162358-07-8

Basic information

• Product Name: Benzene, 1-(2-iodoethyl)-4-octyl-
• Synonyms: Benzene, 1-(2-iodoethyl)-4-octyl-;1-(2-Iodoethyl)-4-octylbenzene;Fingo A-4 1-(2-iodoethyl)-4-octylbenzene;1-(2-lodoethyl)-4-octylbenzen
• CAS NO: 162358-07-8
• Molecular Formula: C₁₆H₂₅I
• Molecular Weight: 344
• Product Categories: Aromatics
• Mol File: 162358-07-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 367.927 °C at 760 mmHg
• Flash Point: 152.798 °C
• Appearance: /
• Density: 1.261
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: Benzene, 1-(2-iodoethyl)-4-octyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(2-iodoethyl)-4-octyl-(162358-07-8)
• EPA Substance Registry System: Benzene, 1-(2-iodoethyl)-4-octyl-(162358-07-8)

Safety Data

• Hazardous Substances Data: 162358-07-8(Hazardous Substances Data)

Usage

Chemical Properties

Oil

Uses

2-(4-Octylphenyl)-1-iodoethane (cas# 162358-07-8) is a compound useful in organic synthesis.

InChI:InChI=1S/C16H25I/c1-2-3-4-5-6-7-8-15-9-11-16(12-10-15)13-14-17/h9-12H,2-8,13-14H2,1H3

Synthetic route

4-octylphenethyl methanesulfonate (162358-06-7) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
With lithium iodide In tetrahydrofuran at 20℃; for 4h;	5.37 g
With sodium iodide In butanone for 2h; Iodination; Heating;	16.0 g
With sodium iodide In tetrahydrofuran at 20℃;	70 g
With tetra-(n-butyl)ammonium iodide; sodium iodide for 3h; Inert atmosphere;	150 g
With sodium iodide In acetone at 20℃; for 19h;	0.44 g

p-hydroxyphenethyl alcohol (501-94-0) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 98 percent / NaHSO4 on silica / hexane / 26 h / Heating 2: 94 percent / pyridine / CH2Cl2 / 1 h / 20 °C 3: 20 percent / Fe(acac)3; NMP / tetrahydrofuran / 1 h 4: Et3N / CH2Cl2 / 1 h 5: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C View Scheme

2-(4-hydroxyphenyl)ethyl acetate (58556-55-1) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 20 percent / Fe(acac)3; NMP / tetrahydrofuran / 1 h 3: Et3N / CH2Cl2 / 1 h 4: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C View Scheme

2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 1 h 2: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 1 h / 20 °C 2: 16.0 g / NaI / butan-2-one / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.5 h 1.2: 3 h / 0 - 20 °C 2.1: sodium iodide / tetrahydrofuran / 20 °C View Scheme

acetic acid 2-(4-octylphenyl)ethyl ester (162358-04-5) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 93 percent / NaOMe / methanol / 8 h / 20 °C 2: Et3N / CH2Cl2 / 1 h 3: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 3.40 g / NaOMe; MeOH / 2 h / Heating 2: Et3N / CH2Cl2 / 1 h / 20 °C 3: 16.0 g / NaI / butan-2-one / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sodium methylate / methanol / 3 h / 20 °C 2.1: triethylamine / dichloromethane / 0.5 h 2.2: 3 h / 0 - 20 °C 3.1: sodium iodide / tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide / water; methanol / 0.2 - 0.3 °C 2: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C View Scheme

acetic acid 2-[4-(trifluoromethanesulfonyloxy)phenyl]ethyl ester (712223-57-9) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 20 percent / Fe(acac)3; NMP / tetrahydrofuran / 1 h 2: Et3N / CH2Cl2 / 1 h 3: 5.37 g / LiI / tetrahydrofuran / 4 h / 20 °C View Scheme

n-octanoic acid chloride (111-64-8) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 43 percent / AlCl3 / 1,2-dichloro-ethane / 3 h / 20 °C 2: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 3: 3.40 g / NaOMe; MeOH / 2 h / Heating 4: Et3N / CH2Cl2 / 1 h / 20 °C 5: 16.0 g / NaI / butan-2-one / 2 h / Heating View Scheme
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 0 - 20 °C 2.1: triethylsilane; trifluoroacetic acid / 20 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 4.1: triethylamine / dichloromethane / 0.5 h 4.2: 3 h / 0 - 20 °C 5.1: sodium iodide / tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 0.01 h / 0.25 - 0.3 °C 1.2: 0 h / 0.2 - 0.5 °C 2.1: sodium hydroxide / water; methanol / 1.5 h / 0.1 - 0.3 °C 3.1: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 4.1: sodium hydroxide / water; methanol / 0.2 - 0.3 °C 5.1: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C View Scheme

acetic acid phenethyl ester (103-45-7) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 43 percent / AlCl3 / 1,2-dichloro-ethane / 3 h / 20 °C 2: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 3: 3.40 g / NaOMe; MeOH / 2 h / Heating 4: Et3N / CH2Cl2 / 1 h / 20 °C 5: 16.0 g / NaI / butan-2-one / 2 h / Heating View Scheme
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 0.01 h / 0.25 - 0.3 °C 1.2: 0 h / 0.2 - 0.5 °C 2.1: sodium hydroxide / water; methanol / 1.5 h / 0.1 - 0.3 °C 3.1: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 4.1: sodium hydroxide / water; methanol / 0.2 - 0.3 °C 5.1: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C View Scheme

2-(4-octanoylphenyl)ethyl acetate (162358-03-4) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylsilane; TFA / 1,2-dichloro-ethane / 3 h / 20 °C 2: 3.40 g / NaOMe; MeOH / 2 h / Heating 3: Et3N / CH2Cl2 / 1 h / 20 °C 4: 16.0 g / NaI / butan-2-one / 2 h / Heating View Scheme
Multi-step reaction with 4 steps 1.1: triethylsilane; trifluoroacetic acid / 20 °C 2.1: sodium methylate / methanol / 3 h / 20 °C 3.1: triethylamine / dichloromethane / 0.5 h 3.2: 3 h / 0 - 20 °C 4.1: sodium iodide / tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 4 steps 1: sodium hydroxide / water; methanol / 1.5 h / 0.1 - 0.3 °C 2: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 3: sodium hydroxide / water; methanol / 0.2 - 0.3 °C 4: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C View Scheme

1-(2-bromoethyl)-4-octylbenzene (268557-54-6) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
In butanone

4'-(2-iodoethyl)octanophenone (219307-01-4) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
With triethylsilane In trifluoroacetic acid

1H-imidazole (288-32-4) + ethyl acetate n-hexane + 2-(4-Octylphenyl)ethyl alcohol (162358-05-6) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
With iodine; triphenylphosphine In ether (200 ml)-acetonitrile

Phenyl acetate (122-79-2) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: aluminum (III) chloride / 1,2-dichloro-ethane / 0 - 20 °C 2.1: triethylsilane; trifluoroacetic acid / 20 °C 3.1: sodium methylate / methanol / 3 h / 20 °C 4.1: triethylamine / dichloromethane / 0.5 h 4.2: 3 h / 0 - 20 °C 5.1: sodium iodide / tetrahydrofuran / 20 °C View Scheme

4'-(2-hydroxyethyl)octanophenone (219307-07-0) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / 0 h / 0.4 °C / Autoclave 2: sodium hydroxide / water; methanol / 0.2 - 0.3 °C 3: sodium iodide / butanone / 0.67 h / 0.8 - 0.85 °C View Scheme

4-iodophenethyl alcohol (52914-23-5) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 17 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 17 h / 20 °C 3: triethylamine / dichloromethane / 3 h / 0 - 20 °C 4: sodium iodide / acetone / 19 h / 20 °C View Scheme

n-octyne (629-05-0) → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); copper(l) iodide; triethylamine / 17 h / 20 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 17 h / 20 °C 3: triethylamine / dichloromethane / 3 h / 0 - 20 °C 4: sodium iodide / acetone / 19 h / 20 °C View Scheme

2-(4-(oct-1-yn-1-yl)phenyl)-1-ethanol → 1-(2-iodoethyl)-4-octylbenzene (162358-07-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 17 h / 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: sodium iodide / acetone / 19 h / 20 °C View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 1-ethyl-4-octylbenzene

Conditions	Yield
With water; zinc In acetonitrile at 25℃; for 12h; Sealed tube; Inert atmosphere;	93%
With water; zinc In acetonitrile at 25℃; for 12h; Inert atmosphere; Sealed tube;	93%

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 1-(ethyl-2-d)-4-octylbenzene

Conditions	Yield
With water-d2; zinc In acetonitrile at 25℃; for 12h; Time; Inert atmosphere; Sealed tube;	92%
With water-d2; zinc In acetonitrile at 25℃; for 12h; Inert atmosphere; Sealed tube;	92%

2-acetylaminomalonic acid diethyl ester (1068-90-2) + 1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate (162358-08-9)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; caesium carbonate In dimethyl sulfoxide at 25 - 85℃; Inert atmosphere;	88%
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide for 30h; Stage #2: 2-(4-octylphenyl)-1-iodoethane In N,N-dimethyl-formamide at 50 - 60℃; for 1h;	82%
Stage #1: 2-acetylaminomalonic acid diethyl ester With sodium ethanolate In ethanol at 20℃; for 0.5h; Metallation; Stage #2: 2-(4-octylphenyl)-1-iodoethane In ethanol at 65℃; for 3h; Alkylation; Further stages.;	61%

(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (78342-42-4) + 1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → (2R,5S)-5-isopropyl-3,6-dimethoxy-2-(4-octylphenethyl)-2,5-dihydro-pyrazine

Conditions	Yield
Stage #1: (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: 2-(4-octylphenyl)-1-iodoethane In tetrahydrofuran at -78 - -15℃; for 4h;	83%

diethyl 4-(tetrahydropyran-2-yloxy)butane-1,1-dicarboxylate (22455-91-0) + 1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → diethyl 2-[2-(4-octylphenyl)ethyl]-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]malonate (177260-23-0)

Conditions	Yield
Stage #1: diethyl 4-(tetrahydropyran-2-yloxy)butane-1,1-dicarboxylate With sodium hydride In N,N-dimethyl-formamide for 0.5h; Metallation; Stage #2: 2-(4-octylphenyl)-1-iodoethane In N,N-dimethyl-formamide for 3h; Alkylation; Further stages.;	76%

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) + ethyl 2-acetamido-2-cyanoacetate (90877-70-6, 4977-62-2) → ethyl 2-acetamido-2-cyano-4-(4-octylphenyl)butyrate (296282-66-1)

Conditions	Yield
Stage #1: ethyl 2-acetamido-2-cyanoacetate With sodium ethanolate In ethanol at 20℃; for 0.5h; Metallation; Stage #2: 2-(4-octylphenyl)-1-iodoethane In ethanol at 65℃; for 3h; Alkylation; Further stages.;	75%

diethyl 3-(tetrahydropyran-2-yloxy)propane-1,1-dicarboxylate (25823-84-1) + 1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-[2-(4-octyl-phenyl)-ethyl]-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-malonic acid diethyl ester (1026240-85-6)

Conditions	Yield
Stage #1: diethyl 3-(tetrahydropyran-2-yloxy)propane-1,1-dicarboxylate With sodium hydride In N,N-dimethyl-formamide for 0.5h; Metallation; Stage #2: 2-(4-octylphenyl)-1-iodoethane In N,N-dimethyl-formamide for 3h; Alkylation; Further stages.;

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → fingolimod (162359-55-9)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 61 percent / ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3.1: 8.25 g / pyridine / 16 h / 20 °C 4.1: 2 N aq. LiOH / methanol / 2 h / Heating View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0.45 - 0.5 °C / Inert atmosphere 1.2: 0.4 - 0.45 °C / Inert atmosphere 2.1: calcium chloride / water; isopropyl alcohol / 0 h / 0.2 - 0.3 °C 2.2: 0.01 h / 0 - 0.5 °C 2.3: 0 h / 0.15 - 0.5 °C 3.1: sodium hydroxide / water; methanol / 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate; tetrabutylammomium bromide / toluene / Inert atmosphere; Reflux 2.1: calcium chloride / ethanol; water 2.2: 10 - 15 °C 2.3: Reflux View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-amino-2-hydroxymethyl-4-(4-octyl-phenyl)-butyric acid (296282-46-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 75 percent / ethanol / 3 h / 65 °C 2.1: 54 percent / LiBH4 / tetrahydrofuran / 6 h / Heating 3.1: 66 percent / aq. HCl; AcOH / 7 h / Heating View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 3-isocyanato-3-[2-(4-octyl-phenyl)-ethyl]-dihydro-furan-2-one

Conditions	Yield
Multi-step reaction with 6 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 4.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 5.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 6.1: benzene / 1 h / Heating View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-amino-2-[2-(4-octylphenyl)ethyl]butane-1,4-diol

Conditions

Yield

Multi-step reaction with 11 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 4.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 5.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 6.1: benzene / 1 h / Heating 7.1: benzene / 7 h / Heating 8.1: LiBH4 / tetrahydrofuran / 0.5 h / Heating 9.1: pyridine / 13 h / 20 °C 10.1: Me3SiI / CH2Cl2 / 7 h 10.2: pyridine / 13 h 11.1: 2 M aq. LiOH / tetrahydrofuran; methanol / 2 h / Heating View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → N-[1-cyano-1-hydroxymethyl-3-(4-octylphenyl)propyl]acetamide (296282-78-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 75 percent / ethanol / 3 h / 65 °C 2.1: 54 percent / LiBH4 / tetrahydrofuran / 6 h / Heating View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carboxylic acid (1027589-49-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-amino-2-[2-(4-octylphenyl)ethyl]pentane-1,5-diol

Conditions

Yield

Multi-step reaction with 9 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: 76 percent / dimethylformamide / 3 h 2.1: KOH / ethanol / 6 h / 50 °C 3.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 4.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 5.1: benzene / 1 h / Heating 6.1: benzene / 7 h / Heating 7.1: LiBH4 / tetrahydrofuran / 3 h / Heating 8.1: 5 N aq. KOH / tetrahydrofuran; methanol / 13 h / Heating 9.1: HCl; MeOH / diethyl ether / 0.5 h View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl) butan-2-yl) acetamide (249289-10-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 61 percent / ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate / dimethyl sulfoxide / 3 h / 60 °C / Inert atmosphere 1.2: 60 - 80 °C 2.1: sodium tetrahydroborate / methanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: caesium carbonate; tetrabutylammomium bromide / toluene / Inert atmosphere; Reflux 2.1: calcium acetate / isopropyl alcohol / 0.5 h / 10 - 15 °C 2.2: 10 - 15 °C View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carboxylic acid ethyl ester (1027929-75-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 3-[2-(4-octyl-phenyl)-ethyl]-2-oxo-tetrahydro-furan-3-carbonyl azide

Conditions	Yield
Multi-step reaction with 5 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 4.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 5.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]-γ-butyrolactone (177259-57-3)

Conditions	Yield
Multi-step reaction with 7 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 4.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 5.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 6.1: benzene / 1 h / Heating 7.1: benzene / 7 h / Heating View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]butane 1,4-diol (177258-50-3)

Conditions	Yield
Multi-step reaction with 8 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 4.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C 5.1: aq. NaN3 / tetrahydrofuran / 1 h / 0 °C 6.1: benzene / 1 h / Heating 7.1: benzene / 7 h / Heating 8.1: LiBH4 / tetrahydrofuran / 0.5 h / Heating View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate (162358-09-0)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium ethoxide / ethanol / 0.5 h / 20 °C 1.2: 61 percent / ethanol / 3 h / 65 °C 2.1: LiAlH4 / tetrahydrofuran / 2 h / 20 °C 3.1: 8.25 g / pyridine / 16 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0.45 - 0.5 °C / Inert atmosphere 1.2: 0.4 - 0.45 °C / Inert atmosphere 2.1: calcium chloride / water; isopropyl alcohol / 0 h / 0.2 - 0.3 °C 2.2: 0.01 h / 0 - 0.5 °C 2.3: 0 h / 0.15 - 0.5 °C View Scheme
Multi-step reaction with 3 steps 1.1: caesium carbonate; tetrabutylammomium bromide / toluene / Inert atmosphere; Reflux 2.1: calcium acetate / isopropyl alcohol / 0.5 h / 10 - 15 °C 2.2: 10 - 15 °C 3.1: pyridine / 0.08 h 3.2: 0 - 5 °C View Scheme
Multi-step reaction with 3 steps 1.1: caesium carbonate; tetrabutylammomium bromide / toluene / Inert atmosphere; Reflux 2.1: calcium acetate / isopropyl alcohol / 0.5 h / 10 - 15 °C 2.2: 10 - 15 °C 3.1: pyridine 3.2: 0 - 5 °C View Scheme

1-(2-iodoethyl)-4-octylbenzene (162358-07-8) → C24H34O6

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaH / dimethylformamide / 0.5 h 1.2: dimethylformamide / 3 h 2.1: 1 N aq. HCl / methanol / 5 h 3.1: 0.25 N aq. NaOH / acetone / 1.5 h / 20 °C 4.1: Et3N / tetrahydrofuran / 0.25 h / -5 °C View Scheme

Upstream product

• 268557-54-6 1-(2-bromoethyl)-4-octylbenzene 
• 288-32-4 1H-imidazole 
• 162358-05-6 2-(4-Octylphenyl)ethyl alcohol 
• 629-05-0 n-octyne 
• 52914-23-5 4-iodophenethyl alcohol 
• 219307-07-0 4'-(2-hydroxyethyl)octanophenone 
• 122-79-2 Phenyl acetate 
• 219307-01-4 4'-(2-iodoethyl)octanophenone 
• 162358-03-4 2-(4-octanoylphenyl)ethyl acetate 
• 103-45-7 acetic acid phenethyl ester 
• 111-64-8 n-octanoic acid chloride 
• 712223-57-9 acetic acid 2-[4-(trifluoromethanesulfonyloxy)phenyl]ethyl ester 
• 162358-04-5 acetic acid 2-(4-octylphenyl)ethyl ester 
• 58556-55-1 2-(4-hydroxyphenyl)ethyl acetate 

Downstream Products

• 1026240-85-6 2-[2-(4-octyl-phenyl)-ethyl]-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-malonic acid diethyl ester 
• 177260-23-0 diethyl 2-[2-(4-octylphenyl)ethyl]-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]malonate 
• 162358-08-9 diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate 
• 296282-66-1 ethyl 2-acetamido-2-cyano-4-(4-octylphenyl)butyrate 
• 162358-61-4 ethyl 2-ethoxycarbonyl-4-(4-octylphenyl)butyrate 
• 204008-22-0 1-ethyl-4-octylbenzene 
• 177260-25-2 ethyl 2-methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]-5-(tetrahydro-2H-pyran-2-yloxy)valerate 
• 177260-24-1 2-ethoxycarbonyl-2-[2-(4-octylphenyl)ethyl]-5-(tetrahydropyran-2-yloxy)pentanoic acid 
• 177260-26-3 2-amino-2-[2-(4-octylphenyl)ethyl]-5-(tetrahydro-2H-pyran-2-yloxy)pentanol 
• 177259-09-5 3-Acetamido-3-acetoxymethyl-5-(4-octylphenyl)pentyl acetate 
• 162358-09-0 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate 
• 177258-50-3 2-Methoxycarbonylamino-2-[2-(4-octylphenyl)ethyl]butane 1,4-diol 

Relevant articles and documents

Development of novel PP2A activators for use in the treatment of acute myeloid leukaemia

AAL(S), the chiral deoxy analog of the FDA approved drug FTY720, has been shown to inhibit proliferation and apoptosis in several cancer cell lines. It has been suggested that it does this by activating protein phosphatase 2A (PP2A). Here we report the synthesis of new cytotoxic analogs of AAL(S) and the evaluation of their cytotoxicity in two myeloid cell lines, one of which is sensitive to PP2A activation. We show that these analogs activate PP2A in these cells supporting the suggested mechanism for their cytotoxic properties. Our findings identify key structural motifs required for anti-cancer effects.

FINGOLIMOD HYDROCHLORIDE PROCESS

A process for preparation of diethyl 2-acetamido-2-(4-octyl phenyl)ethyl malonate (III), a key intermediate of fingolimod hydrochloride comprising reaction of 2-(4- octylphenyl)ethyl iodide (IV) with diethyl acetamido malonate in presence of a base and an iodinating agent and in an organic solvent. The compound of formula (III) thus obtained provided fingolimod hydrochloride (la) having associated impurities below the regulatory limits.

Iron-catalyzed cross-coupling reactions. A scalable synthesis of the immunosuppressive agent FTY720

A chemo- and regioselective cross-coupling reaction of the functionalized aryl triflate 5 with octylmagnesium bromide catalyzed by cheap, nontoxic, and environmentally benign Fe(acac)3 sets the basis for a practical and scaleable synthesis of the octylbenzene derivative 6, which serves as a key building block for the preparation of FTY720 (1). This 2-amino-1,3-propanediol derivative shows highly promising immunosuppressive properties and is currently in human clinical phase III trials.