial scale;
Stage #2: With trifluoroacetic acid In tetrahydrofuran; hexane; water; toluene at 0℃; for 3h; Solvent; Reagent/catalyst; Temperature; Industrial scale;

84.23%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: C26H35BrCl8O9

: C44H49Cl8FO9S

Conditions

Conditions	Yield
With n-hexyllithium; lithium bromide; zinc dibromide In hexane; dibutyl ether; toluene at 10 - 80℃; for 12h;	79.1%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 2,3,4,6-O-tetrachloropivaloyl-α-D-bromoglucopyranose

: C44H53Cl4FO9S

Conditions

Conditions	Yield
With n-butyllithium; isopropylmagnesium chloride; lithium chloride In tetrahydrofuran; hexane at -10℃; for 3h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	78.2%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 73183-34-3
bis(pinacol)diborane

: 2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With 10H-phenothiazine; caesium carbonate In acetonitrile for 48h; Irradiation; Sealed tube; Inert atmosphere;	78%

: 75-75-2
methanesulfonic acid

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1358581-37-9
(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; toluene at -85 - -65℃; for 2h; Stage #2: methanesulfonic acid In tetrahydrofuran; methanol; toluene at 20℃; for 16h; Time;	77.5%

...Expand

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1030825-21-8
(3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; toluene at -85 - -65℃; for 2h; Solvent;	77.5%
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -75 - -70℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one at -60℃; for 1h;
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) In tetrahydrofuran at 0 - 5℃; for 1h; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0 - 5℃; for 2h; Stage #3: With methanesulfonic acid In methanol for 2h; Cooling;

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 2,3,4,6-O-tetrakis(3-chloro-2,2-dichloromethylpropionyl)-α-D-bromoglucopyranose

: C44H45Cl12FO9S

Conditions

Conditions	Yield
With n-hexyllithium; lithium bromide; zinc dibromide In hexane; dibutyl ether; toluene at 10 - 80℃; for 12h;	76.1%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 110391-10-1
(4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one

: 1413373-77-9
(1R,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)-1-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)cyclohex-2-enol

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at -10℃; for 1h; Inert atmosphere; Stage #2: (4R,5S,6R)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-2-cyclohexen-1-one In tetrahydrofuran at -10 - 0℃; for 4h; Inert atmosphere;	75.6%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 104-15-4
toluene-4-sulfonic acid

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1358581-37-9
(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; toluene at -85 - -65℃; for 2h; Stage #2: toluene-4-sulfonic acid In tetrahydrofuran; methanol; toluene at 20℃; for 16h;	72.4%

...Expand

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: C44H57FO9S

Conditions

Conditions	Yield
With lithium bromide; zinc dibromide In diethyl ether at -76℃; Temperature; Reagent/catalyst; Solvent;	71%

: 4291-69-4, 6386-24-9, 6564-72-3, 59531-24-7, 69257-52-9, 78184-89-1, 78609-16-2, 78609-17-3, 78609-18-4, 96553-53-6, 104111-61-7, 131347-08-5, 4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-2-ol

Conditions

Conditions	Yield
Stage #1: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose With sodium hydrogencarbonate; acetic acid; potassium bromide In dichloromethane; water at 20℃; for 0.25h; Stage #2: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water at 20 - 35℃; Stage #3: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -70 - -30℃; Concentration; Solvent; Temperature; Inert atmosphere;	70.2%

Yield

Stage #1: 2,3,4,6-Tetra-O-benzyl-D-glucopyranose With sodium hydrogencarbonate; acetic acid; potassium bromide In dichloromethane; water at 20℃; for 0.25h;
Stage #2: With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water at 20 - 35℃;
Stage #3: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -70 - -30℃; Concentration; Solvent; Temperature; Inert atmosphere;

70.2%

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 108-24-7
acetic anhydride

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 866607-35-4
(3R,4R,5S)-2-(acetoxymethyl)-6-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -75 - -70℃; for 1h; Inert atmosphere; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Large scale; Stage #3: acetic anhydride Large scale; Further stages;	60%

Yield

Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With n-butyllithium In tetrahydrofuran; hexane at -75 - -70℃; for 1h; Inert atmosphere; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -60 - 20℃; for 1h; Large scale;
Stage #3: acetic anhydride Large scale; Further stages;

60%

...Expand

: 300-57-2
allylbenzene

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 73183-34-3
bis(pinacol)diborane

: 2-(3-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-3-phenylpropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With [nickel(II)dichloride(dimethoxyethane)]; quinoline; lithium methanolate In 1,4-dioxane at 30℃; Inert atmosphere; Sealed tube; regioselective reaction;	42%

...Expand

: 75-75-2
methanesulfonic acid

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 61259-48-1, 73322-42-6
2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone

: 1358581-37-9
(2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxylmethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran; toluene at -10 - -5℃; for 2h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone In tetrahydrofuran; toluene at -45 - -40℃; for 2h; Inert atmosphere; Stage #3: methanesulfonic acid In methanol at 40℃; for 4h;	37.5%

...Expand

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1132832-76-8
1-[1-hydroxy-2,3,4,6-tetra-O-(trimethylsilyl)-β-D-glucopyranosyl]-4-methyl-3-[[5-(4-fluorophenyl)-2-thienyl]methyl]benzene

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene); (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With trimethylsilylmethyllithium In tetrahydrofuran; hexane at -40℃; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; hexane at -40℃;

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucopyranoside

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With TurboGrignard In tetrahydrofuran at 0 - 5℃; Inert atmosphere; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at 0 - 5℃; Product distribution / selectivity; Inert atmosphere;

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 61259-48-1, 73322-42-6
2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone

: (3(R),4(S),5(R)-triacetoxy-6-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxy-tetrahydro-pyran-2(R)-yl)-methanol acetate

Conditions

Conditions	Yield
Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With sec-butylmagnesium chloride lithium chloride In toluene at -10 - 0℃; for 1.75h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone In tetrahydrofuran; toluene at -35℃; for 1.25h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; water; toluene at -35 - 25℃; Product distribution / selectivity;

Yield

Stage #1: (2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene) With sec-butylmagnesium chloride lithium chloride In toluene at -10 - 0℃; for 1.75h; Inert atmosphere;
Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucono-1,5-lactone In tetrahydrofuran; toluene at -35℃; for 1.25h; Inert atmosphere;
Stage #3: With acetic acid In tetrahydrofuran; water; toluene at -35 - 25℃; Product distribution / selectivity;

: 898566-17-1
(2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene)

: 842133-18-0
canagliflozin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trimethylsilylmethyllithium / toluene; diethyl ether; pentane / 0.75 h / -50 °C / Inert atmosphere 1.2: 1 h / 25 °C 2.1: ethyl acetate; toluene / 21 h / 75 °C / Inert atmosphere 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme
Multi-step reaction with 4 steps 1.1: n-hexyllithium / toluene; hexane; cyclopentyl methyl ether / 1.17 h / -45 - -25 °C / Inert atmosphere 2.1: zinc dibromide; lithium bromide / cyclopropyl methyl ether / -25 - 0 °C 2.2: 48.5 h / 20 - 65 °C 3.1: methanol / 16 h / 20 - 60 °C 4.1: water / 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetic acid; potassium bromide; sodium hydrogencarbonate / water; dichloromethane / 0.25 h / 20 °C 1.2: 20 - 35 °C 1.3: -70 - -30 °C / Inert atmosphere 2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.5 h / -40 - -20 °C / Inert atmosphere 3.1: trimethylsilyl iodide / dichloromethane / 0 - 30 °C View Scheme

2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene Specification

This chemical is called 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene, and its systematic name is thiophene, 2-(4-fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]-. With the molecular formula of C₁₈H₁₄FIS, its molecular weight is 408.27. The CAS registry number of this chemical is 898566-17-1.

Other characteristics of the 2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene can be summarised as followings: (1)ACD/LogP: 7.20; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 7.19; (4)ACD/LogD (pH 7.4): 7.19; (5)ACD/BCF (pH 5.5): 172937.73; (6)ACD/BCF (pH 7.4): 172937.73; (7)ACD/KOC (pH 5.5): 195370.17; (8)ACD/KOC (pH 7.4): 195370.17; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 28.24 Å²; (13)Index of Refraction: 1.643; (14)Molar Refractivity: 96.26 cm³; (15)Molar Volume: 266.1 cm³; (16)Polarizability: 38.16×10^-24cm³; (17)Surface Tension: 46.5 dyne/cm; (18)Density: 1.533 g/cm³; (19)Flash Point: 226.1 °C; (20)Enthalpy of Vaporization: 68.18 kJ/mol; (21)Boiling Point: 450.2 °C at 760 mmHg; (22)Vapour Pressure: 7.13E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
1.SMILES: Cc1ccc(cc1Cc2ccc(s2)c3ccc(cc3)F)I
2.InChI: InChI=1/C18H14FIS/c1-12-2-7-16(20)10-14(12)11-17-8-9-18(21-17)13-3-5-15(19)6-4-13/h2-10H,11H2,1H3
3.InChIKey: MGXZKAYHSITHMW-UHFFFAOYAY

Product Name

2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene

Synthetic route

2-(4-Fluorophenyl)-5-[(5-iodo-2-methylphenyl)methyl]thiophene Specification

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